Resin composition comprising zinc cyanurate and adhesion method

Abstract

[Problem] To provide a resin composition comprising zinc cyanurate that exhibits high adhesive strength, is particularly suitable for adhering metal substrates to each other and adhering a metal substrate and a different substrate, and can maintain adhesive strength even under hot and humid conditions. [Solution] Provided are: resin composition comprising zinc cyanurate, a cyanuric acid derivative, and a resin component; and a joined body of a cured product of the resin composition, in which the joining surface is a metal or a metal oxide.

Description

Resin composition containing zinc cyanurate and adhesion method

[0001] The present invention relates to a resin composition containing zinc cyanurate, a cyanuric acid derivative, and a resin component, a cured product of the resin composition, a bonded body between the cured product and a metal or the like, and a method for producing a mixed powder containing zinc cyanurate.The present invention also relates to an adhesive composition comprising the resin composition, a bonded body formed by bonding using the adhesive composition, and a bonding method using the adhesive composition.

[0002] Due to its high water-resistant adhesion, zinc cyanurate has been proposed for use as a corrosion inhibitor or anti-rust pigment for the surface of iron-based metals. Taking advantage of its high adhesion to metal parts, its use in adhesive compositions has also been proposed. For example, a backing coating composition containing a synthetic resin binder and zinc cyanurate as a lead-free anti-rust pigment has been proposed as a composition for use in a backing coating for an anti-corrosion mirror (Patent Document 1). Other proposals include a composition containing a thermoplastic elastomer, an epoxy resin, and zinc cyanurate as a resin composition for use in resin-metal composite members such as tire bead members, with the aim of improving adhesion and crack resistance to metal members (Patent Document 2); a curable resin composition containing a curable resin and zinc cyanurate, and an adhesive using said composition, with the aim of improving adhesion, long-term heat resistance, and reflow resistance (Patent Document 3); and a curable resin composition containing an epoxy resin, zinc cyanurate, and a curing agent, with the aim of improving adhesion after water immersion, and a structural adhesive using said composition (Patent Document 4).

[0003] Japanese Patent Application Publication No. 2020-90633 International Publication No. 2021 / 117419 International Publication No. 2021 / 193437 Japanese Patent Application Publication No. 2021-147551

[0004] Adhesive compositions containing zinc cyanurate and a resin component such as an epoxy resin have been disclosed. An object of the present invention is to provide a resin composition containing zinc cyanurate that exhibits high adhesive strength, is particularly suitable for bonding metal substrates together, and for bonding metal substrates to different substrates, and can retain adhesive strength even under humid and hot conditions.

[0005] The present inventors conducted extensive research to solve the above-mentioned problems, and as a result, have completed the present invention as described below. Specifically, the present invention is as follows. In a first aspect, the present invention relates to a resin composition containing zinc cyanurate, a cyanuric acid derivative, and a resin component. In a second aspect, the present invention relates to the resin composition according to the first aspect, in which the mass ratio of the zinc cyanurate to the cyanuric acid derivative is 15:1 to 2:1. In a third aspect, the present invention relates to the resin composition according to the first aspect, in which the total mass of the lead cyanurate and the cyanuric acid derivative is 0.1 to 10 parts by mass per 100 parts by mass of the resin component. In a fourth aspect, the present invention relates to the resin composition according to the first aspect, which contains a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, and a resin component, wherein the mixed powder (A) is a powder obtained by heating a mixed powder (B) containing zinc oxide, cyanuric acid, and water at 30 to 300°C. As a fifth aspect, the present invention relates to the resin composition according to the fourth aspect, wherein in the mixed powder (B), a molar ratio of the zinc oxide to the cyanuric acid is equal to or greater than 1 and less than 2. As a sixth aspect, the present invention relates to the resin composition according to the first aspect, which is a resin composition including a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, and a resin component, wherein the mixed powder is a dry powder of a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid. As a seventh aspect, the present invention relates to the resin composition according to the sixth aspect, wherein in the mixed powder (B), a molar ratio of the zinc oxide or basic zinc carbonate to the cyanuric acid is equal to or greater than 1 and less than 2. As an eighth aspect, the present invention relates to the resin composition according to the first aspect, wherein the resin component is one or more selected from the group consisting of a thermoplastic resin and a curable compound. As a ninth aspect, the present invention relates to the resin composition according to the eighth aspect, wherein the resin component is a curable compound.

[0016] In a tenth aspect, the present invention relates to the resin composition according to the ninth aspect, wherein the curable compound is one or more selected from the group consisting of (meth)acrylate compounds, epoxy compounds, oxetane compounds, thermosetting urethane resins, and thermosetting silicone resins. In an eleventh aspect, the present invention relates to the resin composition according to the first aspect, which contains the resin component in an amount of 90 to 99.9% by mass. In a twelfth aspect, the present invention relates to a cured product of the resin composition according to any one of the first to eleventh aspects.The present invention relates to a bonded body with the cured product according to the twelfth aspect, in which the bonding surface is a metal or a metal oxide. The present invention relates to a bonded body according to the thirteenth aspect, in which the metal is one or more selected from the group consisting of copper, iron, aluminum, magnesium, titanium, nickel, tin, zinc, chromium, and stainless steel, or an alloy containing one or more of these. The present invention relates to a bonded body according to the fourteenth aspect, in which the metal is one or more selected from the group consisting of copper, iron, stainless steel, and aluminum, or an alloy containing one or more of these. The present invention relates to a sixteenth aspect, in which an adhesive composition is made from the resin composition according to any one of the first to eleventh aspects. The present invention relates to a seventeenth aspect, in which a first substrate containing metal atoms and a second substrate are bonded together using the adhesive composition according to the sixteenth aspect. An eighteenth aspect relates to the joined body according to the seventeenth aspect, in which the metal atom is one or more selected from the group consisting of copper atoms, iron atoms, aluminum atoms, magnesium atoms, titanium atoms, nickel atoms, tin atoms, zinc atoms, and chromium atoms. A nineteenth aspect relates to the joined body according to the eighteenth aspect, in which the metal atom is one or more selected from the group consisting of copper atoms, iron atoms, aluminum atoms, nickel atoms, and chromium atoms. A twentieth aspect relates to a bonding method comprising bonding a first substrate containing a metal atom and a second substrate using the adhesive composition according to the sixteenth aspect. A twenty-first aspect relates to the bonding method according to the twentieth aspect, in which bonding between the first substrate and the second substrate is achieved by the adhesive composition acting on the substrates through hydrogen bonding and / or chemical adsorption to metal atoms. As a twenty-second aspect, the present invention relates to a method for producing mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, the method comprising: a step of heat-treating mixed powder (B) containing zinc oxide, cyanuric acid, and water in a range of 30 to 300°C in a sealed or open-to-air state; in the mixed powder (B), a molar ratio of the zinc oxide to the cyanuric acid is equal to or greater than 1 and less than 2; the mixed powder (B) has a water content of 9 to 18% by mass; and the mass ratio (residual rate) of cyanuric acid in mixed powder (A) relative to the mass of cyanuric acid in the mixed powder (B) is 5% or greater.As a twenty-third aspect, the present invention relates to a method for producing a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, the method comprising: a step of wet-dispersing a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid using a dispersion medium in a temperature range of 5 to 55°C, wherein in the mixed slurry, a molar ratio of the zinc oxide or basic zinc carbonate to cyanuric acid is equal to or greater than 1 and less than 2, and a mass proportion (residual rate) of cyanuric acid in the mixed powder (A) relative to the mass of cyanuric acid in the mixed slurry is 5% or greater.

[0006] According to the present invention, it is possible to provide a resin composition that not only exhibits high adhesive strength to metal substrates, but also exhibits high adhesive strength between metal substrates and dissimilar substrates, and can maintain high adhesive strength even under humid and hot conditions.

[0007] The resin composition according to the present invention contains zinc cyanurate, a cyanuric acid derivative, and a resin component.

[0008] <Zinc cyanurate> Cyanuric acid is a tribasic acid, and by reacting with divalent zinc, it is possible to produce an acidic salt, a neutral salt, or a basic salt. For example, when the molar ratio of (zinc oxide) / (cyanuric acid) is 1.0, Zn(C ３ N ３ O ３ When the molar ratio of zinc oxide to cyanuric acid is 1.5, Zn ３ (C ３ N ３ O ３ ) ２ A corresponding neutral salt is formed. When the molar ratio of zinc oxide to cyanuric acid is 2.5, Zn ３ (C ３ N ３ O ３ ) ２A basic salt equivalent to 2ZnO is formed. These salts may contain water of crystallization and may form, for example, monohydrate, dihydrate, or trihydrate. In the present invention, zinc cyanurate having a molar ratio of (zinc oxide) / (cyanuric acid) of 1.0 to 5.0, particularly 1 or more and less than 2, can be used. Examples of zinc sources include zinc oxide and basic zinc carbonate, which can be used in the above-mentioned molar ratio when converted to zinc oxide. For example, zinc oxide type 2 manufactured by Sakai Chemical Industry Co., Ltd. can be used as the zinc oxide.

