Resin compositions, cured resin products, and cured resin sheets

Abstract

The object of the present invention is to provide a resin composition and a resin-cured sheet that have high adhesive strength, flexibility, are easily peeled off by an external trigger, and have a viscosity that allows them to be coated or applied in a solvent-free or high-solid state. [Solution] The resin composition of the present invention is characterized by comprising an oligomer or polymer having a dynamic covalent bond and at least one crosslinkable functional group, and comprising a structure derived from a polyol selected from the group consisting of polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, silicone polyols, and polyether polyols, acrylic polyols, and polyurethane polyols, in which the number of carbon atoms in the repeating unit is 4 or more.

Description

[Technical Field]

[0001] This invention relates to resin compositions, cured resin products, and cured resin sheets. [Background technology]

[0002] Adhesives are in increasing demand as structural adhesives for joining transportation equipment and structural components, often used as a substitute for or in combination with rivets. There is a growing need for adhesives with stronger bonding strength, greater durability, and superior vibration and impact resistance, and development is currently underway to achieve even higher performance. On the other hand, in recent years, from the perspective of resource recycling and environmental issues, there has been a growing demand for adhesives that allow bonded structural components to be disassembled by some external stimulus after their service life, in order to reuse the bonded structural components.

[0003] Thermoplastic adhesives, whose constituent resin is a thermoplastic resin, soften when heated, making it relatively easy to dismantle structural members by physically peeling off the adherend. However, they often struggle to exhibit sufficient tensile strength and high durability as adhesives. Another challenge is that they often soften gradually rather than undergoing a rapid change in elastic modulus at a certain temperature. On the other hand, thermosetting adhesives, whose constituent resins are thermosetting resins, have sufficient tensile strength and durability as adhesives, but in principle, it is difficult to break the molecular bonds, and breaking the bonds requires a great deal of energy and can also destroy structural members, so in many cases, dismantling structural members is very difficult. Therefore, there is a need for an adhesive that can achieve both strong adhesion and ease of dismantling structural members.

[0004] However, strong adhesion and easy dismantling after use are conflicting properties, making commercialization difficult, and there have been no publicly reported cases of high-strength structural adhesives being put into practical use.

[0005] As one of the compatible methods, it is conceivable to introduce a cleavable functional group into a thermosetting resin. As such a resin, for example, vitrimer is known (see, for example, Non-Patent Document 1), and those having a Vinylogous urethane bond as a cleavable weak bond (see, for example, Non-Patent Document 2) and those having an imine bond have been reported (see, for example, Patent Document 1) and so on. However, these documents do not describe the evaluation of adhesiveness, and it cannot be said that they have both strong adhesive strength and easy disassembly. There is still much room for improvement in the development of an adhesive that can achieve both easy disassembly (the adherents joined with the adhesive can be easily disassembled) while maintaining adhesive performance. In addition, this document does not consider the simplicity and stability of the process during the actual production and curing of the resin, and there is still room for improvement in the manufacturing method and the like for industrial production.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Non-Patent Documents

[0007]

Non-Patent Document 1

Non-Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0008] Recently, studies on peelable adhesives utilizing dynamic covalent bonding for such applications have begun to be reported in papers and other publications. However, these are still at the research stage, and no product has yet been seen on the market that uses an adhesive composition that is highly adhesive, flexible (e.g., stretches by more than 10%), easily peelable by an external trigger utilizing dynamic covalent bonding, can be produced stably, and is solvent-free or high-solids.

[0009] Against this backdrop, there is a growing demand for adhesive compositions and adhesive sheets that have dynamic covalent bonding units within the molecule, possess high adhesive strength, flexibility (e.g., elongation of 10% or more), are easily peeled off by external triggers utilizing dynamic covalent bonding, can be produced stably, that is, have a pot life of 10 minutes or more before application or coating, and have a viscosity that allows for application or coating without solvents or with high solids.

[0010] Therefore, the object of the present invention is to provide a resin composition that has high adhesive strength, is flexible, is easily peeled off by an external trigger, and has a viscosity that allows it to be coated or applied in a solvent-free or high-solid state. [Means for solving the problem]

[0011] In other words, the present invention is as follows: [1] A resin composition characterized by comprising an oligomer or polymer having a dynamic covalent bond and at least one crosslinkable functional group, and having a structure derived from a polyol selected from the group consisting of polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, silicone polyols, polyether polyols with 4 or more carbon atoms in the repeating unit, acrylic polyols, and polyurethane polyols. [2] The resin composition according to [1], wherein the at least one crosslinkable functional group is a crosslinkable functional group selected from the group consisting of a hydroxyl group, a carboxyl group, a carbonyl group, a thiol group, an amino group, an epoxy group, an oxetane group, an isocyanate group, and a vinyl group. [3] The resin composition according to [1] or [2], wherein the number average molecular weight of the polyol is 200 or more. [4] The resin composition according to any one of [1] to [3], wherein the dynamic covalent bond is at least one selected from the group consisting of vinylogous urethane type, imine type, cyclic acetal type, urethane type, carbonate type, diketoenamine type, silyl ether type, and disulfide type. [5] The resin composition according to any one of [1] to [4], wherein the weight-average molecular weight Mw of the oligomer or polymer is 300 or more. [6] The resin composition according to any one of [1] to [5], wherein the polyester polyol is a polycaprolactone polyol. [7] The resin composition according to any one of [1] to [6], wherein the crosslinkable functional group is at least one selected from the group consisting of a hydroxyl group, a carboxyl group, a carbonyl group, an epoxy group, an oxetane group, an isocyanate group, and a vinyl group. [8] The resin composition according to any one of [1] to [7], wherein the dynamic covalent bond is at least one selected from the group consisting of vinylogous urethane type, imine type, diketoenamine type, and disulfide type. [9] The resin composition according to any one of [1] to [8], wherein the polyol comprises a polycaprolactone polyol, a polycarbonate polyol, and / or a polyether polyol having 4 or more carbon atoms in the repeating unit.

[10] The resin composition according to any one of [1] to [9], wherein the Tg of the resin composition is -10°C or higher.

[11] Furthermore, the resin composition according to any one of [1] to

[10] further comprises a curing agent containing a functional group B that can react with the crosslinkable functional group in the oligomer or polymer.

[12] The resin composition according to

[11] , wherein the molar ratio of the functional group B to the crosslinkable functional group (moles of functional group B / moles of crosslinkable functional group) is 0.05 or more and 2.0 or less.

[13] The resin composition according to

[11] or

[12] , wherein the pot life from immediately after mixing the oligomer or polymer with the curing agent is 10 minutes or more.

[14] The resin composition according to any one of

[11] to

[13] , wherein after mixing the oligomer or polymer with the curing agent, the mixture is heated at a temperature of 50°C to 180°C, and the gel fraction after 168 hours at 23°C is 60% to 100%.

[15] A cured resin product obtained by curing any of the resin compositions described in

[11] to

[14] .

[16] The resin cured product according to

[15] , wherein the elongation measured in a tensile test at 23°C is 10% or more.

[17] The storage modulus G' at 23°C, as measured by dynamic viscoelasticity, is 5.0 × 10⁻⁶. 5 A resin cured product according to

[15] or

[16] , having a Pa of 1 or higher.

[18] A cured resin product as described in any of

[15] to

[17] , wherein the maximum stress measured in a tensile test at 23°C is 1 MPa or more.

