JP2000336320A - Adhesive and bonding method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an adhesive suitable for mutually bonding molded articles of a cross-linked metathesis polymer, excellent in chemical resistance by including a mixture of a raw compound capable of metathesis polymerizing and a catalyst for metathesis polymerization and a liquid or semisolid obtained by mixing the prescribed compound and catalyst. SOLUTION: This adhesive includes (A) a mixture of (i) a raw compound capable of metathesis polymerizing (e.g. dicyclopentadiene, methyltetracyclododecene, etc.), and (ii) a metathesis polymerization catalyst preferably expressed by formulas I or II (M is ruthenium or osmium; Q and Q1 are each H, a 1-20C alkyl, 2-20C alkenyl, etc.,; X and X1 are each an anionic ligand; L and L1 are each an electron donating group), and (B) a liquid or semisolid obtained by mixing the prescribed compound and catalyst at 0-80 deg.C. Preferably, 0.001-20 pts.wt. of the component ii is used to 100 pts.wt. of the prescribed component i.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a metathesis crosslinked polymer, particularly to an adhesive suitable for bonding norbornene-type cycloolefin-based crosslinked polymers and a bonding method using the same.

[0002]

2. Description of the Related Art A cross-linked polymer obtained by subjecting dicyclopentadiene or the like to metathesis polymerization has excellent mechanical properties and chemical resistance, and is therefore used in a septic tank and the like. In the future, application to high value-added products is expected. A method of bulk polymerizing norbornene-type cycloolefins such as dicyclopentadiene using a metathesis catalyst system to obtain a crosslinked polymer molded product is disclosed in, for example,
According to JP-A-127728 and JP-A-58-129003, a solution (first solution) composed of a mixture of a catalyst component and a monomer of a metathesis catalyst system and a mixture of an activator and a monomer of a metathesis catalyst system are used. The resulting solution (second solution) is produced by a reaction injection molding (R1M) method. In this method, when the first liquid and the second liquid are mixed, an exothermic reaction occurs rapidly after a short induction time, and a crosslinked polymer molded article is obtained.

[0003] Unlike the above two-component mixed type metathesis polymerization catalyst, there is also known a method of obtaining a crosslinked polymerized product by bulk-polymerizing norbornene-type cycloolefins using a stable metathesis polymerization catalyst such as a Ru carbene catalyst. (US Pat. No. 5,312,940). When a crosslinked polymer molded article is produced from a cycloolefin using such a metathesis polymerization catalyst, a metathesis polymerization catalyst (usually a solid) is added to the cycloolefin (raw material monomer).
Is added, mixed and reacted, or after dissolving the metathesis polymerization catalyst in an organic solvent, a cycloolefin (raw material monomer) and a catalyst solution are mixed and reacted.

In order to process the thus obtained crosslinked polymer molded article to obtain a more complicated molded article, an adhesive or a bonding method for adhering them to each other is required. Conventionally, as such an adhesive or a bonding method, a method of treating an adhesive surface of a metathesis cross-linked polymer molded article with a pretreatment liquid and then bonding the same using an epoxy adhesive (Japanese Patent Application Laid-Open No. 2-6524) or a specific method is disclosed. A method of bonding using a saturated polyester-based adhesive (JP-A-7-188636) is known.

[0005]

However, the adhesives used in the above methods are all inferior in chemical resistance to the metathesis crosslinked polymer molded article to be adhered. Therefore, there is a problem when the chemical resistance of the bonded metathesis crosslinked polymer molded product (product) is required. The present invention has been made in view of this problem, and provides an adhesive and a bonding method which are suitable for bonding metathesis cross-linked polymer molded articles and have excellent chemical resistance.

[0006]

Means for Solving the Problems In order to achieve the above object, the present inventors have conceived not to use a heterogeneous adhesive but to use a homogeneous adhesive for bonding metathesis crosslinked polymer molded articles. Thus, the present invention has been completed. That is, the present invention provides the following adhesives (1) and (2) and (3) to
It relates to the bonding method (5).

(1) (a) a mixture of a raw material compound capable of metathesis polymerization and a metathesis polymerization catalyst; and / or (b) a liquid material or a semi-finished product obtained by mixing the metathesis polymerization raw material compound and a metathesis polymerization catalyst. An adhesive comprising: a solid;

(2) The above (1) wherein the metathesis polymerization catalyst is a compound represented by the following general formula (A) or (B):
Glue.

