Adhesive composition, light-meltable adhesive, laminate using light-meltable adhesive, and production method using light-meltable adhesive

Abstract

To provide a light-meltable adhesive composition, a laminate, and a method for producing the laminate, which exhibit excellent adhesiveness to adherends of poor adhesion such as polyolefin resins and are capable of melt adhesion upon light irradiation.SOLUTION: A light-meltable adhesive composition comprises a polyolefin resin (A) and a photothermal conversion material (B). The photothermal conversion material (B) is one or more compounds selected from the group consisting of thioxanthones, triazines, and benzophenones.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a light-melt adhesive composition, a laminate, and a method for producing the laminate. [Background technology]

[0002] Polyolefin resins, such as polypropylene, polyethylene, and their copolymers, have excellent moldability and chemical resistance, and are used in a wide range of fields as materials for automobile parts, electronic parts, construction materials, molding coating films for the surfaces of resin molded products, food packaging films, etc. However, polyolefin resins have low polarity, which makes them difficult to adhere to each other or to other materials, or to paint or print on.

[0003] When bonding polyolefin resins, which are difficult to adhere, methods are used in which functional groups such as hydroxyl groups are introduced into the inactive surface by corona treatment, plasma treatment, oxidation with ozone or acid, sputter etching, or the like to modify the surface (e.g., Patent Document 1), or hot melt adhesives are used in which an adhesive composition that is solid at room temperature is heated and melted in dedicated equipment, the molten adhesive composition is applied to the adherend, and then cooled to solidify (e.g., Patent Document 2). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-95684 [Patent Document 2] International Publication No. 2017 / 73153 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the above-mentioned methods require specialized equipment such as a plasma treatment device and a hot melt applicator for heating and melting, which is not economical and places restrictions on processing methods, and often does not provide sufficient adhesiveness.

[0006] The present invention has been made in view of the above circumstances. That is, an object of the present invention is to provide a photomelt adhesive composition that has excellent adhesion to difficult-to-adhere substrates such as polyolefin resins and that can be melt-bonded by irradiation with light, a laminate, and a method for producing the laminate. [Means for solving the problem]

[0007] That is, the present invention relates to a light-melting adhesive composition containing a polyolefin resin (A) and a photothermal conversion material (B), wherein the photothermal conversion material (B) is one or more compounds selected from the group consisting of thioxanthones, triazines, and benzophenones.

[0008] The present invention also relates to the light-melting adhesive composition, wherein the photothermal conversion material (B) is preferably a compound having a peroxide bond in the molecule.

[0009] The present invention also relates to the light-melt adhesive composition, wherein the compound having a peroxide bond in the molecule is preferably one or more compounds selected from the group consisting of the following general formulas (1), (2), (3), and (4): General formula (1): [ka] (In general formula (1), R 1 , R 2 , R 3 and R 4 independently represent a methyl group or an ethyl group, and R 5 represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, and R 6 are independent substituents each representing an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and n represents an integer of 0 to 2. General formula (2): [ka] (In general formula (2), R 7 and R 8 R independently represents a methyl group or an ethyl group. 9 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. X represents a group represented by the following general formula (2-a): Ar 1 , Ar 2 , Ar 3 or Ar 4 n is an integer of 0 to 2. A triazine derivative having a peroxide bond represented by the formula: [ka] (In the general formula (2-a), m represents an integer of 0 to 3. R 10 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (2-b): R 11 represents a substituent represented by -Y-, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. The R 11 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 10 is two adjacent groups of the general formula (2-b): R 11 -Y- may form a 5- or 6-membered ring.) General formula (3): [ka] (In general formula (3), R 12 and R 13 are independently a methyl group or an ethyl group, R 14 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, and R 15represents an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, an optionally substituted acyl group having 1 to 20 carbon atoms, -YR, or -N-RR', where Y represents an oxygen atom or a sulfur atom, and R and R' independently represent a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms. Ar represents a group represented by the following general formula (3-a): Ar 5 , Ar 6 , Ar 7 or Ar 8 The triazine derivative having a peroxide bond represented by the formula (I) is an aryl group represented by the formula (I). [ka] (In general formula (3-a), m represents an integer of 0 to 3. R 16 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (3-b): R 17 represents a substituent represented by -Y-, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. The R 17 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 16 is two adjacent groups of the general formula (3-b): R 17 -Y- may form a 5- or 6-membered ring.) General formula (4): [ka] (In general formula (4), R 18 and R 19 are independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 9 to 12 carbon atoms, and R 20 and R 21are independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 4 to 8 carbon atoms, or an aralkyloxy group having 9 to 12 carbon atoms.

[0010] The present invention also relates to a laminate in which a first adherend and a second adherend are bonded together via an adhesive layer formed from the light-melt adhesive composition.

[0011] The present invention also relates to a method for producing a laminate, comprising the steps of applying the photo-melt adhesive composition to a first adherend, placing a second adherend on the surface of the first adherend on which the photo-melt adhesive composition has been applied, and irradiating the photo-melt adhesive composition with active energy rays to melt the photo-melt adhesive composition, and solidifying the molten photo-melt adhesive composition to obtain a laminate in which the first adherend and the second adherend are adhered together.