[19] A cured resin product according to any one of

[15] to

[18] , wherein the bonding exchange temperature Tv is 50°C or higher.

[20] A cured resin product as described in any of

[15] to

[19] , wherein the tensile shear adhesive strength measured at a speed of 5 mm / min is 1 MPa or more. [twenty one] A resin cured product according to any of

[15] to

[20] , which is an adhesive resin cured sheet. [twenty two] A resin cured sheet having a thickness of 1 μm or more and 3000 μm or less, as described in any of

[15] to

[20] . [Effects of the Invention]

[0012] Because the resin composition of the present invention has the above configuration, it has high adhesive strength, flexibility, is easily peeled off by an external trigger, and has a viscosity that allows for coating and application in a solvent-free or high-solid state. [Modes for carrying out the invention]

[0013] The embodiments for carrying out the present invention will be described in detail below. However, the present invention is not limited to the following description and can be implemented in various modifications within the scope of its essence.

[0014] [Resin composition] The resin composition of this embodiment comprises the following oligomers or polymers. The resin composition of this embodiment may consist only of the above-mentioned oligomers or polymers, or it may further contain other components such as curing agents described later.

[0015] <Oligomer or polymer> The above oligomer or polymer has dynamic covalent bonds and crosslinkable functional groups, and has a structure derived from a polyol selected from the group consisting of polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, silicone polyols, polyether polyols with 4 or more carbon atoms in the repeating unit, acrylic polyols, and polyurethane polyols. The above oligomer or polymer may consist only of the above dynamic covalent bond, the above crosslinkable functional group, and the structure derived from the above polyol, or it may further contain other structures. The above dynamic covalent bond may be one type or a combination of multiple types. The above crosslinkable functional group may be one type or a combination of multiple types. The structure derived from the above polyol may be one type or a combination of multiple types.

[0016] (dynamic covalent bond) The dynamic covalent bond described above is preferably at least one selected from the group consisting of vinylogous urethane type, imine type, cyclic acetal type, urethane type, carbonate type, diketoenamine type, silyl ether type, and disulfide type; more preferably at least one selected from the group consisting of vinylogous urethane type, imine type, diketoenamine type, and disulfide type; even more preferably vinylogous urethane type, imine type, diketoenamine type, or disulfide type; more preferably vinylogous urethane type or imine type; and even more preferably vinylogous urethane type.

[0017] -Vinyl gas urethane type- The above vinyl gas urethane type is: (i) A structure having a bond formed by dehydration condensation between an acetoacetate ester compound having one or more (preferably two or more) acetoacetate ester groups in the molecule and an amine compound having two or more primary or secondary amino groups in the molecule. (ii) A structure having a bond in which an amine compound having two or more primary amino groups in the molecule is attached to a propargyl acid ester derivative, These are some examples. Examples of reactions (i) and (ii) are shown below. In this specification, an acetoacetate ester compound having one or more (preferably two or more) acetoacetate groups in its molecule may be referred to as "(a) acetoacetate ester compound," and a monomer unit derived from an (a) acetoacetate ester compound may be referred to as "a monomer unit." Furthermore, amine compounds having two or more primary amino groups in their molecule are sometimes referred to as "(b)amine compounds," and monomeric units derived from (b)amine compounds are sometimes referred to as "b monomeric units." Furthermore, monomer units derived from (c) propargylate ester derivatives are sometimes referred to as "c monomer units." Note that a monomer unit and c monomer unit may have the same structure. [ka]

[0018] In the above (i) acetoacetate ester method, R1 in the acetoacetate ester is a hydrogen atom or an optionally substituted alkyl group (for example, an optionally substituted alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms), R2 is a hydrogen atom or an optionally substituted hydrocarbon group (for example, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 18 carbon atoms, etc.), R is an optionally substituted alkyl group, alicyclic group or aromatic group (for example, an optionally substituted alkyl group having 1 to 20 carbon atoms, alicyclic group or aromatic group, preferably an alkyl group having 1 to 20 carbon atoms, alicyclic group or aromatic group, etc.), and -X may be a structure derived from a polyol. Examples of the substituents mentioned above include alkyl and alkylene groups having 1 to 20 carbon atoms, aryl and arylene groups having 1 to 20 carbon atoms, halogen atoms, oxygen atoms, sulfur atoms, hydroxyl groups, primary amino groups, secondary amino groups, tertiary amino groups, thiol groups, silyl groups, and combinations thereof.

[0019] The above vinyl gas urethane type (hereinafter sometimes referred to as "vinyl gas urethane bond") may have a structure represented by the following formula (1). [ka] In equation (1), the zigzag lines represent bonding and indicate bonding with any chemical structure. Examples of R4 and R5 are the same as those for R1 and R2 described above.

[0020] The presence and number of vinylogoust urethane bonds can be analyzed by solid-state NMR analysis. The above oligomer or polymer preferably contains a monomer unit and / or a monomer unit and a monomer unit and a monomer unit and a monomer unit, and more preferably contains a monomer unit and

[0021] The above oligomer or polymer preferably contains a monomer unit derived from an acetoacetate compound within its molecule. The α monomer unit contained in the above oligomer or polymer may be one type or multiple types.

[0022] The above (a) acetoacetate ester compound may be an acetoacetate ester compound having one acetoacetate ester group in the molecule, an acetoacetate ester compound having two acetoacetate ester groups in the molecule (bisacetoacetate ester compound), or an acetoacetate ester compound having three or more acetoacetate ester groups in the molecule.

[0023] Acetoacetate ester compounds having one acetoacetate ester group in the molecule are not particularly limited, but examples include esters of alcohols such as monoalcohols, diols, and triols with one acetylacetic acid. From the viewpoint of the viscosity of the resulting oligomer or polymer, adhesive strength as an adhesive, flexibility, and ease of disassembly, among these, esters of a polyhydric alcohol such as polyester polyol, polycarbonate polyol, polyolefin polyol, polyamide polyol, polyamide polyester polyol, silicone polyol, polyether polyol with 4 or more carbon atoms in the repeating unit, acrylic polyol, and polyurethane polyol with one acetylacetic acid are particularly preferred.

[0024] Examples of bisacetoacetate ester compounds include esters of polyols such as diols and triols with two acetylacetic acids. The bisacetoacetate ester compound is not particularly limited, but bisacetoacetate esters of polyhydric alcohols such as polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, and silicone polyols, acrylic polyols, polyurethane polyols, and polyether polyols with 4 or more carbon atoms in the repeating unit, with one acetylacetic acid molecule are preferred. The above-mentioned bisacetoacetate compounds may be used individually or in combination of two or more.

[0025] Examples of monomers having three or more acetoacetic acid ester groups include esters of polyols such as triols with three or more acetylacetic acids. Examples of acetoacetic acid ester compounds having three or more acetoacetic acid ester groups in the molecule include esters of polyols such as triols with three or more acetoacetic acid groups. The acetoacetate ester compound having three or more acetoacetate ester groups in the molecule is not particularly limited, but triacetoacetate esters of a polyhydric alcohol such as polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, and silicone polyols, and polyether polyols having four or more carbon atoms in the repeating unit, with one acetylacetic acid group are preferred. Other polyacetoacetates are not particularly limited, but include pentaerythritol tetrakisacetoacetate and those that can be obtained by the method described in Japanese Patent Publication No. 2017-533088. From the viewpoint of the strength of the resulting oligomer or polymer and the adhesive strength as an adhesive, among these, triacetoacetic acid esters of a polyhydric alcohol such as polyester polyol, polycarbonate polyol, or polyether polyol with 4 or more carbon atoms in the repeating unit, and one acetylacetic acid are particularly preferred.