Embedded image

[0009]

Embedded image In the formulas (A) and (B), M represents ruthenium or osmium, and Q and Q ₁ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, An arginyl group having 2 to 20 carbon atoms, an aryl group, a carboxylate group having 1 to 20 carbon atoms,
20 alkoxy groups, an alkenyloxy group having 2 to 20 carbon atoms, an aryloxy group, an alkoxydicarbonyl group having 2 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or carbon Number 1-2
0 represents an alkylsulfinyl group (where the hydrogen atom attached to the carbon atom may be substituted with an alkyl group having 1 to 5 carbon atoms, halogen, an alkoxy group having 1 to 5 carbon atoms or a phenyl group; The phenyl group may be substituted with a halogen, an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms), X and X ₁ each independently represent an anionic ligand, and L and L ₁ each independently represents a neutral electron donating group.

(3) A method for bonding two or more metathesis crosslinked polymer molded articles to each other by using the adhesive of (1) or (2) above. (4) The bonding method according to the above (3), wherein the bonding is performed together with the heating. (5) The bonding method according to the above (4), wherein the heating is performed by energizing the electrically conductive heating element.

The anionic ligands (X and X ₁ ) are groups having a negative charge when the coordination to the central metal is removed. Such groups include, for example, hydrogen,
Halogen, CF ₃ CO ₂ , CH ₃ CO ₂ , CFH ₂ CO ₂ ,
(CH ₃ ) ₃ CO, (CF ₃ ) ₂ (CH ₃ ) CO, (CF ₃ )
(CH ₃ ) ₂ CO, alkyl group having 1 to 5 carbon atoms, 1 carbon atom
To 5 alkoxy groups, phenyl groups, phenoxy groups, tosyl groups, mesyl groups, trifluoromethanesulfonate groups and the like, and both are preferably halogen (particularly chlorine).

The neutral electron donating groups (L and L ₁ ) are groups having a neutral charge when the coordination to the central metal is removed. Such groups include, for example, PR ² R ³ R ⁴
(Where R ² is a secondary alkyl group or cycloalkyl group, R ³ and R ⁴ are each independently an aryl group, a primary or secondary alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group. Phosphine-based electron donating group represented by the following formula), pyridine, p-fluoropyridine and the like.
Particularly preferred are both -P (cyclohexyl)
₃ , -P (cyclopentyl) ₃ , or -P (isopropyl) ₃ .

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION As a metathesis-polymerizable raw material compound used in the adhesive of the present invention, a typical one is a norbornene-type cycloolefin. This includes substituted or unsubstituted norbornene, dihydrodicyclopentadiene, methylnorbornene, dimethylnorbornene,
Bicyclic norbornenes such as ethyl norbornene, ethylidene norbornene and butyl norbornene, tricyclic norbornenes such as dicyclopentadiene (a dimer of cyclopentadiene), dihydrodicyclopentadiene, methyldicyclopentadiene and dimethyldicyclopentadiene, and tetracyclododecene Pentacyclic or more norbornene, cyclobutene, such as tetracyclic norbornene, such as methyltetracyclododecene, dimethylcyclotetradodecene, etc., tricyclopentadiene (trimer of cyclopentadiene), tetracyclopentadiene (tetramer of cyclopentadiene) , Cyclopentene, cyclooctene, cyclooctadiene, cyclododecene, cyclododecatriene, tetrahydroindene, methyltetrahydroindene and the like.
Further, a compound having two or more norbornene groups, for example, norbornadiene, tetracyclododecadiene, symmetric tricyclopentadiene, or the like can be used as the polyfunctional crosslinking agent. Further, norbornene derivatives such as hymic acid and hymic acid anhydride can also be used. In addition to the norbornene-type cycloolefin, cycloolefins such as cyclooctene, cyclooctadiene, and cyclododetriene can also be used.

Among these, polycyclic cycloolefin compounds such as dicyclopentadiene, methyltetracyclododecene, ethylidene norbornene, tridiclopentadiene, and tetracyclopentadiene are preferred from the viewpoints of high elastic modulus and economy. Are preferably used alone or in combination of two or more. If necessary,
By combining monocyclic cycloolefin compounds such as cyclooctene, cyclooctadiene and cyclododegatriene, it is also possible to obtain a desired elastic modulus.

