JPH01158087A - Tacky agent composition and production thereof - Google Patents

Abstract

PURPOSE:To obtain the tacky agent composition having excellent water resistance, water-vapor resistance and heat resistance, by adding an isocyanate- containing organosilicon compound to an acrylic/ethylenic copolymer. CONSTITUTION:(A) 100 pts.wt. copolymer consisting essentially of (i) usually 50-99.9wt.% acrylic acid alkyl ester and (ii) usually 0.1-10.0wt.% ethylenic unsaturated monomer capable of being reacted with isocyanate group is blended with (B) usually 0.01-10.0 pts.wt. (preferably 0.05-5.0 pts.wt.) isocyanate- containing organosilicon compound to give the aimed composition. The composition is suitable for bonding a substrate such as film or foam subjected to tacky processing with the composition to an inorganic material such as glass.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to an adhesive composition and a method for producing the same. It is an adhesive suitable for adhering to inorganic materials such as glass, and particularly relates to an adhesive composition having excellent water resistance, moisture resistance, and heat resistance, and a method for producing the same.

[Conventional technology]

For example, an acrylic polymer selected from vinyl silane, epoxy silane, and methacryl silane is used as an adhesive composition that adheres to inorganic surfaces such as glass and exhibits excellent adhesion under high temperature, high humidity, or underwater conditions. at least 1
Adhesive composition containing seeds (Japanese Patent Publication No. 62-30233
No.), adhesive compositions comprising acrylic polymers copolymerized with silane compounds such as methacryloxysilane (Japanese Patent Application Laid-open No. 59-96181 and JP-A No. 59-96181)
, a pressure-sensitive adhesive composition (Japanese Unexamined Patent Publication No. 7369/1983) in which an epoxy group-containing silane compound is blended with an acrylic resin having a hydroxyl group capable of reacting with an epoxy group.

° These pressure-sensitive adhesive compositions make it possible to obtain pressure-sensitive adhesive tapes or pressure-sensitive adhesive sheets that exhibit good adhesive properties even under conditions of high temperature and high humidity.

[Problem that the invention seeks to solve]

However, in the adhesive composition (Japanese Patent Publication No. 30233/1983), which contains an acrylic polymer and additives such as vinyl silane, epoxy silane, and methacryl silane,
Because the bond with the acrylic polymer is weak, there is little improvement in adhesive strength. In addition, when methacrylsilane is used as a copolymerization component and an ethylenically unsaturated monomer containing a hydroxyl group or a carboxyl group is blended at the same time, it tends to gel during polymerization, and even if it can be polymerized, it gels during storage, resulting in lack of stability and aging. On the other hand, when a hydroxyl group- or carboxy group-containing ethylenically unsaturated monomer is not blended (JP-A-59-96181), the performance as an adhesive is not necessarily good. Furthermore, when adding an epoxy group-containing silane compound to a hydroxyl group-containing acrylic polymer as a copolymerization component (Japanese Patent Application Laid-Open No. 61-7369), the reaction with the glycidyl group is slow and it is difficult to cure at room temperature. If a basic catalyst is used to speed up curing, water resistance and moisture resistance will be extremely reduced.

This invention was made based on the above-mentioned background, and its purpose is to provide an adhesive composition that has improved room temperature curability, does not deteriorate water resistance and moisture resistance over time, and exhibits excellent cohesive strength. The goal is to provide products and methods of manufacturing them.

[Means for solving problems]

The above problems are solved by the pressure-sensitive adhesive composition and method for producing the same according to the present invention.

That is, the adhesive composition of the present invention comprises a copolymer consisting of an acrylic acid alkyl ester as a main component and an ethylenically unsaturated monomer capable of reacting with an isocyanate group.
It is characterized by containing an isocyanate group-containing organosilicon compound.

In a preferred embodiment of the present invention, the copolymer is substantially reacted with an acrylic acid alkyl ester, an ethylenically unsaturated monomer capable of reacting with an isocyanate group, and an isocyanate group, which are main components having an alkyl group having 1 to 12 carbon atoms. It may consist of non-ethylenically unsaturated monomers.

