JPH05209164A - Tack agent composition - Google Patents

Abstract

PURPOSE:To provide a tack agent composition capable of well-balanced manifestation of both curing rate and storage stability, excellent in workability in its line production, comprising specific two kinds of compounds, hydrosilylating catalyst, tackifying resin, and storage stability improver. CONSTITUTION:The objective composition mainly comprises (A) a compound having in the molecule at least one alkenyl group [e.g. a compound of formula I (R<1> is H or methyl ; R<2> is 1-20C divalent hydrocarbon group which may contain one or more ether linkages; R<3> is aliphatic or aromatic organic group; (a) is a positive integer)], (B) a compound having in the molecule at least two hydrosilyl groups {e.g. a compound of formula II [X is a group having at least one hydrosilyl group (pref. of formula III)]}, (C) a hydrosilylating catalyst (pref., a platinum-olefin complex), (D) a tackifying resin (e.g. phenol resin), and (E) a storage stability improver (e.g. benzothiazole).

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an adhesive composition.
More specifically, a compound having at least one alkenyl group in the molecule, a compound having at least two hydrosilyl groups in the molecule, and a hydrosilylation catalyst as main components are provided with a good balance of curing rate and storage stability. It also relates to an addition-type curable pressure-sensitive adhesive composition.

[0002]

2. Description of the Related Art A pressure-sensitive adhesive is also called a pressure-sensitive adhesive and has the property of easily adhering to the surface of an object with a small pressure such that it is pressed with a fingertip. Such an adhesive is used for adhesive products such as cellophane tape, vinyl tape for electrical insulation, masking tape, adhesive sheet, and adhesive label. In particular, an adhesive tape having a support made of polyvinyl chloride is widely used because it has various excellent properties such as low cost and excellent water resistance and electrical properties.

As the pressure-sensitive adhesive used in the pressure-sensitive adhesive tape, those containing natural rubber, synthetic rubber or the like as a main component, and those containing an acrylic acid ester copolymer as a main component are mainly used. However, these pressure-sensitive adhesive compositions are generally prone to deterioration by heat, light, etc., and when the pressure-sensitive adhesive product using the pressure-sensitive adhesive composition is used outdoors, the weather resistance is insufficient, so that end peeling or the like easily occurs. As a result, the function as an adhesive product cannot be fully achieved. In order to solve this problem, a saturated hydrocarbon polymer having a hydroxyl group or a hydrolyzable group bonded to a silicon atom and having at least one silicon-containing group which can be crosslinked by forming a siloxane bond, and an adhesive A pressure-sensitive adhesive composition containing an imparting resin has been developed (JP-A-1-170681). However, this pressure-sensitive adhesive composition has a problem that the curing speed is slow because it is cured by the condensation reaction of the functional silyl group, which is inconvenient for line production.

In order to solve the problem that the curing rate is slow, the present inventors have (A) a compound having at least one alkenyl group in the molecule and (B) at least two hydrosilyl groups in the molecule. A pressure-sensitive adhesive composition comprising the compound contained therein, the (C) hydrosilylation catalyst, and the (D) tackifying resin was developed (Japanese Patent Application No. 2-268193). However, since only the components (A) to (D) are cured by a functional allylic addition reaction, the curing rate is high,
Although it is suitable for line productivity, it suffers from poor storage stability and thickening and gelation within a few hours even at room temperature.

The present invention has been made to solve the above problems and to provide a pressure-sensitive adhesive composition having a high curing rate and good storage stability, and the following component (A):
The content is a pressure-sensitive adhesive composition containing (E) as a main component. (A) a compound having at least one alkenyl group in the molecule, (B) a compound having at least two hydrosilyl groups in the molecule, (C) a hydrosilylation catalyst,
(D) Tackifying resin, (E) Storage stability improver.

The compound having at least one alkenyl group in the molecule which is the component (A) of the present invention is not particularly limited, and various compounds from low molecular weight compounds to organic polymers can be used. The alkenyl group is not particularly limited, but is of the formula (I)

[0007]

[Chemical 1]

An alkenyl group represented by the formula (wherein R ¹ is hydrogen or a methyl group) is preferable.