The metathesis polymerization catalyst used includes:
There is a compound [ruthenium (or osnium) carbene catalyst] represented by the formula (A) or (B). The pure substances of these compounds are usually solids (powder).

These metathesis polymerization catalysts are different from two-package metathesis polymerization catalyst systems in which a metal catalyst component and an alkylaluminum-based activator are combined, and do not easily lose their catalytic activity due to oxygen or moisture in the air. Can be subjected to ring-opening polymerization by a metathesis reaction. These metathesis catalysts can be used alone or in combination of two or more. The amount used is
From the viewpoints of economy and curing rate, the amount is usually 0.001 to 20 parts by weight, preferably 0.01 to 5 parts by weight, per 100 parts by weight of the raw material compound capable of metathesis polymerization.

In order to produce the adhesive of the present invention, the above-mentioned metathesis-polymerizable raw material compound and a metathesis polymerization catalyst are essential. If necessary, a modifying agent, a polymerization rate regulator, a colorant And a light stabilizer and the like.

As the modifier, for example, an elastomer,
Natural rubber, butadiene rubber, styrene-butadiene copolymer (SBR), styrene-butadiene-styrene block copolymer (SBS), styrene-maleic acid copolymer, ethylene-vinyl acetate copolymer, polymethyl methacrylate , Polyvinyl acetate, polystyrene, and other thermoplastic resins, as well as petroleum resins. Further, these thermoplastic resins may be esterified, or a polar group may be grafted. Further, it can be modified by copolymerizing or dispersing an epoxy-based, urethane-based, polyester-based, or silicon-based prepolymer. Examples of the copolymerized prepolymer include a compound obtained by reacting an epoxy with norbornene monocarboxylic acid, a compound obtained by reacting an isocyanate compound with norbornene-ol, and a hymic acid-modified polyester. Examples of the polymer to be dispersed and modified include epoxy resins, derivatives such as epoxy acrylate, similarly, urethane resins and derivatives such as urethane acrylate, saturated polyester resins, unsaturated polyester resins, phenol resins, polyamide resins, polyimide resins, polyamide imide resins. And thermosetting resins such as polyether resins.

As the petroleum resin, there is a petroleum resin produced using a C5 or C9 fraction purified in an ethylene plant as a raw material. For example, "Quinton" (trade name) manufactured by Zeon Corporation and "Norn Rex" thermoplastic polynorbornene
(Product name). These petroleum resins preferably have a number average molecular weight of 2000 or more, and more preferably have a functional group such as a hydroxyl group or an ester group in the resin skeleton.

When these modifiers are added, the amount thereof is preferably from 0.2 to 95 parts by weight based on 100 parts by weight of the metathesis-polymerizable starting compound in order to exert the effect of the modifier.
Parts by weight, more preferably 0.5 to 60 parts by weight.

Examples of the polymerization rate regulator include those which cause chain transfer such as methylstyrene dimer and the like, and those which inhibit the polymerization reaction of phosphates such as triisopropyl phosphine, triphenyl phosphine and tricyclohexyl phosphine. Is a raw material compound 100 capable of metathesis polymerization
Preferably, 0.005 to 20 parts by weight based on parts by weight can be used. The use of a polymerization rate regulator is for the purpose of controlling the pot life (storage stability) of the adhesive and the polymerization / crosslinking reaction time. In the case of the above polymerization reaction inhibitor, the larger the amount used, the greater the pot life or polymerization / crosslinking. The reaction time becomes longer.

Examples of the coloring agent include inorganic pigments such as titanium dioxide, cobalt blue and cadmium yellow, and organic pigments such as carbon black, aniline black, β-naphthol, phthalocyanine, quinacridone, azo, quinophthalone and indanthrene blue. Yes, depending on the desired color. These may be used in combination of two or more. Usually, when these pigments are added, the amount thereof is preferably 0.1 to 50 parts by weight based on 100 parts by weight of the raw material compound capable of metathesis polymerization.

