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

Abstract

The invention relates to a compound, a curable resin composition, a cured product, and a decomposition method. The present invention relates to 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 2-10. The reactive functional group in R3 in general formula (1) may be at least one selected from the group consisting of a glycidyl group, a (meth) acryloyl group, an epoxy cyclohexyl group, an oxetanyl group, an allyl group, and a vinyl group. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound, a curable resin composition, a cured product, and a decomposition method. Further, 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 high adhesive strength is usually required. However, in recent years, from the viewpoint of resource reuse, a decomposable adhesive that can disassemble the bonded surface after use and enable reuse of the members has been required (Patent Document 1). As curing methods of adhesives, various curing methods such as heat curing and light curing have existed in the past, and the curing method can be selected according to the members and conditions used.

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: International Publication No. 2007 / 083566 Summary of the Invention

[0006] Problems to be Solved by the Invention

[0007] Conventional decomposable adhesives require multi-stage synthesis, and a large amount of labor and cost are required for industrial production. Therefore, the curing methods of conventional decomposable adhesives are limited to a part of curing methods.

[0008] Means for Solving the Problems

[0009] The present inventors conducted intensive studies to solve the above problems, and as a result, found a compound that can be simply synthesized and is decomposable with an oxidizing agent. Further, the present inventors found that a curable resin composition containing the compound forms a cured product having excellent decomposability.

[0010] The gist of the present invention will be described below.

[0011] [1] A compound represented by the following general formula (1).

[0012]

[0013] (In the 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)

[0014] [2] The compound according to [1], wherein R 3The above reactive functional group in is at least one selected from the group consisting of glycidyl group, (meth)acryloyl group, epoxycyclohexyl group, oxetanyl group, allyl group, and vinyl group.

[0015] [3] The compound according to [1], wherein R 1 is a divalent or higher organic group containing one or more aromatic rings.

[0016] [4] A cured product which is 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.

[0017] [5] A curable resin composition containing the compound described in [1] or [2].

[0018] [6] An adhesive, sealant, or coating agent containing the compound described in [1] or [2].

[0019] [7] A cured product which is 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.

[0020] [8] A decomposition method having a step of decomposing the cured product described in [4] using an oxidizing agent.

[0021] [9] The decomposition method according to [8], wherein the above oxidizing agent is an aqueous hypochlorous acid solution.

[0022] Advantages of the Invention

[0023] The compound of the present invention (hereinafter sometimes referred to as "decomposable compound") can be easily synthesized. In addition, the decomposable compound and the cured product obtained from the decomposable compound can be decomposed by an oxidizing agent, and disintegrability can be imparted to a laminate produced using an adhesive, sealant, and coating agent containing the decomposable compound of the present invention. Detailed Description

[0024] The following is a detailed description of the present invention. It should be noted that "X to Y" in this specification means including the values (X and Y) described before and after as the lower limit value and the upper limit value, that is, "X or more and Y or less". In the present invention, a compound having a (meth)acryloyl group means a (meth)acrylate. The (meth)acryloyl group may also be in the form of a (meth)acryloyloxy group. In addition, the term "(meth)acryloyl" includes both acryloyl and methacryloyl. Therefore, 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 acid" includes both acrylic acid and methacrylic acid, and the term "(meth)acrylamide" includes both acrylamide and methacrylamide.

[0025] The decomposable compound of the present invention is represented by the following general formula (1).

[0026]

[0027] (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)

[0028] The decomposable compound of the present invention exhibits excellent solubility (decomposability) in a solution containing an oxidizing agent.

[0029] The compound of general formula (1) can be obtained by reacting a compound having the structure of the following general formula (2) with a compound having the structure of the following general formula (3) or the structure of the following general formula (4).