In a more limited embodiment, the copolymer has an acrylic acid alkyl ester as a main component of 50 to 99% based on the copolymer.
．． 9% by weight, ethylenically unsaturated monomer capable of reacting with isocyanate groups, 0.1 to 1060% by weight, ethylenically unsaturated monomer 4, which is substantially unreactive with isocyanate groups.
The content of the isocyanate group-containing organosilicon compound is 0.01 to 10.0 parts by weight, preferably 0.05 to 5 parts by weight, based on 100 parts by weight of the copolymer.
．． It is 0 parts by weight.

The method for producing the pressure-sensitive adhesive composition according to the present invention consists of a main component of an acrylic acid alkyl ester, an ethylenically unsaturated monomer capable of reacting with isocyanate groups, and optionally an ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups. A saturated monomer is copolymerized using a radical polymerization initiator selected from peroxides, azo compounds, disulfide A, etc., and an isocyanate group-containing organosilicon compound is added to the copolymer by mixing, coating, This includes inclusion by impregnation or the like.

This invention will be explained in more detail below.

Manufacturing method The acrylic acid alkyl ester used as the copolymer raw material in the manufacturing method of the present invention includes, for example, acrylic acid alkyl esters having 1 to 1 carbon atoms.
12 alkyl groups, such as methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, t-butyl acrylate, n-pentyl acrylate, Isopentyl acrylate, n-octyl acrylate, isooctyl acrylate, 2-ethylhexyl acrylate, isononyl acrylate, n-decyl acrylate,
Isodecyl acrylate, isomyristyl acrylate, or a mixture of at least two of these.

The ethylenically unsaturated monomers that can react with isocyanate groups used as other copolymer raw materials in this production method are:
It is an ethylenic monomer having a functional group capable of reacting with an isocyanate group, such as a functional group having active hydrogen (hydroxyl group, carboxyl group, amino group, etc.). Specific examples of such compounds include acrylic acid, methacrylic acid,
Itaconic acid, crotonic acid, maleic anhydride, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, N-methylolacrylamide, N - methylolmethacrylamide or at least two of these
There are mixtures of seeds.

In addition to the above-mentioned polymer components, various other components may be added during polymerization, if necessary.

For example, there are ethylenically unsaturated monomers that are substantially unable to react with isocyanate groups, in other words, ethylenically unsaturated monomers that do not have functional groups that can react with isocyanate groups. Such compounds include vinyl acetate, vinyl propionate, styrene, alkyl methacrylates, benzyl acrylate, vinyltoluene, acrylonitrile, methacrylonitrile, or mixtures of at least two thereof.

The blending amount of each component in the copolymerization can be selected and changed as appropriate depending on the use of the adhesive composition, but for example, based on the copolymer, the main component acrylic acid alkyl ester is 40 to 99.99% % by weight, preferably 50-99.
9% by weight, 0.11-20.0% by weight of ethylenically unsaturated monomers capable of reacting with isocyanate groups, preferably 0
．． 1 to 10.0% by weight, 0 to 49.9% by weight of ethylenically unsaturated monomers that are substantially unreactive with isocyanate groups.
It is.

For copolymerization of the acrylic acid alkyl ester and the ethylenically unsaturated monomer capable of reacting with the isocyanate group, any method such as bulk polymerization, solution polymerization, suspension polymerization, or emulsion polymerization can be used. Examples of polymerization initiators used during polymerization include peroxides such as benzoyl peroxide, lauroyl peroxide 5, cumene peroxide, ammonium persulfate, and potassium persulfate; compounds, disulfides, etc. In the production method of this invention, the obtained copolymer is made to contain an isocyanate-containing organosilicon compound.

The weight average molecular weight of the copolymer used in this invention is 100,000 to 1,500,000, preferably 200,000 to 1,000,000.
It is 0,000,000.

The isocyanate group-containing organosilicon compound used in this step is an organosilicon compound having at least one isocyanate group in its molecule, and is, for example, a compound represented by the following structural formula.

