Moisture curable composition and cured product

Abstract

The purpose of the present invention is to provide a moisture curable composition, a cured product of which has high elongation, high strength, and excellent heat resistance.　The present invention provides a moisture curable composition which contains the following components (A) to (C).　Component (A): an organic polymer which has two or more alkoxysilyl groups in each molecule Component (B): an organic metal catalyst Component (C): an aromatic secondary amine compound

Description

Moisture-curable composition and cured product

[0001] The present invention relates to a moisture-curable composition which provides a cured product with excellent heat resistance, and to the cured product thereof.

[0002] In recent years, in order to reduce the weight of automotive batteries, aluminum is often used as a component, as described in JP 2022-175357 A. Furthermore, in order to improve the production efficiency of batteries, there is a demand for the elimination of heat sources such as hot air drying ovens during manufacturing. Therefore, moisture curing or room temperature curing is required for sealants and adhesives used in batteries. Furthermore, because the temperature inside a battery rises due to heat generation and the influence of the external environment, durability such as heat resistance is required for sealants and adhesives used in batteries.

[0003] However, although the cured products of conventional moisture-curable compositions have high elongation and strength, the rubber physical properties of the cured products change significantly due to thermal degradation, and the heat resistance is insufficient.

[0004] SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide a moisture-curable composition which provides a cured product with high elongation, high strength, and excellent heat resistance.

[0005] The gist of the present invention will be explained below: The present invention overcomes the above-mentioned problems of the conventional art.

[0006] The gist of the present invention is as follows: A first aspect of the present invention is a moisture-curable composition comprising the following components (A) to (C): Component (A): an organic polymer having two or more alkoxysilyl groups in the molecule; Component (B): an organometallic catalyst; and Component (C): an aromatic secondary amine compound.

[0007] A second aspect of the present invention is the moisture-curable composition according to the first aspect, wherein the metal of the component (B) is one or more selected from the group consisting of zinc, titanium, and tin.

[0008] A third aspect of the present invention is the moisture-curable composition according to the second aspect, wherein the metal of the component (B) is zinc.

[0009] A fourth aspect of the present invention is the moisture-curable composition according to any one of the first to third aspects, wherein the component (C) has a structure represented by any one of general formulas 1 to 3 shown below.

[0010] A fifth aspect of the present invention is the moisture-curable composition according to any one of the first to fourth aspects, wherein the component (C) comprises N,N'-di-2-naphthyl-p-phenylenediamine or 4,4'-bis(α,α-dimethylbenzyl)diphenylamine.

[0011] A sixth aspect of the present invention is the moisture-curable composition according to any one of the first to fifth aspects, wherein the main chain of the organic polymer of component (A) is polyoxyalkylene or poly(meth)acrylate.

[0012] A seventh aspect of the present invention is the moisture-curable composition according to any one of the first to sixth aspects, wherein the organic polymer of component (A) is linear and has alkoxysilyl groups at both ends thereof.

[0013] An eighth aspect of the present invention is the moisture-curable composition according to any one of the first to seventh aspects, wherein the content of the component (C) is 0.01 to 20 parts by mass per 100 parts by mass of the component (A).

[0014] A ninth aspect of the present invention is a cured product obtained by curing the moisture-curable composition according to any one of the first to eighth aspects.

[0015] One aspect of the present invention is a moisture-curable composition comprising the following components (A) to (C): component (A): an organic polymer having two or more alkoxysilyl groups in the molecule; component (B): an organometallic catalyst; and component (C): an aromatic secondary amine compound.

[0016] The moisture-curable composition according to the present invention provides a cured product that has high elongation, high strength, and excellent heat resistance.

[0017] The present invention will be described in detail below. In this specification, the expression "X to Y" means that X and Y are numerical values, and X and Y are used to mean the lower limit and upper limit, respectively. In addition, in the present invention, (meth)acrylate means both acrylate and methacrylate.

[0018] <Component (A)> The component (A) that can be used in the present invention is an organic polymer having two or more alkoxysilyl groups in the molecule. In particular, since the cured product has higher elongation and strength, and has better tensile shear adhesive strength to aluminum, it is preferable that the organic polymer is linear and has alkoxysilyl groups at both ends. The alkoxysilyl group undergoes a crosslinking reaction with the component (B) described below and moisture (water) that enters the moisture-curing composition from the outside air. Specific examples of the component (A) include component (A-1) in which the main chain of the organic polymer of component (A) is polyoxyalkylene, and component (A-2) in which the main chain of the organic polymer of component (A) is poly(meth)acrylate. In consideration of heat resistance, the component (A) is preferably component (A-1).

[0019] Examples of the alkoxysilyl group of component (A) include trialkoxysilyl groups such as trimethoxysilyl group, triethoxysilyl group, and triisopropoxysilyl group, dialkoxysilyl groups such as methyldimethoxysilyl group and methyldiethoxysilyl group, and monoalkoxysilyl groups such as dimethylmethoxysilyl group and dimethylethoxysilyl group. As the alkoxysilyl group of component (A), a dialkoxysilyl group or trialkoxysilyl group is preferred, and a trimethoxysilyl group or triethoxysilyl group is most preferred, as these result in a cured product with superior heat resistance.

[0020] From the viewpoint of handling, component (A) is preferably liquid at 25°C. The viscosity of component (A) at 25°C is preferably 0.5 to 500 Pa·s, more preferably 1 to 200 Pa·s, even more preferably 3 to 150 Pa·s, and even more preferably 10 to 100 Pa·s. A viscosity of 0.5 to 500 Pa·s provides the effect of a cured product having high elongation and strength, and excellent tensile shear adhesive strength to aluminum. Unless otherwise specified, the viscosity was measured at 25°C using a cone-plate viscometer in accordance with JIS K6833-1:2008.

[0021] Commercially available products of the component (A-1) are not particularly limited, and examples thereof include SAT010, SAX115, SAT030, SAT200, SAT350, SAT400, SAX220, SAX510, SAX520, SAX530, SAX575, SAX580, SAX710, SAX720, SAX725, SAX750, SAX770, S203, S303, S203H, S303H, S943S, S911S, MA440, MA447, MA451, MA903, MA903M, MA904, S943, MAX923, and MAX951 manufactured by Kaneka Corporation, but are not limited thereto.