[0012] The present invention also relates to a method for producing a laminate, comprising the steps of applying the photo-melt adhesive composition to a first adherend and irradiating the photo-melt adhesive composition with active energy rays to melt the photo-melt adhesive composition, and placing a second adherend on the surface of the molten photo-melt adhesive composition, and solidifying the molten photo-melt adhesive composition to obtain a laminate in which the first adherend and the second adherend are adhered together. [Effects of the Invention]

[0013] According to the present invention, it is possible to provide a photomelt adhesive composition that has excellent adhesion to difficult-to-adhere substrates such as polyolefin resins and that can be melt-bonded by irradiation with light, a laminate, and a method for producing a laminate. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present invention will be described in detail below.

[0015] The photomelt adhesive composition of the present invention contains a polyolefin resin (A) and a photothermal conversion material (B), wherein the photothermal conversion material (B) is one or more compounds selected from the group consisting of thioxanthones, triazines, and benzophenones. The photomelt adhesive composition of the present invention is an adhesive composition that adheres by melting the polyolefin resin using heat generated from the photothermal conversion material (B) upon irradiation with active energy rays. After application to an adherend, the composition exhibits excellent adhesion to the adherend by cooling and solidifying. Hereinafter, the photomelt adhesive composition of the present invention will also be simply referred to as the "adhesive composition."

[0016] <Polyolefin resin (A)> The polyolefin resin (A) of the present invention is not particularly limited as long as it does not impair the effects of the present invention. Examples of the polyolefin resin (A) include known polyolefin resins, such as high-density polyethylene, low-density polyethylene, polypropylene, ethylene-propylene copolymer, ethylene-α-olefin copolymer, ethylene-propylene copolymer, ethylene-butene copolymer, ethylene-dicyclopentene copolymer, ethylene-hexene copolymer, ethylene-octene copolymer, polybutene-1, poly-4-methyl-1-pentene, poly-3-methyl-1-butene, and ethylene-tetracyclododecene copolymer. From the viewpoint of mechanical strength, unmodified polyolefin resins are preferred, and unmodified polypropylene is more preferred.

[0017] The shape of the polyolefin resin (A) is not particularly limited and can be appropriately selected from the viewpoints of dispersibility, fillability, and meltability in the adhesive composition. For example, pellets, beads, powder, flakes, or a combination of these can be used. The melting point of the polyolefin resin (A) is preferably 70°C to 220°C, more preferably 100°C to 190°C. A melting point of the polyolefin resin (A) below 70°C is not preferred because sufficient adhesiveness cannot be ensured. Furthermore, a melting point of the polyolefin resin (A) higher than 220°C is not preferred because the meltability of the polyolefin resin (A) in the adhesive composition is poor. The above melting points are values ​​measured in accordance with JIS K6921-2.

[0018] The average particle size of the polyolefin resin (A) is preferably 1 to 500 μm, more preferably 3 to 100 μm. An average particle size of the polyolefin resin (A) less than 1 μm is undesirable because the polyolefin resin (A) in the adhesive composition tends to aggregate and the flowability decreases. Furthermore, an average particle size of the polyolefin resin (A) greater than 500 μm is undesirable because the melting properties of the polyolefin resin (A) in the adhesive composition deteriorate. The above average particle size is the median diameter (d50) of the volume-based particle size distribution measured by a laser diffraction scattering method using a Microtrac particle size distribution analyzer.

[0019] The content of polyolefin resin (A) in the adhesive composition of the present invention is preferably 0.1 to 99 mass% in the adhesive composition, and more preferably 1 to 95 mass%. If the content of polyolefin resin (A) in the adhesive composition is less than 0.1 mass%, sufficient adhesiveness cannot be ensured, which is not preferred. Similarly, if the content of polyolefin resin (A) in the adhesive composition is more than 99 mass%, sufficient adhesiveness cannot be ensured, which is also not preferred.

[0020] <Photothermal conversion material (B)> The photothermal conversion material (B) of the present invention is capable of converting light energy into thermal energy upon irradiation with active energy rays, and melting the adhesive composition with the generated heat, and is one or more compounds selected from the group consisting of thioxanthones, triazines, and benzophenones.

[0021] Specific examples of the photothermal conversion material (B) include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and thioxanthone derivatives having a peroxide bond represented by the following general formula (1); 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(3,4-dimethoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(4- halomethyltriazine derivatives such as (ethoxynaphthyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, triazine derivatives having a peroxide bond represented by the following general formulas (2) and (3), benzophenone derivatives such as benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, and benzophenone derivatives having a peroxide bond represented by the following general formula (4), etc.

[0022] From the viewpoint of efficiently converting light energy into heat energy, the photothermal conversion material (B) is preferably a compound having a peroxide bond in the molecule, and is particularly preferably one or more compounds selected from the group consisting of the following general formulae (1), (2), (3), and (4):

[0023] General formula (1): [ka] (In general formula (1), R 1 , R 2 , R 3 and R 4 independently represent a methyl group or an ethyl group, and R 5 represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, and R 6 are independent substituents each representing an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and n represents an integer of 0 to 2.

[0024] In general formula (1), R 1 , R 2 , R 3 and R 4 In the present invention, from the viewpoint of improving the stability of the thioxanthone derivative having a peroxide bond represented by general formula (1), R 1 , R 2 , R 3 and R 4 are preferably all methyl groups.

