Compound, curable resin composition, cured product, and decomposition method

Abstract

To provide a degradable compound that can be easily synthesized, wherein the inventive degradable compound and a cured product derived from the degradable compound can be decomposed with an oxidant, thereby enabling impartation of dismantlability to a laminate produced using an adhesive, a sealant, or a coating agent containing the inventive degradable compound.SOLUTION: The present invention provides a compound represented by general formula (1). (In general formula (1), R1 represents a divalent or higher organic group, R2 represents a hydrogen atom or an alkyl group, R3 represents a monovalent organic group including a reactive functional group, and n represents an integer of 2 to 10).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound, a curable resin composition, a cured product, and a decomposition method. The present invention also relates to an adhesive, a sealant, and a coating agent.

Background Art

[0002] An adhesive is used to bond two or more different members, and generally high adhesive strength is required. However, in recent years, from the viewpoint of resource reuse, a dissociable adhesive that can dissociate the bonded surface after use to enable reuse of the members has been required (Patent Document 1). As the curing form of the adhesive, there are various conventional curing forms such as heat curing and photo curing, and the curing form is selected according to the members and conditions used.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] Conventional dissociable adhesives require multi-step synthesis and require a great deal of labor and cost for industrial production. Therefore, the curing forms of conventional dissociable adhesives have been limited to only some curing forms.

Means for Solving the Problems

[0005] As a result of intensive studies to solve the above problems, the present inventors have found a compound that can be easily synthesized and has decomposability with respect to an oxidizing agent. The present inventors have also found that a curable resin composition containing the compound forms a cured product having excellent dissociability.

[0006] The gist of the present invention will be described below. [1] A compound represented by the following general formula (1).

[0007] [Chemical formula]

[0008] (In general formula (1), R 1 represents a divalent or higher organic group, R 2 represents a hydrogen atom or an alkyl group, R 3 represents a monovalent organic group containing a reactive functional group, and n represents an integer from 2 to 10.)

[0009] [2] The compound according to [1], wherein the reactive functional group in R 3 is at least one selected from the group consisting of a glycidyl group, a (meth)acryloyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, and a vinyl group.

[0010] [3] The compound according to [1], wherein R 1 is a divalent or higher organic group containing one or more aromatic rings.

[0011] [4] A cured product obtained by curing the compound of [1] or [2] by at least one selected from the group consisting of heat curing, photocuring, and anaerobic curing.

[0012] [5] A curable resin composition containing the compound described in [1] or [2].

[0013] [6] An adhesive, a sealant, or a coating agent containing the compound described in [1] or [2].

[0014] [7] A cured product obtained by curing the adhesive, sealant, or coating agent described in [6] by at least one selected from the group consisting of heat curing, photocuring, moisture curing, and anaerobic curing.

[0015] [8] A decomposition method having a step of decomposing the cured product described in [4] using an oxidizing agent.

[0016] [9]The decomposition method according to [8], wherein the oxidizing agent is an aqueous solution of hypochlorous acid.

Advantages of the Invention

[0017] The compound of the present invention (hereinafter sometimes referred to as "decomposable compound") can be easily synthesized. Further, the decomposable compound and the cured product obtained from the decomposable compound can be decomposed by an oxidizing agent, and disassemblability can be imparted to a laminate produced using an adhesive, a sealing agent, and a coating agent containing the decomposable compound of the present invention.

Embodiments for Carrying Out the Invention

[0018] The details of the present invention will be described below. In this specification, "X to Y" means including the numerical values (X and Y) described before and after as the lower limit value and the upper limit value, and means "X or more and Y or less". In the present invention, a compound having a (meth)acryloyl group refers to a (meth)acrylate. The (meth)acryloyl group may be in the form of a (meth)acryloyloxy group. Also, the term "(meth)acryloyl" includes both acryloyl and methacryloyl. Thus, for example, the term "(meth)acryloyl group" includes both an acryloyl group (H2C=CH-C(=O)-) and a methacryloyl group (H2C=C(CH3)-C(=O)-). Similarly, the term "(meth)acrylate" includes both acrylate and methacrylate, the term "(meth)acrylic" includes both acrylic and methacrylic, and the term "(meth)acrylamide" includes both acrylamide and methacrylamide.

