JPH07108928B2 - Curable composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a curable composition containing an isobutylene-based polymer having a reactive silicon group at a molecular end as a main component.

[Prior Art] As a rubber polymer having a reactive silicon group, a propylene oxide polymer having a reactive silicon group at a molecular end is known, and a composition containing the polymer as a main component is
It has the interesting property that it becomes a rubber elastic body by being cured by moisture etc. even at room temperature. However, the curable composition does not have sufficient properties such as weather resistance, water resistance, and heat resistance,
There are cases where the use is limited.

[Problems to be Solved by the Invention] The present invention provides the weather resistance, water resistance and heat resistance of a curable composition containing a propylene oxide polymer having a reactive silicon group at the molecular end as a main component as described above. It was made to improve.

[Means for Solving Problems] The present invention provides a polymer having a reactive silicon group at the molecular end by using an isobutylene polymer containing no polar element in place of the propylene oxide polymer, and curing the polymer. When the composition is produced, not only the weather resistance, water resistance, and lack of heat resistance of the curable composition containing a propylene oxide polymer having a reactive silicon group at the molecular end as the main component as described above can be improved, It was made based on the finding that properties such as electric insulation and gas barrier properties can be improved, and the general formula (1): (In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms,
An aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, R ² is a divalent hydrocarbon group having 1 to 10 carbon atoms, R ³ and R ⁴ are alkyl groups having 1 to 20 carbon atoms, carbon An aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or (R ') ₃ S
iO- (R 'is a monovalent hydrocarbon group having 1 to 20 carbon atoms,
May be the same or different), X is a hydroxyl group or a hydrolyzable group, and when two or more are bonded, they may be the same or different. May be a is 0, 1, 22
Or 3, b is 0, 1 or 2, m is 0 or an integer of 1 to 18, A (-B-CH (R ¹ ) -CH _2- ) _y is 50 to 100% of isobutylene units and 50 to 0%. isobutylene and a copolymerizable composed of units derived from units having an average valence isobutylene polymer group y, B is a direct bond or -CH ₂ -, provided that field that contains a plurality is B in one molecule Incidentally, y is not limited to the same group, and y is a curable composition mainly composed of an isobutylene polymer represented by 1.2 to 4) and having a molecular weight of 500 to 30,000.

[Examples] A polymer forming a skeleton of an isobutylene-based polymer having a reactive silicon group at a molecular end used in the present invention is produced by a cationic polymerization method containing an isobutylene monomer as a main component.

In the polymerization, the main component, that is, a cationically polymerizable carbon number of 4 to 5 in addition to the isobutylene monomer contained in the polymer in an amount of 50% (wt%, the same below) or more, preferably 70% or more
Twelve olefins, conjugated dienes, vinyl ethers, aromatic vinyl compounds, vinylsilanes, allylsilanes, etc. can be copolymerized. Specific examples of such a copolymerization component include, for example, 1-butene, 2-butene, 2-methyl-
1-butene, 3-methyl-1-butene, pentene, 4-
Methyl-1-pentene, hexene, vinylcyclohexane, butadiene, isoprene, methyl vinyl ether,
Ethyl vinyl ether, isobutyl vinyl ether, styrene, α-methylstyrene, dimethylstyrene, monochlorostyrene, dichlorostyrene, β-pinene, indene, vinyltrichlorosilane, vinylmethyldichlorosilane, vinyldimethylchlorosilane, vinyldimethylmethoxysilane, vinyltrimethylsilane, Divinyldichlorosilane, divinyldimethoxysilane, divinyldimethylsilane, 1,3-divinyl-1,1,3,3, -tetramethyldisiloxane, trivinylmethylsilane, tetravinylsilane, allyltrichlorosilane, allylmethyldichlorosilane, allyl Dimethylchlorosilane, allyldimethylmethoxysilane, allyltrimethylsilane, diallyldichlorosilane, diallyldimethoxysilane, diallyldimethylsilane, γ- Taku Leroy Le trimethoxysilane, etc. γ- methacryloyloxypropyl methyl dimethoxysilane and the like.