[0025] In general formula (1), R 5 is an alkyl group having 1 to 6 carbon atoms or a phenyl group. The alkyl group may be a straight chain or a branched chain. 5 Specific examples of R include a methyl group, an ethyl group, a propyl group, a 2,2-dimethylpropyl group, and a phenyl group. Among these, from the viewpoint of ease of synthesis of a thioxanthone derivative having a peroxide bond, R 5 is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably one selected from a methyl group, an ethyl group, and a propyl group. From the viewpoint of efficiently converting light energy into thermal energy, R 5 is more preferably a methyl group or an ethyl group.

[0026] In general formula (1), the substitution position of the dialkyl peroxide on the thioxanthone is not particularly limited. From the viewpoint of efficiently converting light energy into thermal energy, the substitution is preferably at the 2nd, 3rd, or 4th position of the thioxanthone skeleton, and from the viewpoint of ease of synthesis, the substitution is more preferably at the 2nd or 3rd position of the thioxanthone skeleton.

[0027] In general formula (1), R 6are independent substituents and represent an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom. These substituents improve the light absorption characteristics of the thioxanthone derivative having a peroxide bond due to the push-pull effect of these substituents at the emission wavelength of the light source used, enabling efficient conversion of light energy into thermal energy.

[0028] In the general formula (1), n ​​represents an integer of 0 to 2. Among these, n is preferably an integer of 0 to 1, and more preferably 0, from the viewpoint of easily synthesizing a thioxanthone derivative having a peroxide bond.

[0029] In general formula (1), when n is an integer of 1 to 2, R 6 The substitution position of is not particularly limited, but from the viewpoint of efficiently converting light energy into thermal energy, it is preferably the 6th or 7th position of the thioxanthone skeleton, and from the viewpoint of easily synthesizing a thioxanthone derivative having a peroxide bond, it is more preferably the 7th position of the thioxanthone skeleton.

[0030] R 6 Specific examples of R include alkyl groups such as methyl, ethyl, isopropyl, and n-butyl; alkoxy groups such as methoxy, ethoxy, n-propyloxy, sec-butyloxy, and tert-butyloxy; and chlorine atoms. Among these, from the viewpoint of efficiently converting light energy into thermal energy, R 6 is more preferably a methoxy group or an ethoxy group.

[0031] General formula (2): [ka] (In general formula (2), R 7 and R 8 R independently represents a methyl group or an ethyl group. 9 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. X represents a group represented by the following general formula (2-a): Ar 1 , Ar 2 , Ar3 or Ar 4 n is an integer of 0 to 2. A triazine derivative having a peroxide bond represented by the formula: [ka] (In the general formula (2-a), m represents an integer of 0 to 3. R 10 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (2-b): R 11 represents a substituent represented by -Y-, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. The R 11 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 10 is two adjacent groups of the general formula (2-b): R 11 -Y- may form a 5- or 6-membered ring.)

[0032] In general formula (2), R 7 and R 8 R independently represents a methyl group or an ethyl group. 7 and R 8 is preferably a methyl group, from the viewpoint of increasing the stability of the triazine derivative having a peroxide bond.

[0033] In general formula (2), R 9 R is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. The alkyl group may be either a straight chain or a branched chain. 9Specific examples of the group include a methyl group, an ethyl group, a propyl group, a 2,2-dimethylpropyl group, a phenyl group, and an isopropylphenyl group. Among these, from the viewpoint of facilitating synthesis of a triazine derivative having a peroxide bond, a methyl group, an ethyl group, a propyl group, a 2,2-dimethylpropyl group, and a phenyl group are preferred. From the viewpoint of efficiently converting light energy into thermal energy, a methyl group and an ethyl group are more preferred.

[0034] In the general formula (2), n represents an integer of 0 to 2. From the viewpoint of easiness in synthesis of a triazine derivative having a peroxide bond, n is preferably 0 or 1. When n is 0, X is preferably Ar 2 , Ar 3 , or Ar 4 and when n is 1, X is Ar 1 is more preferable from the viewpoint of efficiently converting light energy into heat energy.

[0035] In general formula (2-a), m represents an integer of 0 to 3. From the viewpoint of easiness in synthesis of a triazine derivative having a peroxide bond, m is preferably 0 to 2, and from the viewpoint of efficient conversion of light energy into thermal energy, m is more preferably 1.

[0036] In general formula (2-a), R 10 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (2-b): R 11 represents a substituent represented by -Y-, a nitro group, or a cyano group. Y represents an oxygen atom or a sulfur atom. R 11 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 10 is two adjacent general formula (2-b): R 11 -Y- may form a 5- or 6-membered ring.

[0037] R 10 is an independent substituent, from the viewpoint of efficiently absorbing active energy rays, an alkyl group having 1 to 6 carbon atoms, or a group represented by the general formula (2-c): R 11´ represents a substituent represented by -Y-, where Y represents an oxygen atom, and R 11´ is preferably a hydrocarbon group having 1 to 6 carbon atoms which may have one or more of an ether bond and a hydroxyl group at a terminal in the carbon skeleton, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. 10 is two adjacent general formula (2-c)R 11´ It is preferred that —Y— forms a 5- or 6-membered ring.