[0009] Zinc cyanurate generally has an elongated particle shape, such as a needle or plate. In the resin composition according to the present invention, zinc cyanurate can be preferably used in the form of a powder (zinc cyanurate powder) or particles (zinc cyanurate particles). For example, as the zinc cyanurate powder (particles), a zinc cyanurate powder (particles) can be used in which, as measured by transmission electron microscope observation, the length of the major axis of the primary particle is 400 nm to 3,000 nm, the length of the minor axis of the primary particle is 10 nm to 300 nm, and the ratio of the length of the major axis to the length of the minor axis (major axis / minor axis) is 1.3 to 300. Furthermore, the zinc cyanurate powder (particles) can have a specific surface area of, for example, 10 m ２ / g to 100m ２ / g can be used. For example, zinc cyanurate powder (particles) can be used in which the major axis length of the primary particles is 400 nm to 1,000 nm, or 400 nm to 800 nm, or 400 nm to 600 nm, the minor axis length of the primary particle diameter is 10 to 300 nm, or 10 nm to 90 nm, or 30 nm to 90 nm, and the ratio of the major axis length to the minor axis length (major axis / minor axis) is 1.3 to 100. Also, for example, zinc cyanurate powder (particles) can be used in which the major axis length of the primary particles is 1,000 nm to 3,000 nm, or 2,000 nm to 3,000 nm, the minor axis length of the primary particle diameter is 80 to 300 nm, or 100 nm to 300 nm, and the ratio of the major axis length to the minor axis length (major axis / minor axis) is 3.3 to 37.5.

[0010] Furthermore, the average particle diameter of zinc cyanurate powder (particles) in the aqueous dispersion can be measured by dispersing the powder or a dispersion containing the powder in pure water and using a laser diffraction particle size distribution analyzer (for example, Shimadzu Corporation, product name SALD-7500nano). In the measurement by laser diffraction method, the average particle diameter of the zinc cyanurate powder (particles) in the aqueous dispersion is, for example, 80 nm to 20,000 nm.

[0011] There are two methods for producing zinc cyanurate powder (particles): one is a method in which raw materials are dispersed in water and subjected to a liquid-phase reaction in a slurry state, and the other is a method in which raw materials are subjected to a solid-phase reaction in a powder state.

[0012] A production method in which raw materials are dispersed in water and subjected to a liquid-phase reaction in a slurry state is, for example, a method in which zinc oxide or basic zinc carbonate, cyanuric acid, and water are blended together so that the cyanuric acid concentration is, for example, 0.1% by mass to 10.0% by mass, and the mixed slurry is wet-dispersed using a submerged disperser at a temperature of 5°C to 55°C. This procedure results in the reaction and dispersion of the product, resulting in a slurry (dispersion) of zinc cyanurate powder. The ratio of zinc oxide or basic zinc carbonate to cyanuric acid is not particularly limited, but the molar ratio (total of zinc oxide or basic zinc carbonate in terms of zinc oxide / cyanuric acid) can be 1.0 to 5.0, for example, 1 or more and less than 2. Note that cyanuric acid dissolved in water reacts quickly with zinc oxide or basic zinc carbonate, promoting particle growth, and therefore the product zinc cyanurate tends to become large particles. Therefore, it is preferable to carry out the reaction at 55°C or below, or 45°C or below.

[0013] The wet dispersion can be carried out using a dispersion medium. By carrying out the wet dispersion using a dispersion medium, the mechanical energy generated by the collision of the dispersion media can cause a mechanochemical reaction between at least one selected from zinc oxide and basic zinc carbonate and cyanuric acid. The mechanochemical reaction refers to a chemical reaction in which mechanical energy is applied from multiple directions to zinc oxide, basic zinc carbonate, and cyanuric acid through the collision of the dispersion media. Examples of the dispersion media include stabilized zirconia beads, quartz glass beads, soda-lime glass beads, alumina beads, and mixtures thereof. Considering the contamination caused by collisions between dispersion media and their shattering, it is preferable to use glass beads or stabilized zirconia beads as the dispersion media. The size of the dispersion media can be, for example, 0.1 mm to 10 mm in diameter, preferably 0.5 mm to 2.0 mm in diameter. If the diameter of the dispersion media is less than 0.1 mm, the collision energy between the grinding media is small, and the mechanochemical reactivity tends to be weak. Furthermore, if the diameter of the dispersion media is larger than 10 mm, the collision energy between the dispersion media will be too large, causing the dispersion media to break and resulting in a lot of contamination, which is undesirable.

[0014] The apparatus (pulverizing apparatus) for wet dispersion using the dispersion media is not particularly limited, as long as it can add the mixed slurry to a container containing the dispersion media, stir the mixture, and then collide the dispersion media with the zinc oxide, basic zinc carbonate, or cyanuric acid to cause a mechanochemical reaction between the zinc oxide or basic zinc carbonate and the cyanuric acid. Examples include ball mills such as Sand Grinder (manufactured by Imex Co., Ltd.), Apex Mill (manufactured by Hiroshima Metal & Machinery Co., Ltd. (Chemtech Division)), Attritor (manufactured by Nippon Coke & Engineering Co., Ltd.), and Pearl Mill (manufactured by Ashizawa Finetech Co., Ltd.), as well as bead mills and sand mills. The rotation speed and reaction time of the apparatus for stirring the dispersion media can be appropriately adjusted according to the desired particle size, etc.

[0015] In the obtained dispersion of zinc cyanurate powder, the zinc cyanurate powder is contained in the dispersion (slurry) in an amount of 0.10% by mass to 50% by mass, or 0.1% by mass to 20% by mass, or 0.1% by mass to 10% by mass, or 0.1% by mass to 5% by mass, as a solid content.

[0016] Furthermore, in order to reduce the particle size of the zinc cyanurate powder in the obtained dispersion, the zinc cyanurate powder can be subjected to a pulverization treatment process using the pulverization treatment device. The rotation speed and reaction time of the device for stirring the dispersion medium can be appropriately adjusted according to the desired particle size, etc. The zinc cyanurate powder obtained by this production method can have, for example, a primary particle having a major axis length of 100 nm to 800 nm, a minor axis length of 10 nm to 60 nm, a ratio of the major axis length to the minor axis length (major axis / minor axis) of 5 to 25, as measured by transmission electron microscope observation, and an average particle size of 80 nm to 900 nm as measured by laser diffraction method. The zinc cyanurate particles obtained by drying the aqueous dispersion slurry of this zinc cyanurate powder at 110°C can have a specific surface area of, for example, 10 m ２ / g to 100m ２ / g.

[0017] Another production method for solid-phase reaction of raw materials in a powder state is, for example, a method of heat-treating a mixed powder consisting of zinc oxide, cyanuric acid, and water, in which the sieve residue on a 1,000 μm mesh is less than 1% by mass, the molar ratio of zinc oxide to cyanuric acid [(zinc oxide) / (cyanuric acid)] being 1.0 to 5.0, for example, 1 or more but less than 2, and the moisture content of the mixed powder being 9% to 18% by mass, at 30°C to 300°C in a sealed or open-to-air environment. Since the resulting zinc cyanurate powder contains approximately 10% by mass of moisture, heat treatment can be performed in an open-to-air environment to remove the moisture. For example, Starfine (trade name) manufactured by Nissan Chemical Industries, Ltd. can be used as a zinc cyanurate powder (zinc cyanurate particles) with a moisture content of less than 1.0% by mass. In the case of industrial mass production, the heat treatment can be performed using a powder mixer equipped with a mixing means and a heating means. Specific examples include open or closed heated reaction vessels capable of stirring and mixing, such as a vibration dryer, a Henschel mixer, a Lödige mixer, a Nauta mixer, and a rotary kiln. Furthermore, to reduce the particle size of the resulting zinc cyanurate powder, the zinc cyanurate powder can be subjected to a pulverization process using the pulverization processing device described above. The rotation speed and reaction time of the device for stirring the dispersion medium can be appropriately adjusted according to the desired particle size. The zinc cyanurate powder obtained by this production method can have, for example, a sieve residue of less than 10% by mass, primary particle major axis lengths of 400 nm to 3,000 nm and minor axis lengths of 10 nm to 300 nm as measured by a transmission electron microscope, a ratio of the major axis length to the minor axis length (major axis / minor axis) of 1.3 to 300, and an average particle size of 0.5 μm to 20 μm as measured by laser diffraction. The specific surface area of ​​the obtained zinc cyanurate powder is, for example, 10 m ２ / g to 100m ２ / g.

[0018] <Cyanuric Acid Derivatives> Cyanuric acid derivatives include compounds represented by the following formula (1) in addition to cyanuric acid. In the above formula (1), R １ , R２ , R ３ may be independently or identically present, and examples thereof include a hydrogen atom, an unsubstituted or substituted hydrocarbon group having 1 to 10 carbon atoms, and a halogen atom (such as a fluorine atom, a chlorine atom, or a bromine atom). The hydrocarbon group may be linear, branched, or cyclic, and may have at least one double bond or a triple bond. When the hydrocarbon group is an alkyl group, examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-pentyl group, an n-nonyl group, an n-decyl group, a cyclohexylmethyl group, and a cyclopentylmethyl group. Examples of the hydrocarbon group other than an alkyl group include a benzyl group, an allyl group, and a propargyl group. Examples of the substituent of the hydrocarbon group include a halogen atom and a hydroxyl group. Examples of the compound represented by formula (1) include a compound represented by formula (1) and R １ ~R ３ wherein at least one of R is a hydrogen atom, or １ ~R ３ and R １ ~R ３ In the resin composition according to the present invention, the cyanuric acid derivative can be preferably used in the form of a powder (cyanuric acid derivative powder).