[0030]

[0031] (In general formula (2), R 1 represents a divalent or higher organic group, and n is an integer from 2 to 10)

[0032]

[0033] (In 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)

[0034]

[0035] (In general formula (4), R 2is a hydrogen atom or an alkyl group, R 4 is a divalent organic group, R 5 is a reactive functional group)

[0036] In the above general formula (1) and the above general formula (2), preferably R 1 is an aliphatic hydrocarbon group and / or an aromatic hydrocarbon group. Specific examples of the compound of general formula (2) include: aliphatic hydrocarbons such as adipic dihydrazide, sebacic dihydrazide, dodecanedioic dihydrazide, azelaic dihydrazide, malonic dihydrazide, 7,11-octadecadiene-1,18-dicarboxylic dihydrazide; aromatic hydrocarbons such as isophthalic dihydrazide, terephthalic dihydrazide; alicyclic hydrocarbons such as 1,3-bis(hydrazinocarbonylethyl)-5-isopropylhydantoin, etc. From the viewpoint of the decomposability when reacting with the compound of general formula (3), preferably R 1 is a hydrocarbon group, more preferably R 1 contains an aromatic hydrocarbon group (i.e., contains one or more aromatic rings), and most preferably the compound of general formula (2) is isophthalic dihydrazide.

[0037] As the commercially available products of the compound of the above general formula (2), there is no particular limitation, and examples include ADH, SDH, DDH, IDH, SAH (manufactured by Otsuka Chemical Co., Ltd.), AJICURE VDH, UDH (manufactured by Ajinomoto Fine-Techno Co., Inc.), etc.

[0038] As the reactive functional group in the above general formula (1), the above general formula (3) and the above general formula (4), examples include, for example, glycidyl group, (meth)acryloyl group, epoxycyclohexyl group, oxetanyl group, allyl group, vinyl group, etc., but the reactive functional group is not limited to these. By selecting the reactive functional group, curing can be carried out in various curing methods.

[0039] Specific examples of the compound of the above general formula (3) or (4) include compounds having two or more (meth)acryloyl groups, or compounds having one or more (meth)acryloyl groups and having one or more reactive functional groups different from the (meth)acryloyl group in one molecule, etc., but the compound of the above general formula (3) or (4) is not limited to these. Specific examples of the above reactive functional group include glycidyl group, epoxycyclohexyl group, oxetanyl group, allyl group, vinyl group, etc. By selecting the above reactive functional group, the decomposable compound of general formula (1) obtained by reacting with the compound of general formula (2) can be cured by various curing methods such as heat curing, photocuring, moisture curing, anaerobic curing, etc.

[0040] As the compound having two or more (meth)acryloyl groups, a compound having both acryloyl group and methacryloyl group is preferred.

[0041] The cured product of the present invention can be obtained by curing the compound of the present invention by at least one selected from the group consisting of heat curing, photocuring, moisture curing, and anaerobic curing.

[0042] 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 to these.

[0043] 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 to these.

[0044] 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 to these.

[0045] 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 to these.

[0046] 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 to these.

[0047] It should be noted that the vinyl group includes a vinyl ether group (CH2=CH-O-).

[0048] Examples of the compound having two or more (meth)acryloyl groups in one molecule include, for example, 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, dimethyloltricyclodecane di(meth)acrylate, EO adduct of bisphenol A di(meth)acrylate, PO adduct of bisphenol A di(meth)acrylate, hydroxypivalic acid neopentyl glycol (meth)acrylate adduct, 2-hydroxy-3-acryloyloxypropyl methacrylate, 2-hydroxy-3-methacryloylpropyl acrylate, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, ethoxylated glycerol tri(meth)acrylate, tris(2-acryloyloxyethyl) isocyanurate, bis(2-acryloyloxyethyl) isocyanurate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, di(trimethylolpropane) tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated dipentaerythritol poly(meth)acrylate, and the like. They can be used alone or in combination of two or more. Among them, from the viewpoint of balancing the adhesive strength and the dissolvability, it is preferable to contain at least one compound selected from the group consisting of trimethylolpropane tri(meth)acrylate, dimethyloltricyclodecane di(meth)acrylate, and polyethylene glycol di(meth)acrylate, more preferably to contain at least one compound selected from the group consisting of trimethylolpropane triacrylate, dimethyloltricyclodecane diacrylate, polyethylene glycol diacrylate, and 2-hydroxy-3-methacryloylpropyl acrylate, and most preferably to contain 2-hydroxy-3-methacryloylpropyl acrylate.

[0049] The 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.