(In the formula, l and n are integers of 1 to 3, m is an integer of 0 to 2, provided that 1+m+n-4 is satisfied, and R has carbon atoms of 1 to 10, preferably 1 to 5, more preferably is 1
~3 linear or branched alkyl group, k is an integer of 0 or 1 or more) Specific examples of organosilicon compounds include methoxysilane triisocyanate, dimethoxysilane diisocyanate, and ethoxysilane triisocyanate. , jetoxysilane diisocyanate,
Trimethoxysilane propyl isocyanate, dimethoxymethylsilane propyl isocyanate, triethoxysilane propyl isocyanate, jetoxymethylsilane propyl isocyanate, tripropoxysilane propyl isocyanate, dipropoxymethylsilane propyl isocyanate, or combinations thereof. Among these compounds, particularly preferred are silane compounds having two or more isocyanate groups in the molecule, such as methoxysilane triisocyanate, ethoxysilane triisocyanate, dimethoxysilane diisocyanate, jetoxysilane diisocyanate, and the like.

The content of the silane compound having an isocyanate group is 0.01 to 10.0 parts by weight, preferably 0.05 to 5.0 parts by weight, based on 100 parts by weight of the copolymer.

Other additives added to the copolymer include commonly used crosslinking agents, such as polyisocyanates, epoxy resins, metal compounds, etc., to further increase the cohesive strength of the copolymer, and also to improve adhesion. There are tackifier resins, etc.

In the production method of the present invention, the silane compound having an isocyanate group is incorporated into the copolymer by kneading the silane compound into the copolymer, by applying the silane compound to the copolymer, and by applying the silane compound to the copolymer. There is an embodiment in which a silane compound is impregnated.

Adhesive Composition The adhesive composition of the present invention obtained by the above-mentioned production method comprises an acrylic acid alkyl ester as a main component, an ethylenically unsaturated monomer capable of reacting with an isocyanate group, and an isocyanate group as required. It contains an isocyanate group-containing organosilicon compound in a copolymer made of a substantially unreactable ethylenically unsaturated monomer, and contains various additives as optional components.

This adhesive composition can be applied to various substrates. Base materials include plastic films such as polyethylene film, polyester film, polypropylene film, polyvinyl chloride film, polycarbonate film, polyamide film, and polystyrene film, plastic foam, paper, nonwoven fabric, cloth, metal foil, or composite sheets of these. and so on.

The pressure-sensitive adhesive composition of the present invention can be coated in various ways. For example, the copolymer according to the present invention is kneaded with an isocyanate group-containing organosilicon compound before or immediately before coating, and a kneaded product is coated on the base material. There are embodiments in which the copolymer is directly coated, and embodiments in which the copolymer is first coated on the base material and then the isocyanate group-containing organosilicon compound is coated on the copolymer layer.

Adhesive tapes, adhesive sheets, adhesive boards, etc. coated with the adhesive composition of the present invention can be used for various purposes, but are preferably used for adhesion to inorganic surfaces such as glass, ceramics, and tiles. It is particularly suitable for use in locations where moisture resistance, water resistance, and heat resistance are required.

[For production]

The present invention having the above configuration operates and functions as follows.

Since the copolymer according to the present invention is modified with a functional group capable of reacting with an isocyanate group, the isocyanate group-containing organosilicon compound quickly reacts with the functional group.

In particular, silicon compounds have the property of gathering at interfaces, so
Many of these bonds occur near the interface with the adhesive phase, improving adhesiveness.

The adhesion mechanism of this pressure-sensitive adhesive composition is explained when it is attached to an inorganic surface such as a glass metal.The bond between the silanol group derived from the alkoxysilane of an organosilicon compound and the inorganic surface is generated. Improves adhesion with. Particularly, organosilicon compounds, especially those having two or more isocyanate groups, have a large crosslinking effect, and - impart excellent cohesive force and adhesive properties to the pressure-sensitive adhesive.

〔Effect of the invention〕

This invention having the above configuration and operation has the following effects.

The reactivity between the copolymer and the silane compound is improved, making it possible to cure at room temperature. In addition, the adhesive polymer and the adherend material can be bonded reliably, allowing reliable adhesion even at bonding locations where moisture resistance, water resistance, and heat resistance are required. Furthermore, the adhesive and cohesive force can be further improved due to the crosslinking properties of the silane compound used in the present invention.

〔Example〕

The invention will be specifically explained with reference to the following examples.