[0019] <Resin Component> The resin component is not particularly limited as long as it can be mixed with zinc cyanurate or cyanuric acid to form a resin composition, and may be, for example, one or more types selected from the group consisting of thermoplastic resins and curable compounds.

[0020] [Curable Compound] The curable compound is not particularly limited as long as it is a compound that is cured by heat or light. In this specification, the term "curable compound" includes curable monomers and curable resins.

[0021] Examples of curable compounds include (meth)acrylate compounds (acrylic resins), epoxy compounds (epoxy resins), oxetane compounds, silicone resins, phenolic resins, thermosetting polyimide resins, (poly)urethane resins, melamine resins, urea resins (urea resins), unsaturated polyester resins, etc. These can be used alone or in combination of two or more. When used, a curing agent (polymerization initiator, etc.) is generally used together with the curable compound, and a curing accelerator, etc. can be used as needed. Among these, (meth)acrylate compounds (acrylic resins), epoxy compounds (epoxy resins), oxetane compounds, thermosetting urethane resins, and thermosetting silicone resins are preferably used.

[0022] Examples of the (meth)acrylate compound include methyl (meth)acrylate, ethyl (meth)acrylate, ethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane trioxyethyl (meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, tricyclodecanyl di(meth)acrylate, and trimethylolpropane. Examples of the acrylate include trioxypropyl (meth)acrylate, tris-2-hydroxyethyl isocyanurate tri(meth)acrylate, tris-2-hydroxyethyl isocyanurate di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, pentaerythritol di(meth)acrylate, glycerin methacrylate acrylate, pentaerythritol tri(meth)acrylate, trimethylolpropane trimethacrylate, allyl (meth)acrylate, vinyl (meth)acrylate, epoxy (meth)acrylate, polyester (meth)acrylate, urethane (meth)acrylate, and isobornyl (meth)acrylate, and these can be used alone or in combination of two or more. Commercially available epoxy (meth)acrylate products include, for example, the EBECRYL series (products 3605, 600, 605, 645, 648, 3500, 3608, 3700, 3701, 3702, 3703, 3708, 3603, 5848, 860, etc. (all manufactured by Daicel-Allnex Co., Ltd.)) and the Epoxy Ester series (products M-600A, 40EM, 70PA, 200PA, 80MFA, 3002M(N), 3002A(N), 3000MK, 3000A, etc. (all manufactured by Kyoeisha Chemical Co., Ltd.)).Commercially available polyester (meth)acrylates include, for example, EBECRYL series (bifunctional polyester acrylates such as 524, 525, 571, and 851, trifunctional polyester acrylates such as 436, 438, 811, 852, 853, 884, 812, 888, and 893, and 800, 810, 450, 820, 846, 870, 1830, and LEO Examples of suitable polyester acrylates include tetrafunctional or higher polyester acrylates such as 10801 (all manufactured by Daicel Allnex Corporation), trade names UF-3003, UF-3123M, UF-3999BA, UF-3000AM, etc. (all manufactured by Kyoeisha Chemical Co., Ltd.), and trade names M-6000 series, M-7000 series, M-8000 series, and M-9000 series (all manufactured by Toagosei Co., Ltd.). Specific examples of commercially available urethane (meth)acrylates include the EBECRYL series (bifunctional aliphatic urethane acrylates such as 230, 270, 280 / 15IB, 284, 4491, 4683, 4858, 8307, 8402, 8409, 8411, 8413, 8804, 8807, 9270, and 8800), 294 / 25HD, 4220, and 45 trifunctional aliphatic urethane acrylates such as 13, 4738, 4740, 4820, 8311, 8465, 9260, 8701, 465, 4587, etc.; tetrafunctional aliphatic urethane acrylates such as 4666, 4680, 8210, 8405, 8606, etc.; hexafunctional or higher aliphatic urethane acrylates such as 1290, 5129, 8254, 8301R, etc.; aromatic urethane acrylate), trade name KRM series (difunctional aliphatic urethane acrylates such as 9465, 9556, 2000, 7735, 8961, 8191, etc.; trifunctional aliphatic urethane acrylates such as 8667, 8296, etc.; tetrafunctional aliphatic urethane acrylates such as 8528, etc.; hexafunctional or higher aliphatic urethane acrylates such as 8200, 8200AE, 8530, 8904, 8531A, 8452, etc.) (all manufactured by Daicel Allnex Corporation), trade names AH-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, DAUA-167, etc. (all manufactured by Kyoeisha Chemical Co., Ltd.), trade names M-1100, M-1200, etc. (all manufactured by Toagosei Co., Ltd.), etc.The curing (polymerization) of these (meth)acrylate compounds can be carried out by irradiation with light or heating in the presence of a photoradical initiator or a thermal radical initiator. Examples of photoradical polymerization initiators include acetophenones, benzophenones, Michler's benzoyl benzoate, amyloxime ester, tetramethylthiuram monosulfide, and thioxanthones. Photocleavage-type photoradical polymerization initiators are particularly preferred, and photocleavage-type photoradical polymerization initiators are described in "Latest UV Curing Technology" (page 159, published by Kazuhiro Takasuki, published by Technical Information Association, Inc., 1991). Examples of thermal radical initiators include peroxides such as acetyl peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, 1,1-bis(3,3-dimethylbutylperoxy)cyclohexane, hydrogen peroxide, t-butyl hydroperoxide, cumene hydroperoxide, di-t-butyl peroxide, dicumyl peroxide, dilauroyl peroxide, t-butyl peroxyacetate, t-butyl peroxypivalate, and t-butylperoxy-2-ethylhexanoate (t-butyl 2-ethylhexaneperoxoate); 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvalerate), and the like. azo compounds such as 2,2'-azobis(2,4,4-trimethylpentane), 2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, (1-phenylethyl)azodiphenylmethane, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), dimethyl 2,2'-azobisisobutyrate, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(1-cyclohexanecarbonitrile), 2-(carbamoylazo)isobutyronitrile, 2,2'-azobis(2,4,4-trimethylpentane), 2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, and 2,2'-azobis(2-methylpropane); and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate, but are not limited to these.

[0023] The epoxy compound may be any compound (resin) containing an epoxy group and capable of being cured, and examples thereof include monoepoxy compounds, polyepoxy compounds, etc. Examples of monoepoxy compounds include butyl glycidyl ether, hexyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, para-butylphenyl glycidyl ether, para-xylyl glycidyl ether, glycidyl acetate, glycidyl butyrate, glycidyl hexoate, and glycidyl benzoate. Examples of polyepoxy compounds include bisphenol-type epoxy resins, epoxy resins obtained by glycidylating polyphenol compounds, novolac-type epoxy resins, aliphatic ether-type epoxy resins, ether ester-type epoxy resins, ester-type epoxy resins, amine-type epoxy resins, and alicyclic epoxy resins. Among polyepoxy compounds, specific examples of bisphenol-type epoxy resins include epoxy resins obtained by glycidylating bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol F, tetramethylbisphenol AD, tetramethylbisphenol S, tetrabromobisphenol A, tetrachlorobisphenol A, and tetrafluorobisphenol A with epichlorohydrin or the like. For example, commercially available bisphenol A-type epoxy resins include the jER (formerly Epicoat) series (807, 815, 825, 827, 828, 834, 1001, 1004, 1007, 1009, etc. (all manufactured by Mitsubishi Chemical Corporation)), D.E.R. series (330, 301, 361, etc. (all manufactured by The Dow Chemical Company)), trade names YD8125 and YDF8170 (all manufactured by Nippon Steel Chemical & Material Co., Ltd.), and the like.Specific examples of epoxy resins obtained by glycidylating polyhydric phenol compounds include epoxy resins obtained by glycidylating dihydric phenol compounds such as biphenol, dihydroxynaphthalene, and 9,9-bis(4-hydroxyphenyl)fluorene, epoxy resins obtained by glycidylating trisphenol compounds such as 1,1,1-tris(4-hydroxyphenyl)methane, and epoxy resins obtained by glycidylating tetrakisphenol compounds such as 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane. Specific examples of novolac-type epoxy resins include epoxy resins obtained by glycidylating novolac compounds such as phenol novolac, cresol novolac, bisphenol A novolac, brominated phenol novolac, and brominated bisphenol A novolac. For example, commercially available phenol novolac epoxy resins include the jER (formerly Epicoat) series (products 152 and 154, etc., manufactured by Mitsubishi Chemical Corporation), the EPPN-201 series (manufactured by Nippon Kayaku Co., Ltd.), and the DEN-438 series (manufactured by The Dow Chemical Company). Commercially available o-cresol novolac epoxy resins include the YDPN / YDCN series (products YDPN-638, YDCN-700-10, YDCN-701, YDCN-702, YDCN-703, YDCN-704, etc., manufactured by Nippon Steel Chemical & Material Co., Ltd.), and the EOCN series (products 102S, 103S, 104S, 1012, 1025, 1027, etc., manufactured by Nippon Kayaku Co., Ltd.). Specific examples of aliphatic ether-type epoxy resins include epoxy resins obtained by glycidylating polyhydric alcohols such as glycerin and polyethylene glycol. Specific examples of ether ester-type epoxy resins include epoxy resins obtained by glycidylating hydroxycarboxylic acids such as parahydroxybenzoic acid. Specific examples of ester-type epoxy resins include epoxy resins obtained by glycidylating polycarboxylic acids such as phthalic acid and terephthalic acid. Specific examples of amine-type epoxy resins include epoxy resins obtained by glycidylating amine compounds such as 4,4'-diaminodiphenylmethane and m-aminophenol.Specific examples of alicyclic epoxy resins include 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, 1,2-epoxy-4-vinylcyclohexane, bis(3,4-epoxycyclohexylmethyl)adipate, limonene diepoxide, and 3,4-epoxycyclohexylmethanol.