[0022] Commercially available products of the component (A-2) include SA110S, SA100S, SA120S, and OR110S manufactured by Kaneka Corporation, but are not limited to these.

[0023] <Component (B)> The component (B) that can be used in the present invention is an organometallic catalyst. Component (B) is a catalyst that cures the moisture-curable composition. Component (B) promotes dealcoholization condensation between components (A) themselves, between component (A) and a silane compound having an alkoxysilyl group (excluding component (A)) described below, or between silane compounds having an alkoxysilyl group (excluding component (A)). Specific examples of the curing catalyst component (B) include organotin catalysts, organotitanium catalysts, organozirconium catalysts, and organozinc catalysts. From the viewpoints of the variety of usable catalyst types, reactivity, and cost, organotin catalysts, organotitanium catalysts, or organozinc catalysts are preferred, and organozinc catalysts are most preferred. That is, the metal of component (B) is preferably one or more selected from the group consisting of zinc, titanium, and tin, and more preferably zinc. Furthermore, from the viewpoint of preventing interference between the ligands of each component and thereby reducing catalytic activity, it is preferable to use one type of component (B) alone without mixing them.

[0024] Specific examples of organotin catalysts include divalent organotin compounds such as tin octoate and tin naphthenate, tetravalent organotin compounds such as dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin dimaleate, dibutyltin distearate, dioctyltin dilaurate, dioctyltin diversatate, dibutyltin oxide, and dibutyltin bis(triethoxysilicate), and chelate tin compounds such as tin-based chelate compounds such as dibutyltin bis(acetylacetonate), but are not limited to these.

[0025] Specific examples of organic titanium catalysts include, but are not limited to, tetraisopropyl titanate, tetra-normal-butyl titanate, butyl titanate dimer, tetraoctyl titanate, titanium acetylacetonate, titanium octylene glycolate, titanium tetraacetylacetonate, titanium ethyl acetoacetate, polyhydroxytitanium stearate, titanium lactate, titanium triethanolaminate, and titanium diisopropoxybis(ethyl acetoacetate).

[0026] Component (B) may be an organic zirconium catalyst. Specific examples of the organic zirconium catalyst include, but are not limited to, tetra-normal-propoxy zirconium, tetra-normal-butoxy zirconium, zirconium tetraacetylacetonate, zirconium monobutoxyacetylacetonate bis(ethylacetoacetate), zirconium dibutoxybis(ethylacetoacetate), and zirconium tributoxystearate.

[0027] Specific examples of organozinc catalysts include zinc(1-butylimidazole). ２ (acetate) ２ , zinc(1-methylimidazole) ２ (acetate) ２ , zinc (imidazole) ２ (acetate) ２ , zinc(1,2-dimethylimidazole) ２ (acetate) ２ , zinc (tetramethylguanidine)２ (acetate) ２ , zinc (DBN) ２ (acetate) ２ , zinc (DBU) ２ (acetate) ２ , zinc(1-butylimidazole) ２ (acetate) ２ , zinc(1-methylimidazole) ２ (Formate) ２ , zinc (imidazole) ２ (Formate) ２ , zinc(1,2-dimethylimidazole) ２ (Formate) ２ , zinc (tetramethylguanidine) ２ (Formate) ２ , zinc (DBN) ２ (Formate) ２ , zinc (DBU) ２ (Formate) ２ , zinc(1-butylimidazole) ２ (Neodecanoate) ２ , zinc(1-methylimidazole) ２ (Neodecanoate) ２ , zinc (imidazole) ２ (Neodecanoate) ２ , zinc(1,2-dimethylimidazole) ２ (Neodecanoate) ２ , zinc (tetramethylguanidine) ２ (Neodecanoate) ２ , zinc (DBN) ２ (Neodecanoate) ２ , zinc (DBU) ２ (Neodecanoate) ２ Here, DBN represents 1,5-diazabicyclo[4.3.0]non-5-ene, and DBU represents 1,8-diazabicyclo[5.4.0]undec-7-ene, but is not limited thereto.

[0028] Examples of the organozinc catalyst include a complex compound having zinc (divalent) as the central metal. When the component (B) contains a ligand, examples of the ligand include amine compounds, carboxylate compounds, β-ketoester compounds, and β-diketone compounds, with amine compounds and carboxylate compounds being preferred.

[0029] Examples of the carboxylate compounds include acetic acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, neodecanoic acid, etc. Examples of the β-ketoester compounds include methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, isopropyl acetoacetate, n-butyl acetoacetate, sec-butyl acetoacetate, t-butyl acetoacetate, etc. Examples of the β-diketone compounds include acetylacetone, hexane-2,4-dione, heptane-2,4-dione, heptane-3,5-dione, octane-2,4-dione, nonane-2,4-dione, 5-methyl-hexane-2,4-dione, etc. Examples of amine compounds include alkylamine compounds such as n-propylamine, isopropylamine, n-butylamine, n-hexylamine, n-octylamine, 2-ethylhexylamine, n-decylamine, and n-dodecylamine. These may be used alone or in combination of two or more. Zinc alkylamine complexes are particularly preferred as component (B). A zinc alkylamine complex is an organozinc catalyst in which an alkylamine compound is coordinated to zinc.

[0030] The component (B) may be added in the form of a composition mixed with a curing accelerator, a plasticizer, a solvent, etc., which will be described later.

[0031] Commercially available organozinc catalysts are not particularly limited, and examples thereof include K-KAT 670 and K-KAT XK-648 manufactured by KING INDUSTRIES, and Borchi (registered trademark) Kat 0244, Borchi (registered trademark) Kat 15, and Borchi (registered trademark) Kat 22 manufactured by OMG Borchers GmbH, but are not limited thereto.