Example 1 Components having the following composition were reacted in ethyl acetate for 7 hours to obtain a copolymer.

Butyl acrylate 65% by weight Ethyl acrylate 32% by weight Acrylic acid 2
-Hydroxylethyl 3% by weight Azobisisobutyronitrile 0.2% by weight This acrylic copolymer solution had a nonvolatile content of 35% and a viscosity of 52 poise/25°C.

An adhesive composition was obtained by adding 1.0 parts by weight of trimethoxysilane propyl isocyanate to 100 parts by weight of the acrylic copolymer.

Example 2 To 100 parts by weight of the same acrylic copolymer as in Example 1, 0.53 parts by weight of trimethoxysilaneprobyl isocyanate and 0.5 parts by weight of polyisocyanate (Coronate L1 manufactured by Nippon Polyurethane Co., Ltd.) were added. A pressure-sensitive adhesive composition was obtained.

Example 3 To 100 parts by weight of the same acrylic copolymer as in Example 1, 0.0% of ethoxysilane triisocyanate was added. A pressure-sensitive adhesive composition was obtained by adding 5 parts by weight.

Comparative Example 1 To 100 parts by weight of the same acrylic copolymer as in Example 1, 0.5 parts by weight of polyisocyanate (Coronate 1 manufactured by Nippon Polyurethane Co., Ltd.) was added to obtain an adhesive composition.

Comparative Example 2 γ was added to 100 parts by weight of the same acrylic copolymer as in Example 1.
-1.0 parts by weight of glycidoxypropyltrimethoxysilane was added to obtain an adhesive composition.

Comparative Example 3 To 100 parts by weight of the same acrylic copolymer as in Example 1, 0.5 parts by weight of methylsilyl triisocyanate was added to obtain a pressure-sensitive adhesive composition.

Comparative Example 4 A pressure-sensitive adhesive composition was obtained using 100 parts by weight of the same acrylic copolymer as in Example 1 without adding anything.

Adhesion and holding power test The adhesive composition obtained above was coated on a separator,
The sample was dried at 100° C. for 2 minutes and transferred to a 25 μm polyester film. This was heated at 20℃, 65%R
The measurement was performed after being left in an H atmosphere for 7 days.

In addition, the adhesion test was conducted in accordance with J I 5ZO237.
Ordinary glass was used as the adherend, and the tensile speed was 300 II.
ls/win, ■Normal adhesive strength (measured for 24 hours after applying the sample), ■Moisture and heat resistant adhesive strength (after applying the sample, 60°C/90%)
RH (measured after 7 days) and (2) water-resistant adhesive strength (after applying the sample, immersed in water for 7 days, then measured). The results are shown in Table 1.゛In addition, the holding force test was performed by attaching a glass plate with an area of 20 x 20 II rrr, applying a load of I kg in an atmosphere of 40 ° C, and measuring the time until it falls or 60
The distance deviated after 1 minute was measured. The results are shown in Table 1.

Table 1 Adhesive strength (g/25m) Example Normal state Humid heat resistance Water resistance Holding power Example 1
1020 980 1090 80'-1,2mm Example 2 920 g4o 11120 60°
-0rnra Example 3 850 820 780
80'-Off1m Comparative Example 1 98050 or less 5
0 or less 60°-0aua Comparative Example 2 1130 990
90ri 4° Comparative Example 3 85050 or less 15
0 80'-0mm Comparative Example 4 1220 50 or less
50 or less 4゜From the above results, it can be seen that the adhesive of the present invention is excellent in both water resistance, moisture and heat resistance adhesive strength, and holding power (cohesive strength).

Procedural amendment January 1986 - 1 Mr. Kunio Ogawa, Commissioner of the Patent Office.

1 Indication of the case 1988 Patent Application No. 317896 2 Name of the invention Adhesive composition and its manufacturing method 3 Person making the amendment Relationship with the case Patent applicant Soken Kagaku Co., Ltd. "Scope" and "Detailed Description of the Invention"
Each column.

8. Contents of amendment (1) The scope of claims in the description is corrected as shown in the attached sheet.

(2) "Number of carbons 1 to 12" on page 9, line 17 of the specification
is corrected to "carbon number 1-14".