Examples of the stabilizer include an ultraviolet absorber, a light stabilizer and an antioxidant. Examples of the ultraviolet absorber include salicylic acid-based ultraviolet absorbers such as phenyl salicylate and para-t-butylphenyl salicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, and 2,2′-dihydroxy-4,4. Benzophenone-based ultraviolet absorbers such as' -dimethoxybenzophenone, 2- (2'-hydroxy-5'-methylphenyl)
Benzotriazole, 2- (2′-hydroxy-3 ′,
5′-di-t-butylphenyl) benzotriazole,
Benzotriazole ultraviolet absorbers such as 2- (2′-hydroxy-3 ′, 5′-di-t-amylphenyl) benzotriazole, 2-ethylhexyl-2-cyano-3,
3'-diphenyl acrylate, ethyl-2-cyano-
There is a cyanoacrylate ultraviolet absorber such as 3,3'-diphenylacrylate. These may be used alone or in combination of two or more. The amount of these ultraviolet absorbers to be added is appropriately determined depending on the use environment and required characteristics of the adhesive, but is preferably 0.05 to 20 parts by weight based on 100 parts by weight of the metathesis-polymerizable raw material compound.

As the light stabilizer, bis (2,2,6,
6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, dimethyl-1- (2-hydroxyethyl) -4-hydroxy-2, succinate, There are hindered amine light stabilizers such as 2,6,6-tetramethylpiperidine polycondensate. When these light stabilizers are added, the amount thereof is preferably 0.05 to 20 parts by weight based on 100 parts by weight of the raw material compound capable of metathesis polymerization.

As antioxidants, parabenzoquinone,
Tolquinone, quinones such as naphthoquinone, hydroquinone, hydroquinones such as para-t-butylcatechol, 2,5-di-t-butylhydroquinone, phenols such as di-t-butyl-paracresol hydroquinone monomethyl ether, pyrogallol, Copper salts such as copper naphthenate and copper octenoate; quaternary ammonium salts such as trimethylbenzylammonium chloride, trimethylbenzylammonium maleate and phenyltrimethylammonium chloride; oximes such as quinone dioxime and methyl ethyl ketoxime; triethylamine hydrochloride And amine hydrochlorides such as dibutylamine hydrochloride. When these antioxidants are added, the amount thereof is preferably 10 to the starting compound capable of metathesis polymerization.
-10,000 ppm.

In addition, flame retardant materials, coupling materials,
An antifoaming agent, a wetting agent, a dispersing agent and the like can be used as long as the adhesive strength of the adhesive is not impaired.

The adhesive of the present invention can be prepared by adding a metathesis polymerization catalyst (usually a solid) to a raw compound capable of metathesis polymerization (usually a liquid), or mixing the metathesis polymerization catalyst in an appropriate organic solvent. The catalyst can be easily produced by mixing the prepared catalyst solution with a raw material compound capable of metathesis polymerization. The temperature at the time of mixing is usually 0 to 80 ° C, preferably room temperature to 50 ° C. At this time, if necessary, additives such as the above-mentioned modifier, polymerization rate regulator, colorant, light stabilizer and the like can be contained.

If the mixture thus obtained is left as it is, the polymerization reaction proceeds to a greater or lesser degree, depending on conditions such as the temperature, the type of additive and the amount used. Low viscosity liquid (several centpoise) at the beginning of mixing
However, if the time elapses, it becomes a liquid substance having high viscosity (tens of thousands poise) or a semi-solid substance. Suitable adhesives are those at the beginning of mixing, or those until the reaction proceeds to a liquid or semi-solid having a high viscosity. This is from the time immediately after mixing to about 2 hours when the time (however, when left at room temperature) elapses. If left for more than this time, the polymerization will proceed too much and the function as an adhesive will be reduced. The time until use as an adhesive is appropriately selected depending on the purpose of the bonding operation, quickness, and the like. When the adhesive is in a liquid state, the adhesive is highly reactive, and when heated, the polymerization / crosslinking reaction is accelerated, and the cured product is completed through metathesis polymerization via a semi-solid material.

When the adhesive of the present invention is a semi-solid material having no fluidity (however, the reactivity required for adhesion is left), the semi-solid adhesive is easily applied to a predetermined shape. It is possible to shape. That is, according to the shape of the metathesis cross-linked polymer molded article as the adherend, the semi-solid adhesive is shaped into a suitable shape, for example, a plate, a line, a column, and the like. These can be adhered by sandwiching between the bodies and heating. It is preferable to use the semisolid adhesive before its hardness exceeds 70 (measured with a rubber hardness meter). The semi-solid state is considered to be a state in which the metathesis reaction is not completed (semi-cured state).

The change from a liquid adhesive to a semi-solid adhesive can be easily performed. For example, there is a method of heating at a temperature of about 60 ° C. and storing below freezing when fluidity is lost.