[0024] Examples of curing agents for the epoxy compounds (epoxy resins) include amines, polyamides, acid anhydrides, polysulfides, boron trifluoride, bisphenols having two or more phenolic hydroxy groups per molecule, such as bisphenol A, bisphenol F, and bisphenol S, and phenolic resins, such as phenol novolac resin, bisphenol A novolac resin, and cresol novolac resin. Examples of curing accelerators include imidazoles, dicyandiamide derivatives, dicarboxylic acid dihydrazide, triphenylphosphine, tetraphenylphosphonium tetraphenylborate, 2-ethyl-4-methylimidazole tetraphenylborate, and 1,8-diazabicyclo[5.4.0]undecene-7-tetraphenylborate. These may be used alone or in combination of two or more.

[0025] Examples of the oxetane compound include monofunctional oxetane compounds such as 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol), 2-ethylhexyloxetane, and 3-ethyl-3-(4-hydroxybutyloxymethyl)oxetane; and bifunctional oxetane compounds such as xylylene bisoxetane, (4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl, 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, and (bis[(3-ethyl-3-oxetanyl)methyl]isophthalate.

[0026] Thermosetting urethane resins are made primarily from polyisocyanate compounds (or prepolymers) and polyol compounds, and are obtained by reacting the isocyanate groups of the polyisocyanate compounds with the hydroxyl groups of the polyol compounds. Urethane catalysts and crosslinking agents can also be used in combination to adjust the curing time and improve physical properties.

[0027] Examples of the polyisocyanate compound include aliphatic isocyanates such as hexamethylene diisocyanate (HDI), tetramethylene diisocyanate, and dimer acid diisocyanate; aromatic isocyanates such as 2,4- or 2,6-tolylene diisocyanate (TDI) or mixtures thereof, p-phenylene diisocyanate, xylylene diisocyanate (XDI), 1,5-naphthalene diisocyanate (NDI), diphenylmethane diisocyanate (MDI), and polymeric MDI, which is a polynuclear mixture thereof; and alicyclic isocyanates such as isophorone diisocyanate (IPDI). Note that isocyanate-terminated prepolymers, which are intermediates obtained by reacting the following polyol compounds with an excess of a polyisocyanate compound, are also considered to be polyisocyanate compounds in the broad sense. Examples of the polyol compound include polyester polyols, which are compounds obtained by condensing a dibasic acid such as adipic acid with a polyhydric alcohol such as ethylene glycol and having a hydroxyl group at the end; polyether polyols obtained by addition polymerization of an alkylene oxide such as propylene oxide or ethylene oxide with a low molecular weight compound having two or more hydroxyl groups in the molecule, such as glycol, glycerin, sorbitol, or sucrose (cane sugar); polymer polyols obtained by dispersing polystyrene or polyacrylonitrile in a polyol; and phenolic resins.

[0028] Examples of urethanization catalysts include amine catalysts such as triethylenediamine, tetramethylguanidine, N,N,N',N'-tetramethyl-1,6-hexanediamine, dimethyletheramine, N,N,N',N",N"-pentamethyldipropylenetriamine, N-methylmorpholine, bis(2-dimethylaminoethyl)ether, dimethylaminoethoxyethanol, triethylamine, and 2,2-dimorpholinodiethyl ether; and organotin catalysts such as dibutyltin diacetate, dibutyltin dilaurate, dibutyltin thiocarboxylate, dibutyltin dimaleate, stannous diacetate, stannous dioctoate, stannous dioleate, and stannous dilaurate. Examples of crosslinking agents include polyhydric alcohols such as glycerin, 1,4-butanediol, and diethylene glycol; amines such as ethanolamines and polyethylenepolyamines; and those obtained by adding a small amount of propylene oxide to any of these.

[0029] In the present invention, for example, a urethane resin that corresponds to the definition in the ASTM standard [ASTM D16] for paints and the like as "a paint containing 10 wt% or more of polyisocyanate as a vehicle non-volatile component" can be used, and the urethane resin (paint) may be one-component or two-component. Examples of one-component urethane resins include oil-modified types (those that cure by oxidative polymerization of unsaturated fatty acid groups), moisture-curing types (those that cure by reaction of isocyanate groups with water in the air), block types (those that cure by reaction of the regenerated isocyanate groups with hydroxy groups after dissociation of the blocking agent by heating), and lacquer types (those that cure by evaporation of the solvent and drying). Among these, moisture-curing one-component urethane resins are preferably used from the viewpoint of ease of handling, and examples of commercially available products include "UM-50P" manufactured by Showa Denko K.K. Examples of two-component urethane resins include catalyst-curing types (which cure when an isocyanate group reacts with water in the air in the presence of a catalyst), and polyol-curing types (which cure when an isocyanate group reacts with a hydroxy group of a polyol compound).

[0030] In the polyol-curing two-component urethane resin, specific examples of the polyol compound and the isocyanate compound include those mentioned above, and the compounding ratio thereof can be, for example, a hydroxy group / isocyanate group molar equivalent ratio in the range of 0.7 to 1.5. Furthermore, in the polyol-curing type, the urethane-forming catalyst can generally be compounded in an amount of 0.01 to 10 parts by mass per 100 parts by mass of the polyol compound.

[0031] Examples of thermosetting silicone resins include silicone resins that are liquid at room temperature and silicone resins that are solid at room temperature. Examples of silicone resins and silicone oligomers, such as methylsilicone, methyl / phenylsilicone, and phenylsilicone, which are primarily composed of three-dimensional siloxane bonds and whose organic substituents are methyl and / or phenyl groups, are also available. Examples of organic resin-modified silicone resins, such as hybrid resins of epoxy resins, polyester resins, alkyd resins, urethane resins, and acrylic resins, are also available. Silicone resins can be broadly classified into condensation and addition types based on their curing system, and UV-curable types are also included. They can also be classified into one-component and two-component types based on the presence or absence of a catalyst.

[0032] The condensation type may be a dehydration condensation type that utilizes a dehydration condensation reaction between silanol groups, and cures by heating using a metal-based curing agent or the like as needed, or a dealcoholization condensation type that utilizes a hydrolysis / condensation reaction between a hydrolyzable group such as an alkoxy group and a silanol group, or between the hydrolyzable groups themselves, and cures at room temperature in the presence of an acid, alkali, metal-based catalyst, or the like. Examples of the curing agent (catalyst) include metal-based curing agents such as zinc dioctoate, iron octoate, cobalt octoate, manganese octoate, tin naphthenate, tin caprylate, and tin oleate, and organic tin compounds such as dimethyltin dioleate, dimethyltin dilaurate, dibutyltin diacetate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin dioleate, diphenyltin diacetate, dibutyltin oxide, dibutyltin dimethoxide, dibutylbis(triethoxysiloxy)tin, and dioctyltin dilaurate; and reactive curing agents such as silane coupling agents (aminosilanes).In addition, examples of the hydrolysis catalyst that can be used in the hydrolysis / condensation reaction include metal chelate compounds, organic acids, inorganic acids, organic bases, and inorganic bases.

[0033] Furthermore, the above-mentioned addition type utilizes an addition reaction between a silicone having a vinylsilyl group and a silicone having a hydrosilyl group, and uses an addition reaction catalyst such as platinum, and can be cured at either room temperature or heat. Examples of silicones having vinylsilyl groups include polydimethylsiloxane in which a vinyl group is substituted on each terminal silicon atom, a dimethylsiloxane-diphenylsiloxane copolymer in which a vinyl group is substituted on each terminal silicon atom, a polyphenylmethylsiloxane in which a vinyl group is substituted on each terminal silicon atom, and a vinylmethylsiloxane-dimethylsiloxane copolymer in which a trimethylsilyl group is substituted on each terminal. Examples of silicones containing hydrosilyl groups include a methylhydrosiloxane-dimethylsiloxane copolymer in which a trimethylsilyl group is substituted on each terminal. Polydimethylsiloxane in which a hydrogen atom is bonded to each terminal can also be used in combination. As the addition reaction catalyst, platinum-based catalysts such as platinum black, platinic chloride, chloroplatinic acid, reaction products of chloroplatinic acid and monohydric alcohols, complexes of chloroplatinic acid and olefins, platinum group metal catalysts such as palladium-based catalysts and rhodium-based catalysts are mainly used. The mixing ratio of silicone having a vinyl group to silicone having a hydrosilyl group is adjusted, for example, so that the number of moles of hydrosilyl groups relative to the number of moles of vinyl groups is about 0.5 to 5.0. The amount of addition reaction catalyst added can be adjusted, for example, so that the content of platinum group metal elements is within the range of 1 to 500 ppm by mass.