[0032] Component (B) of the present invention is particularly preferably an organic zinc catalyst. When the organic zinc catalyst is combined with components other than component (B), such as components (A) and (C) of the present invention, the cured product can have even more remarkable effects, such as high elongation, high strength, and excellent heat resistance.

[0033] In the moisture-curable composition of the present invention, the blending amount of component (B) (the total amount when two or more types are included) is, for example, in the range of 0.01 to 25 parts by mass, more preferably 0.01 to 20 parts by mass, even more preferably 0.01 to 10 parts by mass, and still more preferably 1 to 5 parts by mass, per 100 parts by mass of component (A) (the total amount when two or more types are included). By being within the above range, the moisture-curable composition will produce a cured product with even higher elongation, higher strength, and excellent heat resistance.

[0034] <Component (C)> The component (C) that can be used in the present invention is an aromatic secondary amine compound. The component (C) has the effect of an antioxidant. Note that the component (C) does not include the component (B) described above. Specifically, the component (C) is preferably a compound having a structure represented by any one of the following general formulas 1 to 3:

[0035]

[0036] In general formulas 1 to 3, each Ar independently represents an aromatic hydrocarbon group, and each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group.

[0037] In the above general formulas 1 to 3, the aromatic hydrocarbon groups represented by Ar can each independently be a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group. Specific examples of Ar include groups derived from a benzene ring or a naphthalene ring. Preferably, each Ar is independently a benzene ring group or a naphthalene ring group. Note that, in the above general formulas 1 to 3, the aromatic hydrocarbon group represented by Ar may have a substituent on the aromatic ring other than N or R in the above formula, but preferably does not have any other substituents. Furthermore, the aromatic hydrocarbon group represented by Ar may have a linking group between the aromatic ring and N or R in the above formula, but preferably does not have a linking group.

[0038] In the above general formulas 1 to 3, each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group. Examples of alkyl groups include alkyl groups having 1 to 10 carbon atoms. Examples of cycloalkyl groups include cycloalkyl groups having 3 to 10 carbon atoms. Examples of alkenyl groups include alkenyl groups having 1 to 10 carbon atoms. Examples of alkynyl groups include alkynyl groups having 1 to 10 carbon atoms.

[0039] Examples of the substituents on the alkyl group, cycloalkyl group, alkenyl group, and alkynyl group include, but are not limited to, a halogen atom, a hydroxy group, an amino group, an alkoxy group, an alkylamino group, an alkylsulfonyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, a substituted or unsubstituted aryl group, or a group containing an aromatic ring such as a substituted or unsubstituted arylalkyl group.

[0040] The addition of component (C) has the effect of providing a cured product with high elongation, high strength, and excellent heat resistance. Specific examples of component (C) include, but are not limited to, phenylenediamine-based antioxidants and diphenylamine-based antioxidants. Of these, phenylenediamine-based antioxidants represented by general formula 1 or 3 and diphenylamine-based antioxidants represented by general formula 2 are preferred, and in consideration of the hardness, tensile strength, elongation, and tensile shear adhesive strength of the cured product in a heat resistance test, phenylenediamine-based antioxidants represented by general formula 1 or 3 are most preferred. Only one type of component (C) may be used, or two or more types may be used in combination.

[0041] Specific examples of the phenylenediamine-based antioxidant represented by the general formula 1 include, but are not limited to, N,N'-di-2-naphthyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, etc. N,N'-di-2-naphthyl-p-phenylenediamine is particularly preferred because of its superior heat resistance.

[0042] Specific examples of the diphenylamine antioxidant represented by the general formula 2 above include, but are not limited to, 4,4'-bis(α,α-dimethylbenzyl)diphenylamine, 4,4'-distyryldiphenylamine, 4,4'-dioctyldiphenylamine, octylated diphenylamine, 4-(α-phenylethyl)diphenylamine, 4,4'-bis(α-phenylethyl)diphenylamine, di-tert-butyldiphenylamine, N-phenyl-1-naphthylamine, etc. In terms of superior heat resistance, 4,4'-bis(α,α-dimethylbenzyl)diphenylamine, 4,4'-distyryldiphenylamine, 4,4'-dioctyldiphenylamine, and octylated diphenylamine are preferred, and 4,4'-bis(α,α-dimethylbenzyl)diphenylamine is particularly preferred.

[0043] Specific examples of the phenylenediamine antioxidant represented by the general formula 3 above include N-isopropyl-N'-phenyl-p-phenylenediamine, N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-p-phenylenediamine, 2-[(mercaptoacetyl)oxy]ethyl-3-[[4-(phenylamino)phenyl]amino]butanate, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, phenyl-octyl-p-phenylenediamine, bis(phenyl-isopropylidene)-4,4-diphenylamine, N-(3-methacryloyloxy-2-hydroxypropyl)-N'-phenyl-p-phenylenediamine, and N-isopropyl-N'-p-phenylenediamine. In view of excellent heat resistance, N-isopropyl-N'-phenyl-p-phenylenediamine or N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-p-phenylenediamine is preferred.

[0044] It is also possible to use, as component (C), aromatic secondary amine compounds other than the compounds represented by the above general formulas 1 to 3. Examples of such aromatic secondary amine compounds include N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N-bis(1,4-dimethylpentyl)-p-phenylenediamine, 2,4,6-tris(N-1,4-dimethylpentyl-p-phenylenediamino)1,3,5-triazine, diallyl-p-phenylenediamine mixture, p-(p-toluenesulfonylamido)diphenylamine, and 4-(anilinophenyl)methacrylamide.

[0045] Commercially available products of component (C) include, for example, the Nocrac series manufactured by Ouchi Shinko Chemical Industry Co., Ltd., including Nocrac PA (N-phenyl-1-naphthylamine), Nocrac ODA, Nocrac ODA-N, Nocrac AD-F (octylated diphenylamine), Nocrac CD (4,4'-bis(α,α-dimethylbenzyl)diphenylamine), Nocrac TD (p-(p-toluenesulfonylamido)diphenylamine), Nocrac White (N,N'-di-2-naphthyl-p-phenylenediamine), and the like. amine), Nocrac 810-NA (N-isopropyl-N'-p-phenylenediamine), Nocrac 6C (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine), Nocrac G-1 (N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-N'-phenyl-p-phenylenediamine), and the like, as well as Nonflex OD-3, Nonflex DCD, and Steerer LAS manufactured by Seiko Chemical Co., Ltd., but are not limited thereto.