[0019] The decomposable compound of the present invention is represented by the following general formula (1).

[0020]

Chemical formula

[0021] (In general formula (1), R 1 represents a divalent or higher organic group, and R2 represents a hydrogen atom or an alkyl group, and R 3 represents a monovalent organic group containing a reactive functional group, and n represents an integer of 2 to 10.)

[0022] The decomposable compound of the present invention exhibits excellent solubility (decomposability) in a solution containing an oxidizing agent.

[0023] The compound of the general formula (1) can be obtained by reacting a compound having the structure of the following general formula (2) and a compound having the structure of the following general formula (3) or the structure of the following general formula (4).

[0024]

Chemical formula

[0025] (In the general formula (2), R 1 represents a divalent or higher organic group, and n is an integer of 2 to 10.)

[0026]

Chemical formula

[0027] (In the general formula (3), R 2 is a hydrogen atom or an alkyl group, and R 3 is a monovalent organic group containing a reactive functional group.)

[0028]

Chemical formula

[0029] (In the general formula (4), R 2 is a hydrogen atom or an alkyl group, R 4 is a divalent organic group, and R 5 is a reactive functional group.)

[0030] In the general formula (1) and the general formula (2), R 1is preferably an aliphatic hydrocarbon group and / or an aromatic hydrocarbon group. Specific examples of the compound of the general formula (2) include aliphatic hydrocarbons such as adipic acid dihydrazide, sebacic acid dihydrazide, dodecanoic acid dihydrazide, azelaic acid dihydrazide, malonic acid dihydrazide, 7,11-octadecadiene-1,18-dicarboxylic dihydrazide, aromatic hydrocarbons such as isophthalic acid dihydrazide, terephthalic acid dihydrazide, and alicyclic hydrocarbons such as 1,3-bis(hydrazinocarbonoethyl)-5-isopropylhydantoin. From the perspective of the decomposability when reacting with the compound of the general formula (3), R 1 is preferably a hydrocarbon group, and it is more preferable that R 1 contains an aromatic hydrocarbon group (that is, contains one or more aromatic rings), and it is most preferable that the compound of the general formula (2) is isophthalic acid dihydrazide.

[0031] Commercially available products of the compound of the general formula (2) are not particularly limited, and examples include ADH, SDH, DDH, IDH, SAH (manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, UDH (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and the like.

[0032] Examples of the reactive functional groups in the general formula (1), the general formula (3), and the general formula (4) include, for example, a glycidyl group, a (meth)acryloyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, a vinyl group, etc., but the reactive functional groups are not limited to these. By selecting the reactive functional group, curing in various curing forms becomes possible.

[0033] Specific examples of the compound of the general formula (3) or (4) include compounds having two or more (meth)acryloyl groups, or compounds having one or more (meth)acryloyl groups and one or more reactive functional groups different from the (meth)acryloyl group in one molecule, etc., but the compound of the general formula (3) or (4) is not limited thereto. Specific examples of the reactive functional group include a glycidyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, a vinyl group, etc. By selecting the reactive functional group, it becomes possible to select various curing forms such as heat curing, photocuring, moisture curing, and anaerobic curing for the decomposable compound of the general formula (1) obtained by reacting with the compound of the general formula (2). As the compound having two or more (meth)acryloyl groups, a compound having both an acryloyl group and a methacryloyl group is preferable. The cured product of the present invention is obtained by curing with at least one selected from the group consisting of heat curing, photocuring, moisture curing, and anaerobic curing of the compound of the present invention.

[0034] Specific examples of the compound having one or more (meth)acryloyl groups and containing a glycidyl group as a reactive functional group include glycidyl (meth)acrylate, 4-hydroxybutyl acrylate glycidyl ether, etc., but the compound is not limited thereto.