In the cationic polymerization, an acid such as H ₂ SO ₄ , Cl ₃ CCO ₂ H, or a Friedel-Crafts catalyst such as SnCl ₄ or TiCl ₄ may be used as an initiator, but a polymer having a functional group at the molecular end may be used. U.S. Pat. No. 4,276,394 in that it may be manufactured into a coalescence.
It is preferably produced by the following inifer method described in the specification.

What is the Inifer method? (In the above formula, Y is a halogen atom, R ^{5 to} R ⁸ are hydrogen atoms, a lower alkyl group or a phenyl group, R ⁹ is a divalent hydrocarbon group, and R ^{10 to} R ¹³ are monovalent ones having 1 to 20 carbon atoms. Hydrocarbon groups of,
R ^14, R ¹⁵ is a hydrogen atom, represents a hydrocarbon group or a halogen atom having 1 to 20 carbon atoms, never both R ^14, R ¹⁵ is a halogen atom, and a set of R ¹⁴ and R ¹⁵ The combination is not a halogen atom and a hydrogen atom, and n is 0 or 1.
A compound having a structure such as BCl ₃ , SnCl ₄ , TiCl ₄ , SbCl ₆ , FeCl ₃ , and AlCl ₃ with organic halogen compounds that can generate stable carbon cations such as
It is a cationic polymerization method using a combination with a Friedel-Crafts acid catalyst as a polymerization co-initiator.

In the inifer method, saturated hydrocarbon solvents such as ethane, propane, butane, pentane, and hexane, halogenated hydrocarbon solvents such as methyl chloride, methylene chloride, and 1,1-dichloroethane, or those at +10 to -130 ° C. A polymer having the halogen atom in the organic halogen compound at the molecular end can be produced by polymerizing the above-mentioned cationically polymerizable monomer in the mixture.

To give an example of the Inifer method, And BCl ₃ are used as a polymerization co-initiator and the isobutylene monomer is polymerized in methylene chloride at −70 ° C. It is possible to produce a polymer having Furthermore, at both ends By treating a polymer having OH with a strong base such as t-BuOK, it is possible to selectively carry out the deHCl reaction, and Can be converted to an isobutylene polymer. This polymer can be suitably used for a radical addition reaction with a mercaptan compound having a reactive silicon group, as described later.

Examples of the reactive silicon group in the isobutylene polymer having a reactive silicon group at the molecular end used in the present invention include a hydrolyzable silicon group and a silanol group.

The hydrolyzable silicon group referred to in the present specification means a group in which a hydrolyzable group capable of being hydrolyzed by moisture in the presence or absence of a silanol condensation catalyst is bonded to a silicon atom. Specific examples of the functional group include commonly used groups such as a hydrogen atom, an alkoxy group, an acyloxy group, a ketoximate group, an amino group, an amido group, an aminooxy group, a mercapto group and an alkenyloxy group. Among these, an alkoxy group is particularly preferable because it has mild hydrolyzability and is easy to handle. The hydrolyzable group has 1 to 1 silicon atom.
It can bind in the range of 3 to 3, and when two or more bind, they may be the same or different.

The number of silicon atoms forming the silicon source forming the hydrolyzable silicon group may be one or two or more, but in the case of silicon atoms connected by a siloxane bond or the like, 20 It is preferably up to one.