[0031] Two or more metathesis cross-linked polymer moldings can be easily bonded using the adhesive of the present invention. A liquid or semi-solid adhesive is applied or affixed to an adhesive portion between the metathesis crosslinked polymer molded products. The application of the liquid adhesive can be performed by spraying, roll coating, bristling, extrusion from a gun, spray coating with an applicator, or the like. In addition, the application of the semi-solid adhesive may be manual application or mechanical application. The amount of the liquid or semi-solid adhesive can be appropriately determined according to the breaking strength of the adhesive, the shape of the bonding surface, and the like.

In order to sufficiently exhibit the chemical resistance and adhesive strength of the bonded molded article, it is preferable that the degree of cure of the adhesive after bonding is 94% or more. However, the degree of cure (%) is represented by (100%-[% of weight loss at 400 ° C.]). In order to make the degree of curing of the adhesive 94% or more, a heating operation is preferably performed. The heating operation can be performed by one-stage, two-stage or multi-stage heating by external heating. In the case of one-stage heating, the temperature is preferably 4
0-200 ° C. In the case of two-stage heating, the temperature of the first stage is preferably 40 to 80 ° C. (the polymerization time can be appropriately determined depending on the amount of the catalyst and the polymerization temperature, but usually 1 minute to 50 hours). The eye temperature is preferably 100 to 180 ° C. (the polymerization time can be appropriately determined depending on the amount of the catalyst and the polymerization temperature, but is usually 1 minute to 50 ° C.).
Time). In the case of multi-stage heating, the heating temperature is gradually increased based on the above-described two-stage heating temperature range.

As a heating method for curing the liquid or semi-solid adhesive, a method of placing the adhesive in a furnace, a method of blowing warm air, a method of providing a heating element in the bonding portion in advance and heating by heating. It can be performed by a method in which an energizing heating element is arranged in advance in a semi-solid adhesive and energized and heated, or a method in which an energizing heating element is arranged between semi-solid adhesives and energized and heated. Of these heating methods,
In particular, a method using an energizing heating element is preferable because the work is simple.

Here, silver, copper,
Examples include various metals such as aluminum, iron, and nichrome, and conductors such as carbon. Various shapes such as a linear shape, a plate shape, a column shape, and a powder shape can be used. In addition, the amount of the conductive heating element that arranges the conductive heating element in the adhesive is appropriately determined in consideration of the adhesive area, the thickness, the shape, and the like of the adhesive, and the amount suitable for the adhesive to be cured is appropriately determined. be able to.

[0035]

The present invention will be described below in more detail with reference to examples. The production of the metathesis crosslinked polymer molded article of the adherend plate used in the test was performed as follows. Commercially available 99% by weight of dicyclopentadiene (hereinafter referred to as DCPD) is added to about 40%.
After heating to 100 ° C., 0.13 parts by weight of triphenylphosphine (hereinafter referred to as TPP) was added to and dissolved in 100 parts by weight of DCPD, and the Ru carbene catalyst of formula (C) was dissolved in 0.1 part by weight.
1 part by weight is melted, poured into a mold, the mold is placed in a high-temperature bath, and subjected to two-stage heating at 40 ° C., 3 hours, and 125 ° C. for 1 hour, and has a width of 25 mm, a length of 125 mm, and a thickness of 5 mm. A board was made.

[0036]

Embedded image (L 'is tricyclohexylphosphine, Ph is a phenyl group)

Example 1 100 parts by weight of DCPD, 0.13 part by weight of TPP and 0.1 part by weight of a Ru carbene catalyst of the formula (C) were added at 35 ° C. for 10 hours.
After mixing for a minute, a liquid adhesive was obtained. As shown in FIG. 1, this liquid adhesive is dropped onto the bonding surfaces of the adherend plates (two sheets) with a dropper, and then the two are adhered to each other, and the plate is sandwiched and fixed with a commercially available eyeball clip. Put in a thermostat, 40
After two-stage heating at 3 ° C., 3 hours, and 125 ° C. for 1 hour, the mixture was cooled at room temperature. As a result of performing a tensile shear test (based on JIS-K6850) of this adhesive test piece, the tensile shear force was about 68 kgf / square cm, indicating a high adhesive strength.