[0035] Specific examples of the compound having one or more (meth)acryloyl groups and containing an epoxycyclohexyl group as a reactive functional group include 3,4-epoxycyclohexylmethyl (meth)acrylate, etc., but the compound is not limited thereto.

[0036] Specific examples of the compound having one or more (meth)acryloyl groups and containing an oxetanyl group as a reactive functional group include (3-ethyloxetan-3-yl)(meth)acrylate, etc., but the compound is not limited thereto. Specific examples of the compound having one or more (meth)acryloyl groups and containing an allyl group as a reactive functional group include 2-propenyl (meth)acrylate, etc., but the compound is not limited thereto.

[0037] Specific examples of the compound having one or more (meth)acryloyl groups and containing a vinyl group as a reactive functional group include vinyl (meth)acrylate, 2-[2-(vinyloxy)ethoxy]ethyl (meth)acrylate, etc., but the compound is not limited thereto. Note that the vinyl group includes a vinyl ether group (CH2=CH-O-).

[0038] Examples of the compound having two or more (meth)acryloyl groups in one molecule include triethylene glycol di(meth)acrylate, polyethylene glycol #200 di(meth)acrylate, polyethylene glycol #400 di(meth)acrylate, polyethylene glycol #600 di(meth)acrylate, polyethylene glycol #1000 di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol #400 di(meth)acrylate, polypropylene glycol #700 di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, dimethylol tricyclodecane di(meth)acrylate, EO adduct of bisphenol A di(meth)acrylate, PO adduct of bisphenol A di(meth)acrylate, neopentyl glycol hydroxypivalate (meth)acrylate adduct, 2-hydroxy-3-acryloyloxypropyl methacrylate, 2-hydroxy-3-methacryloylpropyl acrylate, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, ethoxylated glycerin tri(meth)acrylate, tris(2-acryloxyethyl) isocyanurate, bis(2-acryloxyethyl) isocyanurate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated dipentaerythritol poly(meth)acrylate, etc. These may be used alone or in combination of two or more kinds.Among them, from the viewpoint of achieving both high adhesive strength and easy disassembly, it is preferably to contain at least one compound selected from the group consisting of trimethylolpropane tri(meth)acrylate, dimethylol-tricyclodecane di(meth)acrylate, and polyethylene glycol di(meth)acrylate. More preferably, it contains at least one compound selected from the group consisting of trimethylolpropane triacrylate, dimethylol-tricyclodecane diacrylate, polyethylene glycol diacrylate, and 2-hydroxy-3-methacryloxypropyl acrylate. Most preferably, it contains 2-hydroxy-3-methacryloxypropyl acrylate.

[0039] Commercially available products of the compound having two or more (meth)acryloyl groups in one molecule are not particularly limited, and examples include Light Acrylate 9EG-A, Light Acrylate 14EG-A, TMP-A, DCP-A (manufactured by Kyoeisha Chemical Co., Ltd.), NK Ester A-200, A-400, A-600, A-1000, A-DCP, A-TMPT, 701A (manufactured by Shin-Nakamura Chemical Co., Ltd.), and the like. In addition, R 1 Specific examples of the divalent or higher organic group of are, for example, a divalent methylene group having 1 to 15 carbon atoms, a divalent aryl group, and a divalent organic group containing an aromatic group. R 2 Specific examples of the alkyl group of are, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. n is preferably 1 or 2. R 4 Specific examples of the divalent organic group of are, for example, a divalent methylene group, and the divalent methylene group preferably contains a hydroxyl group or an ether group.

[0040] When reacting the compound of general formula (2) with the compound of general formula (3) or general formula (4), as the functional group equivalent ratio, the equivalent ratio of the hydrazide group derived from general formula (2) to the (meth)acryloyl group derived from general formula (3) or general formula (4) (hydrazide group:(meth)acryloyl group) is preferably 1.0:1.0 to 1.0:3.0, more preferably 1.0:1.2 to 1.0:2.8, and most preferably 1.0:1.5 to 1.0:2.5. By having the functional group equivalent ratio be 1.0:1.0 to 1.0:3.0, the yield of the degradable compound can be improved.