Claim 1: An acrylic acid alkyl ester as a main component, an ethylenically unsaturated monomer capable of reacting with an isocyanate group,
An adhesive composition comprising an isocyanate group-containing organosilicon compound in a copolymer consisting of the following.

2. The pressure-sensitive adhesive composition according to claim 1, wherein the acrylic acid alkyl ester has an alkyl group having 1 to 14 carbon atoms.

3. Claim 1 in which the copolymer consists of an acrylic acid alkyl ester as a main component, an ethylenically unsaturated monomer capable of reacting with isocyanate groups, and an ethylenically unsaturated monomer substantially incapable of reacting with isocyanate groups. Or the pressure-sensitive adhesive composition according to item 2.

4. The copolymer contains, based on the copolymer, 50 to 99.9% by weight of an acrylic acid alkyl ester as a main component, and 0.1% of an ethylenically unsaturated monomer capable of reacting with an isocyanate group.
4. The pressure-sensitive adhesive composition according to claim 3, comprising 10.0% by weight of an ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups.

56 The content of the isocyanate group-containing organosilicon compound is 0.01 to 10.0% with respect to 100 parts by weight of the copolymer.
The pressure-sensitive adhesive composition according to any one of claims 1 to 4, which contains 0 parts by weight.

6. The content of the isocyanate group-containing organosilicon compound is 0.05 to 5.0 per 100 parts by weight of the copolymer.
The pressure-sensitive adhesive composition according to any one of claims 1 to 4, which is in parts by weight.

7. The adhesive composition according to any one of claims 1 to 6, wherein the isocyanate group-containing organosilicon compound is represented by the following structural formula.

(In the formula, l and n are integers of 1 to 3, m is an integer of 0 to 2, provided that l + m + n-4 is satisfied, and R
is an alkyl group having 1 to 3 carbon atoms, and k is an integer of 0 or 1 or more. isobutyl acid, acrylic acid t
-butyl, n-pentyl acrylate, isopentyl acrylate, n-octyl acrylate, isooctyl acrylate, 2-ethylhexyl acrylate, isononyl acrylate, n-decyl acrylate, isodecyl acrylate, or isomyristyl acrylate, or The adhesive composition according to any one of claims 1 to 7, which is selected from a mixture of at least two of these.

9. Ethylenically unsaturated monomers capable of reacting with isocyanate groups include acrylic acid, methacrylic acid, itaconic acid,
Crotonic acid, maleic anhydride, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, N
- methylol acrylamide, or N-methylol methacrylamide, or at least two of these.
Claims 1 to 8 selected from a mixture of species
The pressure-sensitive adhesive composition according to any one of the above items.

10. The ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups is selected from vinyl acetate, vinyl propionate, styrene, alkyl methacrylate, benzyl acrylate, or a mixture of at least two of these. The adhesive composition according to any one of claims 1 to 9.

11. The isocyanate group-containing organosilicon compound is
The pressure-sensitive adhesive composition according to any one of claims 1 to 10, which contains one or more isocyanate groups.

12. A pressure-sensitive adhesive composition comprising copolymerizing an acrylic acid alkyl ester as a main component with an ethylenically unsaturated monomer capable of reacting with an isocyanate group, and incorporating an isocyanate group-containing organosilicon compound into the copolymer. Manufacturing method.

13. The method for producing an adhesive composition according to claim 12, which comprises copolymerizing using a radical polymerization initiator selected from peroxides, azo compounds, and disulfides.

14. Acrylic acid alkyl ester as main component 50-9
9.9% by weight, 0.1 to 10.0% by weight of ethylenically unsaturated monomers capable of reacting with isocyanate groups, and less than 49.9% by weight of ethylenically unsaturated monomers that are substantially unreactive with isocyanate groups. A method for producing an adhesive composition according to claim 12 or 13, which comprises polymerizing.

15. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by kneading the organosilicon compound into the copolymer. Method for producing agent composition.

16. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by applying the organosilicon compound to the copolymer. Method for producing agent composition.

17. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by impregnating the copolymer with the organosilicon compound. Method for producing agent composition.