[0038] R 10 Specific examples of the alkyl group include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, and n-hexyl; methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, cyclopentyloxy, n-hexyloxy, cyclohexyloxy, 2-hydroxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-butoxyethoxy, 2-(2-hydroxyethoxy)ethoxy, 2-(2-ethoxyethoxy)ethoxy, 1,2-dihydroxypropoxy, and methylenedioxy. Examples of such functional groups include alkoxy groups such as oxy, dimethylmethylenedioxy, and ethylenedioxy; aryloxy groups such as phenyloxy and 4-isopropylphenyloxy; alkylsulfanyl groups such as methylsulfanyl, ethylsulfanyl, hexylsulfanyl, 2-methoxyethylsulfanyl, and 2-(2-methoxyethoxy)ethylsulfanyl; arylsulfanyl groups such as phenylsulfanyl, 2-methylphenylsulfanyl, and 4-methylphenylsulfanyl; and acyl groups such as acetyl, n-butanoyl, 2-ethylhexanoyl, benzoyl, and 2-methylbenzoyl. Compounds having these functional groups and represented by general formula (2) are preferred because they efficiently convert light energy into thermal energy.

[0039] Furthermore, among these, triazine derivatives having a peroxide bond are easy to synthesize and are suitable for efficiently converting light energy into heat energy. 10 is more preferably a methoxy group, an ethoxy group, or a 2-hydroxyethoxy group.

[0040] R 10 The substitution position of X is not particularly limited, but 1 In the case of R 10 Preferably, at least one of the following is substituted at the 4-position of the benzene ring substituted with the triazine group. 2 In the case of R 10 Preferably, at least one of the following is substituted at the 4-position of a benzene ring other than the benzene ring substituted with the triazine group. 3 In the case of R 10 is preferably substituted at the 4-position of the triazine group substituted at the 1-position. 4 In the case of R 10 In terms of efficient conversion of light energy into heat energy, it is preferable that at least one of the above is substituted at the 4-position of a benzene ring other than the benzene ring substituted with the triazine group.

[0041] General formula (3): [ka] (In general formula (3), R 12 and R 13 are independently a methyl group or an ethyl group, R 14 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, and R 15represents an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, an optionally substituted acyl group having 1 to 20 carbon atoms, -YR, or -N-RR', where Y represents an oxygen atom or a sulfur atom, and R and R' independently represent a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms. Ar represents a group represented by the following general formula (3-a): Ar 5 , Ar 6 , Ar 7 or Ar 8 The triazine derivative having a peroxide bond represented by the formula (I) is an aryl group represented by the formula (I). [ka] (In general formula (3-a), m represents an integer of 0 to 3. R 16 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (3-b): R 17 represents a substituent represented by -Y-, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. The R 17 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 16 is two adjacent groups of the general formula (3-b): R 17 -Y- may form a 5- or 6-membered ring.)

[0042] In general formula (3), R 12 and R 13 are independently a methyl group or an ethyl group, and a methyl group is preferred from the viewpoint of increasing the stability of the triazine derivative having a peroxide bond.

[0043] In general formula (3), R 14represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. The alkyl group may be either a straight chain or a branched chain. R 14 Specific examples of the group include a methyl group, an ethyl group, a propyl group, a 2,2-dimethylpropyl group, a phenyl group, and an isopropylphenyl group. Among these, from the viewpoint of facilitating the synthesis of a triazine derivative having a peroxide bond, a methyl group, an ethyl group, a propyl group, a 2,2-dimethylpropyl group, and a phenyl group are preferred. From the viewpoint of increasing the stability of a triazine derivative having a peroxide bond and efficiently converting light energy into thermal energy, a methyl group and an ethyl group are more preferred.

[0044] In general formula (3), R 15 represents an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, an optionally substituted acyl group having 1 to 20 carbon atoms, -YR, or -N-RR', where Y represents an oxygen atom or a sulfur atom, and R and R' independently represent a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms. The "substituent" in the above "optionally substituted" includes a halogen atom, an aliphatic hydrocarbon group which may have an ether bond or a thioether bond in the carbon skeleton, an aromatic hydrocarbon group, a heterocyclic ring-containing group, an acyl group, a cyano group, a nitro group, a carboxyl group, an epoxy group, a hydroxyl group, and the like. The above R 15is preferably an optionally substituted aliphatic hydrocarbon group of 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group of 6 to 20 carbon atoms, an optionally substituted heterocyclic ring-containing group of 2 to 20 carbon atoms, an optionally substituted acyl group of 1 to 20 carbon atoms, or -YR, from the viewpoint of high stability, and is more preferably -OR, in which R is an optionally substituted aliphatic hydrocarbon group of 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group of 6 to 20 carbon atoms, or an optionally substituted heterocyclic ring-containing group of 2 to 20 carbon atoms, from the viewpoint of ease of synthesis.

[0045] In general formula (3-a), m represents an integer of 0 to 3. From the viewpoint of easiness in synthesis of a triazine derivative having a peroxide bond, m is preferably 0 to 2, and from the viewpoint of efficient conversion of light energy into thermal energy, m is more preferably 1.

[0046] In general formula (3-a), R 16 are independent substituents, and are alkyl groups having 1 to 18 carbon atoms, and are represented by the general formula (3-b): R 17 R represents a substituent represented by -Y-, a nitro group, or a cyano group. Y represents an oxygen atom or a sulfur atom. 17 represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a terminal hydroxyl group in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. 16 is two adjacent general formula (2-b): R 17 -Y- may form a 5- or 6-membered ring.

[0047] R 16 is an independent substituent, from the viewpoint of efficiently absorbing active energy rays, an alkyl group having 1 to 6 carbon atoms, or a group represented by the general formula (2-c): R 17´ represents a substituent represented by -Y-, where Y represents an oxygen atom, and R 17´is preferably a hydrocarbon group having 1 to 6 carbon atoms which may have one or more of an ether bond and a hydroxyl group at a terminal in the carbon skeleton, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. 16 is two adjacent general formula (2-c)R 17´ It is preferred that —Y— forms a 5- or 6-membered ring.