To describe the component (A) concretely, firstly,
Formula (II)

[0010]

[Chemical 2]

(R ¹ is hydrogen or methyl, R ² is 1 to 1 carbon atoms
Twenty divalent hydrocarbon groups may contain one or more ether bonds. R ³ is an aliphatic or aromatic organic group, and a is a positive integer. The compound which has the ether bond represented by these is mentioned.

In the formula (II), R ² represents a divalent hydrocarbon group having 1 to 20 carbon atoms, but R ² may contain one or more ether bonds. In particular,

[0013]

[Chemical 3]

And the like. Due to ease of synthesis
CH ₂ - is preferred.

In the formula (II), R ³ is an aromatic or aliphatic organic group. Specifically,

[0016]

[Chemical 4]

[0017]

[Chemical 5]

[0018]

[Chemical 6]

And the like. Of these, the following are preferred.

[0020]

[Chemical 7]

R ³ may be an organic polymer, and various kinds can be used.

First, as the polyether polymer, for example, polyoxyethylene, polyoxypropylene, polyoxytetramethylene, polyoxyethylene-polyoxypropylene copolymer and the like are preferably used. Other polymers having a main chain skeleton include adipic acid and the like 2.
Polyester polymer obtained by condensation of basic acid and glycol, or ring-opening polymerization of lactones, ethylene-propylene copolymer, polyisobutylene, copolymer of isobutylene and isoprene, etc., polychloroprene, polyisoprene Hydrogenated copolymers of isoprene with butadiene, acrylonitrile, styrene, etc., polybutadiene, copolymers of butadiene with styrene, acrylonitrile, etc., polyisoprene, polybutadiene, isoprene or copolymers of butadiene with acrylonitrile, styrene, etc. Polyolefin polymer obtained by radical polymerization of monomers such as ethyl acrylate and butyl acrylate.
Acrylic ester-based copolymers of acrylic acid esters such as ethyl acrylate and butyl acrylate with vinyl acetate, acrylonitrile, methyl methacrylate, styrene and the like, and graft polymers obtained by polymerizing vinyl monomers in the organic polymer. , Polysulfide polymer, nylon 6 by ring-opening polymerization of ε-caprolactam, nylon 66 by condensation polymerization of hexamethylenediamine and adipic acid, nylon 610 by condensation polymerization of hexamethylenediamine and sebacic acid, condensation of ε-aminoundecanoic acid Polyamide-based polymers such as nylon 11 by polymerization, nylon 12 by ring-opening polymerization of ε-aminolaurolactam, and copolymerized nylon having two or more components among the above-mentioned nylons, for example, polycondensation from bisphenol A and carbonyl chloride. Polycarbonate-based polymer produced Te, diallyl phthalate polymers are exemplified.

Next, the general formula (III)

[0024]

[Chemical 8]

(R ¹ is hydrogen or a methyl group, R ² has 1 carbon atom
It is a divalent hydrocarbon group of -20 and may contain one or more ether bonds. R ⁴ is an aliphatic or aromatic organic group, and a is a positive integer. The compound which has an ester bond represented by these is mentioned. In formula (III), R ² is the same as R ² in formula (II).

R ⁴ is 1 of aromatic or aliphatic type.
Is a tetravalent organic group. Specifically,

[0027]

[Chemical 9]

[0028]

[Chemical 10]

And the like. Of these, the following are preferred.

[0030]

[Chemical 11]

R ⁴ may be an organic polymer and has the formula (II)
All of the organic polymers exemplified as the ether compound of can be preferably used. Next, the general formula (IV)

[0032]

[Chemical 12]

(R ¹ is hydrogen or a methyl group, R ⁵ is an aliphatic or aromatic organic group, and a is a positive integer). In formula (IV), R ⁵ represents an aliphatic or aromatic organic group, and specifically,

[0034]

[Chemical 13]

[0035]

[Chemical 14]

Is preferred. Furthermore, − (CH ₂ ) _n − (n = 1
0) is particularly preferable. R ⁵ may be an organic polymer,
All the organic polymers exemplified in the explanation of the formula (II) can be preferably used.