[0034] [Thermoplastic Resin] Examples of thermoplastic resins include diene rubbers and hydrogenated products thereof, polyolefin resins, polystyrene resins, polycarbonate resins, vinyl chloride resins, polyamide resins and polyamide elastomers, polyimide resins, thermoplastic polyurethane resins, (meth)acrylic resins, polyester resins and polyester thermoplastic elastomers, polyphenylene ether resins, modified polyphenylene ether resins, polyacetal resins, polyvinyl acetal resins, polysulfone resins, polyphenylene sulfide (PPS) resins, polyvinyl alcohol resins, polyglycolic acid, modified starch, cellulose acetate, cellulose triacetate, chitin, chitosan, and lignin, and these may be used alone or in combination of two or more.

[0035] Examples of the diene rubber and hydrogenated products thereof include diene rubbers such as butadiene rubber (BR), isoprene rubber (IR), butyl rubber (IIR), styrene-butadiene rubber (SBR), acrylonitrile-butadiene rubber (NBR), styrene-isoprene-styrene (SIS) block copolymer, styrene-butadiene-styrene (SBS) block copolymer, and styrene-butadiene-butylene-styrene (SBBS) block copolymer; and hydrogenated products of diene rubbers such as styrene-ethylene-butylene-styrene (SEBS) block copolymer, styrene-ethylene-propylene-styrene (SEPS) block copolymer, and hydrogenated styrene-butylene rubber (HSBR).

[0036] Examples of the polyolefin resin include olefin polymers (homopolymers) such as polyethylene (PE) and polypropylene (PP), copolymers of ethylene and α-olefins (propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, etc.), copolymers of propylene and α-olefins (ethylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, etc.), acid-modified olefin resins such as maleic anhydride-modified polyethylene and maleic anhydride-modified polypropylene; ethylene / vinyl acetate copolymer (EVA) and partially saponified products thereof; ethylene / (meth)acrylic acid copolymer, ethylene / maleic anhydride copolymer, propylene / maleic anhydride copolymer; Examples of the copolymer include ethylene / (meth)acrylic acid ester copolymers and partially saponified products thereof [ethylene / methyl methacrylate copolymers and partially saponified products thereof, ethylene / ethyl methacrylate copolymers and partially saponified products thereof, ethylene / methyl acrylate copolymers and partially saponified products thereof, ethylene / ethyl acrylate copolymer (EEA) and partially saponified products thereof, ethylene / glycidyl (meth)acrylate copolymers, etc.]; ethylene / (meth)acrylic acid ester / (meth)acrylic acid ester copolymers such as ethylene / glycidyl (meth)acrylate / methyl (meth)acrylate copolymers [ethylene / glycidyl (meth)acrylate / methyl (meth)acrylate copolymers, etc.]; ethylene / (meth)acrylic acid ester / vinyl acetate copolymers [ethylene / glycidyl (meth)acrylate / vinyl acetate copolymers, etc.]; ethylene / (meth)acrylic acid ester / maleic anhydride copolymers [and ethylene / methyl (meth)acrylate / maleic anhydride copolymers, etc.], and resins of metal salts thereof.

[0037] Examples of the polystyrene resin include PS (polystyrene), HIPS (high impact polystyrene), AS (acrylonitrile-styrene copolymer), ABS (acrylonitrile-butadiene-styrene copolymer), and MS (methyl methacrylate-styrene copolymer).

[0038] Examples of the polyamide resin include polyamide 6, polyamide 46, polyamide 66, polyamide 610, polyamide 11, polyamide 12, and copolymers thereof. Examples of the polyamide elastomer include copolymers of these polyamide resins with polyesters, polyalkylene ether glycols, and the like.

[0039] Examples of the (meth)acrylic resin include copolymers of (meth)acrylic acid esters such as PMMA (polymethyl methacrylate), such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, hexyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl acrylate, butyl methacrylate, isobutyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, 2-ethylhexyl methacrylate, and lauryl methacrylate, and copolymers of the above-mentioned (meth)acrylic acid esters with acrylonitrile (acrylic rubber).

[0040] Examples of polyester resins include polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN), polybutylene naphthalate (PBN), polylactic acid (PLA), poly-3-hydroxybutyric acid, polycaprolactone, polybutylene succinate, polyethylene succinate / adipate, terephthalic acid / isophthalic acid / 1,4-butanediol copolymer polyester resin, terephthalic acid / isophthalic acid / 1,6-hexanediol copolymer polyester resin, terephthalic acid / isophthalic acid / polyethylene glycol copolymer polyester resin, terephthalic acid / isophthalic acid / ethylene glycol / 1,4-butanediol copolymer polyester resin, terephthalic acid / isophthalic acid / adipic acid / 1,4-butanediol copolymer polyester resin, and terephthalic acid / isophthalic acid / 1,4-butanediol / diethylene glycol copolymer polyester resin. Examples of the polyester thermoplastic elastomer include copolymers of the above polyester resins and polyalkylene ether glycols.

[0041] [Resin Composition] In the resin composition according to the present invention, the mass ratio of zinc cyanurate to cyanuric acid derivative is not particularly limited, but can be, for example, zinc cyanurate:cyanuric acid derivative = 15:1 to 2:1. In the resin composition, the mixing ratio of the resin component to the zinc cyanurate and cyanuric acid derivative can be 0.1 to 10 parts by mass in terms of the total mass of the zinc cyanurate and the cyanuric acid derivative per 100 parts by mass of the resin component. In the resin composition, the resin component can be, for example, 90 to 99.9% by mass.

[0042] In the resin composition according to the present invention, zinc cyanurate and a cyanuric acid derivative can be blended into the composition as separate components. That is, when preparing the resin composition, for example, zinc cyanurate and a cyanuric acid derivative can be added separately to the resin component and then mixed to prepare the composition. Alternatively, zinc cyanurate and a cyanuric acid derivative can be blended into the composition as a mixed component. That is, when preparing the resin composition, for example, zinc cyanurate and a cyanuric acid derivative can be added as a mixture (mixed powder) to the resin component and then mixed to prepare the composition.

[0043] The mixture (mixed powder) of zinc cyanurate and a cyanuric acid derivative may be a mixture of zinc cyanurate (powder) and a cyanuric acid derivative (powder). For example, zinc cyanurate (powder) and a cyanuric acid derivative (powder) may be prepared separately and mixed together in advance. Alternatively, in the present invention, the reaction product obtained after preparing zinc cyanurate using zinc oxide or basic zinc carbonate and cyanuric acid may be used as the mixture (mixed powder). In this embodiment, in addition to the zinc cyanurate product, unreacted cyanuric acid and zinc oxide (or basic zinc carbonate) may remain in the system after the preparation of zinc cyanurate. This reaction product containing multiple compounds is used as the mixture (mixed powder) without purification. More specifically, the mixture (mixed powder) of zinc cyanurate and a cyanuric acid derivative may be a mixed powder (A) obtained by heating a mixed powder (B) consisting of zinc oxide, cyanuric acid, and water at 30 to 300°C. The ratio of zinc oxide to cyanuric acid in this case, in terms of molar ratio, zinc oxide / cyanuric acid, can be 1.0 to 5.0, for example, 1 or more and less than 2. Alternatively, as the mixture (mixed powder) of zinc cyanurate and a cyanuric acid derivative, a mixed powder (A) that is a dry powder of a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid can be used. In this case, the ratio of zinc oxide or basic zinc carbonate to cyanuric acid in terms of molar ratio, total amount of zinc oxide or basic zinc carbonate converted to zinc oxide / cyanuric acid, can be 1.0 to 5.0, for example, 1 or more and less than 2. In this case, the resin composition according to the present invention can be in an embodiment including the mixed powder (A) of zinc cyanurate and a cyanuric acid derivative and a resin component.

[0044] The present invention also relates to a method for producing a mixed powder containing zinc cyanurate for use in the resin composition. Specifically, the method for producing a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative according to the present invention includes a step of heat-treating a mixed powder (B) consisting of zinc oxide, cyanuric acid, and water at a temperature ranging from 30 to 300°C, either sealed or open to the atmosphere. In this case, the molar ratio of zinc oxide to cyanuric acid in the mixed powder (B) may be 1 or more and less than 2, the water content of the mixed powder (B) may be 9 to 18% by mass, and the mass proportion (residual rate) of cyanuric acid in the mixed powder (A) relative to the mass of cyanuric acid in the mixed powder (B) may be 5% or more. The mass proportion (residual rate) of cyanuric acid in the mixed powder (A) may be, for example, 7.5% or more, or, for example, 9.5% or more, and may be 30% or less. The method for producing the mixed powder can use the same procedures and apparatus as those described for the method for producing zinc cyanurate, in which raw materials are subjected to a solid-phase reaction in a powder state. Alternatively, the method for producing a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative according to the present invention includes a step of wet-dispersing a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid using a dispersion medium at a temperature range of 5 to 55°C. In this case, the molar ratio of the zinc oxide or basic zinc carbonate to cyanuric acid in the mixed slurry can be 1 or more and less than 2, and the mass proportion (residual rate) of cyanuric acid in the mixed powder (A) relative to the mass of cyanuric acid in the mixed slurry can be 5% or more. The mass proportion (residual rate) of cyanuric acid in the mixed powder (A) can be, for example, 7.5% or more, or, for example, 9.5% or more, or 30% or less. The mixed powder can be produced by the same procedures and apparatuses as those used in the above-mentioned method for producing zinc cyanurate, in which raw materials are dispersed in water in a slurry state and then subjected to a liquid phase reaction.

