JPS636041A - Curable composition - Google Patents

Abstract

PURPOSE:To provide a curable compsn. having excellent resistance to weather, water and heat, electrical insulating properties and gas barrier properties, consisting of an isobutylene polymer having a reactive silicone group at the terminal to its molecular chain. CONSTITUTION:An isobutylene polymer having at least one unsaturated bond of formula I (wherein R<1> is H, a 1-8C alkyl, an 8-20C aryl or a 7-20C aralkyl) at the terminal of its molecular chain and a hydrogenated silicone compd. of formula II [wherein R<2> and R<3> are each a 1-20C alkyl, a 6-20C aryl, a 7-20C aralkyl or a triorganosiloxy group of formula III (wherein R<1> is a 1-20C monovalent hydrocarbon group); X is hydroxyl or a hydrolyzable group and when two or more X groups exist, they may be the same groups; a is a number of 0-3; b is a number of 0-2; and m is a number of 0-18], are subjected to a hydrosilylating reaction in the presence of a catalyst such as H2PtCl5.6H2O, etc., at 0-150 deg.C to obtain a curable compsn. mainly composed of an isobutylene polymer having an MW of 500-30,000 and at least one reactive silicone group of formula IV at the terminal of its molecular chain.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a curable composition containing as a main component an isobutylene polymer having at least one reactive silicon group at the end of the molecule.

[Prior Art] As a rubber-based polymer having a reactive silicon group, a propylene oxide-based polymer having a reactive silicon group at the molecular end is known, and a composition containing this polymer as a main component is
It has an interesting property of being hardened by moisture even at room temperature and becoming a rubber elastic body. 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 aims to improve the weather resistance, water resistance, and heat resistance of a curable composition whose main component is a propylene oxide polymer having a reactive silicon group at the molecular end as described above. This was done to improve deficiencies such as deficiencies.

[Means for Solving the Problems] The present invention uses an isobutylene polymer that does not contain a polar element instead of a propylene oxide polymer to produce a polymer having a reactive silicon group at the end of the molecule. By producing the composition, it is possible to not only improve the deficiencies in weather resistance, water resistance, and heat resistance of the curable composition mainly composed of a propylene oxide polymer having a reactive silicon group at the molecular end as described above, but also It was developed based on the discovery that it could improve properties such as electrical insulation and gas barrier properties, and it is made mainly of isobutylene polymers that have at least one reactive silicon group at the end of the molecule. The present invention relates to a curable composition.

[Example] The isobutylene polymer that forms the backbone of the isobutylene polymer having at least one reactive silicon group at the end of the molecule used in the present invention is produced by a cationic polymerization method using inbutylene monomer as the main component. Ru.

During polymerization, in addition to the isobutylene monomer that is contained as a main component, that is, 50% (by weight, the same applies hereinafter) or more, preferably 70% or more, in the inbutylene polymer,
Cation polymerizable olefins having 4 to 12 carbon atoms, conjugated dienes, vinyl ethers, aromatic vinyl compounds, vinylsilanes, allylsilanes, etc. can be copolymerized.

Specific examples of such copolymer components include l
-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, inbutyl 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, allyldimethylchlorosilane, allyldimethylmethoxysilane, allyltrimethylsilane, diallyl Examples include dichlorosilane, diallyldimethoxysilane, diallyldimethylsilane, γ-methacryloyloxypropyltrimethoxysilane, γ-methacryloyloxypropylmethyldimethoxysilane, and the like.

In the cationic polymerization, H2SO4, CCI s
Although acids such as C02II and Friedel-Craft catalysts such as 5nCI4 and TlClJ may be used as initiators, U.S. Pat. Preferably, it is produced by the Vinifer method described in the specification below.

The Inif 7-method is (In the above formula, Y is a halogen atom, R4-R7 is a hydrogen atom, a lower alkyl group or a phenyl group, Re is a divalent hydrocarbon group, and R9-R12 is a carbon number of 1 to 20. Monovalent hydrocarbon group, R13 and Re4 are hydrogen atoms, 1 having 1 to 20 carbon atoms
Represents a valent hydrocarbon group or halogen atom, Re3,
Both Re4 are not halogen atoms, and R
Compounds with a structure such that the combination of e3 and Re4 is neither a halogen atom nor a hydrogen atom, and n represents 0 or an integer from 1 to 20), specifically CH3Cl
Organohalogen compounds that can generate stable carbon cations such as CH3 and BCf3.5nCI4, TIC
fa, 5bCf6, PeCl3, AlCl3
This is a cationic polymerization method that uses a combination of Friedelkraut and other hydrofluoric acid catalysts as polymerization co-initiators.