[0050] It should be noted that as the R 1 specific examples of the divalent or higher organic group of, 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 can be cited.

[0051] As the R 2 specific examples of the alkyl group of, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl can be cited.

[0052] n is preferably 1 or 2.

[0053] As the R 4 specific examples of the divalent organic group of, for example, divalent methylene, divalent methylene preferably contains a hydroxyl group or an ether group.

[0054] As the functional group equivalent ratio when reacting the compound of the general formula (2) with the compound of the general formula (3) or the general formula (4), the equivalent ratio of the hydrazide group from the general formula (2) to the (meth)acryloyl group from the general formula (3) or the 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 setting the functional group equivalent ratio to 1.0:1.0 to 1.0:3.0, the yield of the decomposable compound can be increased.

[0055] The reaction can be carried out by stirring in the presence of a solvent. As the solvent, formamide, sulfolane, N,N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoramide, N-methyl-2-pyrrolidone, tetrahydrofuran, dimethylacetamide, etc. can be cited, but the solvent is not limited to these.

[0056] As the reaction temperature, as long as it is not the temperature at which the solvent volatilizes, there is no particular limitation, and the compound of the present invention can be reacted at 100 to 200 °C.

[0057] As the reaction time, as long as it is 30 minutes or more, there is no particular limitation, and it is preferably 30 minutes to 24 hours.

[0058] <Curable resin composition>

[0059] Since a reactive functional group of the reactive functional group from the general formula (3) or (4) is present in one molecule of the compound of the present invention, a curable resin composition can be obtained by containing a curing agent capable of reacting with the reactive functional group. Moreover, the curable resin composition can be cured by various curing methods to obtain a cured product, and the cured product can be disintegrated using an oxidizing agent.

[0060] It should be noted that 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.

[0061] When the reactive functional group in the general formula (1) is at least one selected from the group consisting of a glycidyl group, an epoxycyclohexyl group, and an oxetanyl group, as the curing agent, 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 cationic initiator, a cationic photoinitiator, etc. can be used. They can be used alone or two or more of them can be used in combination.

[0062] When the reactive functional group in the general formula (1) is a (meth)acryloyl group, as the curing agent, a photo radical initiator, a thermal radical initiator, an anaerobic curable catalyst, etc. can be used.

[0063] As a specific example of the compound containing a (meth)acryloyl group as the above reactive functional group, 2-hydroxy-3-methacryloylpropyl acrylate etc. can be cited. From the viewpoint of the yield of the decomposable compound, the compound of the general formula (3) or (4) preferably 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.

[0064] When the reactive functional group in the general formula (1) is an allyl group, a radical initiator that generates radical species by cleavage caused by light and heat through an ene-thiol reaction can be used. At this time, as the curing agent, a polythiol compound etc. can be used.

[0065] When the reactive functional group in the general formula (1) is a vinyl group, as the curing agent, a metal catalyst etc. can be used. As the compound containing a vinyl group as the reactive functional group, 2-[2-(vinyloxy)ethoxy]ethyl (meth)acrylate etc. can be cited, but the compound is not limited to these.

[0066] When synthesizing the decomposable compound of the present invention, it is preferably not to use an epoxy resin that does not have a (meth)acryloyl group. The epoxy resin in this specification means a compound that does not have a (meth)acryloyl group and has one or more epoxy groups in one molecule. If an epoxy resin is used, there is a possibility that the epoxy group reacts with the compound of the general formula (2) and the cured product does not exhibit disintegratability, so it is not preferred.

[0067] The curable resin composition of the present invention contains the decomposable compound of the present invention. A cured product can be obtained by curing the decomposable compound of the present invention or the curable resin composition of the present invention using a curing agent. The curable resin composition of the present invention may contain additives such as organic fillers, colorants, plasticizers, silane coupling agents, leveling agents, and rheology control agents within the range that does not impair the characteristics of the present invention.

[0068] In the curable resin composition, to the extent that its characteristics are not lost, in addition to the decomposable compound of the present invention, 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 may also be contained. The mass ratio of the decomposable 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 100:0 to 50:50, and most preferably 100:0.