[0045] [Other Components] The resin composition may contain other components within a range that does not impair the effects of the present invention. Examples of other components include, but are not limited to, fillers, reinforcing agents, UV absorbers, antioxidants, stabilizers (antigelling agents), plasticizers, leveling agents, antifoaming agents, silane coupling agents, antistatic agents, flame retardants, lubricants, viscosity reducers, shrinkage reducing agents, dispersants, storage stabilizers, precipitation inhibitors, anti-bleeding agents, colorants (pigments, dyes, etc.), water repellents, and desiccants.

[0046] [Cured Product and Bonded Product] The resin composition can be cured by heat or light, and the cured product can be composited with a metal or the like. That is, a bonded product can be formed with the cured product, in which the bonding surface is a metal or metal oxide, and such a bonded product and cured product are also within the scope of the present invention. Examples of the metal include one or more metals selected from the group consisting of copper, iron, aluminum, magnesium, titanium, nickel, tin, zinc, chromium, and stainless steel, and examples of the metal include one or more metals selected from the group consisting of copper, iron, stainless steel, and aluminum. Examples of the metal oxide include oxides of these metals. Examples include copper and copper oxide. The bonding surface may be an alloy containing the metal.

[0047] [Adhesive Composition and Joint] The resin composition can also be used for bonding multiple substrates together, i.e., as an adhesive composition. For example, a joint can be formed by bonding a first substrate containing metal atoms to a second substrate using the adhesive composition. This joint and adhesive composition are also within the scope of the present invention. Examples of metal atoms contained in the first substrate include at least one selected from the group consisting of copper, iron, aluminum, magnesium, titanium, nickel, tin, zinc, and chromium atoms, and at least one selected from the group consisting of copper, iron, aluminum, nickel, and chromium atoms, particularly copper atoms. Examples of the second substrate include the first substrate containing the metal atoms, as well as resin substrates and glass substrates. Examples of resin substrates include the various resins listed above under [Thermoplastic Resins], as well as fiber-reinforced plastic materials made from these thermoplastic resins. The first substrate and the second substrate may be made of the same material or different materials.

[0048] [Bonding Method] The present invention also relates to a bonding method for bonding a first substrate containing the above-described metal atoms to a second substrate using the adhesive composition. The bonding method may involve placing the first substrate and the second substrate via the adhesive composition, and then subjecting them to a curing treatment (heat treatment, UV irradiation, etc.) depending on the resin component contained in the adhesive composition (resin composition).

[0049] The adhesion between the first substrate and the second substrate is believed to be achieved by the adhesive composition acting on the substrates through hydrogen bonding and / or chemical adsorption to metal atoms.

[0050] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.

[0051] In the examples, the apparatus and conditions used for sample preparation and analysis of physical properties are as follows: (1) Quantitative determination of zinc oxide Apparatus: Aeris benchtop X-ray diffractometer (manufactured by Spectris Co., Ltd.), scanning conditions: 15 to 42° (10 minutes 36 seconds), step width: 0.0217329° Quantitative determination method: A calibration curve was drawn based on the intensity of the zinc oxide peak at 36.2°, and the amount of zinc oxide was quantified. (2) Quantitative Determination of Cyanuric Acid Apparatus: High-performance liquid chromatography [Agilent 1100 (Agilent Technologies, Inc.)], Column: Hypercarb [Thermo Fisher Scientific K.K., Particle Size: 3 μm, HPLC Column, Length: 100 mm, ID: 4.6 mm], Column temperature: 40° C., Eluent: 0.1% aqueous phosphoric acid:acetonitrile=90:10, Flow rate: 0.5 mL / min (Injection amount: 5 μL), Detector: UV 200 nm Sample preparation: 0.1 g of a sample was added to 10 g of dimethyl sulfoxide, the mixture was sonicated, and the filtered product was used for quantitative determination. (3) Stirrer Apparatus: Three-One Motor [BL600 manufactured by Shinto Scientific Co., Ltd.] (4) Tensile Shear Adhesion Strength Apparatus: Desktop Precision Universal Testing Machine Autograph AGS-10kNX [manufactured by Shimadzu Corporation] Measurement Method: Measured based on JIS K 6850.

[0052] The details of each component and abbreviation used in the examples are as follows: Zinc oxide powder: zinc oxide type 2 [manufactured by Sakai Chemical Industry Co., Ltd.] Cyanuric acid powder: water content 3.83 mass% [manufactured by Nissan Chemical Industries, Ltd.] EBECRYL 8402: urethane acrylate [manufactured by Daicel Allnex Corporation, EBECRYL (registered trademark) 8402] IBXA: isobornyl acrylate [manufactured by Osaka Organic Chemical Industry Ltd.] Perhexa HC: organic peroxide (polymerization initiator) [manufactured by NOF Corporation, Perhexa (registered trademark) HC, 1,1-bis(3,3-dimethylbutylperoxy)cyclohexane] jER828: bisphenol A-type epoxy resin [manufactured by Mitsubishi Chemical Corporation, jER (registered trademark) 828, epoxy equivalent: 185 g / eq. ] 2E4MZ: 2-ethyl-4-methylimidazole (curing accelerator) [manufactured by Tokyo Chemical Industry Co., Ltd.] Polyol: polypropylene glycol Isocyanate: diphenylmethane diisocyanate DMDEE: 2,2-dimorpholinodiethyl ether (curing catalyst)

[0053] [Production of Mixed Powder of Zinc Cyanurate and Cyanuric Acid] (Reference Example 1) 45.00 g of zinc oxide powder and 33.25 g of cyanuric acid powder were added to a 1 L four-neck flask containing 903 g of water. The mixture was stirred for 6 hours at 230 rpm using a Three-One motor. The suspension in the flask was subjected to suction filtration using a Kiriyama Funnel (without a ground joint) Buchner type S-95 and Kiriyama Funnel filter paper φ95 mm, No. 5A. The residue remaining on the filter paper was washed with water and removed. The washed residue was dried in a dryer at 110°C for 12 hours and then pulverized in a mortar to obtain 84.71 g of a flowable white powder. The zinc oxide content of this white powder was quantified by powder X-ray diffraction, and the cyanuric acid content was quantified by high-performance liquid chromatography. The obtained white powder contained 1.8% by mass of cyanuric acid, 0.7% by mass of zinc oxide, and 97.5% by mass of zinc cyanurate, and the mass ratio of the zinc cyanurate powder to the cyanuric acid powder was 54.17:1.

[0054] Example 1 38.48 g of zinc oxide powder and 33.25 g of cyanuric acid powder were added to a 1 L four-neck flask containing 903 g of water. The mixture was stirred for 6 hours at 230 rpm using a Three-One motor. The suspension in the flask was subjected to suction filtration using a Kiriyama Funnel (without a ground joint) Buchner type S-95 and Kiriyama Funnel filter paper φ95 mm, No. 5A. The residue remaining on the filter paper was washed with water and removed. The washed residue was dried in a dryer at 110°C for 12 hours and then pulverized in a mortar to obtain 67.21 g of a flowable white powder. The zinc oxide content of this white powder was quantified by powder X-ray diffraction, and the cyanuric acid content was quantified by high-performance liquid chromatography. The obtained white powder contained 7.5% by mass of cyanuric acid, 0.6% by mass of zinc oxide, and 91.9% by mass of zinc cyanurate, and the mass ratio of the zinc cyanurate powder to the cyanuric acid powder was 12.25:1.

[0055] (Examples 2 to 4, Comparative Example 1) Mixed powders containing zinc cyanurate and cyanuric acid of Examples 2 to 4 and Comparative Example 1 were obtained in the same manner as in Example 1, except that the amounts of each component were changed as shown in Table 1.

[0056]

[0057] [Preparation of Resin Compositions] (Examples 5 to 9, Comparative Examples 2 to 3) As shown in Table 2, mixed powders A to F containing zinc cyanurate and cyanuric acid, a resin (acrylic monomer), and a polymerization initiator were weighed and thoroughly mixed to obtain the resin compositions of Examples 5 to 9 and Comparative Examples 2 to 3.