In the Yefer method, at a temperature of +lθ to -130°C,
Saturated hydrocarbon solvents such as ethane, propane, butane, pentane, hexane, methyl chloride, methylene chloride, 1.
By polymerizing the above-mentioned cationic polymerizable monomer in a halogenated hydrocarbon solvent such as 1-dichloroethane or a mixture thereof, a polymer in which the halogen atom in the organic halogen compound is present at the molecular end is produced. can do.

An example of the Binifer method is to use CH3CI+3 as an initiator and polymerize isobutylene monomer in methylene chloride at -70°C to produce -C11,3CH3 on the molecular side. Furthermore, Cl has -C-CI groups at both ends.
3. By treating the polymer with a strong base such as t-BuOK, a selective HCf removal reaction can be carried out. It can be converted into a polymer.

This polymer can be suitably used in a hydrosilylation reaction as described below.

Examples of the reactive silicon group in the isobutylene polymer having at least one reactive silicon group at the molecular terminal used in the present invention include a hydrolyzable silicon group or a silanol group.

The term "hydrolyzable silicon group" as used herein refers to a group in which a hydrolyzable group that can be hydrolyzed by moisture in the presence or absence of a silanol condensation catalyst is bonded to a silicon atom. Specific examples of the functional groups include commonly used groups such as a hydrogen atom, an alkoxy group, an acyloxy group, a ketoximate group, an amino group, an amide group, an aminooxy group, a mercapto group, and an alkenyloxy group. Among these, alkoxy groups are particularly preferred because they are mildly hydrolyzable and easy to handle.

One to three hydrolyzable groups can be bonded to one silicon atom, and when two or more are bonded, they may be the same or different.

The number of silicon atoms forming the hydrolyzable silicon group may be one or two or more, but in the case of silicon atoms connected by siloxane bonds etc., the number may be up to 20. is preferred.

Although there are no particular limitations on the method of introducing reactive silicon groups into the molecules of the isobutylene polymer used in the present invention,
General formula (2): % formula % (2) (wherein R1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms,
An isobutylene polymer having at least one unsaturated bond represented by an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms at the molecular end;
): (wherein, R2 and R3 are both an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 2 o carbon atoms, or an aryl group having 7 carbon atoms.
~20 aralkyl groups or (R”)JSIO-(R
" is a monovalent hydrocarbon group having 1 to 20 carbon atoms, which may be the same or different), and which may be the same or different, may be used, X is a hydroxyl group or a hydrolyzable group,
When two or more are combined, they may be the same or different, and a is 0. 1.2 or 3, b is 0.1 or 2, I is 0 or an integer from 1 to 18), for example) 12 PtCf
6 ・81120, pt metal, RhCf (PPh
3) 3, Rh (J 3, Rh/Aj 203, Ru
CIg,, IrCf3, PeCl3, MCl3,
PdC12・2H20, NLCN 2 , Ti(J 4
A useful method is to introduce such a compound at the end of the molecule by a so-called hydrosilylation reaction using a compound such as the above as a catalyst.

The hydrosilylation reaction is generally carried out at a temperature range of 0 to 150°C, and n-pentane, n-hexane, n-hebutane, or benzene may be added as necessary to adjust the reaction temperature or the viscosity of the reaction system. , toluene, xylene, and the like may be used.

At least one unsaturated bond represented by the general formula ('2J)
Among the polymers contained in the individual molecules, the isobutylene polymer obtained by the Vinifer method described above is the
S? Therefore, it is preferable. Isobutylene polymers having 10-CH2 groups at the molecular ends are those in which as many H3 -C-C)12 groups are introduced at the molecular ends as more reactive silicon groups are present at the molecular ends during the hydrosilylation reaction. This is preferable because it reduces the number of terminals that are introduced and do not participate in curing, and the number is preferably in the range of 1.4 to 4.5, accounting for 70% or more of the terminals. If this number is less than 1.4, it is difficult to introduce reactive silicon groups into all unsaturated double bonds, making it impossible to introduce at least one reactive silicon group at the end of the molecule. In some cases, the curing of the composition after introduction of the reactive silicon group may become insufficient. In addition, in the case of a cured product in which five or more reactive silicon groups are introduced into one molecule, the rubbery properties may be insufficient. The number of heavy bonds in one molecule is preferably up to 4.5.