Specific examples of the component (A) include general formula (V)

[0038]

[Chemical 15]

(R ¹ is hydrogen or methyl group, R ² is carbon number 1
It is a divalent hydrocarbon group of -20 and may contain one or more ether bonds. R ⁶ is an aliphatic or aromatic organic group, and a is a positive integer. The compound which has the carbonate bond represented by these is mentioned. Wherein, R ² is the same as R ² in formula (II). Also, as R ⁶ ,

[0040]

[Chemical 16]

[0041]

[Chemical 17]

[0042]

[Chemical 18]

And the like. Of these, the following are particularly preferable.

[0044]

[Chemical 19]

R ⁶ may be an organic polymer and has the formula (II)
All of the organic polymers exemplified in the above description can be preferably used.

When an organic polymer is used as the component (A), various proposed methods can be used for introducing an alkenyl group into the polymer.
It can be roughly classified into a method introduced after polymerization and a method introduced during polymerization.

As a method for introducing an alkenyl group after polymerization, for example, a polymer having a functional group such as a hydroxyl group or an alkoxide group at the terminal, main chain or side chain, an active group reactive with the above functional group, By reacting an organic compound having an alkenyl group, the alkenyl group can be introduced into the terminal, main chain or side chain. Examples of the organic compound having an active group and an alkenyl group reactive with the above functional group include C ₃ -C ₂₀ unsaturated such as acrylic acid, methacrylic acid, vinyl acetic acid, acrylic acid chloride, and acrylic acid bromide. Fatty acids, acid halides,
Acid anhydrides, C ₃ -C ₂₀ unsaturated fatty acid-substituted carbonic acid halides such as allyl chloroformate, allyl bromoformate, allyl chloride, allyl bromide, vinyl (chloromethyl) benzene, allyl (chloromethyl) benzene, allyl (Bromomethyl) benzene, allyl (chloromethyl) ether, allyl (chloromethoxy) benzene, 1-butenyl (chloromethyl) ether, 1-hexenyl (chloromethoxy) benzene, allyloxy (chloromethyl) benzene and the like can be mentioned.

As a method of introducing an alkenyl group during the polymerization, for example, in the case of producing by a radical polymerization method, a vinyl monomer having an alkenyl group having a low radical reactivity in a molecule such as allyl methacrylate and allyl acrylate, allyl mercaptan, etc. An alkenyl group can be introduced into the main chain or terminal of the polymer by using the radical chain transfer agent.

The alkenyl group-containing organic polymer may be linear or branched and has a molecular weight of 500 to 50,000.
Any of the above can be preferably used, but 1000 to 200
Particularly preferred is 00. The alkenyl group may be at the molecular end or in the molecule, but when a rubber-like cured product is prepared using the composition of the present invention, the effective network chain length becomes longer at the molecular end. Therefore, it is preferable.

The component (B) of the present invention, which is an organic compound having at least two hydrosilyl groups in the molecule, is not particularly limited, but a specific example of the group containing a hydrosilyl group is -Si. (H) _n (CH ₃ ) _3-n , − Si (H) _n (C
₂ H ₅ ) _3-n , − Si (H) _n (C ₆ H ₅ ) _3-n (n = 1 to 3), − SiH
₂ (C ₆ H ₁₃₎ hydrosilyl group containing only one silicon atom, such _{as, -Si (CH 3) 2 Si} (CH 3) 2 H, -Si (CH 3) 2 CH 2 CH 2 Si (C
H ₃ ) ₂ H, −Si (CH ₃ ) ₂ SiCH ₃ H ₂ ,

[0051]

[Chemical 20]

(In the formula, R is a group selected from H, OSi (CH ₃ ) ₃ and an organic group having 1 to 10 carbon atoms, and each R may be the same or different. M and n are positive) Is an integer and 2
≦ m + n ≦ 50)

[0053]

[Chemical 21]

(Where R is the same as above, m is a positive integer,
n, p, and q are 0 or a positive integer, and 1 ≦ m + n + p
+ Q ≦ 50)

[0055]

[Chemical formula 22]

(Where R is the same as above, m is a positive integer,
n is 0 or a positive integer, and examples thereof include a group derived from various linear, branched or cyclic polyvalent hydrogen siloxanes represented by 2 ≦ m + n ≦ 50).