[0058] [Adhesion Test Piece Preparation and Adhesion Test] Copper substrates [Standard Test Piece Co., Ltd., C1020P (½H): 25 mm wide x 100 mm long x 1.6 mm thick] (35 pairs prepared, two in total) were degreased (wiped) with ethanol, immersed in 1 vol.% sulfuric acid for 1 minute, washed with pure water, and air-dried. The resin composition of Examples 5 to 9 or Comparative Examples 2 to 3 was applied to the surface of one of the copper substrates in a pair. The other copper substrate was positioned so that it overlapped the coated portion. The two copper substrates were overlapped so that the overlapping portion measured 25 mm wide x 12.5 mm long x 0.05 mm thick and secured with clips. The resin composition was then cured in a 150°C oven for 30 minutes, and then left to stand at room temperature for 24 hours to obtain test pieces in which the two copper substrates were bonded together with the cured resin composition (five test pieces were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are also shown in Table 2.

[0059]

[0060] As shown in Tables 1 and 2, the compositions of Examples 5 to 9 containing zinc cyanurate and cyanuric acid exhibited a tensile shear bond strength exceeding 1,500 N, which was higher than that of the composition containing only resin (Comparative Example 1: 602 N) or the composition containing zinc cyanurate but not cyanuric acid (Comparative Example 2: 710 N). In particular, the compositions of Examples 6 to 9, which used mixed powders B to E in which the mass ratio of zinc cyanurate to cyanuric acid was in the range of 15:1 to 2:1, exhibited an adhesive test strength 1.5 times or more higher than that of the composition of Example 6, which used mixed powder A in which the mass ratio was outside the above range.

[0061] [Preparation of Adhesion Test Pieces and Evaluation of Adhesion Retention Rate After Humidity and Heat Test] (Example 10, Comparative Example 4) As shown in Table 3, mixed powder G containing zinc cyanurate and cyanuric acid (see Table 3), resin (acrylic monomer), and polymerization initiator were each weighed and thoroughly mixed to obtain resin compositions of Example 10 and Comparative Example 4. Mixed powder G containing zinc cyanurate and cyanuric acid contained 94.4 mass% zinc cyanurate, 3.1 mass% cyanuric acid, and 2.5 mass% zinc oxide, and was produced in accordance with the production method of carrying out a solid-phase reaction in a powder state disclosed in Japanese Patent No. 6,521,262.

[0062] [Adhesion Test Piece Preparation and Adhesion Test] Copper substrates [Standard Test Piece Co., Ltd., C1020P (1 / 2H): width 25 mm × length 100 mm × thickness 1.6 mm] (2 sheets per set, a total of 10 sets prepared) were prepared. The surfaces of these copper substrates were degreased (wiped) with ethanol, then immersed in 1% by volume sulfuric acid for 1 minute, washed with pure water, and air-dried. The resin composition of Example 10 or Comparative Example 4 was applied to the surface of one of the copper substrates in a pair of copper substrates. The other copper substrate was positioned so that it overlapped the coated portion. The two copper substrates were overlapped so that the overlapping portion was 25 mm wide × 12.5 mm long × 0.05 mm thick and secured with clips. The resin composition was then cured in a 150 ° C. oven for 30 minutes, and then left to stand at room temperature for 24 hours to obtain test pieces in which two copper substrates were bonded together with the cured resin composition (five test pieces were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces), and this was recorded as the adhesive test strength before the moist heat test. A similarly prepared test piece was left to stand in a thermo-hygrostat [SH-222, manufactured by Espec Corporation] under an environment of 40°C and 95% RH for 168 hours, and then the tensile shear adhesive strength was measured, and this was recorded as the adhesive test strength after the moist heat test. From the adhesive test strength values ​​before and after the moist heat test, the adhesive retention after the moist heat test was calculated using the following formula. The obtained results are also shown in Table 3. Adhesion retention after moist heat test (%) = [adhesion test strength after moist heat test / initial adhesive test strength] × 100

[0063] [Table 3]

[0064] As shown in Table 3, the composition of Example 10, which contained a mixed powder containing zinc cyanurate and cyanuric acid, showed a higher adhesion retention rate after the wet heat test than the composition of Comparative Example 4, which did not contain the mixed powder.

[0065] [Preparation of Resin Compositions] (Examples 11 to 12, Comparative Example 5) As shown in Table 4, mixed powder G containing zinc cyanurate and cyanuric acid (see Table 4), resin (epoxy resin), and curing accelerator were each weighed and thoroughly mixed to obtain the resin compositions of Examples 11 to 12 and Comparative Example 5.

[0066] [Adhesion Test Piece Preparation and Adhesion Test] Copper substrates [Standard Test Piece Co., Ltd., C1020P (½H): 25 mm wide x 100 mm long x 1.6 mm thick] (2 substrates per set, 15 sets prepared in total) were immersed in 1% by volume sulfuric acid for 1 minute, washed with pure water, and then air-dried. The resin composition of Examples 11-12 or Comparative Example 5 was applied to the surface of one of the copper substrates in a pair of copper substrates. The other copper substrate was positioned so that it overlapped the applied portion. The two copper substrates were overlapped so that the overlapping portion measured 25 mm wide x 12.5 mm long x 0.05 mm thick and secured with clips. The resin composition was then cured in a 150°C oven for 120 minutes, and then left to stand at room temperature for 24 hours to obtain test specimens in which the two copper substrates were bonded together with the cured resin composition (five test specimens were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are shown in Table 4.

[0067] The surfaces of cold-rolled steel (SPCC) substrates [Standard Test Piece Co., Ltd., SPCC-SD: 25 mm wide x 100 mm long x 1.6 mm thick] (15 pairs prepared, total) were degreased (wiped) with acetone and then air-dried. The resin composition of Examples 11-12 or Comparative Example 5 was applied to the surface of one of the two SPCC substrates. The other SPCC substrate was positioned so that it overlapped the coated portion. The two SPCC substrates were overlapped so that the overlapping area measured 25 mm wide x 12.5 mm long x 0.05 mm thick and secured with clips. The resin composition was then cured in a 150°C oven for 120 minutes, and then left to stand at room temperature for 24 hours to obtain test specimens in which the two SPCC substrates were bonded together with the cured resin composition (five test specimens were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are shown in Table 4.

[0068]

[0069] As shown in Table 4, even in systems using an epoxy resin as the resin component, the compositions of Examples 11 and 12, which contained a mixed powder containing zinc cyanurate and cyanuric acid, showed adhesive test strengths equal to or greater than that of the composition of Comparative Example 5, which did not contain the mixed powder.

[0070] [Preparation of Resin Composition] (Example 13) Mixed Powder H containing zinc cyanurate and cyanuric acid (see Table 5), a resin (epoxy resin), and a curing accelerator were each weighed out as shown in Table 5 and thoroughly mixed to obtain the resin composition of Example 13. Mixed Powder H containing zinc cyanurate and cyanuric acid contains 87.8 mass % zinc cyanurate, 10.1 mass % cyanuric acid, and 2.1 mass % zinc oxide, and is a powder produced in accordance with the production method of carrying out a solid-phase reaction in a powder state disclosed in Japanese Patent No. 6,521,262.

[0071] [Preparation of Adhesion Test Pieces and Adhesion Tests] The surfaces of SUS304 stainless steel substrates [Standard Test Piece Co., Ltd., SUS304 (2B), one side polished with #120HL: width 25 mm × length 100 mm × thickness 2.0 mm] (pairs of two, a total of 10 sets prepared) were degreased (wiped) with acetone and then air-dried. The resin composition of Example 13 or Comparative Example 5 was applied to the surface of one of the SUS304 substrates, and the other SUS304 substrate was positioned so that it overlapped the coated portion. The two SUS304 substrates were overlapped so that the overlapping portion measured 25 mm width × 12.5 mm length × 0.05 mm thickness, and secured in place with clips. The resin compositions were then cured in a 150°C oven for 120 minutes, and then left to stand at room temperature for 24 hours to obtain test pieces in which two SUS304 substrates were bonded together by the cured resin composition (five test pieces were prepared for each resin composition).The tensile shear bond strength of these test pieces was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation).The results are shown in Table 5.

[0072] The surfaces of SUS430 stainless steel substrates (2B, manufactured by Standard Test Piece Co., Ltd., polished on one side with #120HL polishing: width 25 mm × length 100 mm × thickness 2.0 mm) (two substrates per set, a total of 10 sets) were degreased (wiped) with acetone and then air-dried. The resin composition of Example 13 or Comparative Example 5 was applied to the surface of one of the two SUS430 substrates, and the other SUS430 substrate was positioned so that it overlapped the coated portion. The two SUS430 substrates were overlapped so that the overlapping portion measured 25 mm width × 12.5 mm length × 0.05 mm thickness, and then secured in place with clips. The resin compositions were then cured in a 150°C oven for 120 minutes, and then left to stand at room temperature for 24 hours to obtain test pieces in which two SUS430 substrates were bonded together by the cured resin composition (five test pieces were prepared for each resin composition).The tensile shear bond strength of these test pieces was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation).The results are shown in Table 5.

[0073] The surfaces of surface-treated aluminum alloys [Standard Test Piece Co., Ltd., A5052P (H34), sulfuric acid anodized / sealed: width 25 mm × length 100 mm × thickness 1.6 mm] (two sheets per set, a total of 10 sets prepared) were degreased (wiped) with acetone and then air-dried. The resin composition of Example 13 or Comparative Example 5 was applied to the surface of one of the two surface-treated aluminum alloy substrates. The other surface-treated aluminum alloy substrate was positioned so that it overlapped the coated portion. The two surface-treated aluminum alloy substrates were overlapped so that the overlapping portion measured 25 mm × length 12.5 mm × thickness 0.05 mm and secured with clips. The resin composition was then cured in a 150°C oven for 120 minutes, and then left to stand at room temperature for 24 hours to obtain test specimens in which the two surface-treated aluminum alloy substrates were bonded together with the cured resin composition (five test specimens were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are shown in Table 5.