[0026] When the acetoacetate compound contains a monoacetoacetate compound, the monomer units derived from the monoacetoacetate compound are preferably greater than 0 parts by mass and 25 parts by mass or less, more preferably greater than 0 parts by mass and 20 parts by mass or less, even more preferably greater than 0 parts by mass and 15 parts by mass or less, and most preferably greater than 0 parts by mass and 10 parts by mass or less, based on 100 parts by mass of the total amount of the oligomer or polymer. When the content of monomer units derived from the monoacetoacetate compound is within the above range, the three-dimensional crosslinks formed by the condensation reaction between the acetoacetate group of monomer units derived from a polyfunctional acetoacetate compound having two or more acetoacetate groups and the primary or secondary amino group of the amine compound are appropriately controlled, and high mechanical properties and strong adhesive strength tend to be obtained. When the acetoacetate compound contains a bisacetoacetate compound, the monomer units derived from the bisacetoacetate compound are preferably 20 parts by mass or more and 100 parts by mass or less, based on 100 parts by mass of the total amount of the oligomer or polymer, more preferably 30 parts by mass or more and 100 parts by mass or less, more preferably 40 parts by mass or more and 100 parts by mass or less, even more preferably 80 parts by mass or more and 100 parts by mass or less, even more preferably 85 parts by mass or more and 100 parts by mass or less, and even more preferably 90 parts by mass or more and 100 parts by mass or less. When the content of monomer units derived from the bisacetoacetate compound is within the above range, the three-dimensional crosslinks formed by the condensation reaction between the acetoacetate group of the bisacetoacetate compound and the primary or secondary amino group of the amine compound are appropriately controlled, and high mechanical properties and strong adhesive strength tend to be obtained. When the acetoacetate ester compound includes an acetoacetate ester compound having three or more acetoacetate groups in its molecule, the monomer units derived from the acetoacetate ester compound having three or more acetoacetate groups in its molecule are preferably greater than 0 parts by mass and 60 parts by mass or less, more preferably greater than 0 parts by mass and 50 parts by mass or less, more preferably greater than 0 parts by mass and 40 parts by mass or less, more preferably greater than 0 parts by mass and 30 parts by mass or less, and more preferably greater than 0 parts by mass and 20 parts by mass or less, based on 100 parts by mass of the total amount of the oligomer or polymer. When the content of monomer units derived from the acetoacetate ester compound having three or more acetoacetate groups in its molecule is within the above range, the three-dimensional crosslinks formed by the condensation reaction between the acetoacetate group of the acetoacetate ester compound having three or more acetoacetate groups in its molecule and the primary or secondary amino group of the amine compound are appropriately adjusted, and high mechanical properties and strong adhesive strength tend to be obtained.

[0027] The above oligomer or polymer preferably contains (b) monomer units derived from an amine compound having two or more primary or secondary amino groups in the molecule. (b) An amine compound having two or more primary amino groups in its molecule is a compound having two or more -NH2 groups in its molecule.

[0028] (b) The amine compound having two or more primary amino groups in the molecule may be a diamine, a triamine, or a polyamine, and may be an aromatic amine, an aliphatic amine, or a compound having both an aliphatic amino group and an aromatic amino group, but an aliphatic amine is more preferred from the viewpoint of providing flexibility. (b) Amine compounds having two or more primary or secondary amino groups in the molecule may be used alone or in combination of two or more types.

[0029] Examples of aromatic diamines include o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 3,5-diaminotoluene, 1,4-diamino-2-methoxybenzene, 2,5-diamino-p-xylene, 1,3-diamino-4-chlorobenzene, 3,5-diaminobenzoic acid, 1,4-diamino-2,5-dichlorobenzene, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-2,2'-dimethylbibenzyl, 4,4'-diaminodiphenylmethane, 3, 3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 2,2'-diaminostilbene, 4,4'-diaminostilbene, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminobenzophenone, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene Benzene, 1,4-bis(4-aminophenoxy)benzene, 3,5-bis(4-aminophenoxy)benzoic acid, 4,4'-bis(4-aminophenoxy)bibenzyl, 2,2-bis[(4-aminophenoxy)methyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, 1,1-bis(4-aminophenyl)cyclohex Sun, α,α'-bis(4-aminophenyl)-1,4-diisopropylbenzene, 9,9-bis(4-aminophenyl)fluorene, 2,2-bis(3-aminophenyl)hexafluoropropane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4'-diaminodiphenylamine, 2,4-diaminodiphenylamine, 1,8-diaminonaphthalene, 1,5-diaminonaphthalene, 1,5-diaminoanthraquinone, 1,3-diaminopyrene, 1,6-diaminopyrene, 1,8-diaminopyrene, 2,7-diaminofluorene, 1,3-Bis(4-aminophenyl)tetramethyldisiloxane, benzidine, 2,2'-dimethylbenzidine, 1,2-bis(4-aminophenyl)ethane, 1,3-bis(4-aminophenyl)propane, 1,4-bis(4-aminophenyl)butane, 1,5-bis(4-aminophenyl)pentane, 1,6-bis(4-aminophenyl)hexane, 1,7-bis(4-aminophenyl)heptane, 1,8-bis(4-aminophenyl)octane, 1,9-bis(4-aminophenyl)nonane, 1,1 0-Bis(4-aminophenyl)decane, 1,3-Bis(4-aminophenoxy)propane, 1,4-Bis(4-aminophenoxy)butane, 1,5-Bis(4-aminophenoxy)pentane, 1,6-Bis(4-aminophenoxy)hexane, 1,7-Bis(4-aminophenoxy)heptane, 1,8-Bis(4-aminophenoxy)octane, 1,9-Bis(4-aminophenoxy)nonane, 1,10-Bis(4-aminophenoxy)decane, Di(4-aminophenyl)propane-1,3-GioA To, di(4-aminophenyl)butane-1,4-dioate, di(4-aminophenyl)pentane-1,5-dioate, di(4-aminophenyl)hexane-1,6-dioate, di(4-aminophenyl)heptane-1,7-dioate, di(4-aminophenyl)octane-1,8-dioate, di(4-aminophenyl)nonane-1,9-dioate, di(4-aminophenyl)decane-1,10-dioate, 1,3-bis[4-(4-aminophenoxy)phenoxy]propane, 1,4- Examples include bis[4-(4-aminophenoxy)phenoxy]butane, 1,5-bis[4-(4-aminophenoxy)phenoxy]pentane, 1,6-bis[4-(4-aminophenoxy)phenoxy]hexane, 1,7-bis[4-(4-aminophenoxy)phenoxy]heptane, 1,8-bis[4-(4-aminophenoxy)phenoxy]octane, 1,9-bis[4-(4-aminophenoxy)phenoxy]nonane, and 1,10-bis[4-(4-aminophenoxy)phenoxy]decane.