[0046] In the moisture-curable composition of the present invention, the amount of component (C) added (content, total amount when two or more types are included) is preferably 0.01 to 20 parts by mass, more preferably 0.5 to 5 parts by mass, and even more preferably 0.5 to 2 parts by mass, per 100 parts by mass of component (A) (total amount when two or more types are included). When 0.01 part by mass or more of component (C) is added per 100 parts by mass of component (A), the heat resistance of the cured product is further improved, and when the amount added is 20 parts by mass or less, the cured product has higher elongation and strength.

[0047] <Optional Components> Additives such as curing accelerators, thioether-based antioxidants, fillers, silane compounds having an alkoxysilyl group (excluding component (A)), plasticizers, solvents, light stabilizers, heavy metal deactivators, tackifiers, antifoaming agents, dyes, pigments, rust inhibitors, leveling agents, dispersants, rheology modifiers, and surfactants can be used in the moisture-curable composition of the present invention, provided they do not impair the object of the present invention.

[0048] Examples of the curing accelerator include amine compounds. Specific examples include primary amines, secondary amines, and tertiary amines. However, the curing accelerator excludes the aforementioned component (B). Furthermore, the curing accelerator excludes the aforementioned component (C). Examples of the primary amine include N-propylamine, N-isopropylamine, N-butylamine, N-benzylamine, N-hexylamine, N-cyclohexylamine, N-n-octylamine, N-(2-ethylhexyl)amine, N-(2-phenylethyl)amine, N-(3-methoxypropyl)amine, N-decylamine, N-dodecylamine, and ethylenediamine. Examples of the secondary amines include N,N-dipropylamine, N,N-diisopropylamine, N,N-dibutylamine, N,N-dihexylamine, N,N-dicyclohexylamine, N,N-bis(2-methoxyethyl)amine, N,N-dioctylamine, N,N-bis(2-ethylhexyl)amine, N,N-diisononylamine, N,N-bis(tridecyl)amine, morpholine, 2,2,6,6-tetramethylpiperidine, N,N'-dimethylethylenediamine, N,N'-diethylethylenediamine, and N,N'-diisopropylethylenediamine. Examples of the tertiary amines include 3-diethylaminopropylamine, imidazole, 1-methylimidazole, 1-butylimidazole, 1,2-dimethylimidazole, tetramethylguanidine, DBU, and DBN.

[0049] The moisture-curable composition of the present invention may further contain a thioether-based antioxidant. When combined with the component (C) of the present invention, the thioether-based antioxidant has the effect of providing a cured product with even higher elongation, strength, and heat resistance. Examples of thioether-based antioxidants include pentaerythritol tetrakis[3-(dodecylthio)propionate], pentaerythrityl tetrakis(3-laurylthiopropionate), dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, and distearyl-3,3'-thiodipropionate. The thioether-based antioxidant may be used alone or in combination with two or more types. Commercially available thioether-based antioxidants include, for example, Adeka STAB AO-503, AO-26, and AO-412S (manufactured by ADEKA Corporation).

[0050] When the moisture-curable composition contains a thioether-based antioxidant, the amount of thioether-based antioxidant added (the total amount when two or more types are included) is not particularly limited, but is preferably 0.1 to 10 parts by mass, and more preferably 0.5 to 5 parts by mass, per 100 parts by mass of component (A) (the total amount when two or more types are included). Furthermore, the content of the thioether-based antioxidant (the total amount when two or more types are included) per part by mass of component (C) (the total amount when two or more types are included) is preferably 0.1 to 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass. Amounts within the above range have the effect of further improving the heat resistance of the cured product.

[0051] Specific examples of the filler include talc powder, silica powder, clay powder, calcium carbonate powder, magnesium carbonate powder, calcium silicate powder, glass powder, alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, boron nitride powder, and aluminum hydroxide powder. The filler may be surface-treated with a fatty acid soap or the like. These fillers may be used alone or in combination. Among these, talc powder, silica powder, clay powder, calcium carbonate powder, magnesium carbonate powder, calcium silicate powder, and glass powder are preferred for imparting a high modulus to the cured product, with calcium carbonate powder being particularly preferred. The calcium carbonate powder is preferably surface-treated with a fatty acid soap or the like. It is even more preferred to use a combination of surface-treated and non-surface-treated calcium carbonate powder, as this provides the cured product with even higher elongation, strength, and heat resistance. For the purpose of imparting thermal conductivity to the moisture-curable composition, preferred fillers have thermal conductivity, such as alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, and boron nitride powder, and for the purpose of imparting flame retardancy to the moisture-curable composition, aluminum hydroxide powder is preferred. By imparting thermal conductivity to the moisture-curable composition, it can be used as a heat-dissipating agent that exhibits thermal conductivity.

[0052] The average particle size of the filler is preferably 0.001 to 90 μm, more preferably 0.005 to 50 μm, and most preferably 0.01 to 20 μm, from the viewpoint of achieving high elongation, high strength, and excellent heat resistance in the cured product. Furthermore, it is preferable to mix a filler having an average particle size of 0.5 μm to 90 μm with a filler having an average particle size of 0.001 μm to less than 0.5 μm. For 100 parts by mass of the filler having an average particle size of 0.5 μm to 90 μm, the filler having an average particle size of 0.001 μm to less than 0.5 μm is preferably contained in an amount ranging from 100 to 300 parts by mass, more preferably from 150 to 250 parts by mass, and even more preferably from 200 to 240 parts by mass. In the present invention, the average particle size is the particle size at 50% cumulative in the particle size distribution measured by laser diffraction / scattering. The particle size at 50% cumulative in the measured particle size distribution is also called the 50% average particle size or D50.