Among the various hydrosilyl groups described above, the molecular weight of the group constituting the hydrosilyl group is 500 because the hydrosilyl group-containing compound of the present invention is less likely to impair the compatibility with the component (A). The following are preferable, and the following are preferable in consideration of the reactivity of the hydrosilyl group.

[0058]

[Chemical formula 23]

(Where p is a positive integer, q is 0 or a positive integer, and 2≤p + q≤4).

[0060]

[Chemical formula 24]

When two or more hydrosilyl group-containing groups are present in the same molecule, they may be the same or different. The total number of hydrosilyl groups contained in the component (B) may be at least 2 in one molecule, but is preferably 2 to 15 and particularly preferably 3 to 12. When the compound containing a hydrosilyl group of the present invention is mixed with a compound containing an alkenyl group (component (A)) in the presence of a hydrosilylation catalyst to cure by a hydrosilylation reaction, the number of hydrosilyl groups is 2 or more. If the amount is small, curing failure often occurs. Also,
When the number of the hydrosilyl groups exceeds 15, (B)
The stability of the components becomes poor, and in addition, a large amount of hydrosilyl groups remain in the cured product even after curing, causing voids and cracks.

The hydrosilyl group-containing compound as the component (B) is not particularly limited, but various compounds ranging from low molecular weight compounds to polymers can be used. Illustrating specifically, the formula (VI)

[0063]

[Chemical 25]

[0064] (wherein, X is a group having at least one hydrosilyl group of ^{the, R 1, R 2, R} 3 is, R ¹ in Formula (II),
The same thing as R ² and R ³ can be used. ) A compound having an ether bond represented by the formula:

[0065]

[Chemical formula 26]

[0066] (wherein, X is a group having at least one hydrosilyl group of ^{the, R 1, R 2, R} 4 is, R ¹ in formula (III),
The same thing as R ² and R ⁴ can be used. ) A compound having an ester bond represented by the formula:

[0067]

[Chemical 27]

[0068] In (wherein, X is a group having at least one hydrosilyl group of the, R ^1, R ⁵ may be used as the same respectively as R ^1, R ⁵ in formula (IV).) Table A hydrocarbon-based compound of formula (IX)

[0069]

[Chemical 28]

[0070] (wherein, X is a group having at least one hydrosilyl group of ^{the, R 1, R 2, R} 6 is, R ¹ in Formula (V), at
The same ones as R ² and R ⁶ can be used. The compound which has a carbonate bond represented by these can be mentioned.

When an organic polymer is used as the component (B), the polymer may be linear or branched and has a molecular weight of 5
Any of 00 to 50000 can be preferably used,
Those of 500 to 20,000 are particularly preferable. The hydrosilyl group as the component (B) may be present at the molecular end or in the molecule, but when a rubber-like cured product is produced using the composition of the present invention, it is more effective at the molecular end. It is preferable because the network chain length becomes long.

The method for producing the component (B) is not particularly limited, and any method may be used. For example, (i) a method of treating an organic compound having a Si—Cl group in the molecule with a reducing agent such as LiAlH ₄ or NaBH ₄ to reduce the Si—Cl group in the compound to a Si—H group, (ii) ) A method of reacting an organic compound having a functional group X present in the molecule with a compound having at the same time a functional group Y reactive with the functional group and a hydrosilyl group in the molecule,
(Iii) A method in which a polyhydrosilane compound having at least two hydrosilyl groups is selectively hydrosilylated with respect to an organic compound having an alkenyl group so that the hydrosilyl group remains in the molecule of the compound after the reaction can be considered. . Of these, the method (iii) is particularly preferable.

As the combination of the components (A) and (B), any combination can be used.
It is preferable that one or both of the component and the component (B) be an organic polymer, and among them, a polypropylene oxide polymer is preferable. When both the component (A) and the component (B) are low molecular weight compounds, the resulting cured product has a high crosslink density and a reduced viscosity, which is not preferable as a pressure-sensitive adhesive composition.