[0069] <Method for curing the curable resin composition>

[0070] As the method for curing the above curable resin composition, arbitrary conditions can be set according to the curing mode of the curable resin composition. For example, in the case of heat-curing the curable resin composition, it is preferably cured at 50°C to 300°C, 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, more preferably 1 to 100 minutes. In the case of a curable resin composition curable by active energy rays, 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, 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 amount is preferably 5 to 50 kJ / m 2 and more preferably 7 to 40 kJ / m 2 . In the case of a moisture-curable resin composition, it is preferably cured at 10°C to 50°C, and the humidity is preferably 30% to 80%. The curing time in the case of moisture curing is preferably one day to two weeks, more preferably three days to one week. The anaerobic curable resin composition can be cured by blocking air (oxygen) and contacting with metal ions.

[0071] <Decomposition method>

[0072] The decomposition method of the present invention has a step of decomposing the cured product using an oxidizing agent.

[0073] 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, for example, chlorine, bromine, hydrogen peroxide, or hypochlorous acid or its salts. From the viewpoint of versatility, an aqueous solution of a hypochlorite is preferably used, and an aqueous solution of sodium hypochlorite is more preferably used. The concentration of the aqueous solution of sodium hypochlorite is preferably 1 to 10% by mass.

[0074] <Decomposition conditions>

[0075] From the viewpoint of safety, the suitable decomposition temperature of the decomposable compound and the cured product obtained by curing the decomposable compound in the decomposition method of the present invention is preferably 5 to 70°C, more preferably 10 to 60°C, and most preferably 20 to 50°C. The contact time with the oxidizing agent required for decomposition is not particularly limited, and is preferably 10 seconds to 24 hours, more preferably 1 minute to 24 hours, and most preferably 30 minutes to 20 hours.

[0076] <Adherend>

[0077] 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, for example, iron, aluminum, SUS, nickel, zinc, magnesium, gold, silver, copper, titanium, etc. Examples of plastics include, for example, fiber reinforced plastics (FRP), glass fiber reinforced plastics (GFRP), carbon fiber reinforced plastics (CFRP), polyacrylic acid, 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, for example, nitrile rubber, urethane rubber, silicone rubber, EPDM, etc. Among them, metals generally tend to exhibit high bonding strength and are thus usually difficult to disassemble. However, by using the curable resin composition of the present invention, they can be easily disassembled, and thus are suitable.

[0078] <Uses>

[0079] The compounds and curable resin compositions of the present invention can be incorporated into adhesives, sealants, and coating agents and applied to a variety of uses. In addition, the adhesives, sealants, and coating agents can be cured by at least one selected from the group consisting of heat curing, photocuring, moisture curing, and anaerobic curing to obtain cured products. As specific uses to which the compounds and curable resin compositions of the present invention can be applied, they can be used for: bonding, sealing, casting, coating, etc. of switch parts, headlamps, engine internal components, electrical components, drive engines, brake oil tanks, front hoods, fenders, body panels such as car doors, and windows in the automotive field; bonding, sealing, casting, coating, etc. of 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. in the field of electronic materials; bonding, sealing, coating, etc. of lithium batteries, lithium ion batteries, manganese batteries, alkaline batteries, fuel cells, silicon solar cells, dye-sensitized batteries, organic solar cells, etc. in the field of batteries; bonding, sealing, coating, etc. of optical fiber materials, optical passive components, optical circuit components, and around optoelectronic integrated circuits around optical switches and around optical connectors in the field of optical components; bonding, 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 field of optical instruments; bonding, lining materials, sealing, coating materials, etc. of gas pipes, water pipes, etc. in the infrastructure field.

[0080] Examples

[0081] Next, examples are given to illustrate the present invention in more detail, but the present invention is not limited to these examples.

[0082] Synthesized products 1 to 5 as decomposable compounds were prepared by the following method.

[0083] [Example 1]

[0084] 10.8 g (1.1 eq) of isophthalic dihydrazide and 20.2 g (2.0 eq) of 4-hydroxybutyl acrylate glycidyl ether were heated and stirred in a DMF (N,N-dimethylformamide) solvent at 150 °C for 1 hour. DMF was removed by vacuum distillation to obtain synthesized product 1.