[0053] In a preferred embodiment, the moisture-curable composition contains, as fillers, a non-surface-treated calcium carbonate powder having an average particle size of 0.5 μm to 90 μm and a calcium carbonate powder surface-treated with a fatty acid soap having an average particle size of 0.001 μm to 0.5 μm. In this case, the calcium carbonate powder surface-treated with a fatty acid soap having an average particle size of 0.001 μm to 0.5 μm is preferably contained in an amount ranging from 100 to 300 parts by mass, more preferably from 150 to 250 parts by mass, and even more preferably from 200 to 240 parts by mass, per 100 parts by mass of the non-surface-treated calcium carbonate powder having an average particle size of 0.5 μm to 90 μm.

[0054] The amount of filler (total amount when two or more types are included) is preferably in the range of 2 to 400 parts by mass, more preferably 10 to 300 parts by mass, even more preferably 30 to 200 parts by mass, still more preferably 100 to 200 parts by mass, and particularly preferably 140 to 180 parts by mass, per 100 parts by mass of component (A) (total amount when two or more types are included). By keeping the amount within the above range, the cured product will have even higher elongation, higher strength, and excellent heat resistance.

[0055] When a thermally conductive filler such as alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, or boron nitride powder is used as the filler, the content of the thermally conductive filler is not particularly limited, but is preferably 55 to 95 mass %, and more preferably 60 to 90 mass %, relative to the total amount of the moisture-curable composition.

[0056] It is preferable to use two or more types of thermally conductive fillers with different average particle sizes in combination. This allows for a moisture-curing composition with even better thermal conductivity of the cured product. For example, it is preferable to use a thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm in combination with a thermally conductive filler with an average particle size of 5 μm or more and 90 μm or less. In this case, the content of the thermally conductive filler with an average particle size of 5 μm or more and 90 μm or less per 100 parts by mass of the thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm is, for example, 10 to 700 parts by mass, preferably 100 to 500 parts by mass.

[0057] In another preferred embodiment, a thermally conductive filler having an average particle size of 0.001 μm or more and less than 5 μm, a thermally conductive filler having an average particle size of 5 μm or more and less than 20 μm, and a thermally conductive filler having an average particle size of 20 μm or more and less than 90 μm can be used in combination. In this case, the content of the thermally conductive filler having an average particle size of 5 μm or more and less than 20 μm per 100 parts by mass of the thermally conductive filler having an average particle size of 0.001 μm or more and less than 5 μm is, for example, 5 to 600 parts by mass, preferably 110 to 200 parts by mass. Furthermore, the content of the thermally conductive filler having an average particle size of 20 μm or more and less than 90 μm per 100 parts by mass of the thermally conductive filler having an average particle size of 0.001 μm or more and less than 5 μm is, for example, 5 to 600 parts by mass, preferably 200 to 400 parts by mass.

[0058] The silane compound having an alkoxysilyl group refers to a silane compound, excluding component (A), particularly having a molecular weight of 1,000 or less. Specific examples of the silane compound having an alkoxysilyl group include silicate compounds represented by methyl silicate, ethyl silicate, propyl silicate, and butyl silicate; silane coupling agents having an alkyl group such as dimethyldimethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, and hexyltrimethoxysilane; vinyl group-containing silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; silane coupling agents having a phenyl group such as phenyltrimethoxysilane, diphenyldimethoxysilane, and phenyltriethoxysilane; N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyltrimethoxysilane, and N-2-(aminoethyl)-3-aminopropylmethyltriethoxysilane; Examples of suitable coupling agents include silane coupling agents having an amino group, such as silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and N-phenyl-3-aminopropyltrimethoxysilane; silane coupling agents having a glycidyl group, such as 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxysilyltriethoxysilane; and silane coupling agents having a (meth)acryloyl group, such as 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, and 3-(meth)acryloxypropyltriethoxysilane. Among these, silane coupling agents having an amino group and silane coupling agents having a glycidyl group are preferred because the cured product has even higher elongation, higher strength, and better heat resistance.The amount of the silane compound having an alkoxysilyl group (the total amount when two or more types are included) is preferably in the range of 0.1 to 25 parts by mass, more preferably 0.3 to 20 parts by mass, and particularly preferably 0.5 to 18 parts by mass, per 100 parts by mass of component (A) (the total amount when two or more types are included). Amounts within the above ranges are preferred because the cured product has even higher elongation, strength, and heat resistance.

[0059] Specific examples of the plasticizers are broadly classified into phthalate ester plasticizers and non-phthalate plasticizers, with non-phthalate ester plasticizers being preferred due to their low carcinogenicity and the ability to maintain the effects of the present invention. Examples of the non-phthalate plasticizers include, but are not limited to, (meth)acrylic polymer plasticizers obtained by polymerizing (meth)acrylic monomers; polyether polyol plasticizers such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol; polyester plasticizers obtained from dibasic acids such as sebacic acid and adipic acid and dihydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, and propylene glycol; process oil plasticizers; alkylsulfonic acid phenyl esters; and acetyl tributyl citrate. The viscosity of the plasticizers at 25°C is not particularly limited, but is, for example, 0.1 to 5 Pa·s. The amount of plasticizer added (the total amount when two or more types are included) is preferably in the range of 5 to 300 parts by mass, more preferably 10 to 150 parts by mass, and particularly preferably 12 to 75 parts by mass, per 100 parts by mass of the component (A) of the present invention (the total amount when two or more types are included). By being within the above range, the cured product will have even higher elongation, higher strength, and better heat resistance.

[0060] Specific examples of the solvent include ketone-based solvents, alcohol-based solvents, glycol-based solvents, hydrocarbon-based solvents, and ester-based solvents.

[0061] The dispersant is not particularly limited, but a hydroxyl group-containing carboxylic acid ester is preferred from the viewpoint of easily improving the dispersibility of the above components (A) to (C). The dispersant may be either a synthetic product or a commercially available product. Specific examples of commercially available products include the DISPER BYK (registered trademark) series manufactured by BYK. The content of the dispersant is not particularly limited, but is, for example, 0.01 to 20 parts by mass per 100 parts by mass of component (A).