[0041] The reaction can be carried out by stirring in the presence of a solvent. Examples of the solvent include formamide, sulfolane, N,N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoramide, N-methyl-2-pyrrolidone, tetrahydrofuran, dimethylacetamide, etc., but the solvent is not limited thereto.

[0042] The reaction temperature is not particularly limited as long as it is not the temperature at which the solvent volatilizes, but the compound of the present invention can be reacted at 100 to 200 °C.

[0043] The reaction time is not particularly limited as long as it is 30 minutes or more, but is preferably 30 minutes to 24 hours.

[0044] <Curable resin composition> Since there is a reactive functional group derived from the reactive functional group of general formula (3) or (4) in one molecule of the compound of the present invention, a curable resin composition can be obtained by including a curing agent that can react with the reactive functional group. Further, the curable resin composition can be cured by various curing methods to obtain a cured product, and the cured product can be disassembled by an oxidizing agent. The curable resin composition contains the compound of the present invention. The content of the compound of the present invention in the curable resin composition is preferably 1 to 90% by mass, more preferably 5 to 60% by mass, and most preferably 10 to 50% by mass.

[0045] When at least one of the reactive functional groups in the general formula (1) is selected from the group consisting of a glycidyl group, an epoxycyclohexyl group, and an oxetanyl group, for example, a latent curing agent, an amine compound, an acid anhydride, an imidazole compound, a hydrazide compound, a thiol compound, a urea compound, dicyandiamide, a microcapsule type curing agent, a cation initiator, a photo cation initiator, etc. can be used as the curing agent. These may be used alone or in combination of two or more.

[0046] When the reactive functional group in the general formula (1) is a (meth)acryloyl group, a photo radical initiator, a thermal radical initiator, an anaerobic curable catalyst, etc. can be used as the curing agent.

[0047] Specific examples of the compound containing a (meth)acryloyl group as the reactive functional group include 2-hydroxy-3-methacryloylpropyl acrylate. From the viewpoint of the yield of the decomposable compound, it is preferable that the compound of the general formula (3) or (4) has both an acryloyl group and a methacryloyl group, and the functional group equivalent ratio of the acryloyl group to the methacryloyl group is preferably 3:7 to 7:3.

[0048] When the reactive functional group in the general formula (1) is an allyl group, a radical initiator that generates radical species by cleavage by light and heat can be used by an ene-thiol reaction. In that case, a polythiol compound etc. can be used as the curing agent. When the reactive functional group in the general formula (1) is a vinyl group, a metal catalyst etc. can be used as the curing agent. Examples of the compound containing a vinyl group as the reactive functional group include 2-[2-(vinyloxy)ethoxy]ethyl (meth)acrylate, but the compound is not limited thereto.

[0049] When synthesizing the degradable compound of the present invention, it is preferable not to use an epoxy resin having no (meth)acryloyl group. The epoxy resin in the present specification is a compound having no (meth)acryloyl group and having one or more epoxy groups in one molecule. When an epoxy resin is used, the epoxy group may react with the compound of the general formula (2), and there is a risk that the cured product will not exhibit disintegrability, which is not preferable.

[0050] The curable resin composition of the present invention contains the degradable compound of the present invention. By curing the degradable compound of the present invention or the curable resin composition of the present invention using a curing agent, a cured product can be obtained. The curable resin composition of the present invention may contain additives such as an organic filler, a colorant, a plasticizer, a silane coupling agent, a leveling agent, and a rheology control agent within a range that does not impair the characteristics of the present invention. The curable resin composition may contain, to the extent that its properties are not lost, a compound having at least one group selected from the group consisting of a glycidyl group, a (meth)acryloyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, and a vinyl group, in addition to the degradable compound of the present invention. The mass ratio of the degradable compound of the present invention to the compound having at least one group selected from the group consisting of a glycidyl group, a (meth)acryloyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, and a vinyl group is preferably from 100:0 to 50:50, and most preferably 100:0.