[0030] Examples of aromatic-aliphatic diamines include 3-aminobenzylamine, 4-aminobenzylamine, 3-amino-N-methylbenzylamine, 4-amino-N-methylbenzylamine, 3-aminophenethylamine, 4-aminophenethylamine, 3-amino-N-methylphenethylamine, 4-amino-N-methylphenethylamine, 3-(3-aminopropyl)aniline, 4-(3-aminopropyl)aniline, 3-(3-methylaminopropyl)aniline, 4-(3-methylaminopropyl)aniline, 3-(4- Examples include minobutyl)aniline, 4-(4-aminobutyl)aniline, 3-(4-methylaminobutyl)aniline, 4-(4-methylaminobutyl)aniline, 3-(5-aminopentyl)aniline, 4-(5-aminopentyl)aniline, 3-(5-methylaminopentyl)aniline, 4-(5-methylaminopentyl)aniline, 2-(6-aminonaphthyl)methylamine, 3-(6-aminonaphthyl)methylamine, 2-(6-aminonaphthyl)ethylamine, and 3-(6-aminonaphthyl)ethylamine.

[0031] Examples of heterocyclic diamines include 2,6-diaminopyridine, 2,4-diaminopyridine, 2,4-diamino-1,3,5-triazine, 2,7-diaminodibenzofuran, 3,6-diaminocarbazole, 2,4-diamino-6-isopropyl-1,3,5-triazine, and 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole.

[0032] Examples of aliphatic diamines include 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,3-diamino-2,2-dimethylpropane, 1,6-diamino-2,5-dimethylhexane, and 1,7-diamino Examples include no-2,5-dimethylheptane, 1,7-diamino-4,4-dimethylheptane, 1,7-diamino-3-methylheptane, 1,9-diamino-5-methylheptane, 1,12-diaminododecane, 1,18-diaminooctadecane, 1,2-bis(3-aminopropoxy)ethane, and tetraethyl=2,2'-[(2-methylpentane-1,5-diyl)diimino]disuccinate.

[0033] Examples of alicyclic diamines include 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 4,4'-diaminodicyclohexylmethane, 4,4'-diamino-3,3'-dimethyldicyclohexylamine, isophoronediamine, (2S,2'S)-tetraethyl=2,2'-{[methylenebis(cyclohexane-4,1-diyl)]bis(azandiyl)}disuccinate, and (2S,2'S)-tetraethyl=2,2'-{[methylenebis(2-methylcyclohexane-4,1-diyl)]bis(azandiyl)}disuccinate.

[0034] From the viewpoint of improving reactivity, among these aliphatic diamines, those in which the amino group is located at the end of the molecular chain are preferred.

[0035] From the viewpoint of high mechanical properties, adhesive strength, and flexibility, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, and 1,8-diaminooctane are preferred among these. Furthermore, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, and 1,8-diaminooctane are preferred, with 1,5-diaminopentane and 1,6-diaminohexane being the most preferred. The above diamine compounds may be used individually or in combination of two or more.

[0036] Specific examples of aromatic triamines include 1,3,5-triaminobenzene, tris(3-aminophenyl)amine, tris(4-aminophenyl)amine, tris(3-aminophenyl)benzene, tris(4-aminophenyl)benzene, 1,3,5-tris(3-aminophenoxy)benzene, 1,3,5-tris(4-aminophenoxy)benzene [TAPOB], 1,3,5-tris(aminophenyl)benzene [TAPB], or 1,3,5-tris(4-aminophenoxy)triazine.

[0037] Furthermore, it is also possible to use aromatic triamines having a predetermined asymmetric structure represented by the following general formula (1). [ka] (In the formula, -Z- is -O-, -CO-, -S-, -SO2-, -CH2-, -C(CH3)2-, -C(CF3)2-, or a single bond. Ra and Rb are independently a hydrogen atom, a halogen atom, a hydroxyl group, or a hydrocarbon group. m is an integer from 0 to 3, and n is an integer from 0 to 4.)

[0038] Specific examples of aromatic triamines having a predetermined asymmetric structure represented by the above general formula (1) include 2,3',4-triaminobiphenyl, 2,4,4'-triaminobiphenyl, 3,3',4-triaminobiphenyl, 3,3',5-triaminobiphenyl, 3,4,4'-triaminobiphenyl, 3,4',5-triaminobiphenyl, 2,3',4-triaminodiphenyl ether, 2,4,4'-triaminodiphenyl ether, 3,3',4-triaminodiphenyl ether, 3,3',5-triaminodiphenyl ether, and 3,4,4'-triaminodiphenyl ether. Triaminodiphenyl ether, 3,4',5-triaminodiphenyl ether, 2,3',4-triaminobenzophenone, 2,4,4'-triaminobenzophenone, 3,3',4-triaminobenzophenone, 3,3',5-triaminobenzophenone, 3,4,4'-triaminobenzophenone, 3,4',5-triaminobenzophenone, 2,3',4-triaminodiphenyl sulfide, 2,4,4'-triaminodiphenyl sulfide, 3,3',4-triaminodiphenyl sulfide, 3,3',5-triaminodiphenyl sulfide 3,4,4'-triaminodiphenyl sulfide, 3,4',5-triaminodiphenyl sulfide, 2,3',4-triaminodiphenyl sulfone, 2,4,4'-triaminodiphenyl sulfone, 3,3',4-triaminodiphenyl sulfone, 3,3',5-triaminodiphenyl sulfone, 3,4,4'-triaminodiphenyl sulfone, 3,4',5-triaminodiphenyl sulfone, 2,3',4-triaminodiphenylmethane, 2,4,4'-triaminodiphenylmethane, 3,3',4-triaminodiphenyl Tan, 3,3',5-triaminodiphenylmethane, 3,4,4'-triaminodiphenylmethane, 3,4',5-triaminodiphenylmethane, 2-(2,4-diaminophenyl)-2-(3-aminophenyl)propane, 2-(2,4-diaminophenyl)-2-(4-aminophenyl)propane, 2-(3,4-diaminophenyl)-2-(3-aminophenyl)propane, 2-(3,5-diaminophenyl)-2-(3-aminophenyl)propane, 2-(3,Examples include 5-diaminophenyl)-2-(4-aminophenyl)propane, 2-(2,4-diaminophenyl)-2-(3-aminophenyl)hexafluoropropane, 2-(2,4-diaminophenyl)-2-(4-aminophenyl)hexafluoropropane, 2-(3,4-diaminophenyl)-2-(3-aminophenyl)hexafluoropropane, 2-(3,5-diaminophenyl)-2-(3-aminophenyl)hexafluoropropane, 2-(3,4-diaminophenyl)-2-(4-aminophenyl)hexafluoropropane, and 2-(3,5-diaminophenyl)-2-(4-aminophenyl)hexafluoropropane.

[0039] Among the aromatic triamines mentioned above, those exhibiting a symmetrical molecular structure are preferred.

[0040] Aliphatic triamines are not particularly limited, but examples include 1,2,3-triaminopropane, 1,3,5-triaminocyclohexane, and tris(2-aminoethyl)amine.

[0041] Specific examples of amine compounds having both aliphatic and aromatic amino groups include 5-(2-aminoethyl)benzene-1,3-diamine and 2-((4-aminophenoxy)methyl)propane-1,3-diamine.