The method for introducing a reactive silicon group into the molecule of the isobutylene polymer used in the present invention is not particularly limited,
General formula (2): (In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms). The isobutylene-based polymer having the general formula (3): (In the formula, R ² is a divalent hydrocarbon group having 1 to 10 carbon atoms, R ³ and R ⁴ are all alkyl groups having 1 to 20 carbon atoms, and 6 to 6 carbon atoms.
A 20-aryl group, a C 7-20 aralkyl group or (R ′) ₃ SiO— (R ′ is a C 1-20 monovalent hydrocarbon group, which may be the same or different. Good)
Is a triorganosiloxy group, which may be the same or different, X is a hydroxyl group or a hydrolyzable group, and when two or more are bonded, they may be the same or different. May be, a is 0, 1, 2 or 3, b is 0, 1 or 2, m is 0 or an integer of 1 to 18)
A method in which a mercaptan compound having a reactive silicon group represented by is introduced into an unsaturated bond site of an isobutylene polymer by a radical addition reaction in the presence of a radical initiator and / or a radical generation source is useful. is there.

Among the isobutylene-based polymers having at least one unsaturated bond represented by the general formula (2) in the molecule, the isobutylene-based polymer obtained by the above-mentioned inifer method is at the molecular end. Is preferable because it has At the end of the molecule The isobutylene-based polymer having What is introduced as much as possible, the reactive silicon group is introduced more at the molecular end during the radical addition reaction with the mercaptan compound having a reactive silicon group, and is preferable because the number of terminals not involved in curing is reduced, and the terminal 70 %more than Are particularly preferred.

The average number per 1 molecule is preferably 1.4 to 4.5. When this number is less than 1.4, unsaturated 2
It is not easy to introduce a mercaptan compound having a reactive silicon group in all of the heavy bonds, and it sometimes occurs that one reactive silicon group cannot be introduced at the end of the molecule. The composition may be insufficiently cured. Further, in the case of a cured product in which five or more reactive silicon groups are introduced in one molecule, the rubber-like property may be insufficient. The number of double bonds is preferably up to 4.5 in one molecule.

Specific examples of the mercaptan-based compound having a reactive silicon group represented by the general formula (3) include, for example, However, the present invention is not limited to these. The reactive silicon group of the mercaptan-based compound may be introduced into the isobutylene-based polymer and then converted appropriately according to the purpose of use.

Examples of the radical initiator include azo compounds such as azobisisobutyronitrile and phenylazotriphenylmethane, and organic peroxides such as tert-butyl peroxide and benzoyl peroxide.

Radical sources include, for example, sun rays, ultraviolet rays,
X-rays, β-rays, γ-rays and the like are exemplified, and when these are used, a compound having a photosensitizing action such as benzophenone and acetophenone may be used in combination, if necessary.

The reaction temperature is preferably in the range of 20 to 200 ° C when a radical initiator is used, and in the range of -20 to 200 ° C when a radical generating source such as light is used. In addition, you may use a radical initiator and a radical generation source together.

If necessary, a solvent such as n-pentane, n-hexane, n-heptane, benzene, toluene or xylene may be used for controlling the reaction temperature and the viscosity of the reaction system.

The molecular weight of the isobutylene polymer having 1.2 to 4 reactive silicon groups at the molecular end used in the present invention is 500 to 30,00.
It is preferably about 0, and particularly the molecular weight is 1,000 to 15,000.
A liquid substance of a certain degree is preferable because it is easy to handle. When the number of reactive silicon groups contained in the molecular ends is less than 1.2 on average, the curing becomes insufficient and it becomes difficult to exhibit good rubber elastic behavior. The reactive silicon group needs to be present at the molecular end, and when the reactive silicon group is present at the molecular end, the effective network chain amount of the isobutylene-based polymer component contained in the cured product to be formed is Since the amount is large, it becomes easy to obtain a rubber-like cured product having high strength and high elongation.

If the isobutylene-based polymer having a reactive silicon group at the molecular end used in the present invention does not contain any unsaturated bond except the aromatic ring in the molecule, the composition of the present invention is an oxypropylene-based polymer or other It has significantly better weather resistance than a composition comprising an organic polymer having a saturated bond. Further, since the polymer is also a hydrocarbon polymer, it has good water resistance, and once the surface is cured, the inside can be kept uncured, and by extension, it has excellent adhesion performance to various base materials. The composition may be made.