[0048] R 16 Specific examples of the alkyl group include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, and n-hexyl; methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, cyclopentyloxy, n-hexyloxy, cyclohexyloxy, 2-hydroxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-butoxyethoxy, 2-(2-hydroxyethoxy)ethoxy, 2-(2-ethoxyethoxy)ethoxy, 1,2-dihydroxypropoxy, and methylenedioxy. Examples of such functional groups include alkoxy groups such as oxy, dimethylmethylenedioxy, and ethylenedioxy; aryloxy groups such as phenyloxy and 4-isopropylphenyloxy; alkylsulfanyl groups such as methylsulfanyl, ethylsulfanyl, hexylsulfanyl, 2-methoxyethylsulfanyl, and 2-(2-methoxyethoxy)ethylsulfanyl; arylsulfanyl groups such as phenylsulfanyl, 2-methylphenylsulfanyl, and 4-methylphenylsulfanyl; and acyl groups such as acetyl, n-butanoyl, 2-ethylhexanoyl, benzoyl, and 2-methylbenzoyl. Compounds having these functional groups and represented by general formula (3) are preferred because they efficiently convert light energy into thermal energy.

[0049] Furthermore, among these, triazine derivatives having a peroxide bond are easy to synthesize and are suitable for efficiently converting light energy into heat energy. 16 is more preferably a methoxy group, an ethoxy group, or a 2-hydroxyethoxy group.

[0050] R 16 The substitution position of X is not particularly limited, but 1 In the case of R 16 Preferably, at least one of the following is substituted at the 4-position of the benzene ring substituted with the triazine group. 2 In the case of R 16 Preferably, at least one of the following is substituted at the 4-position of a benzene ring other than the benzene ring substituted with the triazine group. 3 In the case of R 16 Preferably, at least one of the following is substituted at the 4-position of the triazine group substituted at the 1-position. 4 In the case of R 16 In terms of efficient conversion of light energy into heat energy, it is preferable that at least one of the above is substituted at the 4-position of a benzene ring other than the benzene ring substituted with the triazine group.

[0051] General formula (4): [ka] (In general formula (4), R 18 and R 19 are independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 9 to 12 carbon atoms, and R 20 and R 21 are independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 4 to 8 carbon atoms, or an aralkyloxy group having 9 to 12 carbon atoms.

[0052] In general formula (4), R 18 and R 19 are independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 9 to 12 carbon atoms, and among these, a tertiary alkyl group having 4 to 8 carbon atoms is preferred from the viewpoint of efficiently converting light energy into thermal energy.

[0053] In general formula (4), R 20 and R21 are independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 4 to 8 carbon atoms, or an aralkyloxy group having 9 to 12 carbon atoms, and among these, a tertiary alkoxy group having 4 to 8 carbon atoms is preferred from the viewpoint of efficiently converting light energy into thermal energy.

[0054] Examples of the compound represented by general formula (4) include 3,3',4,4'-tetra-(tert-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(tert-amylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(tert-hexylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(tert-octylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(cumylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(p-isopropylcumylperoxycarbonyl)benzophenone, 3,3'-di-(meth Examples of the peroxycarbonyl group include 3,4'-di-(tert-butylperoxycarbonyl)benzophenone, 3,4'-di-(methoxycarbonyl)-4,3'-di-(tert-butylperoxycarbonyl)benzophenone, and 4,4'-di-(methoxycarbonyl)-3,3'-di-(tert-butylperoxycarbonyl)benzophenone. Among these, from the viewpoint of efficiently converting light energy into thermal energy, 3,3',4,4'-tetra-(tert-butylperoxycarbonyl)benzophenone and 3,3',4,4'-tetra-(tert-amylperoxycarbonyl)benzophenone are preferred.

[0055] The compounds represented by the general formulas (1) to (4) may be used alone or in combination of two or more kinds.

[0056] The content of the photothermal conversion material (B) in the adhesive composition of the present invention is preferably 1 to 2000 parts by mass, more preferably 5 to 1500 parts by mass, per 100 parts by mass of the polyolefin resin (A). A content of less than 1 part by mass of the photothermal conversion material (B) per 100 parts by mass of the polyolefin resin (A) is undesirable because the thermal energy generated is too small to sufficiently melt the adhesive composition. Furthermore, a content of more than 2000 parts by mass of the photothermal conversion material (B) per 100 parts by mass of the polyolefin resin (A) is undesirable because the thermal energy generated is so large that the temperature rises when the adhesive composition melts, placing a heavy load on the adherend.

[0057] <Other additives, etc.> The adhesive composition may further contain a resin having an ethylenically unsaturated bond. Examples of resins having an ethylenically unsaturated bond include (meth)acrylic acid esters, styrene, maleic acid esters, fumaric acid esters, itaconic acid esters, cinnamic acid esters, crotonic acid esters, vinyl ethers, vinyl esters, vinyl ketones, allyl ethers, allyl esters, N-substituted maleimides, N-vinyl compounds, unsaturated nitriles, and olefins. Among these, it is preferable to contain a (meth)acrylic acid ester.