[0042] As amine compounds having three or more primary amino groups in the molecule, commercially available products can also be used. Examples include JEFFAMINE T-403, JEFFAMINE T-3000, and JEFFAMINE T-5000 from Huntsman, as well as Polyment NK-350 from Nippon Shokubai Co., Ltd. and Hexatran 110 from Ascend. Furthermore, amine compounds having three or more primary amino groups in their molecule include amino group-modified polysiloxanes. For example, X-22-3939A manufactured by Shin-Etsu Silicone Co., Ltd. is one such example.

[0043] Amine compounds having two or more primary amino groups in their molecule may also contain a secondary amino group.

[0044] From the viewpoint of high mechanical properties and thermal stability, among these, trifunctional amines having three primary amino groups in the molecule are particularly preferred, and it is even more preferable that they do not contain heteroatoms other than the three primary amino groups. The amine compounds having three or more primary amino groups in the molecule may be used individually or in combination of two or more types.

[0045] (b) The molar proportion of primary amino groups in monomer units derived from amine compounds is preferably 60 mol% to 100 mol%, more preferably 65 mol% to 100 mol%, more preferably 70 mol% to 100 mol%, more preferably 75 mol% to 100 mol%, more preferably 80 mol% to 100 mol%, more preferably 83 mol% to 100 mol%, and even more preferably 85 mol% to 99.99 mol%, when the total amount of acetoacetate groups in monomer units derived from acetoacetate compounds having one or more acetoacetate groups in the molecule is taken as 100 mol%,. When the amount of primary amino groups is within the above range, the formation of a three-dimensional crosslinked structure formed by the condensation reaction between the acetoacetate group of the acetoacetate compound and the primary amino group of the amine compound, as well as bond exchange, are appropriately regulated, which tends to result in high mechanical properties, high adhesive strength, and easy dismantling.

[0046] When the acetoacetate compound contains an acetoacetate compound having three or more acetoacetate groups in its molecule, the monomer units derived from the amine compound are preferably more than 0 parts by mass and 90 parts by mass or less, more preferably more than 0 parts by mass and 80 parts by mass or less, even more preferably 0 to 70 parts by mass, even more preferably 0 to 65 parts by mass, and even more preferably 0 to 60 parts by mass, based on 100 parts by mass of the total amount of the oligomer or polymer. When the content of monomer units derived from the amine compound is within the above range, the formation of the three-dimensional crosslinked structure formed by the condensation reaction between the acetoacetate group of the acetoacetate compound and the primary amino group of the amine compound is appropriately controlled, and high mechanical properties, high adhesive strength, and easy disassembly tend to be obtained.

[0047] The above oligomer or polymer preferably contains monomer units derived from an amine compound having two or more primary amino groups in the molecule, but may also contain monomer units derived from a monoamine. Examples of monoamines include n-butylamine and benzylamine.

[0048] The above (c) propargyl ester derivative may be a propargyl ester derivative having one propargyl ester group in the molecule, a propargyl ester derivative having two propargyl ester groups in the molecule, or a propargyl ester derivative having three or more propargyl ester groups in the molecule.

[0049] Propargylic acid ester derivatives having one propargyl acid ester group in the molecule are not particularly limited, but examples include esters of propargyl acid with alcohols such as monoalcohols, diols, and triols. Among these, from the viewpoint of adhesive strength, esters of one propargyl acid with polyhydric alcohols such as ethylene glycol monopropargyl ester and polypropylene glycol monopropargyl ester are particularly preferred.

[0050] Examples of bispropargyl ester derivatives include esters of polyols such as diols and triols with two propargyl acids. Examples of bispropargyl ester derivatives are not particularly limited, but include ethylene glycol-1,2-bispropargyl ester, propanediol-1,3-bispropargyl ester, propanediol-1,2-bispropargyl ester, butanediol-1,4-bispropargyl ester, hexanediol-1,6-bispropargyl ester, decanediol-1,10-bispropargyl ester, and other alkanediol bispropargyl esters; diethylene glycol bispropargyl ester, triethylene glycol bispropargyl ester, polyethylene glycol bispropargyl ester, polypropylene glycol bispropargyl ester, and other oxyalkylenediol bispropargyl esters; and 1,4-cyclohexanedimethanol bispropargyl ester. From the viewpoint of adhesive strength, among these, ethylene glycol-1,2-bispropagilate, polyethylene glycol bispropagilate, polypropylene glycol bispropagilate, and 1,4-cyclohexanedimethanol bispropagilate are particularly preferred. The above-mentioned bispropargyl ester derivatives may be used individually or in combination of two or more types.

[0051] Examples of propargyl ester derivatives having three or more propargyl ester groups in the molecule include esters of three or more propargyl acids with polyols such as triols. Propargylate compounds having three or more propargyl ester groups in the molecule are not particularly limited, but examples include polypropargyl esters such as trispropargyl ester and tetrakispropargyl ester. Examples of trispropargyl esters are not particularly limited, but include trimethylolpropane trispropargylate, trispropargylate-1,2,3-propanetriol, trispropargylate-1,2,4-butanetriol, and trispropargylate-1,2,6-hexanetriol.

[0052] The above oligomer or polymer is preferably three-dimensionally crosslinked by (i) a condensation reaction between the acetoacetic acid group of (a) an acetoacetic acid ester compound and the primary amino group of (b) an amine compound to form a vinylogous urethane bond, or (ii) a condensation reaction between the propagilate ester group of (c) a propagilate ester compound and the primary amino group of (b) an amine compound to form a vinylogous urethane bond. Vinyl gas urethane bonds are dynamic covalent bonds that can be reversibly exchanged by external stimuli such as heat (temperature), light, and catalysts. Among oligomers or polymers having dynamic covalent bonds, oligomers or polymers having vinyl gas urethane bonds are preferred from the viewpoint of having high adhesive strength and flexibility as oligomers or polymers, good disassembly, and on the other hand, softening as the oligomer or polymer relaxes under stress, resulting in a short disassembly time. Furthermore, since the bond exchange reaction proceeds even without a catalyst, there is no need to worry about catalyst bleed-out over time, making them even more preferable.

[0053] The reactions of vinylogous urethane include the formation of vinylogous urethane bonds, as well as amine exchange and hydrolysis, as shown below. Reversible dissociation and bonding are possible through the formation of vinylogous urethane bonds, amine exchange reactions, and hydrolysis reactions. In the reaction equations below, R1, R2, and R3 each independently represent arbitrary chemical structures. [ka]

[0054] The three-dimensional cross-linked structure (polymer network structure) formed by vinylogous urethane bonds is a strong structure, and therefore oligomers or polymers having vinylogous urethane bonds have good mechanical strength and adhesive strength. Furthermore, stress relaxation and softening occur due to the hydrolysis of vinylogous urethane or amine exchange reaction with monofunctional primary amines, so oligomers or polymers having vinylogous urethane bonds exhibit excellent decomposition properties.

[0055] -Imine bond- The imine bond described above may be a vitrimer that utilizes a reversible bond exchange reaction between imine and amine. The imine bond described above is, for example, a bond obtained by a condensation reaction between the carbonyl group of an aldehyde compound or ketone compound and the primary amino group of an amine compound, and is reversibly dissociated and bonded by an imine-amine exchange reaction or the like. Oligomers or polymers having imine bonds as dynamic covalent bonds can be synthesized, for example, by referring to the method described in Polym. Chem. 7, 7052-7056 (2016).