[0062] <Curing Method and Cured Product> The moisture-curable composition of the present invention can be a one-component or two-component composition. Here, two-component refers to a form in which the composition is cured by mixing two components when used. The composition can be cured by the humidity and temperature of the ambient air. It can also be cured by heating using a hot air drying oven or the like. Specific curing conditions include, for example, a temperature of preferably 5 to 50°C, a humidity of preferably 40 to 70% RH, and a curing time of preferably 5 minutes to 10 days. A cured product obtained by curing the moisture-curable composition of the present invention is also an aspect of the present invention. That is, the present invention also provides a cured product obtained by curing the moisture-curable composition.

[0063] <Applications> The moisture-curable composition of the present invention provides a cured product having high elongation, high strength, and excellent heat resistance, and is therefore preferably used in a variety of applications such as adhesives, sealing agents, sealants, potting agents, coating agents, thermally conductive resins, flame-retardant resins, and conductive pastes, and is particularly used in applications such as automobile parts, electric and electronic parts, and building materials.

[0064] Examples of the automobile parts include oil pans, transmissions, oil pressure switches, air flow meters, cam position sensors, water temperature sensors, crank position sensors, intake air temperature sensors, vehicle speed sensors, in-vehicle electronic boards, nickel batteries, Li batteries, and fuel cells, and adhesives, sealants, and potting agents using the moisture-curable composition of the present invention can be suitably used for these parts.

[0065] Furthermore, when thermal conductivity is imparted to the moisture-curable composition of the present invention, it can be used in a variety of applications, such as heat dissipation from electronic substrates, heat dissipation from electronic devices such as mobile phones and personal computers, heat dissipation from lighting such as LEDs, heat dissipation from optical pickup modules, heat dissipation from camera modules, heat dissipation from sensing devices, heat dissipation from power semiconductors, heat dissipation from inverters, heat dissipation from converters, and heat dissipation from ECU parts.

[0066] The moisture-curable composition of the present invention can be used for bonding various adherends. In particular, because of its excellent adhesion to aluminum, it is suitable for use as an adhesive or sealant in applications where aluminum is used. Examples of applications where aluminum is used include backsheets containing an aluminum layer used in solar cells, heat dissipation fins, battery cases, etc.

[0067] <Method of Use> Sealing methods using the moisture-curing composition of the present invention are not particularly limited, but representative examples include FIPG (formed-in-place gasketing). FIPG is a method of applying the moisture-curing composition of the present invention to a flange of a sealed part using an automatic application device or the like, and then bonding the flange to the other flange and curing the moisture-curing composition to form an adhesive seal. More specifically, this is a method of sealing at least a portion of the space between at least two flanges of a sealed part having at least two flanges, comprising the steps of applying the moisture-curing composition to the surface of at least one of the flanges, bonding the one flange coated with the moisture-curing composition to the other flange via the moisture-curing composition, and curing the moisture-curing composition to seal at least a portion of the space between the at least two flanges.

[0068] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Hereinafter, the moisture-curable composition will also be simply referred to as the composition.

[0069] Examples 1 to 8 and Comparative Examples 1 to 4 Preparation of Moisture-Curable Compositions The following components were prepared to prepare moisture-curable compositions. Component (A): Organic polymer having two or more alkoxysilyl groups in the molecule; Linear polyoxyalkylene having trimethoxysilyl groups at both ends and having a viscosity of 50 Pa·s at 25°C (Silyl (registered trademark) SAX575, manufactured by Kaneka Corporation); Component (B): Organometallic catalyst; Zinc alkylamine complex (K-KAT 670, manufactured by KING INDUSTRIES); Titanium diisopropoxybis(ethyl acetoacetate) (TC-750, manufactured by Matsumoto Fine Chemical Co., Ltd.); Dioctyltin dilaurate (Neostan U-810, manufactured by Nitto Kasei Co., Ltd.); Component (C): Aromatic secondary amine compound; N,N'-di-2-naphthyl-p-phenylenediamine (Nocrac White, manufactured by Ouchi Shinko Chemical Industry Co., Ltd.); 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (Nocrac CD, manufactured by Ouchi Shinko Chemical Industry Co., Ltd.) Component (C'): antioxidant other than component (C) Liquid thioether antioxidant (AO-26, manufactured by ADEKA Corporation) Tetrakis[3-(dodecylthio)propionic acid]pentaerythritol (AO-412S, manufactured by ADEKA Corporation) Tetrakis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionic acid] (AO-60, manufactured by ADEKA Corporation) Filler Untreated calcium carbonate powder with an average particle size of 1.3 μm (Softon 1800, manufactured by Bihoku Funka Kogyo Co., Ltd.) Calcium carbonate powder with an average particle size of 0.05 μm that has been surface-treated with fatty acid soap (Calcine 500, Maruo Calcium Co., Ltd.).

[0070] Component (A), component (C) (and / or component (C')), and a filler were weighed into a stirring vessel and stirred with a stirrer at 25°C for 60 minutes while vacuum degassing. Component (B) was then weighed and added, and the mixture was stirred for 30 minutes in a 25°C atmosphere while vacuum degassing to obtain a moisture-curable composition. The detailed amounts prepared are shown in Table 1, and all values ​​are expressed in parts by mass. In Table 1, the total is the combined amount of components (A) to (C) and component (C'). In Table 1, blank spaces indicate that the corresponding component was not included.

[0071]

[0072] <Evaluation> The moisture-curable compositions of Examples 1 to 8 and Comparative Examples 1 to 4 were subjected to hardness measurement, tensile strength measurement, elongation percentage (elongation at break) measurement, and tensile shear adhesive strength measurement, and further each measurement was performed after a heat resistance test. The results are summarized in Table 2.