In the present invention, various silane compounds may be used as a physical property modifier in order to widely control physical properties such as strength and elongation of the cured product.

Specific examples of such compounds include (CH ₃ ) ₃ Si
_{OH, (CH 3 CH 2)} 3 SiOH, (CH 3 CH 2 CH 2) 3 SiOH, _{(CH 3) 2 Si (OCH} 3) 2, (CH 3 CH 2) 2 Si (OCH 3) 2, (CH 3) 2 Si (OCH 2
_{CH 3) 2, (CH 3} CH 2) 2 Si (OCH 2 CH 3) 2, _{(CH 3) 2 Si (OCH} 2 CH 2 OCH 3) 2, (CH 3 CH 2) 2 Si (OCH 2 CH 2 OCH 3) 2, (CH 3) (CH 3 CH 2) Si (OCH 3) 2 , Examples thereof include, but are not limited to, silicon compounds containing one or more hydrolyzable groups and silanol groups. In the formula, R is a hydrogen atom or has 1 carbon atom.
~ 20 hydrocarbon groups.

There are roughly three methods for adding these silicon compounds.

One is a method in which the compound is simply added to the isobutylene polymer. Depending on the properties of the compound, if necessary, it may be uniformly dispersed and dissolved by heating and stirring.
In this case, it is not necessary to make it completely uniform and transparent,
Even if it is in an opaque state, the object can be sufficiently achieved if it is dispersed. If necessary, a dispersibility improving agent such as a surfactant may be used in combination.

The second method is a method in which a predetermined amount of the compound is added and mixed when the product is finally used. For example, when used as a two-component type sealing material, the compound may be mixed and used as a third component in addition to the base and the curing agent.

In the third method, the compound is reacted with the isobutylene polymer in advance, and a tin catalyst, a titanate ester catalyst, an acid or a basic catalyst may be used in combination if necessary. In the case of a compound which produces a compound containing a silanol group due to moisture, the object can be achieved by adding a necessary amount of water and heating and devolatilizing under reduced pressure.

Specific examples of the catalyst that can be used in this case include titanic acid esters such as tetrabutyl titanate and tetrapropyl titanate; tin carboxylates such as dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, tin octylate and tin naphthenate. Lead octylate; butylamine, octylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine,
Triethylenetetramine, oleylamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine,
Guanidine, diphenylguanidine, 2,4,6-tris (dimethylaminomethyl) phenol, morpholine, N
-Amine compounds such as methylmorpholine and 1,3-diazabicyclo (5,4,6) undecene-7 (DBU) or salts thereof such as carboxylic acids; low molecular weight obtained from excess polyamine and polybasic acid Polyamide resin; reaction product of excess polyamide and epoxy compound; silane coupling agent having amino group, for example, silanol condensation catalyst such as γ-aminopropyltrimethoxysilane and N- (β-aminoethyl) aminopropylmethyldimethoxysilane Can be given. These catalysts may be used alone or in combination of two or more.

The curable composition of the present invention, in addition to the isobutylene-based polymer having a reactive silicon group at the molecular end which is the main component, of course, it is possible to use various silane compounds as a physical property modifier, if necessary, Furthermore, various fillers, plasticizers,
Silanol condensation catalysts usually used to cure the isobutylene-based polymer component having a reactive silicon group as the main component, water, antioxidants, ultraviolet absorbers, lubricants, pigments, foaming agents, adhesion promoters, etc. It can be added if necessary.

Examples of the filler that can be used in the present invention include wood flour, pulp, cotton chips, asbestos, glass fiber, carbon fiber, mica, walnut shell powder, chaff powder, graphite, diatomaceous earth, clay, fume silica, and precipitated silica. Silicic acid anhydride, carbon black, calcium carbonate, clay,
Examples thereof include talc, titanium oxide, magnesium carbonate, quartz, fine aluminum powder, flint powder and zinc dust. These fillers may be used alone or in combination of two or more.