Specific examples of hydrogenated silicon compounds represented by general formula (3) include halogenated silanes such as trichlorosilane, methyldichlorosilane, dimethylchlorosilane, and trimethylsiloxydichlorosilane; trimethoxysilane, triethoxysilane, and methyldimethoxysilane; Silane, phenyldimethoxysilane, 1,3.3.5.5,7
．． Alkoxysilanes such as 7-hebutamethyl-1,1-dimethoxytetrasiloxane; Acyloxysilanes such as methyldiacetoxysilane and trimethylsiloxymethylacetoxysilane; Bis(dimethylketoximate)methylsilane, bis(cyclohexylketoxymate) ketoximate silanes such as methylsilane, bis(diethylketoximate)trimethylsiloxysilane;
Dimethylsilane, trimethylsiloxymethylsilane, 1
, 1,3.3-tetramethyldisiloxane, ■, 3゜5
-81 in molecules such as trimethylcyclotrisiloxane
Examples include, but are not limited to, hydrosilanes having two or more -H bonds; alkenyloxysilanes such as methyldi(isopropenyloxy)silane; and the like. Among these compounds, chlorosilanes such as trichlorosilane, methyldichlorosilane, and dimethylchlorosilane, which have high activity in hydrosilylation reactions, are particularly preferred. However, isobutylene polymers having chlorosilyl groups obtained by hydrosilylation reactions using chlorosilanes produce hydrogen chloride gas or hydrochloric acid when condensed and cured, which may cause practical problems. In addition, the generated chlorine ions act as a catalyst for the condensation reaction of reactive silicon groups, and may adversely affect the storage stability of polymers having such groups. Therefore, it is preferable to use the chlorosilyl group after converting the chlorine atom into an alkoxy group, acyloxy group, aminooxy group, alkenyloxy group, hydroxyl group, or the like. Among these, alkoxy groups are particularly preferred since they are mildly hydrolyzable and easy to handle.

The molecular weight of the isobutylene polymer having at least one, preferably 1.2 to 4 reactive silicon groups in the molecule used in the present invention is preferably about 500 to 30,000, particularly about 1,000. A liquid material of about 15,000 to 15,000 is preferred because it is easy to handle. When the number of thick silicon groups contained in the molecule is less than 1, the curability becomes insufficient and it becomes difficult to exhibit good rubber elastic behavior.

It is necessary that the reactive silicon group be present at the end of the molecule. When a reactive silicon group is present at the molecular end, the effective network chain amount of the inbutylene polymer component contained in the cured product increases, resulting in a rubber-like cured product with high strength and high elongation. become more susceptible to

If the isobutylene-based polymer having a reactive silicon group used in the present invention does not contain any unsaturated bonds in the molecule that are not aromatic rings, the composition of the present invention may contain oxypropylene-based polymers or other unsaturated bonds. It has significantly better weather resistance than compositions made of organic polymers. In addition, since the polymer is a hydrocarbon polymer, it has good water resistance and -
Once the surface of the foot is cured, the interior can remain uncured, making it possible to create a composition that has excellent adhesion performance to various substrates.

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

Specific examples of such compounds include (CH3
”)s 31011, (C)I3CI!2) 3310
11゜(C)13 Cll2CH2)35IO11,I c Margin below] (C)(3)281 (OCHJ) 2, (CH3
CH2) 2 81 (OCH3):! , (CH3
)25l (OCH2CH3)2, (CH3CH2)2
5i(OCIhCH3)2, (CHI)2Si
(OCII2C)120C)13 )2, (CH3CH
I2 )2 Sl (OCII2CH2QC)13)
2, (CHI) (C113C82) S 1 (O
CRg)2, (x +y -0~18) (x +y = 0~18) (CH3hSINSl(CH3)3, (CH3)3
SIN(CHa)2, (C)13)35l-N-C
Examples include, but are not limited to, silicon compounds containing a hydrolyzable group such as -N-91(CHI3) 3 and one or more silanol groups. Note that R in the formula is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.