Example 2 The liquid adhesive obtained in Example 1 was applied with a thickness of 1 mm and a width of 100 mm.
When poured into a mold having a height of 50 mm and left in a thermostat at 40 ° C. for 3 hours, a semi-solid adhesive having no fluidity was obtained. This had a hardness of 11 as measured by a rubber hardness tester, and could be easily formed into a predetermined shape. This was cut into a shape having a width of 25 mm, a height of 25 mm, and a thickness of 1 mm, and the adherend plates (two sheets) were bonded in the same manner as in Example 1 using this as an adhesive. The tensile shear force of the adhesive test piece was about 65 kgf / cm 2, indicating high adhesive strength.

Example 3 A nichrome wire having a diameter of 0.8 mm and a resistance of 2.16 Ω / m was placed in a mold having a thickness of 1 mm, a width of 100 mm, and a height of 50 mm. A solid adhesive was prepared. Next, the semi-solid adhesive containing the nichrome wire was cut out to a width of 25 mm, a height of 25 mm and a thickness of 1 mm (FIG. 2).
), And the adherend plates (two sheets) were bonded in the same manner as in Example 2. The tensile shear force of the adhesive test piece is about 65 kgf /
Square cm and showed high adhesive strength.

[0040]

The adhesives according to claims 1 and 2 are excellent in chemical resistance and can easily bond metathesis crosslinked polymer molded articles with good workability. According to the bonding method of claims 3 to 5, the metathesis crosslinked polymer molded products can be easily bonded to each other with good workability, and the bonded products have high adhesive strength and excellent chemical resistance. Also, when the bonding operation is performed outdoors, the handling is easy.

[Brief description of the drawings]

FIG. 1 is a diagram in which two metathesis crosslinked polymer molded products (flat plates) are adhered with the adhesive of the present invention. (A) is a sectional view, and (B) is a plan view.

FIG. 2 is a diagram of a semi-solid adhesive containing an electric conductor (Nichrome wire). (A) is a plan view and (B) is a side view.

[Explanation of symbols]

 1a, 1b: adherend plate 2: adhesive (liquid and semi-solid) 3: semi-solid adhesive 4: electric conductor (Nichrome wire)

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Toru Kimura 1250 Shimoedori, Shimodate-shi, Ibaraki Pref.Hitachi Chemical Industry Co., Ltd.Yuki Plant (72) Inventor Akio Aihara 48 Wadai, Tsukuba City, Ibaraki Prefecture Hitachi Chemical Co. (72) Inventor Akira Sasaki 1250 Shimoe-ren, Shimodate-shi, Ibaraki F-term (reference) 4Y040 DK011 DK021 FA191 HD43 JA01 JA08 KA14 LA07 MA10 MA11 PA30 PA32

Claims (5)

[Claims] 1. A liquid or semisolid obtained by mixing (a) a metathesis-polymerizable raw material compound and a metathesis polymerization catalyst; and / or (b) a metathesis-polymerizable raw material compound and a metathesis polymerization catalyst. An adhesive comprising: a shaped article; 2. A metathesis polymerization catalyst represented by the following general formula (A):
Or the adhesive represented by (B). Embedded image Embedded image [In the formulas (A) and (B), M represents ruthenium or osmium; Q and Q ₁ each independently represent a hydrogen atom, a carbon number of 1 to 2;
0 alkyl group, alkenyl group having 2 to 20 carbon atoms, arginyl group having 2 to 20 carbon atoms, aryl group, 1 to 2 carbon atoms
0 carboxylate group, C1-C20 alkoxy group, C2-C20 alkenyloxy group, aryloxy group, C2-C20 alkoxydicarbonyl group, C1-C20 alkylthio group, carbon Represents an alkylsulfonyl group having 1 to 20 carbon atoms or an alkylsulfinyl group having 1 to 20 carbon atoms (where the hydrogen atom attached to the carbon atom is an alkyl group having 1 to 5 carbon atoms, halogen,
X may be substituted with a halogen, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. ₁ independently represents an anionic ligand; L and L ₁ each independently represent a neutral electron donating group. ] 3. A method for adhering two or more metathesis crosslinked polymer molded articles, wherein the two or more metathesis crosslinked polymer molded articles are adhered to each other using the adhesive of claim 1 or 2. 4. The bonding method according to claim 3, wherein the bonding is performed together with the heating. 5. The bonding method according to claim 4, wherein the heating is performed by energizing a conductive heating element.