[0051] <Curing method of curable resin composition> As the method for curing the curable resin composition, arbitrary conditions can be set according to the curing form of the curable resin composition. For example, in the case of a heat-curable resin composition, it is preferably cured at 50°C to 300°C, and more preferably cured at 70°C to 200°C. The curing time in the case of heat curing is preferably 0.1 to 200 minutes, and more preferably 1 to 100 minutes. In the case of a radiation-curable resin composition, the light source is not particularly limited, and a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a black light lamp, a microwave-excited mercury lamp, a metal halide lamp, a sodium lamp, a halogen lamp, a xenon lamp, an LED, a fluorescent lamp, sunlight, an electron beam irradiation device, etc. can be used. The irradiation dose is preferably 5 to 50 kJ / m 2 is preferable, and 7 to 40 kJ / m 2 is more preferable. In the case of a moisture-curable resin composition, it is preferably cured at 10 to 50°C, and the humidity is preferably 30 to 80%. The curing time in the case of moisture curing is preferably 1 day to 2 weeks, and more preferably 3 days to 1 week. The anaerobic curable resin composition can be cured by blocking air (oxygen) and bringing it into contact with a metal ion.

[0052] <Decomposition method> The decomposition method of the present invention has a step of decomposing the cured product using an oxidizing agent. The cured product containing the decomposable compound of the present invention can be easily decomposed and / or disassembled by an oxidizing agent. Examples of the oxidizing agent that can be used in the decomposition method of the present invention include chlorine, bromine, hydrogen peroxide solution, hypochlorous acid or its salts, etc. From the viewpoint of versatility, it is preferable to use an aqueous solution of a hypochlorite, and more preferable to use an aqueous solution of sodium hypochlorite. The concentration of the aqueous solution of sodium hypochlorite is preferably 1 to 10% by mass.

[0053] <Decomposition conditions> In the decomposition method of the present invention, the preferable decomposition temperature of the decomposable compound and the cured product obtained by curing the decomposable compound is preferably 5 to 70°C, more preferably 10 to 60°C, and most preferably 20 to 50°C from the viewpoint of safety. The contact time with the oxidizing agent required for decomposition is not particularly limited, but is preferably 10 seconds to 24 hours, more preferably 1 minute to 24 hours, and most preferably 30 minutes to 20 hours.

[0054] <Adherend> The type of adherend to which the curable resin composition of the present invention can be applied is not particularly limited, and examples include metals, plastics, rubbers, etc. Examples of metals include iron, aluminum, SUS, nickel, zinc, magnesium, gold, silver, copper, titanium, etc. Examples of plastics include fiber-reinforced plastics (FRP), glass fiber-reinforced plastics (GFRP), carbon fiber-reinforced plastics (CFRP), polyacryl, polyester, polyamide, acrylonitrile-butadiene-styrene copolymer (ABS), 6 nylon, 6,6-nylon, polycarbonate, polyacetal, polyethylene terephthalate, polybutylene terephthalate (PBT), polyphenylene sulfide, polyphenylene ether, polyether ether ketone, polyethylene, polypropylene, etc. Examples of rubbers include nitrile rubber, urethane rubber, silicone rubber, EPDM, etc. Among them, metals are generally likely to exhibit adhesive strength and are usually difficult to disassemble, but it is suitable because it can be easily disassembled by using the curable resin composition of the present invention.