[0056] Oligomers or polymers that have imine bonds as dynamic covalent bonds tend to have shorter degradation times. An example of a reversible reaction involving an imine bond is the imine-amine exchange reaction shown below. In the reaction equation below, R7, R8, and R9 each independently represent arbitrary chemical structures. [ka] By dissociating the bond through an imine-amine exchange reaction, the polymer network structure can be returned to a monomer or a chain-like low-molecular-weight derivative. Therefore, it is possible to separate the members from the composition in a structure where two members are bonded together using a composition containing an oligomer or polymer having imine bonds as dynamic covalent bonds.

[0057] Oligomers or polymers having imine bonds as dynamic covalent bonds can be obtained, for example, by condensing an aldehyde or ketone compound having two or more carbonyl groups in the molecule with an amine compound having two or more primary amino groups in the molecule and optionally other monomers that do not contradict the purpose of the invention. Alternatively, they can be obtained by reacting an imine-bonded oligomer with a crosslinking agent.

[0058] Examples of amine compounds having two or more primary amino groups in the molecule include those similar to those listed above as raw materials for synthesizing oligomers or polymers having vinylogous urethane bonds. Amine compounds having two or more primary amino groups in their molecule may be used individually or in combination of two or more.

[0059] Examples of aldehyde compounds having two or more carbonyl groups in the molecule include terephthalaldehyde, isophthalaldehyde, 2,5-diformylfuran, 3,4-diformylthiophene, 2,4-diformylimidazole, and 3,4-diccarboxyaldehyde pyrrole. Aldehyde compounds having two or more carbonyl groups in their molecule may be used individually or in combination of two or more.

[0060] The amount of primary amino groups in monomer units derived from amine compounds having two or more primary amino groups in the molecule is preferably 0.7 to 1.0 equivalents, more preferably 0.75 to 1.0 equivalents, and even more preferably 0.80 to 1.0 equivalents, relative to the amount of carbonyl groups in monomer units derived from aldehyde compounds or ketone compounds. Even more preferably, it is 0.85 to 0.99 equivalents. When the amount of primary amino groups is within the above range, the density of the three-dimensional cross-linked structure formed by the condensation reaction between the carbonyl group of the aldehyde compound or ketone compound and the primary amino group of the amine compound is appropriately adjusted, and high mechanical properties and good disassembly properties tend to be obtained.

[0061] Oligomers or polymers having imine bonds as dynamic covalent bonds can be produced, for example, by dissolving the above-mentioned aldehyde compound or ketone compound, the above-mentioned amine compound, and optionally other monomers within a range that does not contradict the purpose of the invention in an organic solvent (e.g., methanol, ethanol, etc.), and then mixing and stirring them.

[0062] The above-mentioned imine-linked oligomer may be an oligomer containing at least one non-terminal imine portion such that the imine portion is located within the oligomer skeleton. The above imine-linked oligomer may be linear or branched. The above imine-linked oligomer preferably contains at least one secondary amine within its oligomer skeleton. The above-mentioned imine-linked oligomers can be prepared from a monofunctional or polyfunctional amine and a monofunctional or polyfunctional aldehyde or carbonyl. For example, polyfunctional aldehydes or carbonyls include terephthalaldehyde, 2,5-diformylfuran, diformylthiophene, diformylpyrrole, diformylimidazole, and combinations thereof. The above-mentioned polyfunctional carbonyls include aldehydes, ketones, carboxylic acid esters, amides, enones, acid anhydrides, imides, and combinations thereof. The above-mentioned polyfunctional aldehydes or carbonyls may be derived from renewable biological sources.

[0063] The above crosslinking agent may be a compound that chemically reacts with and covalently bonds with oligomers and / or polymers. Examples of the crosslinking agents include compounds containing a reactive moiety selected from the group consisting of epoxy, isocyanate, bismaleimide, sulfide, polyurethane, acid anhydride, polyester, and combinations thereof. For example, novolac resin, bisphenol (e.g., bisphenol A (BPA)), monoglycidyl, diglycidyl or triglycidyl molecules, N-containing triglycidyl molecules, cresol or SU-8 photoresist containing epoxy, isocyanate, bismaleimide, sulfide, polyurethane, acid anhydride, and / or polyester functional groups.

[0064] Examples of catalysts that promote imine-amine exchange reactions in oligomers or polymers having imine bonds as dynamic covalent bonds include sulfuric acid, p-toluenesulfonic acid, p-toluenesulfonic acid monohydrate, ethylphosphinic acid, phenylphosphinic acid, ethylphosphonic acid, phenylphosphonic acid, zinc(II) chloride, zinc(II) acetate, iron(II) chloride, iron(III) chloride, diethylamine, diisopropylamine, triethylamine, tributylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,5-diazabicyclo[4.3.0]non-5-yne, 1,5,7-triazabicyclo[4.4.0]deca-5-ene, ammonium chloride, ammonium acetate, ammonium carbamate, and the like. The amount of the catalyst added is preferably 0 to 6 parts by mass, more preferably 0.1 to 5 parts by mass, and even more preferably 0.1 to 3 parts by mass, based on 100 parts by mass of the total amount of the oligomer or polymer having an imine bond.

[0065] -Disulfide type- The above disulfide type (hereinafter sometimes referred to as a disulfide bond) may be a vitrimer that utilizes a reversible bond exchange reaction between disulfides. The above disulfide bond can be reversibly dissociated and bonded, for example, under the conditions of a redox reaction with a thiol. Oligomers or polymers having disulfide bonds as dynamic covalent bonds can be synthesized, for example, by referring to the methods described in ACS Macro Lett. 8, 255-260 (2019).

[0066] Examples of reversible reactions of disulfide bonds include the reactions shown below. Note that in the reaction equations below, R 10 , R 11 , R 12 , R 13 Each of these independently represents an arbitrary chemical structure. [ka]

[0067] Oligomers or polymers having disulfide bonds as dynamic covalent bonds can be obtained, for example, by thermal curing a resin such as epoxy or urethane using a curing agent containing disulfide units.

[0068] Examples of the above-mentioned oligomer or polymer include MDS-EPO, which is obtained by thermally curing an isosorbide-based epoxy resin (IS-EPO) (IS-EPO) obtained by reacting isosorbide (1,4:3,6-dianhydro-d-glucitol) and epichlorohydrin in the presence of a concentrated aqueous solution of NaOH) using 4,4'-disulfanediyldianiline (MDS) as a curing agent.

[0069] -Diketoenamine type- A diketoenamine bond (hereinafter sometimes referred to as a diketoenamine bond) is a bond obtained, for example, by condensing a triketone compound and an amine compound, and is capable of reversible dissociation and bonding through an exchange reaction involving an amino group. Oligomers or polymers having a diketoenamine bond as a dynamic covalent bond can be synthesized, for example, by referring to the method described in Nature Chemistry 11, 442-448 (2019). Specifically, an example of a reversible reaction of diketoenamine bonding is the diketoenamine-amine exchange reaction shown below. Note that in the reaction equation below, R 14 ~R 16 Each of these independently represents an arbitrary chemical structure. [ka]

[0070] A carbonate bond is a bond obtained, for example, by ring-opening polymerization of a biscyclic carbonate compound in the presence of a polyol and optionally other monomers to produce an oligomer or polymer, and is reversible dissociation and bonding possible through carbonate exchange reactions or the like.