Examples of the hydrosilylation catalyst which is the component (C) of the present invention include platinum simple substance, solid platinum supported on a carrier such as alumina, silica, carbon black, chloroplatinic acid, chloroplatinic acid and alcohol, Complexes with aldehydes, ketones, etc., platinum-olefin complexes {for example, Pt (CH ₂ = C
_{H 2) 2 (PPh 3)} 2 Pt (CH 2 = CH 2) 2 Cl 2}; platinum - vinylsiloxane complex {for _{example, Pt n (ViMe 2 SiOSiMe 2} Vi) m, Pt [(MeV
iSiO) ₄ ] _m }; platinum-phosphine complex {for example, Pt (PPh
_{3) 4,} Pt (PBu _{3) 4};} platinum - phosphite complex (e.g., Pt [P (OPh _{3] 4)} (in the formula, Me represents a methyl group, Bu a butyl group, Vi represents a vinyl group, Ph is A phenyl group, m and n are integers), dicarbonyldichloroplatinum, and Ashby U.S. Pat. Nos. 3,159,601 and 3,
159662, a platinum-hydrocarbon composite, as well as Lamoreaux U.S. Pat. No. 322.
Mention may also be made of the platinum alcoholate catalysts described in 0972. Additionally, the platinum chloride-olefin composites described in Modic US Pat. No. 3,516,946 are also useful in the present invention.

Examples of catalysts other than platinum compounds include RhCl (PPh ₃ ) ₃ , RhCl ₃ , RhlAl ₂ O ₃ , RuCl ₃ , IrCl ₃ and FeC.
Examples include l ₃ , AlCl ₃ , PdCl ₂ · 2H ₂ O, NiCl ₂ and TiCl ₄ . These catalysts may be used alone or in combination of two or more. Chloroplatinic acid, a platinum-olefin complex, and a platinum-vinylsiloxane complex are preferable from the viewpoint of catalytic activity.

The amount of catalyst is not particularly limited, but (A)
10 ^-1 to 10 ^-8 mo for ¹ mol of alkenyl group in the component
It is recommended to use in the range of l. Preferably 10 ^-3 to 10 ^-6
It is recommended to use it in the mol range. If it is less than 10 ^-8 mol, curing will not proceed sufficiently. Further, the hydrosilylation catalyst is generally expensive and corrosive, and since a large amount of hydrogen gas may be generated and the cured product may foam, 10 ^-1 mol
It is better not to use more. In the present invention, the pressure-sensitive adhesive composition has a Si for alkenyl group using a noble metal catalyst.
Since it is cured by the addition reaction of —H group, the curing rate is very fast, which is convenient for line production.

The tackifying resin which is the component (D) of the present invention is not particularly limited, and those usually used can be used.
Specific examples include, for example, phenol resin, modified phenol resin (for example, cashew oil modified phenol resin, tall oil modified phenol resin, etc.), terpene phenol resin, xylene-phenol resin, cyclopentadiene-phenol resin, xylene resin, petroleum resin, phenol. Modified petroleum resins, rosin ester resins, low molecular weight polystyrene resins, terpene resins and the like can be mentioned. These may be used alone or in combination of two or more. The amount of the tackifying resin used is preferably 10 to 140 parts by weight, more preferably 15 to 80 parts by weight, based on 100 parts by weight of the total amount of the components (A) and (B).