[0058] The (meth)acrylic acid ester may be a monofunctional compound or a polyfunctional compound. Examples of the monofunctional compound include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, and stearyl (meth)acrylate; cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and dicyclopentenyloxyethyl (meth)acrylate. Acrylate, 2-ethyl-2-adamantyl (meth)acrylate and other (meth)acrylic acid ester compounds with alicyclic alcohols; phenyl (meth)acrylate, benzyl (meth)acrylate and other aryl (meth)acrylates; 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene Monomers having a hydroxy group, such as polyethylene glycol mono(meth)acrylate; methoxyethyl(meth)acrylate, methoxypolyethylene glycol(meth)acrylate, phenoxypolyethylene glycol(meth)acrylate, 2-phenylphenoxyethyl(meth)acrylate, tetrahydrofurfuryl(meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl(meth)acrylate, (3-ethyloxetan-3-yl)methyl(meth)acrylate, cyclic trimethylol Monomers having a chain or cyclic ether bond, such as dipropylpropaneformal (meth)acrylate; monomers having a nitrogen atom, such as N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethyl(meth)acrylamide, N-methylol(meth)acrylamide, N-isopropyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide, diacetone(meth)acrylamide, (meth)acryloylmorpholine, and N-(meth)acryloyloxyethylhexahydrophthalimide;Monomers having an isocyanate group such as 2-(meth)acryloyloxyethyl isocyanate; monomers having an epoxy group such as glycidyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate glycidyl ether; monomers having a phosphorus atom such as 2-((meth)acryloyloxy)ethyl phosphate; monomers having a silicon atom such as 3-(meth)acryloxypropyltrimethoxysilane; monomers having a fluorine atom such as 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3,3-pentafluoropropyl (meth)acrylate, and 2-(perfluorohexyl)ethyl (meth)acrylate; and monomers having a carboxyl group such as (meth)acrylic acid, mono(2-(meth)acryloyloxyethyl) succinate, mono(2-(meth)acryloyloxyethyl) phthalate, mono(2-(meth)acryloyloxyethyl) maleate, and ω-carboxy-polycaprolactone mono(meth)acrylate.

[0059] Examples of polyfunctional compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, glycerin di(meth)acrylate, glycerin tri(meth)acrylate, glycerin propoxy tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol di(meth)acrylate monostearate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and neopentyl glycol hydroxypivalate. Polyhydric alcohols such as ricol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, 2,2-bis(4-(meth)acryloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypolyethoxyphenyl)propane, 9,9-bis(4-(2-(meth)acryloyloxyethoxy)phenyl)fluorene, and 9,9-bis(4-(2-(2-(meth)acryloyloxyethoxy)ethoxy)phenyl)fluorene; Ester compounds with (meth)acrylic acid; bis(4-(meth)acryloxyphenyl)sulfide, bis(4-(meth)acryloylthiophenyl)sulfide, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene bis(meth)acrylamide, zinc (meth)acrylate, zirconium (meth)acrylate, aliphatic urethane acrylate, aromatic urethane acrylate, epoxy acrylate, polyester acrylate, and the like.

[0060] In addition to the above-described components, the adhesive composition of the present invention may contain various additives as needed, provided that the effects of the present invention are not impaired. Examples of additives include known additives such as sensitizers (anthracene derivatives such as 9,10-dibutoxyanthracene; coumarin derivatives such as coumarin and ketocoumarin; acridine derivatives such as acridine orange and 9-phenylacridine; benzoate derivatives such as ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and (2-dimethylamino)ethyl benzoate; alkylamine derivatives such as triethanolamine and methyldiethanolamine; camphorquinone), tackifiers (unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, maleic anhydride, itaconic anhydride, and fumaric anhydride; rosin derivatives, polyterpene resins, petroleum resins, and oil-soluble phenols), fillers, colorants (pigments, dyes, and the like), antioxidants, plasticizers, softeners, surfactants, and antistatic agents.

[0061] <Method for preparing adhesive composition> The adhesive composition can be prepared by placing the polyolefin resin (A), the photothermal conversion material (B), and, if necessary, other additives, etc., into a container and dissolving or dispersing them in a conventional manner using a paint shaker, bead mill, sand grind mill, ball mill, attritor mill, two-roll mill, three-roll mill, etc.

[0062] <Laminate> In the laminate of the present invention, a first adherend and a second adherend are bonded together via an adhesive layer formed from a light-melt adhesive composition.

[0063] Various materials can be used as the first and second adherends, including inorganic materials, metals, plastics, and paper. Inorganic materials include glass, metals, mortar, concrete, and stone. Metals include steel plates, metals such as aluminum and chromium, and metal oxides such as zinc oxide (ZnO) and indium tin oxide (ITO). Specific examples of plastics include polyolefin resins, such as polypropylene, polyethylene, and their copolymers; ABS resins; polyvinyl alcohol; cellulose acetate resins such as triacetyl cellulose and diacetyl cellulose; acrylic resins; polyethylene terephthalate; polycarbonate; polyarylate; polyethersulfone; cyclic polyolefin resins containing cyclic olefins such as norbornene as monomers; polyvinyl chloride; epoxy resins; and polyurethane resins. Among these adherends, the adhesive layer is preferably applied to difficult-to-adhere substrates such as polyolefin resins because of its excellent adhesion. If necessary, the surface of the adherend may be subjected to adhesion-enhancing treatments such as corona discharge treatment, plasma treatment, blasting, and chemical etching, antistatic treatments, and coloring treatments.