[0073] [Hardness Measurement] A 2 mm thick frame was made as a spacer on a release-treated steel plate, and the moisture-curable composition was applied to a uniform thickness. The applied moisture-curable composition was left for 7 days in an atmosphere of 23°C and 50% RH to produce a cured product. Three sheets of the cured product were stacked to produce a test piece. Using a durometer hardness tester (A hardness), a hardness meter was pressed against the test piece at a pressure of 10 N, and the average value of five measurements was taken as the "hardness (unitless)." Details are in accordance with JIS K 6249:2003. The results are shown in Table 2. When the moisture-curable composition does not contain a thermally conductive filler, the hardness (initial) of the cured product is preferably softer than A50 (hardness less than 50) in consideration of flexibility.

[0074] [Tensile Strength Measurement] A 2 mm thick frame was made as a spacer on a release-treated steel plate, and the moisture-curable composition was applied to a uniform thickness. The applied moisture-curable composition was left to stand for 7 days in an environment of 23°C and 50% RH to produce a cured product. The cured product was punched out with a No. 5 dumbbell to produce a test piece. Both ends of the test piece were fixed to chucks. The test piece was pulled at a pulling rate of 500 mm / min, and the maximum load was measured. The results are shown in Table 2. The strength at the maximum load was defined as "tensile strength (MPa)." Details were in accordance with JIS K 6251 (2010). The tensile strength (initial) of the cured product is preferably 1.6 MPa or more, more preferably 1.7 MPa or more.

[0075] [Measurement of Elongation (Elongation at Break)] A 2 mm thick frame was made on a release-treated steel plate as a spacer, and the moisture-curable composition was applied to a uniform thickness. The applied moisture-curable composition was left for 7 days in an environment of 23 °C and 50% RH to produce a cured product. The cured product was punched out with a No. 5 dumbbell to prepare a test piece, and benchmark lines were written on the test piece at 25 mm intervals. Both ends of the test piece were fixed to the chuck in the same manner as in the measurement of tensile strength, and the test piece was pulled at a pulling rate of 500 mm / min until the test piece broke. Since the test piece stretched during measurement and the gap between the benchmark lines widened, the gap between the benchmark lines was measured with a vernier caliper until the test piece broke. The percentage of the gap between the benchmark lines, based on the initial gap between the benchmark lines, was defined as the "elongation (%)." Evaluation was performed based on the following criteria, and the results are shown in Table 2. Furthermore, when the moisture-curable composition does not contain a thermally conductive filler, the elongation (initial) of the cured product is preferably 250% or more, more preferably 350% or more, and even more preferably 400% or more, from the viewpoint of high extensibility.

[0076] [Measurement of Tensile Shear Adhesion Strength] Two aluminum plates (A1050P) measuring 25 mm wide x 100 mm long x 1 mm thick were prepared, and the moisture-curable composition was applied to one of the aluminum plates. The other aluminum plate was then attached and fixed so that the overlapping portion was 25 mm wide x 10 mm long x 1 mm thick. The test piece was then left to stand for 7 days in an environment of 23°C and 50% RH to obtain a test piece. The test piece was fixed to the chuck of a universal tensile tester and pulled at a pulling rate of 50 mm / min. The "tensile shear adhesion strength (MPa)" was measured from the maximum strength and adhesive area. Details were in accordance with JIS K 6850:1999. The results are shown in Table 2. In the present invention, the tensile shear adhesion strength (initial) of the cured product is preferably 1.3 MPa or more.

[0077] [Heat Resistance Test] Test pieces for hardness, tensile strength, elongation, and tensile shear bond strength measurements were prepared using the above procedures, and then the hardness, tensile strength, elongation, and tensile shear bond strength at 0 hours (initial) were measured. Another test piece was prepared and placed in a hot air drying oven set at 120°C. After 500 hours and 1000 hours of exposure, it was removed and returned to room temperature, and then the hardness, tensile strength, elongation, and tensile shear bond strength measurements were performed using the above procedures. The results are shown in Table 2. In Table 2, initial, 500 hours, and 1000 hours represent the measurements at the initial, 500-hour, and 1000-hour exposures, respectively. The "percent change" was calculated using the formula "percent change = [(measured value after 1000 hours exposure - initial measurement) / initial measurement] × 100" and is shown in Table 2. The percent change after 1000 hours is preferably -60 to 60%, and more preferably -30 to 30%.

[0078] In Table 2, "-" indicates that the sample was in a state where it could not be measured when exposed to the atmosphere for the heat resistance test. The hardness, tensile strength, and elongation could not be measured because the cured product of a specific shape had become brittle. The tensile shear adhesive strength could not be measured because the cured product could not be sandwiched and held between the aluminum plates that served as the adherend.

[0079]

[0080] Comparing Examples 1 to 8 with Comparative Examples 1 to 4, while Examples 1 to 8 showed a change rate of -60 to 60% for all test items, Comparative Examples 1 to 4 showed thermal degradation, with all test items becoming unmeasurable after 500 hours in Comparative Examples 1 and 2, and after 1000 hours in Comparative Examples 3 and 4. It was found that the use of component (C) in Examples 1 to 8 resulted in good heat resistance, while the absence of component (C), as in Comparative Examples 1 to 4, did not exhibit sufficient heat resistance. The mere use of component (C') without component (C), as in Comparative Examples 3 and 4, did not improve heat resistance. In particular, Example 1, in which N,N'-di-2-naphthyl-p-phenylenediamine was added as component (C), was particularly preferable because the change rate for all test items in Table 2 was -30 to 30%.

[0081] Example 9 Preparation of Moisture-Curable Composition The following components were prepared to prepare a moisture-curable composition. Component (A): Organic polymer having two or more alkoxysilyl groups in the molecule; Linear polyoxyalkylene having dimethoxysilyl groups at both ends and having a viscosity of 50 Pa·s at 25°C (Silyl (registered trademark) SAX750, manufactured by Kaneka Corporation); Component (B): Organometallic catalyst; Zinc alkylamine complex (K-KAT 670, manufactured by KING INDUSTRIES); Component (C): Aromatic secondary amine compound; 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (Nocrac CD, manufactured by Ouchi Shinko Chemical Industry Co., Ltd.); Filler; Alumina powder having an average particle size of 0.5 μm (referred to as Filler 1 in Table 3 below); Alumina powder having an average particle size of 5.4 μm (referred to as Filler 2 in Table 3 below); Alumina powder having an average particle size of 40 μm (referred to as Filler 3 in Table 3 below); Plasticizer Acrylic polymer having a viscosity of 3.5 Pa·s in an atmosphere of 25°C and a weight average molecular weight of 2,500 (referred to as plasticizer 1 in Table 3 below) Silane coupling agent Methyltrimethoxysilane (reagent) Dispersant Hydroxyl group-containing carboxylic acid ester (referred to as dispersant 1 in Table 3 below).