When the hydrosilyl group-containing compound which is the component (B) is produced by the selective hydrosilylation described above, the hydrosilylation catalyst is contained in the component (B) even after the reaction, so that its stability is generally good. However, when left for a long period of time or when moisture is mixed, conversion of Si-H groups to Si-OH groups occurs, and phenomena such as viscosity increase and gelation are observed. Therefore, the composition further contains a storage stability improver which is the component (E). As such a compound, a compound containing an aliphatic unsaturated bond, an organic phosphorus compound, an organic sulfur compound, a nitrogen-containing compound, a tin compound, an organic peroxide and the like can be preferably used.
Specific examples thereof include benzothiazole, thiazole, dimethylmalate, 2-pentenenitrile, and 2,3-dichloropropene, and thiazole is particularly preferable in terms of compatibility of pot life and fast curability. It is not limited. The storage stability improver can be used in an almost arbitrary amount as long as it is uniformly dispersed in the component (A) and the component (B).
It is preferably used in the range of 10 ⁻⁶ to 10 ⁻¹ mol with ^respect to ¹ mol of the H group-containing compound. This is less than 10 ^-6 mol not improved sufficiently storage stability of component (B), 10 ^-1 mo
This is because if it exceeds l, curing is hindered. The storage stability improvers may be used alone or in combination of two or more. The order of adding the component (E) is not particularly limited, but it is desirable not to directly mix the component (C) alone. This is because direct mixing of the (C) component and the (E) component produces a precipitate due to complex formation and the like, which makes it difficult to uniformly disperse it in the composition.

The composition of the present invention may further contain various supports (plastic film, metal foil,
Nitrogen-containing silane compounds, plasticizers and softeners, fillers, antioxidants, ultraviolet absorbers, pigments, surfactants, solvents, silicon compounds, etc. for improving the adhesiveness to paper) . Specific examples of the nitrogen-containing silane compound include, for example, H ₂ NCH ₂ CH ₂ CH ₂ Si (OCH ₃ ) ₃ , H ₂ NCH ₂ CH.
₂ NCH ₂ CH ₂ CH ₂ Si (OCH ₃ ) ₃ , H ₂ NCH ₂ CH ₂ NCH ₂ CH ₂ CH ₂ Si (CH ₃ ) (OC
H ₃ ) ₂ , (C ₂ H ₅ O) ₃ SiCH ₂ CH ₂ CH ₂ NHCH ₂ CH ₂ NHCH ₂ CH ₂ CH ₂ Si (OC ₂ H
₅ ) ₃ , an amino group- and / or imino group-containing alkoxysilane such as the above, and an amino group- and / or imino group-containing alkoxysilane,

[0080]

[Chemical 29]

CH ₂ ═C (CH ₃ ) COOCH ₂ CH ₂ CH ₂ Si (OCH ₃ ) ₃ , CH ₂ with a reaction product of an epoxysilane compound such as the above, an alkoxysilane containing an amino group and / or an imino group. =
Examples thereof include reaction products with a methacryloxysilane compound such as C (CH ₃ ) COOCH ₂ CH ₂ CH ₂ Si (OCH ₂ CH ₂ OCH ₃ ) ₃ . The amount of the nitrogen-containing silane compound used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the total amount of the components (A) and (B).

Specific examples of the plasticizers and softeners include dioctyl phthalate, butyl benzyl phthalate, polypropylene glycol, chlorinated paraffin, and liquid polybutadiene. Specific examples of the filler include fine silica powder, calcium carbonate, clay, talc, titanium oxide, zinc oxide, diatomaceous earth, barium sulfate, and carbon black. Among these fillers, especially silica fine powder, especially particle size 70 to 50 nm (BET specific surface area 50 to 380 m ² /
Finely divided silica of about g) is preferable, and among them, hydrophobic silica subjected to surface treatment is particularly preferable because it has a large effect of improving strength in a preferable direction.

[0083]

EXAMPLES Next, the composition of the present invention will be specifically described by way of examples, but the present invention is not limited to these examples.

Synthesis Example 1 According to the method disclosed in JP-A-53-134095,
A polyoxypropylene having an allyl type olefin group at the end was synthesized. Polyoxypropylene glycol having an average molecular weight of 3000 and powdered caustic soda were stirred at 60 ° C., and bromochloromethane was added to carry out a reaction to increase the molecular weight. Next, add allyl chloride to give 11
The end was allyl etherified at 0 ° C. This was treated with aluminum silicate to synthesize a purified terminal allyl etherified polyoxypropylene. The average molecular weight of this polyether is 7960, 92% of the end of the iodine value
Was an olefin group. The viscosity by E type viscosity system is 13
It was 0 poise (40 ° C.).