[0055] <Use> The compounds and curable resin compositions of the present invention can be incorporated into adhesives, sealants, and coating agents and applied to a wide variety of uses. Further, it is possible to obtain a cured product by curing the adhesive, sealant, and coating agent with at least one selected from the group consisting of heat curing, photocuring, moisture curing, and anaerobic curing. Specific uses to which the compounds and curable resin compositions of the present invention can be applied include adhesion, sealing, casting, coating, etc. of switch parts for automobiles, headlamps, engine internal parts, electrical parts, drive engines, brake oil tanks, front hoods, fenders, door and other body panels, windows, etc.; in the field of electronic materials, flat panel displays (liquid crystal displays, organic EL displays, light emitting diode display devices, field emission displays), video discs, CDs, DVDs, MDs, pickup lenses, hard disks, etc. for adhesion, sealing, casting, coating, etc.; in the field of batteries, lithium batteries, lithium ion batteries, manganese batteries, alkaline batteries, fuel cells, silicon-based solar cells, dye-sensitized solar cells, organic solar cells, etc. for adhesion, sealing, coating, etc.; in the field of optical components, adhesion, sealing, coating, etc. of optical fiber materials around optical switches and around optical connectors, optical passive components, optical circuit components, and around optoelectronic integrated circuits; in the field of optical devices, adhesion, sealing, coating, etc. of camera modules, lens materials, viewfinder prisms, target prisms, viewfinder covers, light receiving sensor parts, photographic lenses, projection lenses of projection TVs, etc.; in the infrastructure field, it can be used for adhesion, lining materials, sealing, coating materials, etc. of gas pipes, water pipes, etc.

Examples

[0056] Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples only.

[0057] Compounds 1 to 5 were prepared as decomposable compounds by the following method.

[0058] [Example 1] 10.8 g (1.1 eq) of isophthalic acid dihydrazide and 20.2 g (2.0 eq) of 4-hydroxybutyl acrylate glycidyl ether were heated and stirred at 150 °C for 1 hour in a DMF (N,N-dimethylformamide) solvent. DMF was removed by distillation under reduced pressure to obtain Compound 1.

[0059] [Example 2] 10.3 g (1.1 eq) of isophthalic acid dihydrazide, 20.6 g (2.0 eq) of 2-hydroxy-3-methacryloxypropyl acrylate, and 0.05 g (0.01 eq) of hydroquinone were heated and stirred at 150 °C for 1 hour in a DMF solvent. DMF was removed by distillation under reduced pressure to obtain Compound 2.

[0060] [Example 3] 10.9 g (1.1 eq) of isophthalic acid dihydrazide and 20.1 g (2.0 eq) of 3,4-epoxycyclohexylmethyl methacrylate (Cyclomer M100 manufactured by Daicel Ornex Co., Ltd.) were heated and stirred at 170 °C for 1 hour in a DMF solvent. DMF was removed by distillation under reduced pressure to obtain Compound 3.

[0061] [Example 4] 72 g (1.1 eq) of isophthalic acid dihydrazide and 120 g (2.0 eq) of (3-ethyloxetan-3-yl) methacrylate (OXE-10 manufactured by Toagosei Co., Ltd.) were heated and stirred at 170 °C for 1 hour in a DMF solvent. DMF was removed by distillation under reduced pressure to obtain Compound 4.

[0062] [Example 5] 20 g (1.1 eq) of isophthalic acid dihydrazide, 38.4 g (2.0 eq) of 2-[2-(vinyloxy)ethoxy]ethyl acrylate, and 0.1 g of hydroquinone were heated and stirred at 150 °C for 1 hour in a DMF solvent. DMF was removed by distillation under reduced pressure to obtain Compound 5.

[0063] [Confirmation of degradability] 1 g of Composites 1 to 5 was weighed, immersed in warm water at 40 °C or a 6 mass% aqueous sodium hypochlorite solution at 40 °C for 24 hours, filtered, and the weight loss of the composite after drying was measured. The results are shown in Table 1.

[0064]

Table 1

[0065] As shown in Table 1, significant weight loss was confirmed in Composites 1 to 5 immersed in a 6 mass% aqueous sodium hypochlorite solution as an oxidizing agent compared to Composites 1 to 5 immersed in warm water. From this, it can be seen that the decomposable compounds of Composites 1 to 5 are decomposable with respect to the oxidizing agent.