Claims (1)

[Claims] 1. A copolymer consisting of an acrylic acid alkyl ester as a main component and an ethylenically unsaturated monomer capable of reacting with an isocyanate group, containing an isocyanate group-containing organosilicon compound. Characteristic adhesive composition. 2. The pressure-sensitive adhesive composition according to claim 1, wherein the acrylic acid alkyl ester has an alkyl group having 1 to 12 carbon atoms. 3. Claim 1 in which the copolymer consists of an acrylic acid alkyl ester as a main component, an ethylenically unsaturated monomer capable of reacting with isocyanate groups, and an ethylenically unsaturated monomer substantially incapable of reacting with isocyanate groups. Or the pressure-sensitive adhesive composition according to item 2. 4. The copolymer contains, based on the copolymer, 50 to 99.9% by weight of an acrylic acid alkyl ester as the main component, and 0.1 to 0.1 to 99.9% by weight of an ethylenically unsaturated monomer capable of reacting with an isocyanate group.
4. The pressure-sensitive adhesive composition according to claim 3, comprising 10.0% by weight of an ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups and less than 49.9% by weight of an ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups. 5. According to any one of claims 1 to 4, the content of the isocyanate group-containing organosilicon compound is 0.01 to 10.0 parts by weight based on 100 parts by weight of the copolymer. The adhesive composition described. 6. Any one of claims 1 to 4, wherein the content of the isocyanate group-containing organosilicon compound is 0.05 to 5.0 parts by weight based on 100 parts by weight of the copolymer.
The pressure-sensitive adhesive composition described in . 7. The adhesive composition according to any one of claims 1 to 6, wherein the isocyanate group-containing organosilicon compound is represented by the following structural formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, l and n are integers of 1 to 3, m is an integer of 0 to 2, provided that l + m + n = 4, and R is a carbon number of 1 to 3, k is an integer of 0 or 1 or more) 8. Acrylic acid alkyl ester is methyl acrylate, propyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, acrylic acid t-butyl, n-pentyl acrylate, isopentyl acrylate, n-octyl acrylate, isooctyl acrylate, 2-ethylhexyl acrylate, isononyl acrylate, n-decyl acrylate, isodecyl acrylate, or isomyristyl acrylate, or a mixture of at least two thereof. 9. Ethylenically unsaturated monomers capable of reacting with isocyanate groups include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic anhydride, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 2-hydroxy methacrylate. Ethyl, 2-hydroxypropyl methacrylate, dimethylaminoethyl methacrylate, N-
The adhesive composition according to any one of claims 1 to 8, which is selected from methylol acrylamide, N-methylol methacrylamide, or a mixture of at least two thereof. 10. The ethylenically unsaturated monomer that is substantially unreactive with isocyanate groups is selected from vinyl acetate, vinyl propionate, styrene, alkyl methacrylate, benzyl acrylate, or a mixture of at least two of these. The adhesive composition according to any one of claims 1 to 9. 11. The pressure-sensitive adhesive composition according to any one of claims 1 to 10, wherein the isocyanate group-containing organosilicon compound contains one or more isocyanate groups. 12. A pressure-sensitive adhesive composition comprising copolymerizing an acrylic acid alkyl ester as a main component with an ethylenically unsaturated monomer capable of reacting with an isocyanate group, and incorporating an isocyanate group-containing organosilicon compound into the copolymer. Manufacturing method. 13. The method for producing an adhesive composition according to claim 12, which comprises copolymerizing using a radical polymerization initiator selected from peroxides, azo compounds, and disulfides. 14. Main component acrylic acid alkyl ester 50-99
．． 9% by weight, 0.1 to 10.0% by weight of ethylenically unsaturated monomers capable of reacting with isocyanate groups, and less than 49.9% by weight of ethylenically unsaturated monomers substantially incapable of reacting with isocyanate groups. , a method for producing an adhesive composition according to claim 12 or 13. 15. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by kneading the organosilicon compound into the copolymer. Method for producing agent composition. 16. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by applying the organosilicon compound to the copolymer. Method for producing agent composition. 17. The adhesive according to any one of claims 12 to 14, wherein the isocyanate group-containing organosilicon compound is added to the copolymer by impregnating the copolymer with the organosilicon compound. Method for producing agent composition.