As the plasticizer, polybutene, hydrogenated polybutene, α
-Methylstyrene oligomer, biphenyl, triphenyl, triaryldimethane, alkylenetriphenyl,
Hydrocarbon compounds such as liquid polybutadiene, hydrogenated liquid polybutadiene, alkyldiphenyl, and partially hydrogenated terphenyl; chlorinated paraffins; dibutyl phthalate, diheptyl phthalate, di (2-ethylhexyl) phthalate, butyl benzyl phthalate, butyl phthalyl Phthalates such as butyl glycolate;
Non-aromatic dibasic acid esters such as dioctyl adipate and dioctyl sebacate; polyalkylene glycol esters such as diethylene glycol benzoate and triethylene glycol dibenzoate; phosphoric acid esters such as tricresyl phosphate and tributyl phosphate. To be These may be used alone or in combination of two or more. These plasticizers may be used in place of the solvent for the purpose of adjusting the reaction temperature and adjusting the viscosity of the reaction system when introducing the reactive silicon group into the isobutylene polymer.

In order to cure the isobutylene-based polymer component having a reactive silicon group, which is the main component of the curable composition of the present invention, a silanol condensation catalyst can be used if necessary. Examples of such condensation catalysts include titanic acid esters such as tetrabutyl titanate and tetrapropyl titanate; tin carboxylates such as dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, tin octylate and tin naphthenate; dibutyltin oxide and phthalate. Reaction products with acid esters; dibutyltin diacetylacetonate; organoaluminum compounds such as aluminum triscetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethylacetoacetate; zirconium tetraacetylacetonate, titanium tetraacetylacetonate, etc. Chelate compounds; lead octylate; butylamine, monoethanolamine, triethylenediamine, guanidinium , 2-ethyl-4-methylimidazole, 1,3-diazabicyclo (5,4,6) undecene -7 (DB
Examples thereof include amine compounds such as U) or salts thereof such as carboxylic acids; and other known silanol catalysts such as other acidic catalysts and basic catalysts.

The curable composition of the present invention may be used in combination with various adhesion-imparting agents for the purpose of further improving the adhesiveness. Specifically, various silane coupling agents such as epoxy resin, phenol resin, aminosilane compound, epoxysilane compound, etc., alkyl titanates, aromatic polyisocyanates and the like can be used alone or in combination of two or more to obtain various kinds of compounds. It is possible to improve the adhesiveness to the body.

The curable composition of the present invention can be suitably used as an adhesive, a pressure-sensitive adhesive, a paint, a sealing material composition, a waterproof material, a spraying material, a molding material, a cast rubber material and the like.

Next, the curable composition of the present invention will be described based on Examples.

Production Example 1 20 g of an isobutylene polymer having an isopropenyl group and a molecular weight of about 5,000 and 1 g of toluene were weighed in a 200 ml four-necked flask at a ratio of about 92% at the molecular end, and devolatilized under reduced pressure at 90 ° C. for 2 hours. did. Next, under a nitrogen atmosphere, at room temperature, 5.8 ml of dry heptane and 1.88 g of γ-mercaptopropylmethyldimethoxysilane were added and heated to 90 ° C. To the reaction mixture, 0.2 ml of an acetone solution of azobisisobutyronitrile (AIBN) (a solution of 1 g of AIBN dissolved in 5 g of acetone) was added 10 times every about 2 hours. At this point, when the amount of residual isopropenyl group of the isobutylene polymer in the reaction solution was quantified by IR spectrum analysis, it was about 15% of the original amount.

Next, in order to remove the solvent and unreacted silane compound in the reaction system, depressurization under reduced pressure was performed at 90 ° C. for 2 hours. The components remaining in the flask are It is an isobutylene polymer that has about 75% of the molecular ends according to the NMR method. Was introduced.