Synthesis Example 2 A 200 ml four-necked flask was equipped with a cooling tube with a three-way cock.
A pressure equalizing dropping funnel, a thermometer, a magnetic tip, and a glass stopper were attached. Cyclic polyhydrogen siloxane under N ₂ atmosphere

[0086]

[Chemical 30]

(LS 8600, manufactured by Shin-Etsu Chemical Co., Ltd.) 12.
03 g (50 mmol) and 20 ml of toluene were charged into the flask. 1.76 g of 1,9-decadiene (20 mmo
l), 20 μl of a chloroplatinic acid catalyst solution (a solution of 1 g of H ₂ PtCl ₆ .6H ₂ O dissolved in 1 g of ethanol and 9 g of 1,2-dimethoxyethane) dissolved in 30 ml of toluene was charged into a dropping funnel. The flask was placed in an oil bath at 50 ° C., and the toluene solution was dropped into the flask over 2 hours under N ₂ atmosphere. When the IR spectrum was measured at the time when the reaction was further continued at 50 ° C. for 1 hour after the completion of the dropping, the absorption of the olefin near 1640 cm ⁻¹ had completely disappeared, so the reaction was ended at this time. After the reaction, the toluene solution was added to a saturated aqueous solution of ammonium chloride (1
After washing with 00 ml × 2) and exchanged water (100 ml × 1), Na ₂ S
Dry with O ₄ . Na ₂ SO ₄ was removed by filtration, benzothiazole (13 μl, 0.12 mmol) was added, and the volatile matter was removed by evaporation, and then degassed under reduced pressure at 80 ° C. to obtain 9.11 g of a colorless transparent liquid. It was The hydrosilyl group in the hydrocarbon compound was confirmed as a strong absorption at 2170 cm ^-1 . In addition, the proton intensity ratio between the Si— H peak and Si— CH ₃ at 300 MHz NMR (measured value 0.2
16) and the calculated intensity ratio, the compound has an average structure of the following formula [n = 1 (MW = 998) 53%, n = 2 (MW = 1377) 47%] It was found to be a mixture. Based on this, the number of Si--H groups in the unit weight was calculated to be 0.769 mol / 100 g.

Examples 1 to 5 Organic polymer obtained in Synthesis Example 1 and Si-obtained in Synthesis Example 2
H group-containing compound, tackifying resin [terpene-phenol resin (Yasuhara Yushi Co., Ltd., trade name: YS Polystar T
-115)]], hindered phenolic antioxidant (Irganox 1010 manufactured by Ciba Geigy), storage stability improver (thiazole) and chloroplatinic acid catalyst solution (H ₂ PtCl ₆・ 6H ₂
1.0 g of O dissolved in 99 g of ethanol / 1,2-dimethoxyethane (1/9 V / V) was weighed as shown in Table 1, thoroughly mixed, and then degassed under reduced pressure. The pressure-sensitive adhesive composition of the obtained pressure-sensitive adhesive composition and the snap-up time (time until it becomes a rubber elastic body) were measured. The results are shown in Table 1. From Table 1, the adhesive composition of the present invention,
It can be seen that the composition is fast-curing at high temperature and has good storage stability.

Comparative Example 1 In Examples 1 to 5, the amounts shown in Table 1 were weighed with the same composition except that the storage stability improver was removed, and after mixing well, degassing was performed under reduced pressure. The viscosity and the snap-up time of the obtained pressure-sensitive adhesive composition were measured in the same manner. The results are shown in Table 1.

[0090]

[Table 1]

[0091]

As is clear from the results shown in Table 1, the pressure-sensitive adhesive composition of the present invention is a composition capable of exhibiting both a curing rate and storage stability in a well-balanced manner and having excellent workability during line production. .

Claims (1)

[Claims] 1. A pressure-sensitive adhesive composition comprising the following components (A) to (E) as main components; (A) a compound having at least one alkenyl group in a molecule, and (B) at least two in a molecule. A compound containing a hydrosilyl group of (C), a hydrosilylation catalyst,
(D) Tackifying resin, (E) Storage stability improver.