[0085] [Example 2]

[0086] 10.3 g (1.1 eq) of isophthalic dihydrazide, 20.6 g (2.0 eq) of 2-hydroxy-3-methacryloylpropyl acrylate, and 0.05 g (0.01 eq) of hydroquinone were heated and stirred in a DMF solvent at 150 °C for 1 hour. DMF was removed by distillation under reduced pressure to obtain Compound 2.

[0087] [Example 3]

[0088] 10.9 g (1.1 eq) of isophthalic dihydrazide and 20.1 g (2.0 eq) of 3,4-epoxycyclohexylmethyl methacrylate (CYCLOMER M100 manufactured by DAICEL-ALLNEX Co., Ltd.) were heated and stirred in a DMF solvent at 170 °C for 1 hour. DMF was removed by distillation under reduced pressure to obtain Compound 3.

[0089] [Example 4]

[0090] 72 g (1.1 eq) of isophthalic dihydrazide and 120 g (2.0 eq) of (3-ethyloxetane-3-yl) methacrylate (OXE-10 manufactured by Toagosei Co., Ltd.) were heated and stirred in a DMF solvent at 170 °C for 1 hour. DMF was removed by distillation under reduced pressure to obtain Compound 4.

[0091] [Example 5]

[0092] 20 g (1.1 eq) of isophthalic dihydrazide, 38.4 g (2.0 eq) of 2-[2-(vinyloxy)ethoxy]ethyl acrylate, and 0.1 g of hydroquinone were heated and stirred in a DMF solvent at 150 °C for 1 hour. DMF was removed by distillation under reduced pressure to obtain Compound 5.

[0093] [Confirmation of Decomposability]

[0094] 1 g of Compounds 1 to 5 was weighed and immersed in warm water at 40 °C or a 6 mass% aqueous sodium hypochlorite solution at 40 °C for 24 hours, and the weight loss of the filtered and dried compounds was measured. The results are shown in Table 1.

[0095]

[0096] As shown in Table 1, a significant weight loss was confirmed for Compounds 1 to 5 immersed in a 6 mass% aqueous sodium hypochlorite solution as an oxidant compared to Compounds 1 to 5 immersed in warm water. From this, it was found that the decomposable compounds of Compounds 1 to 5 are decomposable with respect to oxidants.

[0097] Furthermore, curable resin compositions were prepared using Compound 1 and Compound 2, respectively.

[0098] [Example 6]

[0099] Take 5 g of Composition 2, add 14 g of dimethylacrylamide and 0.4 g of diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, and mix for 15 minutes using a mixer in a light-shielded environment.

[0100] [Example 7]

[0101] Take 5 g of Composition 4, add 2 g of 3-ethyl-3-hydroxymethyloxetane (trade name: OXT-101, manufactured by Toagosei Co., Ltd.), 3.5 g of a 7:3 mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride (trade name: RIKACID 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.), and mix for 15 minutes using a mixer.

[0102] [Example 8]

[0103] Take 5 g of Composition 4, add 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: EPOLIGHT 400E), 3.5 g of urethane-modified epoxy resin (trade name: ADEKA RESIN EPU-73B, manufactured by ADEKA Corporation), 10.3 g of a 7:3 mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride (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, and mix for 15 minutes using a mixer.

[0104] [Comparative Example 1]

[0105] Use 2-hydroxy-3-methacryloylpropyl acrylate instead of Composition 1, and prepare the composition in the same manner as in Example 6.

[0106] [Comparative Example 2]

[0107] Add 10 g of urethane-modified epoxy resin (trade name: ADEKA RESIN EPU-73B, manufactured by ADEKA Corporation), 6.7 g of a 7:3 mixture of 4-methylhexahydrophthalic anhydride and hexahydrophthalic anhydride (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, and mix for 15 minutes using a mixer.

[0108] [Disassembly Confirmation]

[0109] Weigh 1 g of the compositions of Example 6 and Comparative Example 1, and use an ultraviolet belt conveyor irradiation device to produce a cured product with an accumulated light quantity of 30 kJ / m 2 Immerse the produced cured product in 400 mL of 6 mass% hypochlorous acid aqueous solution at 50 °C or warm water at 50 °C filled in a 500 mL beaker, leave it standing for 12 hours, and observe the state of the cured product. The results are shown in Table 2.