Production Example 2 20 g of the same isobutylene polymer having an isopropenyl group at the molecular end and having a molecular weight of about 5000 as in Production Example 1 was used.
The mixture was weighed in a 00 ml four-necked flask and degassed under reduced pressure at 90 ° C. for 2 hours. Next, in a nitrogen atmosphere, dry heptane 20 ml, γ-
1.44 g of mercaptopropylmethyldimethoxysilane and 10 mg of benzophenone were added. The mixture was reacted for 40 hours at room temperature while externally irradiating it with a UV lamp (Mitsubishi Electric Co., Ltd., MIS53, 15W × 2). When the amount of residual isopropenyl groups in the isobutylene polymer in the reaction solution was quantified by IR spectrum analysis, it was about 20% of the original amount.

Next, the solvent in the reaction system and the unreacted silane compound are removed under reduced pressure by volatilization to remove An isobutylene polymer having According to the NMR method, about 70% of the molecular ends Was introduced.

Production Example 3 Average molecular weight with allyl ether groups introduced at 97% of all terminals
800 g of 8000 polypropylene oxide was placed in a pressure-resistant reaction vessel equipped with a stirrer, and 19 g of methyldimethoxysilane was added. Then, chloroplatinic acid catalyst solution (8.9 g of H ₂ PtCl ₆ .6H ₂ O was added to 18 ml of isopropyl alcohol and 160 m of tetrahydrofuran).
0.34 ml of a solution dissolved in 1) was added, and the mixture was reacted at 80 ° C. for 6 hours.

When the amount of residual silicon hydride groups in the reaction solution was quantified by the IR spectrum analysis method, almost no residue remained. The reactive silicon groups introduced by the NMR method were quantified and found to be about 85% of the molecular ends. Was introduced.

Example 1 At the molecular end obtained in Production Example 1 With 100 parts of isobutylene polymer, 50 parts of hydrogenated polybutene (manufactured by Idemitsu Petrochemical Co., Ltd., trade name Polybutene OH, used as a plasticizer), 50 parts of fatty acid-treated colloidal calcium carbonate (produced by Shiraishi Industry Co., Ltd., trade name CCR 100 parts (used as a filler), 2.0 parts diphenylsilanediol (used as a physical property modifier), 0.5 parts water, hindered phenolic antioxidant (Ouchi Shinko Chemical Co., Ltd., trade name Nocrac)
NS-6) 1 part was weighed out and mixed well, and after 3 paint rolls were passed 3 times to thoroughly knead, a silanol condensation catalyst consisting of 3 parts of tin octylate and 0.75 parts of laurylamine prepared separately Was added and kneaded thoroughly. The composition was poured into a mold having a thickness of about 3 mm so as to prevent bubbles from entering inside. 4 days at room temperature, then
After curing at 50 ° C for 4 days, a cured product was obtained.

A No. 3 dumbbell conforming to JIS K 6301 was punched out from the cured product sheet and subjected to a tensile test at a tensile speed of 500 mm / min. The strength at break was 6.0 kg / cm ² and the elongation at break was 450%.

Example 2 A cured product sheet was prepared in the same manner as in Example 1 except that the polymer obtained in Production Example 2 was used instead of the polymer obtained in Production Example 1, and the tensile speed was 500 mm / It was subjected to a tensile test for minutes. The strength at break was 5.5 kg / cm ² and the elongation at break was 420%.

Example 3 At the molecular end obtained in Production Example 1 100 parts of the isobutylene polymer having the above, 0.5 parts of water and 50 parts of toluene were well stirred to form a uniform toluene solution.
Pour this solution into a mold with a thickness of about 3 mm, and at room temperature for 1 day,
After curing at 50 ° C. for 4 days, it was devolatilized at 50 ° C. under reduced pressure (2 to 3 mmHg) for 2 hours to completely volatilize toluene.

Place the obtained cured product sheet on a sunshine carbon arc weather meter (120 minute cycle, spray 18 minutes) 3
It was exposed for 00 hours and the weather resistance was measured. The surface of the sheet was not deteriorated at all, and the sheet itself was not resinized or softened at all.