There are roughly three methods for adding these silicon compounds.

One is a method of simply adding the compound to the isobutylene polymer. Depending on the properties of the compound, it may be uniformly dispersed and dissolved by heating and stirring, if necessary. In this case, it is not necessary to have a completely uniform and transparent state; even in an opaque state, as long as it is dispersed, the purpose can be achieved. Further, if necessary, a dispersibility improver such as a surfactant may be used in combination.

The second method is to add and mix a predetermined amount of the compound when the product is finally used.

For example, when used as a two-component sealant, the compound may be mixed as a third component in addition to the base and curing agent.

The third method is to react the compound with the isobutylene polymer in advance, and if necessary, a tin-based, titanate-based, acid or basic catalyst may be used in combination. In the case of a compound that generates a silanol group-containing compound due to moisture, the objective can be achieved by adding the required amount of water and devolatilizing it by heating under reduced pressure.

Specific examples of catalysts that can be used in this case include titanate 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, jetanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, Guanidine, diphenylguanidine, 2.4.8-tris(dimethylaminomethyl)phenol, morpholine, N
-Methylmorpholine, 1,3-diazabicyclo(5,4
, 8) Amine compounds such as undecene-7 (DBU) or their salts with carboxylic acids; low molecular weight polyamide resins obtained from excess polyamines and polybasic acids; reaction products between excess polyamines and epoxy compounds thing;
A silane coupling agent having an amino group, such as γ-
Examples include silanol condensation catalysts such as aminopropyltrimethoxysilane and N-(β-aminoethyl)aminopropylmethyldimethoxysilane. These catalysts may be used alone or in combination of two or more.

In the curable composition of the present invention, in addition to the main component, an isobutylene polymer having at least one reactive silicon group at the end of the molecule, various silane compounds as physical property modifiers may be used as necessary. Of course, there are also various fillers, plasticizers, silanol condensation catalysts commonly used to cure the isobutylene polymer component with reactive silicon groups, water, anti-aging agents, ultraviolet absorbers, and lubricants. , pigments, foaming agents, adhesion promoters, etc. may be added as necessary.

Fillers that can be used in the present invention include, for example, wood flour, bulbs, cotton chips, asbestos, glass fiber, carbon fiber, mica, walnut flour, rice flour, graphite, diatomaceous earth, clay, hume silica, precipitated silica, and silicic anhydride. , carbon black, calcium carbonate, clay, talc, titanium oxide, magnesium carbonate, quartz, fine aluminum powder, flint powder, zinc powder, etc.

These fillers may be used alone or in combination of two or more.

Plasticizers include polybutene, hydrogenated polybutene, α
-methylstyrene oligomer, biphenyl, triphenyl, triaryl dimethane, alkylene triphenyl,
Hydrocarbon compounds such as liquid polybutadiene, hydrogenated liquid polybutadiene, alkyldiphenyl, partially hydrogenated terphenyl; chlorinated paraffins; dibutyl phthalate, dibutyl phthalate, di(2-ethylhexyl)
Phthalate esters such as phthalate, butyl benzyl phthalate, butyl phthalyl butyl glycolate; Non-aromatic dibasic acid esters such as dioctyl adipate and dioctyl sebacate; Polyalkylene glycols such as diethylene glycol benzoate and triethylene glycol dibenzoate. Esters: Examples include phosphoric acid esters such as tricresyl phosphate and tributyl phosphate. These may be used alone or in combination of two or more. These plasticizers may be used in place of a solvent for the purpose of adjusting the reaction temperature, adjusting the viscosity of the reaction system, etc. when introducing reactive silicon groups into the isobutylene polymer.

In order to cure the isobutylene polymer component containing reactive silicon groups, which is the main component of the curable composition of the present invention,
A silanol condensation catalyst can be used if necessary. Such condensation catalysts include, for example, titanate esters such as tetrabutyl titanate and tetrapropyl titanate;
dibutyltin dilaurate, dibutyltin maleate,
Tin carboxylates such as dibutyltin diacetate, tin octylate, and tin naphthenate; reaction product of dibutyltin oxide and phthalate ester, nidibutyltin diacetylacetonate; aluminum trisacetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethyl Organoaluminum compounds such as acetoacetate; chelate compounds such as zirconium tetraacetylacetonate and titanium tetraacetylacetonate; lead octylate; butylamine, monoethanolamine, triethylenetetramine, guanidine, 2-ethyl-4-methylimidazole , 1,3-diazabicyclo(5,4,8)undecene-
Examples include amine compounds such as 7 (DBU) or salts thereof such as carboxylic acids; and other known silanol catalysts such as acidic catalysts and basic catalysts.