[0066] Furthermore, curable resin compositions were prepared using Composite 1 and Composite 2, respectively.

[0067] [Example 6] 5 g of Composite 2 was collected, 14 g of dimethylacrylamide and 0.4 g of diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide were added, and the mixture was stirred for 15 minutes using a mixer in a light-shielded environment.

[0068] [Example 7] 5 g of Composite 4 was collected, 2 g of 3-ethyl-3-hydroxymethyloxetane (trade name: OXT-101, manufactured by Toagosei Co., Ltd.), 3.5 g of a mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride 7:3 (trade name: Licacid MH700G, manufactured by Shin Nippon Rika Co., Ltd.), 0.1 g of potassium 2-ethylhexenoate, 0.2 g of C15 crown ether, and 0.25 g of fumed silica (trade name: Aerosil RY200, manufactured by Nippon Aerosil Co., Ltd.) were added, and the mixture was stirred with a mixer for 15 minutes.

[0069] [Example 8] 5 g of the composite 4 was collected, and 2 g of 3-ethyl-3-hydroxymethyloxetane (trade name: OXT-101, manufactured by Toagosei Co., Ltd.), 3.5 g of polyethylene glycol #400 diglycidyl ether (trade name: Epolite 400E), 3.5 g of urethane-modified epoxy resin (trade name: Adeka Resin EPU-73B, manufactured by Adeka Corporation), 10.3 g of a mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride in a ratio of 7:3 (trade name: Rikacid MH700G, manufactured by Shin Nippon Rika Co., Ltd.), 0.8 g of potassium 2-ethylhexenoate, and 1.6 g of C15 crown ether were added, and the mixture was mixed with a mixer for 15 minutes.

[0070] [Comparative Example 1] A composition was prepared in the same manner as in Example 6, except that 2-hydroxy-3-methacryloxypropyl acrylate was used instead of the composite 1.

[0071] [Comparative Example 2] 10 g of urethane-modified epoxy resin (trade name: Adeka Resin EPU-73B, manufactured by Adeka Corporation), 6.7 g of a mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride in a ratio of 7:3 (trade name: Rikacid MH700G, manufactured by Shin Nippon Rika Co., Ltd.), 0.2 g of potassium 2-ethylhexenoate, and 0.4 g of C15 crown ether were added, and the mixture was mixed with a mixer for 15 minutes.

[0072] [Confirmation of Disintegrability] 1 g of the compositions of Example 6 and Comparative Example 1 was weighed, and a cured product was prepared using an ultraviolet belt conveyor irradiation device with an integrated light amount of 30 kJ / m 2 . The prepared cured product was immersed in 400 mL of a 6% by mass aqueous sodium hypochlorite solution at 50 °C or warm water at 50 °C contained in a 500 mL beaker, allowed to stand for 12 hours, and the state of the cured product was observed. The results are shown in Table 2.

[0073] [Table 2]

[0074] As shown in Table 2, for the cured product of Example 6, the cured product immersed in the oxidizing agent (aqueous hypochlorous acid solution) dissolved, and no cured product could be visually confirmed. The cured product immersed in warm water only swelled, and the cured product could be confirmed. On the other hand, the cured product of Comparative Example 1 only swelled in both the aqueous hypochlorous acid solution and warm water, and the cured product could be confirmed. From the above, it can be seen that the cured product composed of the composition of Example 6 can be disassembled by an oxidizing agent, and the cured product composed of the composition of Comparative Example 1 does not have disassembly properties.