[0082] The (A) component, the (C) component, the filler, the plasticizer, the silane coupling agent, and the dispersant were weighed into a stirring vessel and stirred with a stirrer at 25 ° C for 60 minutes while vacuum degassing. Then, the (B) component was weighed and added, and the mixture was further stirred for 30 minutes under a 25 ° C atmosphere while vacuum degassing to obtain a moisture-curable composition. The detailed amounts prepared are shown in Table 3, and all values ​​are expressed in parts by mass. In Table 3, the total is the total amount of all components.

[0083]

[0084] <Evaluation> The moisture-curable composition of Example 9 was subjected to hardness measurement, tensile strength measurement, elongation (elongation at break) measurement, and tensile shear bond strength measurement using the same methods as those used in Examples 1 to 8 and Comparative Examples 1 to 4. Thermal conductivity measurement was also performed using the following method. The results obtained are shown in Tables 4 and 5 below as initial hardness, tensile strength, elongation, tensile shear bond strength, and thermal conductivity.

[0085] [Thermal Conductivity Measurement] The thermal conductivity was measured by the following procedure: Apparatus: TRIDENT thermal conductivity measuring apparatus manufactured by C-THERM Test method: ASTM D7984-21 Modified Transient Plane Source (MTPS) Specifically, first, a cured product having a diameter of 18 mm or more and a thickness of 2 mm was prepared (n=3). Next, contact liquid was dropped onto a sensor (resistance temperature detector unit), and the cured product was placed on top of it, and a 500 g weight was placed on top of this. Here, water was used as the contact liquid. Thereafter, the thermal conductivity was measured in an atmosphere of 25°C.

[0086] In addition, in a moisture-curable composition containing a thermally conductive filler, the initial hardness of the cured product is preferably 100 or less. The initial elongation of the cured product is preferably 80% or more. The preferred values ​​of the initial tensile strength and tensile shear bond strength of the cured product are the same as those described above. In addition, the initial thermal conductivity of the cured product is preferably 2.5 W / m K or more.

[0087] Furthermore, for each test piece for measuring hardness, tensile strength, elongation (elongation at break), tensile shear adhesive strength, and thermal conductivity, a heat resistance test was carried out in a 120°C atmosphere in the same manner as in the heat resistance tests in Examples 1 to 8 and Comparative Examples 1 to 4, except that the leaving time was changed to 240 hours, 500 hours, 750 hours, and 1000 hours. The results are summarized in Table 4.

[0088] Furthermore, each test piece for hardness measurement, tensile strength measurement, elongation (elongation at break), tensile shear adhesive strength measurement, and thermal conductivity measurement was placed in a thermo-hygrostat set to an atmosphere of 85°C and 85% RH, and after leaving for 240 hours, 500 hours, 750 hours, and 1000 hours, it was taken out and returned to room temperature, and then hardness measurement, tensile strength measurement, elongation measurement, tensile shear adhesive strength measurement, and thermal conductivity measurement were performed in the same manner as above. The results are summarized in Table 5.

[0089]

[0090]

[0091] As shown in Tables 4 and 5 above, the moisture-curable composition of Example 9 was found to have good performance in all of hardness, tensile strength, elongation (elongation at break), tensile shear adhesive strength, and thermal conductivity. Furthermore, in all of these test items, the rate of change after 1000 hours when a heat resistance test was conducted at 120°C was within the range of -20 to 20%, demonstrating excellent heat resistance. Furthermore, in all of these test items, the rate of change after 1000 hours when a high-temperature, high-humidity resistance test was conducted at 85°C and 85% RH was within the range of -25 to 25%, demonstrating excellent high-temperature, high-humidity resistance.

[0092] The moisture-curable composition of the present invention provides a cured product with high elongation, high strength, and excellent heat resistance, and is therefore suitable for a variety of applications, such as adhesives, sealants, potting agents, coating agents, thermally conductive resins, flame-retardant resins, conductive pastes, etc. Therefore, the moisture-curable composition of the present invention is industrially useful because it can be applied in a wide range of fields.

[0093] This application is based on Japanese Patent Application No. 2023-195483, filed on November 16, 2023, the disclosure of which is incorporated herein by reference in its entirety.

Claims

1. A moisture-curable composition comprising the following components (A) to (C): Component (A): an organic polymer having two or more alkoxysilyl groups in the molecule; Component (B): an organometallic catalyst; and Component (C): an aromatic secondary amine compound.

2. The moisture-curable composition according to claim 1, wherein the metal of component (B) is one or more selected from the group consisting of zinc, titanium and tin.

3. The moisture-curable composition according to claim 2, wherein the metal of component (B) is zinc.

4. The moisture-curable composition according to claim 1, wherein the component (C) has a structure represented by any one of the following general formulas 1 to 3: In general formulas 1 to 3, each Ar independently represents an aromatic hydrocarbon group, and each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group.

5. The moisture-curable composition according to claim 1, wherein said component (C) comprises N,N'-di-2-naphthyl-p-phenylenediamine or 4,4'-bis(α,α-dimethylbenzyl)diphenylamine.

6. The moisture-curable composition according to claim 1, wherein the main chain of the organic polymer of component (A) is a polyoxyalkylene or a poly(meth)acrylate.

7. The moisture-curable composition according to claim 1, wherein the organic polymer of component (A) is linear and has alkoxysilyl groups at both ends thereof.

8. The moisture-curing composition according to claim 1, wherein the content of the component (C) is 0.01 to 20 parts by mass per 100 parts by mass of the component (A).

9. A cured product obtained by curing the moisture-curable composition according to claim 1.

Images