[0110]

[0111] As shown in Table 2, regarding the cured product of Example 6, the cured product immersed in the oxidant (hypochlorous acid aqueous solution) dissolved, and the cured product could not be confirmed visually. The cured product immersed in warm water only swelled, and the cured product could be confirmed. On the other hand, regarding the cured product of Comparative Example 1, only swelling occurred in both the hypochlorous acid aqueous solution and warm water, and the cured product could be confirmed. From the above, it can be seen that the cured product formed from the composition of Example 6 can be disintegrated by an oxidant, and the cured product formed from the composition of Comparative Example 1 does not have disintegrating properties.

[0112] [Measurement of change rate of shear bond strength]

[0113] Use a spacer to coat the curable resin compositions of Example 7, 8, and Comparative Example 2 on an aluminum plate (A1050P) with a width of 25 mm × a length of 100 mm × a thickness of 1 mm so that the coating area is 25 mm × 10 mm and the coating thickness is 1 mm. Overlap another aluminum plate on the coated part, and use a hot air drying oven to cure it under the conditions of 120 °C and 1 hour to obtain a shear bond strength test piece. Immerse the produced shear bond strength test piece in a 500 mL beaker filled with 400 mL of 6 mass% sodium hypochlorite aqueous solution (manufactured by KITCHEN HAITER, Kao Corporation), and leave it standing in a constant temperature bath at 50 °C for 16 hours. Take out the immersed test piece from the beaker, and leave it standing in a fume hood under the atmosphere of 25 °C and 55% RH for 12 hours to dry the test piece. Use the dried test piece as the immersed test piece.

[0114] Use a tensile testing machine to measure the maximum strength (MPa) of the test piece before immersion and the test piece after immersion at a tensile speed of 50 mm / min. Calculate the change rate of shear bond strength by the following formula. The results are shown in Table 3.

[0115] Change rate of shear bond strength = [(maximum strength of the test piece after immersion - maximum strength of the test piece before immersion) / maximum strength of the test piece before immersion] × 100 (%)

[0116] The acceptance criterion for the disassemblability based on the change rate of shear bond strength is -90% or less, preferably -100%.

[0117]

[0118] According to Table 3, the test pieces made of the curable resin compositions of Example 7 and Example 8 were immersed in an oxidizing agent (aqueous hypochlorous acid solution), and detachment occurred even without applying force, and they could be easily disassembled. On the other hand, regarding the test pieces made of the curable resin composition of Comparative Example 2, although a decrease in strength was observed, detachment of the test pieces could not be confirmed. From the above, it can be seen that the cured products formed from the curable resin compositions of Examples 7 and 8 have disassemblability, and the cured products formed from the curable resin composition of Comparative Example 2 do not have disassemblability.

[0119] The present invention has been described in detail with reference to specific embodiments, but it is obvious 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 (Japanese Patent Application No. 2023-214033) filed on December 19, 2023, the content of which is incorporated herein by reference.

[0120] Industrial Applicability

[0121] The synthesis of the decomposable compound of the present invention is simple, and the decomposable compound and the cured product obtained from the compound can be easily decomposed by an oxidizing agent. Moreover, by selecting the reactive functional groups in the decomposable compound, curing can be carried out under various conditions. Therefore, the decomposable compound of the present invention can be applied in various fields such as adhesives, sealants, and coating agents that require disassemblability.

Claims

1. A compound represented by the following general formula (1): In the general formula (1), R 1 represents an organic group with a valence of two or more, R 2 represents a hydrogen atom or an alkyl group, R 3 represents a monovalent organic group including a reactive functional group, and n represents an integer of 2 to 10.

2. The compound according to claim 1, wherein R 3 The reactive functional group 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. The compound according to claim 1 or 2, wherein R 1 It is a divalent or higher valent 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 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 sealant 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 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 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 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 solidified material according to claim 4 using an oxidizing agent.

13. The decomposition method according to claim 12, wherein: The oxidant is an aqueous solution of hypochlorous acid.

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