The curable composition of the present invention may be used in combination with various adhesion promoters for the purpose of further improving adhesiveness. Specifically, by using one or more types of epoxy resins, phenol resins, various silane coupling agents such as a, minosilane compounds, and epoxysilane compounds, alkyl titanates, aromatic polyisocyanates, etc., a wide variety of types can be produced. can improve adhesion to adherends.

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

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

Production Example 1 20 g of an isobutylene polymer having a molecular weight of about 5.000 and having isopropenyl groups at both ends at a ratio of about 92% and 1 g of toluene were weighed into a 500 ml four-loaf flask, and heated at 90°C for 2 hours. Degassed under reduced pressure.

Next, 120 m of hebutane was dried at room temperature under a nitrogen atmosphere.
1. 11.5 g of methyldichlorosilane and 0.1 ml of chloroplatinic acid catalyst solution (lhPt(Js ・8112
01g to 1,2-dimethoxyethane 9g, ethanol I
After adding a solution (dissolved in g-), the mixture was reacted at 90°C for 12 hours.

When the amount of residual inpropenyl groups in the isobutylene polymer in the reaction solution was quantified by IR spectroscopy, it was found that almost no inpropenyl groups remained.

Next, 21.2 g of methyl orthoformate, 8.0 g of methanol.
4 g was added and reacted at 70°C for 3 hours. At this point, the pl of the reaction system was approximately 7, making it neutral.

After distilling off the volatile components under reduced pressure, 50% hexane was added to the remaining components.
ml was added and stirred well, and insoluble components were removed by filtration. CI to distill hexane from the liquid! 3, and an isobutylene polymer having two -91(OCIIx) groups at both ends was changed.

It was found by NMR method that two -31 (Oellx) groups were introduced at about 80% of the terminal ends of the molecule.

Production Example 2 800 g of polypropylene budoxide having an average molecular weight Ml of 80110 and having allyl ether groups introduced into 97% of all terminals was placed in a pressure-resistant reaction vessel equipped with a stirrer, and 19 g of methyldimethoxysilane was added thereto. Then, a chloroplatinic acid catalyst solution (H2Pt
C1a ・61 (8.9 g of 20 and 18 ml of isopropyl alcohol and 180 ml of tetrahydrofuran
After adding 0.34 ml of solution dissolved in
The mixture was allowed to react for 6 hours.

When the amount of silicon hydride groups remaining in the reaction solution was determined by IR spectroscopy, it was found that almost no silicon hydride groups remained. Furthermore, when silicon groups were quantified by NMR method, about 85% of the molecular terminals were H3 (C1130)25iCI12C)12 CI+20-
I found out that it's based on

Example I 13t (OC113) at the end of the molecule obtained in Production Example 1
100 parts of isobutylene polymer having z group, hydrogenated polybutene (manufactured by Idemitsu Petrochemical Oki, trade name: polybutene OH)
, used as a plasticizer) 50 parts, fatty acid-treated colloidal calcium carbonate (manufactured by Shiraishi Kogyo ■, trade name: CCR, used as a filler) 100 parts, diphenylsilanediol (used as a physical property modifier) 2.2 parts, water 0 .5 parts and 1 part of a hindered phenolic antioxidant (manufactured by Iriuchi Shinko Kagaku ■, trade name: Nickrac MS-6) were weighed out, mixed well, and thoroughly kneaded by passing it through three paint rolls three times. Thereafter, a separately prepared silanol condensation catalyst consisting of 3 parts of tin octylate and 0.75 parts of laurylamine was added and thoroughly kneaded. The composition was poured into a mold with a thickness of about 3 m+s so as to avoid bubbles as much as possible, and cured at room temperature for 4 days and then at 50°C for 4 days to obtain a cured product. A No. 3 dumbbell conforming to JIS K 8301 was punched out from the sheet of the cured product and subjected to a tensile test at a tensile speed of 500 mm/min. Strength at break is 7.4kg/cm
2. Elongation at break was 400%.