[0074]

[0075] As shown in Table 5, even in systems in which the metal substrates to be joined were stainless steel and surface-treated aluminum alloy, the composition of Example 13, which contained a mixed powder containing zinc cyanurate and cyanuric acid, showed an adhesive test strength equal to or greater than that of the composition of Comparative Example 5, which did not contain the mixed powder.

[0076] [Preparation of Resin Composition] (Synthesis Example 1) Synthesis of Polyurethane Oligomer with Mixed Powder H Dispersed A predetermined amount of 82 parts by mass of polyol component (polypropylene glycol) and 2.0 parts by mass of mixed powder H (see Table 6) were weighed into a 300 mL separable flask equipped with a three-way stopcock, a nitrogen gas inlet tube, a stirring seal, a stirring blade, and a mechanical stirrer. The mixture was then stirred at 70 °C under reduced pressure to disperse the mixed powder H into the polyol component, and dehydration treatment was performed until the water content in the system was 500 ppm or less. The atmosphere in the flask was replaced with nitrogen gas, and 18 parts by mass of an isocyanate component (diphenylmethane diisocyanate) was added to the flask while stirring under a nitrogen gas stream. The mixture was reacted at 80 °C for 3 hours under a nitrogen atmosphere, yielding an isocyanate-terminated polyurethane oligomer a with mixed powder H dispersed therein. The isocyanate group (NCO group) content in the resulting polyurethane oligomer a was 2.20% as measured by JIS K1603-1 Method A.

[0077] (Synthesis Example 2) Synthesis of polyurethane oligomer not containing mixed powder H Polyurethane oligomer b was synthesized in the same manner as in Synthesis Example 1 above, except that mixed powder H was not contained. The isocyanate group content in the obtained polyurethane oligomer b was 2.20%.

[0078] (Examples 14 to 15, Comparative Example 6) As shown in Table 6, the polyurethane oligomer a or polyurethane oligomer b and the curing catalyst were each weighed in a predetermined amount and thoroughly mixed to obtain the resin compositions of Examples 14 to 15 and Comparative Example 6.

[0079] [Adhesion Test Specimen Preparation and Adhesion Test] The surfaces of aluminum (Al) alloy substrates [Standard Test Piece Co., Ltd., A3003 (H24): 25 mm wide x 100 mm long x 2.0 mm thick] (15 pairs prepared, total) were degreased (wiped) with acetone and then air-dried. The resin composition of Examples 14-15 or Comparative Example 6 was applied to the surface of one of the pairs of aluminum alloy substrates. The other aluminum alloy substrate was positioned so that it overlapped the applied portion. The two aluminum alloy substrates were overlapped so that the overlapping portion measured 25 mm wide x 12.5 mm long x 1.0 mm thick, and secured with clips. The specimens were then aged for one week at 23°C and 50% relative humidity to obtain test specimens in which the two aluminum alloy substrates were bonded together with the cured resin composition (five test specimens were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are shown in Table 6.

[0080] Copper substrates [Standard Test Piece Co., Ltd., C1020P (½H): 25 mm wide x 100 mm long x 1.6 mm thick] (2 sheets per set, 15 sets prepared) were immersed in 1% by volume sulfuric acid for 1 minute, rinsed with pure water, and then air-dried. The resin composition of Examples 14-15 or Comparative Example 6 was applied to the surface of one of the copper substrates in each set. The other copper substrate was positioned so that it overlapped the coated portion. The two copper substrates were overlapped so that the overlapping portion measured 25 mm wide x 12.5 mm long x 1.0 mm thick, and secured in place with clips. The specimens were then aged for 1 week at 23°C and 50% relative humidity to obtain test specimens in which the two copper substrates were bonded together with the cured resin composition (five test specimens were prepared for each resin composition). The tensile shear adhesive strength of this test piece was measured in accordance with JIS K 6850 (tensile speed 1 mm / min, unit N: average value of five test pieces and standard deviation). The results are shown in Table 6.

[0081]

[0082] As shown in Table 6, even in systems using a urethane resin as the resin component, the compositions of Examples 14 and 15, which contained a mixed powder containing zinc cyanurate and cyanuric acid, showed adhesive test strengths equal to or greater than that of the composition of Comparative Example 6, which did not contain the mixed powder.

[0083] This technology enables highly reliable bonding of inorganic surfaces containing resins or metal atoms, and is suitable for use in civil engineering and construction applications, adhesion of structural materials for transportation equipment and construction machinery, and adhesion of electronics components. Specifically, it is suitable for use in automotive structural adhesives, printed wiring board peripheral materials, lithium-ion battery assemblies, etc., but there are no particular limitations as long as water-resistant adhesion is required.

Claims

1. A resin composition comprising zinc cyanurate, a cyanuric acid derivative, and a resin component.

2. The resin composition according to claim 1, wherein the mass ratio of said zinc cyanurate to said cyanuric acid derivative is from 15:1 to 2:

1.

3. The resin composition according to claim 1, wherein the total mass of the lead cyanurate and the cyanuric acid derivative is 0.1 to 10 parts by mass per 100 parts by mass of the resin component.

4. A resin composition comprising a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, and a resin component, wherein the mixed powder (A) is a powder of a mixed powder (B) consisting of zinc oxide, cyanuric acid, and water that has been heat-treated at 30 to 300°C. The resin composition according to claim 1.

5. The resin composition according to claim 4, wherein in said mixed powder (B), a molar ratio of said zinc oxide to said cyanuric acid is 1 or more and less than 2.

6. The resin composition according to claim 1, comprising a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, and a resin component, wherein the mixed powder is a dry powder of a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid.

7. The resin composition according to claim 6, wherein in said mixed powder (B), a molar ratio of said zinc oxide or basic zinc carbonate to said cyanuric acid is 1 or more and less than 2.

8. The resin composition according to claim 1, wherein the resin component is at least one selected from the group consisting of thermoplastic resins and curable compounds.

9. The resin composition according to claim 8, wherein the resin component is a curable compound.

10. The resin composition according to claim 9, wherein the curable compound is at least one selected from the group consisting of (meth)acrylate compounds, epoxy compounds, oxetane compounds, thermosetting urethane resins, and thermosetting silicone resins.

11. The resin composition according to claim 1, comprising 90 to 99.9% by mass of the resin component.

12. A cured product of the resin composition according to any one of claims 1 to 11.

13. A joint with the cured product according to claim 12, wherein the joint surface is a metal or a metal oxide.

14. The joined body according to claim 13, wherein the metal is one or more selected from the group consisting of copper, iron, aluminum, magnesium, titanium, nickel, tin, zinc, chromium and stainless steel, or an alloy containing one or more of these.

15. The joint according to claim 14, wherein the metal is at least one selected from the group consisting of copper, iron, stainless steel, and aluminum, or an alloy containing at least one of these metals.

16. An adhesive composition comprising the resin composition according to any one of claims 1 to 11.

17. A bonded body, comprising a first substrate containing metal atoms and a second substrate bonded together with the adhesive composition according to claim 16.

18. The joint according to claim 17, wherein the metal atom is at least one selected from the group consisting of copper atoms, iron atoms, aluminum atoms, magnesium atoms, titanium atoms, nickel atoms, tin atoms, zinc atoms and chromium atoms.

19. The joint according to claim 18, wherein the metal atom is at least one selected from the group consisting of copper atoms, iron atoms, aluminum atoms, nickel atoms, and chromium atoms.

20. A method for bonding a first substrate containing metal atoms and a second substrate, comprising using the adhesive composition according to claim 16.

21. The method of claim 20, wherein adhesion between the first and second substrates is achieved by the adhesive composition acting on the substrates by hydrogen bonding and / or chemical adsorption to metal atoms.

22. A method for producing a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, comprising the step of heat-treating a mixed powder (B) consisting of zinc oxide, cyanuric acid and water at a temperature in the range of 30 to 300°C, either sealed or open to the atmosphere, wherein the molar ratio of zinc oxide to cyanuric acid in said mixed powder (B) is 1 or more and less than 2, the water content of said mixed powder (B) is 9 to 18 mass%, and the mass ratio (residual rate) of cyanuric acid in said mixed powder (A) to the mass of cyanuric acid in said mixed powder (B) is 5% or more.

23. A method for producing a mixed powder (A) containing zinc cyanurate and a cyanuric acid derivative, comprising: a step of wet-dispersing a mixed slurry containing zinc oxide or basic zinc carbonate and cyanuric acid using a dispersion medium at a temperature range of 5 to 55°C; in the mixed slurry, the molar ratio of the zinc oxide or basic zinc carbonate to cyanuric acid is 1 or more and less than 2; and the mass proportion (residual rate) of cyanuric acid in the mixed powder (A) relative to the mass of cyanuric acid in the mixed slurry is 5% or more.