[0071] A cyclic acetal bond is, for example, a bond obtained from a carbonyl group and a diol compound. Reversible dissociation and bonding are possible depending on reaction conditions such as acid catalyst conditions and temperature.

[0072] (Crosslinkable functional group) The above oligomer or polymer contains at least one crosslinkable functional group. The above crosslinkable functional group is preferably at least one selected from the group consisting of hydroxyl group, carboxyl group, carbonyl group, thiol group, amino group, epoxy group, oxetane group, isocyanate group, and vinyl group. More preferably, from the viewpoint of obtaining an oligomer or polymer with higher shear adhesion strength, higher flexibility, and superior coating properties, it is at least one selected from the group consisting of hydroxyl group, carboxyl group, carbonyl group, epoxy group, oxetane group, isocyanate group, and vinyl group.

[0073] The molar ratio of the above crosslinkable functional groups to 100 mol% of the above oligomer or polymer is preferably 120 mol% to 350 mol%, more preferably 140 mol% to 320 mol%, even more preferably 160 mol% to 310 mol%, and even more preferably 170 mol% to 300 mol%, from the viewpoint of obtaining an oligomer or polymer with higher shear adhesion strength, higher flexibility, easier peeling by external triggers, and superior coating properties. That is, it is preferable that the average number of functional groups in the polymer is 1.7 to 3.0.

[0074] The above-mentioned crosslinkable functional group can be introduced into the oligomer or polymer, for example, when the dynamic covalent bond is of the vinylogas urethane type, by using an amine compound (b) having at least one crosslinkable functional group.

[0075] (Structures derived from polyols) The above oligomer or polymer includes a structure derived from at least one polyol. From the viewpoint of obtaining oligomers or polymers with higher shear bonding strength, greater flexibility, and superior coating properties, polyether polyols, polyester polyols, and / or polycarbonate polyols with 4 or more carbon atoms in the repeating units are preferred. The polyester polyol is preferably a polycaprolactone polyol. The polyol is preferably a polyether polyol, polycaprolactone polyol, and / or polycarbonate polyol, with four or more carbon atoms in the repeating units. Among polyether polyols with four or more carbon atoms, PTMG is preferred.

[0076] The number-average molecular weight Mn of the above polyol is preferably 200 or higher, more preferably 220 or higher, and even more preferably 230 to 12000, from the viewpoint of obtaining an oligomer or polymer with higher shear adhesion strength, higher flexibility, easier peeling by external triggers, and superior coating properties. The above number-average molecular weight Mn can be measured by GPC measurement. (Measurement conditions) Equipment: HLC-802A, manufactured by Tosoh Corporation Column: Tosoh Corporation, G1000HXL x 1 G2000HXL x 1 G3000HXL x 1 Carrier: Tetrahydrofuran Detection method: Differential refractometer

[0077] The above polyol may be a polyfunctional polyol. In particular, bifunctional or trifunctional polyols are preferred from the viewpoint of curability, high adhesive strength, high flexibility, and viscosity that is easy to handle.

[0078] When the above dynamic covalent bond is of the vinylogous urethane type, the oligomer or polymer is preferably a structure obtained by the reaction of the above crosslinkable functional group (b) amine compound and (a) acetoacetate ester compound (preferably an acetoacetate ester compound including a structure derived from the above polyol), from the viewpoint of having even better viscosity, coating properties, adhesion, and flexibility (for example, a structure in which the amino group of the vinylogous urethane type dynamic covalent bond (for example, the amino group of formula (1) above) is derived from the amino group of the above crosslinkable functional group (b) amine compound).

[0079] The above oligomer or polymer preferably has the following structure. [ka] In the above formula, R4, R'4, R5, and R'5 are each independently a hydrogen atom or a hydrocarbon group which may be substituted, namely an alkyl group, an alicyclic group, or an aromatic group (for example, an alkyl group, an alicyclic group, or an aromatic group having 1 to 20 carbon atoms which may be substituted, an alkyl group, an alicyclic group, or an aromatic group having 1 to 20 carbon atoms, etc.). It is preferable that R4 and R'4 are the same. It is preferable that R5 and R'5 are the same. As R7, a single bond, a saturated or unsaturated alkylene group having 1 to 20 carbon atoms which may be substituted, a saturated or unsaturated alkylidene group having 1 to 20 carbon atoms which may be substituted, a cycloalkylene group having 1 to 20 carbon atoms which may be substituted, a saturated or unsaturated cycloalkylidene group having 1 to 20 carbon atoms which may be substituted, an arylene group having 1 to 20 carbon atoms which may be substituted, -S-, -SO2-, -O-, combinations thereof, etc. may be used. Further, it may be a polyether, a polycarbonate, a polyester, or a combination thereof, etc. having 4 or more carbon atoms in the repeating unit. Among them, it is preferable that the above R7 contains a polyether, a polycarbonate, a polycaprolactone-based polyester, a single bond, or a saturated or unsaturated alkylene group having 4 to 20 carbon atoms which may be substituted in the repeating unit. R 12 、R’ 12 are each independently a hydrocarbon group having 1 to 20 carbon atoms which may be substituted, namely an alkyl group, an alicyclic group, or an aromatic group. Examples of the above substituent include a halogen atom, an oxygen atom, a sulfur atom, a hydroxy group, a primary amino group, a secondary amino group, a tertiary amino group, a thiol group, a silyl group, combinations thereof, etc. R 12 and R’ 12 are preferably the same. In the formula, -O-R7-O- may be a structure derived from a polyol. In the formula, R 12 、R’ 12 preferably contain the above crosslinkable functional group.

[0080] (Properties) The properties of the above oligomer or polymer will be described.

[0081] The weight-average molecular weight Mw of the above oligomer or polymer is preferably 300 or more, more preferably 350 to 600,000, and even more preferably 400 to 500,000, from the viewpoint of providing superior adhesive strength, film strength, flexibility, and coating properties, as well as easier peeling by external triggers. The weight-average molecular weight Mw mentioned above can be calculated by GPC measurement.

[0082] <Other ingredients> Other components in the resin composition other than the oligomer or polymer include curing agents, acrylic resins, urethane resins, epoxy resins, silicone resins, fluororesins, tackifiers, surface modifiers, particles, pigments, balloons, silane coupling agents, and the like.

[0083] The mass ratio of the oligomer or polymer to 100% by mass of the resin composition is preferably 30% by mass or more, preferably 35% by mass or more, preferably 40% by mass or more, preferably 45% by mass or more, preferably 50% by mass or more, preferably 55% by mass or more, preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and particularly preferably 100% by mass.

[0084] The Tg of the above resin composition is preferably -10°C or higher, more preferably 0°C to 130°C, and even more preferably 0°C to 120°C, from the viewpoint of providing superior adhesive strength, flexibility, and coating properties, as well as easier peeling by external triggers. The above Tg can be measured by reading the temperature at the top of the tanδ peak in a dynamic viscoelasticity measurement.

[0085] The above resin composition is preferably an adhesive resin composition. The above resin composition can be cured by mixing it with a curing agent to produce adhesive resin cured products, adhesive resin cured sheets, etc.

[0086] The resin composition of this embodiment preferably further comprises a curing agent (which may be simply referred to as "curing agent B" in this specification) containing a functional group B that can react with the crosslinkable functional group in the oligomer or polymer. The above resin composition may also consist only of the above oligomer or polymer and the above curing agent B.