[0064] <Method of manufacturing laminate> Examples of methods for producing laminates include the steps of applying a photo-melt adhesive composition to a first adherend, placing a second adherend on the surface of the first adherend on which the photo-melt adhesive composition has been applied, and irradiating the photo-melt adhesive composition with active energy rays to melt the photo-melt adhesive composition, and solidifying the molten photo-melt adhesive composition to obtain a laminate in which the first and second adherends are bonded together. Examples of methods for producing laminates include the steps of applying a photo-melt adhesive composition to a first adherend, irradiating the photo-melt adhesive composition with active energy rays to melt the photo-melt adhesive composition, and placing the second adherend on the surface of the molten photo-melt adhesive composition, and solidifying the molten photo-melt adhesive composition to obtain a laminate in which the first and second adherends are bonded together.

[0065] Examples of methods for applying the photomelt adhesive composition include spin coating, bar coating, spray coating, dip coating, flow coating, slit coating, doctor blade coating, gravure coating, screen printing, offset printing, inkjet printing, and dispenser printing.

[0066] The amount of the light-melting adhesive composition to be applied may be appropriately selected depending on the intended use, but the film thickness after melting is preferably 1 to 1000 μm, more preferably 3 to 500 μm.

[0067] The active energy rays are not particularly limited, and examples thereof include electron beams, ultraviolet rays, visible light, and radiation.

[0068] Examples of light sources for active energy rays that can be used include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, ultraviolet electrodeless lamps, light-emitting diodes (LEDs), xenon arc lamps, carbon arc lamps, sunlight, solid-state lasers such as YAG lasers, semiconductor lasers, and gas lasers such as argon lasers.

[0069] The exposure dose of the active energy ray should be appropriately set depending on the wavelength and intensity of the active energy ray and the composition of the adhesive composition. For example, the exposure dose in the UV-A region is 1 to 2000 J / cm. 2 is preferably 10 to 1000 J / cm 2 It is more preferable that the exposure dose of the active energy rays is set within the above range, thereby enabling efficient conversion of light energy into heat energy. The irradiation time of the active energy rays is not particularly limited, but is preferably 0.01 seconds to 30 minutes, and more preferably 0.1 seconds to 10 minutes. Setting the irradiation time within the above range enables increased productivity in producing the laminate. The irradiation of the active energy rays may be performed in one go, or may be divided into multiple rounds.

[0070] The photomelt adhesive composition of the present invention can be used in fields where adhesives have traditionally been used, such as structural components (panel parts, frame parts, suspension parts, etc.) for automobiles, building materials, and transportation equipment such as ships and aircraft, electronic materials, and fuel cells, and there are no limitations on its applications. [Example]

[0071] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0072] <Production of Adhesive Composition> Polyolefin resin (A), photothermal conversion material (B), and other additives were mixed in the blending ratios shown in Table 1 to obtain adhesive compositions of Examples 1 to 18 and Comparative Examples 1 and 2. Using these adhesive compositions, laminates as shown below were prepared and adhesive properties were evaluated.

[0073] <Laminate manufacturing method 1> 1.5 mg of the adhesive composition was applied to the first adherend, and the second adherend was placed on the adhesive composition, and the adhesive composition was applied at a pressure of 250 g / cm 2 The second adherend was fixed under a load of 1000 mW. A 365 nm LED light source [primelite ALE / 3 (Advanced Lite Engines)] was used, and the light source was installed 10 mm from the outer surface of the second adherend, with an illuminance of 4.9 W / cm. 2 The adhesive composition was irradiated with ultraviolet light for the time shown in Table 1 to melt the adhesive composition, and after the optical melting, the adhesive composition was allowed to cool naturally to obtain a laminate.

[0074] <Laminate manufacturing method 2> 1.5 mg of the adhesive composition was applied to a first adherend, and a 365 nm LED light source [primelite ALE / 3 (Advanced Lite Engines)] was used, the light source was placed 10 mm from the outer surface of the first adherend, and the illuminance was 4.9 W / cm. 2 The adhesive composition was irradiated with ultraviolet light for the time shown in Table 1 to melt the adhesive composition. After the adhesive composition was irradiated with ultraviolet light, a second adherend was placed on the adhesive composition and a pressure of 250 g / cm 2 After fixing under a load of 1000 kJ / cm, the laminate was naturally cooled to obtain a laminate.

[0075] <Evaluation method> The adhesiveness of the laminates obtained in each of the Examples and Comparative Examples was evaluated by the following method. The evaluation results are shown in Table 1.

[0076] (Adhesiveness) The adhesion strength (MPa) between the first and second adherends was measured using a centrifugal multi-specimen adhesive strength and adhesion strength measuring device (LUMiFrac). A rating of B or higher was considered a pass. A: Adhesion strength of 1.5 MPa or more B: Adhesion strength is 0.5 MPa or more and less than 1.5 MPa C: Adhesion strength is less than 0.5 MPa

[0077] [Table 1]

[0078] Compound 1 of the photothermal conversion material (B) was synthesized according to the method described in International Publication No. 2020 / 067118, compounds 2 to 7 were synthesized according to the method described in International Publication No. 2023 / 054225, compound 8 was synthesized according to the method described in International Publication No. 2018 / 221177, and compound 9 was synthesized according to the method described in Showa 59-197401. The synthesized compounds were analyzed by EI-MS and 1 The compounds were identified by H-NMR. Details of compounds 1 to 9 are shown in Table 2.