Example 4 A cured product sheet was prepared in the same manner as in Example 3 except that the polymer obtained in Production Example 2 was used instead of the polymer obtained in Production Example 1, and the weather resistance was measured. . The surface of the sheet was not deteriorated at all, and the sheet itself was not resinized or softened at all.

Comparative Example 1 The weather resistance was measured in the same manner as in Example 3 except that the polymer obtained in Production Example 3 was used instead of the polymer obtained in Production Example 1 used in Example 3. At the time of exposure for 60 hours, the cured product sheet softened and partly flowed down.

Example 5 The heat resistance was measured using the cured product sheet produced in Example 3. The cured product sheet is placed in a hot air dryer at 150 ° C,
The change in properties over time was observed. There was no change in 30 minutes,
Although there was some coloration even after 5 hours, the surface tack did not increase at all, and neither resinification nor softening was observed at all.

Example 6 Using the cured product sheet prepared in Example 4, heat resistance was measured in exactly the same manner as in Example 5. There was no change at 30 minutes, and there was some coloration even after 5 hours, but the surface tack did not increase at all, and neither resinification nor softening was observed at all.

Comparative Example 2 Using the cured product sheet prepared in Comparative Example 1, heat resistance was measured in exactly the same manner as in Example 5. Softening and melting occurred in 30 minutes, and further 5 hours later, decomposition further proceeded and volatilized.

Example 7 At the molecular end obtained in Production Example 1 With 100 parts of isobutylene polymer, hydrogenated polybutene (Idemitsu Petrochemical Co., Ltd., trade name Polybutene OH) 50
Part, hindered phenolic antioxidant (Ouchi Shinko Chemical Co., Ltd., trade name Nocrac NS-6) 1 part, and dibutyltin dilaurate 2 parts are measured and mixed well,
Pour into a mold with a thickness of about 3 mm for 4 days at room temperature, then 70 ℃
After curing for 10 days, a cured product was obtained. When the cured product was cut out, it was a mastic type cured product in which about 1 mm of the surface layer was cured but the inside was not cured.

[Effects of the Invention] By using the curable composition of the present invention, a cured product having excellent weather resistance, water resistance, heat resistance, electrical insulation and gas barrier properties can be obtained.

Claims (4)

[Claims] 1. General formula (1): (In the formula, R ¹ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms,
An aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, R ² is a divalent hydrocarbon group having 1 to 10 carbon atoms, R ³ and R ⁴ are alkyl groups having 1 to 20 carbon atoms, carbon An aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or (R ') ₃ S
iO- (R 'is a monovalent hydrocarbon group having 1 to 20 carbon atoms,
May be the same or different), X is a hydroxyl group or a hydrolyzable group, and when two or more are bonded, they may be the same or different. May be a is 0, 1, 2
Or 3, b is 0, 1 or 2, m is 0 or an integer of 1 to 18, A (-B-CH (R ¹ ) -CH _2- ) _y is 50 to 100% by weight of isobutylene unit and 50 to 0. An isobutylene-based polymer group having an average valence of y composed of a unit derived from a monomer having a copolymerizability with isobutylene in weight%, B is a direct bond or -CH _2- , but B is plural in one molecule. When they are included, they do not have to be the same group, y is represented by 1.2 to 4) and has a molecular weight of 500 to
A curable composition containing 30,000 isobutylene polymer as a main component. 2. X in the general formula (1) is a hydrogen atom, a hydroxyl group,
An alkoxy group, an acyloxy group, a ketoximate group, an amino group, an amido group, an aminooxy group or an alkenyloxy group, and when two or more X's are bonded, they may be the same or different Patents The curable composition according to claim 1. 3. The curable composition according to claim 1, wherein X in the general formula (1) is an alkoxy group. 4. The curable composition according to claim ¹ , wherein R ¹ in the general formula (1) is a methyl group.