Example 2 -3i (OCIlx) at the end of the molecule obtained in Production Example 1
100 parts of an inbutylene polymer having two groups, 0.5 parts of water, and 50 parts of toluene were thoroughly stirred to form a uniform toluene solution. Pour this solution into a mold with a thickness of about 3 mm,
After curing for 1 day at room temperature and 4 days at 50°C, 11 g of toluene was heated for 2 to 3 times at 50°C to completely volatilize the toluene.
The mixture was devolatilized for 2 hours under reduced pressure.

The obtained cured sheet was exposed to a Sunshine Carbon Arc Weathermeter (120 minute cycle, 18 minute spray) for 300 hours to measure weather resistance. No resinization or softening occurred at all.

Comparative Example 1 Weather resistance was measured in exactly the same manner as in Example 2, except that the polymer obtained in Production Example 2 was used instead of the polymer obtained in Production Example 1 used in Example 2. After 60 hours of exposure, the cured sheet had already softened and -part of it had run off.

Example 3 Heat resistance was measured using the cured sheet produced in Example 2. The cured sheet was placed in a hot air dryer at 150° C., and changes in properties over time were observed.

There was no change at all after 30 minutes, and although there was some coloring after 5 hours, the surface tack had not increased at all and no phenomena of resinization or softening were observed.

Comparative Example 2 The heat resistance of the cured sheet prepared in Comparative Example 1 was measured in exactly the same manner as in Example 3, and it softened in 30 minutes.
Melting occurred, and after 5 hours had passed, the decomposition progressed further and it was volatilized.

Example 4 C)+3 ■ -81(QC)II) at the end of the molecule obtained in Production Example 1
100 parts of isobutylene polymer having 2 M, hydrogenated polybutene (manufactured by Idemitsu Petrochemical ■, trade name Polybutene 01)
1) Weigh out 50 parts, 1 part of bindard phenol antioxidant (manufactured by Iriuchi Shinko Kagaku, trade name: Tsukrak NS-6), and 2 parts of dibutyltin dilaurate, mix well, and then form a mold with a thickness of about 3 mm. A cured product was obtained by pouring the mixture into a container and curing it at room temperature for 4 days and then at 70''C for 10 days.

When the cured product was cut out, about one part of the surface layer was cured, but the inside was not cured and was a mastic type cured product.

[Effects of the Invention] When the curable composition of the present invention is used, a cured product having excellent weather resistance, water resistance, heat resistance, electrical insulation property, gas barrier property, etc. can be obtained.

Procedural amendment (related) June 23, 1986

Claims (1)

[Scope of Claims] 1. A curable composition containing as a main component an isobutylene polymer having at least one reactive silicon group at the end of the molecule. 2 The reactive silicon group in the isobutylene polymer has the general formula (1): ▲There are numerical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1 is a hydrogen atom, an alkyl having 1 to 8 carbon atoms group, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, R^2 and R^3 each have 1 carbon number
-20 alkyl group, C6-20 aryl group, C7-20 aralkyl group or (R^-)_3Si
A triorganosiloxy group represented by O- (R' is a monovalent hydrocarbon group having 1 to 20 carbon atoms and may be the same or different), and may be the same. , may be different, X is a hydroxyl group or a hydrolyzable group, and when two or more are bonded, they may be the same,
may be different, a is 0, 1, 2 or 3, b is 0
, 1 or 2, and m is 0 or an integer from 1 to 18). 3 In the general formula (1), X is a hydrogen atom, a hydroxyl group, an alkoxy group, an acyloxy group, a ketoximate group, an amino group,
The curable composition according to claim 2, which is an amide group, an aminooxy group, a mercapto group, or an alkenyloxy group, and when X is two or more, they may be the same or different. thing. 4. The curable composition according to claim 2, wherein X in general formula (1) is an alkoxy group. 5. The curable composition according to claim 2, wherein R^1 in general formula (1) is a methyl group. 6 An isobutylene polymer whose reactive silicon group has at least one unsaturated bond at the end of the molecule and general formula (3): ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(3) The curable composition according to claim 1 or 2, which is a group formed by a hydrosilylation reaction with a hydrogenated silicon compound represented by the following.