[0079] [Table 2]

[0080] Details of abbreviations used in the examples and comparative examples are as follows: PP1: Polypropylene powder (Seishin Enterprises PPW-5J, average particle size 5 μm) PP2: Polypropylene beads (number average molecular weight (Mn) ~ 67,000, weight average molecular weight (Mw) ~ 250,000, melting point (Tm) 160 ~ 165 °C, average particle diameter 3 mm) Compound 10: 2-Isopropylthioxanthone (manufactured by Tianjin Jiuri New Materials Co., Ltd., Hebei Province) Compound 11: Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (manufactured by IGM Resins BV) MAN: Maleic anhydride (Mitsubishi Chemical) HA: 2-ethylhexyl acrylate (Mitsubishi Chemical) PP: Polypropylene plate (size 15mm x 30mm, thickness 1.0mm) Glass: slide glass (size 15mm x 30mm, thickness 1.0mm)

[0081] As shown in Table 1, the adhesive composition of each Example had excellent adhesive properties. On the other hand, the adhesive composition of each Comparative Example showed results showing poor adhesive properties.

Claims

1. Contains a polyolefin resin (A) and a photothermal conversion material (B), A light-melting adhesive composition, wherein the photothermal conversion material (B) is one or more compounds selected from the group consisting of thioxanthones, triazines, and benzophenones.

2. 2. The light-melting adhesive composition according to claim 1, wherein the photothermal conversion material (B) is a compound having a peroxide bond in the molecule.

3. 3. The light-melt adhesive composition according to claim 2, wherein the compound having a peroxide bond in the molecule is one or more compounds selected from the group consisting of the following general formulas (1), (2), (3), and (4): General formula (1): 【Chemical 1】 (In general formula (1), R １ , R ２ , R ３ and R ４ independently represent a methyl group or an ethyl group, R ５ represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, and R ６ are independent substituents each representing an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a chlorine atom, and n represents an integer of 0 to 2. General formula (2): 【Chemistry 2】 (In general formula (2), R ７ and R ８ R independently represents a methyl group or an ethyl group. ９ represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group. X represents a group represented by the following general formula (2-a): Ar １ , Ar ２ , Ar ３ or Ar ４ and n is an integer of 0 to 2. A triazine derivative having a peroxide bond represented by the formula: 【Chemistry 3】 (In general formula (2-a), m represents an integer of 0 to 3. R １０ are independent substituents, and are alkyl groups having 1 to 18 carbon atoms; １１ represents a substituent represented by —Y—, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. １１ represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a hydroxyl group at a terminal in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. １０ is two adjacent groups of the general formula (2-b): R １１ -Y- may form a 5- or 6-membered ring. General formula (3): 【Chemistry 4】 (In general formula (3), R １２ and R １３ are independently a methyl group or an ethyl group, R １４ represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group; R １５ represents an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, an optionally substituted acyl group having 1 to 20 carbon atoms, -Y-R, or -N-RR', where Y represents an oxygen atom or a sulfur atom, and R and R' independently represent a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic ring-containing group having 2 to 20 carbon atoms. Ar represents the following general formula (3-a): Ar ５ , Ar ６ , Ar ７ or Ar ８ The triazine derivative having a peroxide bond represented by the formula: 【Chemistry 5】 (In general formula (3-a), m represents an integer of 0 to 3. R １６ are independent substituents, and are alkyl groups having 1 to 18 carbon atoms; １７ represents a substituent represented by —Y—, a nitro group, or a cyano group. The Y represents an oxygen atom or a sulfur atom. １７ represents a hydrocarbon group having 1 to 18 carbon atoms which may have one or more of an ether bond, a thioether bond, and a hydroxyl group at a terminal in the carbon skeleton, an aromatic hydrocarbon group having 6 to 9 carbon atoms which may have an alkyl group, or an acyl group having 1 to 8 carbon atoms. １６ is two adjacent groups of the general formula (3-b): R １７ -Y- may form a 5- or 6-membered ring. General formula (4): 【Chemistry 6】 (In general formula (4), R １８ and R １９ are independently an alkyl group having 4 to 8 carbon atoms or an aralkyl group having 9 to 12 carbon atoms, and R ２０ and R ２１ are independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 4 to 8 carbon atoms, or an aralkyloxy group having 9 to 12 carbon atoms.

4. A laminate comprising a first adherend and a second adherend bonded together via an adhesive layer formed from the light-melt adhesive composition according to any one of claims 1 to 3.

5. applying the photomelt adhesive composition according to any one of claims 1 to 3 to a first adherend, placing a second adherend on the surface of the first adherend on which the photomelt adhesive composition has been applied, and irradiating the photomelt adhesive composition with active energy rays to melt the photomelt adhesive composition; a step of solidifying the molten light-melt adhesive composition to obtain a laminate in which the first adherend and the second adherend are fixed together; A method for manufacturing a laminate, comprising:

6. applying the photomelt adhesive composition according to any one of claims 1 to 3 to a first adherend, and irradiating the photomelt adhesive composition with active energy rays to melt the photomelt adhesive composition; a step of placing a second adherend on the surface of the molten photomelt adhesive composition and solidifying the molten photomelt adhesive composition to obtain a laminate in which the first adherend and the second adherend are fixed together; A method for manufacturing a laminate, comprising:

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