[0075] [Measurement of change rate of shear adhesion strength] The curable resin compositions of Example 7, Example 8, and Comparative Example 2 were applied to an aluminum plate (A1050P) with a width of 25 mm × a length of 100 mm × a thickness of 1 mm using a spacer so that the coating area was 25 mm × 10 mm and the coating thickness was 1 mm. Another aluminum plate was overlapped on the coated portion and cured under the conditions of 120 °C for 1 hour using a hot air drying oven to obtain a shear adhesion strength test piece. The shear adhesion strength test piece prepared was immersed in a 500 mL beaker containing 400 mL of 6 mass% sodium hypochlorite aqueous solution (Kitchen Hitter, manufactured by Kao Corporation), and left standing in a constant temperature bath at 50 °C for 16 hours. The immersed test piece was taken out from the beaker and left standing in a draft at 25 °C and 55% RH atmosphere for 12 hours to dry the test piece. The dried test piece was used as the test piece after immersion. The maximum strength (MPa) of the test piece before immersion and the test piece after immersion was measured using a tensile tester at a tensile speed of 50 mm / min. The change rate of shear adhesion strength was calculated by the following formula. The results are shown in Table 3. Change rate of shear adhesion strength = [(Maximum strength of test piece after immersion - Maximum strength of test piece before immersion) / Maximum strength of test piece before immersion] × 100 (%) The pass criterion for disassembly property based on the change rate of shear adhesion strength is -90% or less, preferably -100%.

[0076]

Table 3

[0077] From Table 3, the test pieces prepared using the curable resin compositions of Example 7 and Example 8 were detached by immersion in an oxidizing agent (aqueous hypochlorous acid solution) without applying force, and could be easily disassembled. On the other hand, although a strength decrease was observed in the test piece prepared using the curable resin composition of Comparative Example 2, detachment of the test piece could not be confirmed. From the above, it can be seen that the cured products composed of the curable resin compositions of Example 7 and 8 have disassembly properties, and the cured product composed of the curable resin composition of Comparative Example 2 does not have disassembly properties.

[0078] Although the present invention has been described in detail with reference to specific embodiments, it is apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention. This application is based on a Japanese patent application filed on December 19, 2023 (Japanese Patent Application No. 2023-214033), the content of which is incorporated herein by reference.

Industrial Applicability

[0079] The degradable compound of the present invention is easy to synthesize, and the degradable compound and the cured product obtained from the compound can be easily decomposed by an oxidizing agent. Also, by selecting the reactive functional groups in the degradable compound, curing under various conditions is possible. Therefore, the degradable compound of the present invention can be applied to various fields such as adhesives, sealants, and coating agents that require disassembly properties.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 (In general formula (1), R １ represents a divalent or higher organic group; R ２ represents a hydrogen atom or an alkyl group, R ３ represents a monovalent organic group containing a reactive functional group, and n represents an integer of 2 to 10.

2. R ３ The compound according to claim 1, wherein the reactive functional group in the formula (I) is at least one selected from the group consisting of a glycidyl group, a (meth)acryloyl group, an epoxycyclohexyl group, an oxetanyl group, an allyl group, and a vinyl group.

3. R １ The compound according to claim 1 or 2, wherein is a divalent or higher organic group containing one or more aromatic rings.

4. A cured product obtained by curing the compound according to claim 1 or 2 by at least one method selected from the group consisting of heat curing, light curing, moisture curing, and anaerobic curing.

5. A curable resin composition comprising the compound according to claim 1 or 2.

6. An adhesive comprising the compound according to claim 1 or 2.

7. A sealing agent comprising the compound according to claim 1 or 2.

8. A coating agent comprising the compound according to claim 1 or 2.

9. A cured product obtained by curing the adhesive according to claim 6 by at least one method selected from the group consisting of heat curing, light curing, moisture curing, and anaerobic curing.

10. A cured product obtained by curing the sealant according to claim 7 by at least one method selected from the group consisting of heat curing, light curing, moisture curing, and anaerobic curing.

11. A cured product obtained by curing the coating agent according to claim 8 by at least one method selected from the group consisting of heat curing, light curing, moisture curing, and anaerobic curing.

12. A decomposition method, comprising the step of decomposing the cured product according to claim 4 using an oxidizing agent.

13. The decomposition method according to claim 12, wherein the oxidizing agent is an aqueous solution of hypochlorous acid.

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