[0087] <Hardening agent containing functional group B> Examples of the above-mentioned functional group B include isocyanate groups, amino groups, carboxyl groups, hydroxyl groups, epoxy groups, oxetane groups, and vinyl groups. Among these, epoxy groups, carboxyl groups, and isocyanate groups are desirable from the viewpoint of extending the pot life, with isocyanate groups being more preferred. The functional group B contained in the curing agent may be one type or a combination of multiple types. In a resin composition having a preferred crosslinkable functional group, the crosslinkable functional group is a hydroxyl group, and the functional group B is an isocyanate.

[0088] Examples of the curing agents include polyisocyanates, amines, and epoxy compounds such as isocyanurate-type aliphatic (alicyclic or aromatic) polyisocyanates, urethane adduct-type aliphatic (alicyclic or aromatic) polyisocyanates, amine compounds having 2 to 8 primary or secondary amines in the molecule, and epoxy compounds having 2 to 6 epoxy groups in the molecule. Among these, polyisocyanates are preferred from the viewpoint of extending the pot life and adhesion to the adherend. Furthermore, aliphatic polyisocyanates or alicyclic polyisocyanates are preferred from the viewpoint of being less prone to discoloration, ensuring an even longer pot life, and adhesive strength. In addition, to enhance adhesion to various adherends, it is more preferable to use kyrile diisocyanate, an aromatic polyisocyanate that does not yellow easily. The above-mentioned hardening agent may be one type or a combination of multiple types.

[0089] In the curing agent described above, the molar ratio of the functional group B to the crosslinkable functional group (moles of functional group B / moles of crosslinkable functional group) is preferably 0.05 to 2.0, more preferably 0.10 to 2.00, more preferably 0.20 to 2.00, more preferably 0.30 to 1.90, more preferably 0.40 to 1.80, and more preferably 0.50 to 1.70. More preferably, the values ​​are 0.60 to 1.60, more preferably 0.70 to 1.50, more preferably 0.70 to 1.40, more preferably 0.70 to 1.30, more preferably 0.70 to 1.20, more preferably 0.75 to 1.15, more preferably 0.75 to 1.10, more preferably 0.75 to 1.05, more preferably 0.75 to 1.00, and even more preferably 0.77 to 0.999.

[0090] The total mass ratio of the oligomer, polymer, and curing agent to 100% by mass of the resin composition is preferably 50% by mass or more, preferably 60% by mass or more, preferably 70% by mass or more, preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and particularly preferably 100% by mass.

[0091] The pot life of the above resin composition, immediately after mixing the above oligomer or polymer with the above curing agent, is preferably 10 minutes or more, more preferably 30 minutes to 1440 minutes, even more preferably 40 minutes to 1320 minutes, even more preferably 50 minutes to 1200 minutes, even more preferably 60 minutes to 1080 minutes, even more preferably 80 minutes to 960 minutes, even more preferably 100 minutes to 840 minutes, even more preferably 120 minutes to 720 minutes, even more preferably 140 minutes to 720 minutes, and even more preferably 180 minutes to 720 minutes. The pot life of the resin composition in this embodiment was evaluated as follows: ○ (good) for 10 minutes or more, and ◎ (excellent) for 180 minutes or more. × (poor) indicated that it could not be coated or applied. The above pot life can be measured by the method described in the examples below. If the resin composition contains components other than polymers, oligomers, and curing agents, the value may be measured by mixing the other components together with the oligomers, polymers, and curing agents.

[0092] After mixing the above-mentioned oligomer or polymer with the above-mentioned curing agent of the above-mentioned resin composition, and after heat treatment (which is optional), the gel fraction after curing at 23°C for 168 hours is preferably 60% to 100%, more preferably 65% ​​to 100%, more preferably 70% to 100%, even more preferably 75% to 100%, even more preferably 80% to 100%, even more preferably 83% to 100%, and even more preferably 87% to 100%. The above-mentioned heat treatment may be heating at a temperature of 50°C to 180°C. In this specification, "gel fraction after mixing the oligomer or polymer with the curing agent, heating at a temperature of 50°C to 180°C, and curing at 23°C for 168 hours" may refer to the value measured using an adhesive resin-cured sheet obtained by coating a resin composition, which is a mixture of the oligomer or polymer described in the examples below with the curing agent, onto a PET film to a thickness of 50 μm, drying at 120°C for 30 minutes, and curing at 23°C for 168 hours. If the resin composition contains components other than the polymer, oligomer, and curing agent, the other components may be mixed simultaneously with the oligomer, polymer, and curing agent, and the value measured using the method described above may be used.

[0093] [Cured resin] The cured resin product of this embodiment is a cured product obtained by curing the resin composition of this embodiment described above.

[0094] The curing temperature during the above curing process may be between 23°C and 190°C. The curing time during the above curing process may be between 1 minute and 200 hours.

[0095] The elongation of the above-mentioned cured resin, as measured in a tensile test at 23°C, is preferably 10% or more, more preferably 20% to 1000%, even more preferably 30% to 900%, even more preferably 40% to 800%, even more preferably 45% to 700%, even more preferably 50% to 600%, even more preferably 55% to 500%, even more preferably 60% to 400%, even more preferably 65% ​​to 350%, and even more preferably 70% to 300%. The above elongation rate can be measured by the method described in the examples below.

[0096] The storage modulus G' of the above-mentioned cured resin at 23°C, measured by dynamic viscoelasticity measurement, is 5.0 × 10⁻⁶, from the viewpoint of adhesive strength. 5 It is preferable that it is Pa or higher, and more preferably 7.0 × 10 5 Pa or more 1.0×10 10 Pa or less, more preferably 1.0 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 1.2 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 1.4 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 1.6 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 1.8 × 10⁻⁶ 6 Pa or more 1.0×10 10 Pa or less, more preferably 2.0 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 2.2 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 2.5 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 3.0 × 10 6 Pa or more 1.0×10 10 Pa or less, more preferably 3.5 × 10 6Pa or more 1.0×10 10 Pa or less, more preferably 3.8 × 10 6 Pa or more 9.0×10 9 Pa or less, more preferably 4.0 × 10 6 Pa or more 9.0×10 9 Pa or less, more preferably 5.0 × 10 6 Pa or more 8.0×10 9 Pa or less, more preferably 7.0 × 10 6 Pa or more 7.0×10 9 Pa or less, more preferably 9.0 × 10 6 Pa or more 6.0×10 9 Pa or less, more preferably 1.0 × 10 7 Pa or more 5.0×10 9 Pa or less, more preferably 1.2 × 10 7 Pa or more 3.0×10 9 Pa or less, more preferably 1.3 × 10 7 Pa or more 2.0×10 9 Pa or less, more preferably 1.4 × 10 7 Pa or more 1.0×10 9 Pa or less, more preferably 1.6 × 10 7 Pa or more 9.0×10 8 It is below Pa. The above storage modulus G' can be measured by the method described in the examples below.

[0097] The maximum stress measured in the tensile test of the above-mentioned cured resin at 23°C is preferably 1 MPa or more, more preferably 2 MPa or more, more preferably 2.2 MPa to 100 MPa, and even more preferably 2.5 MPa to 100 MPa, from the viewpoint of increasing adhesive strength. The above-mentioned maximum stress can be measured by the method described in the examples below.

[0098] The above-mentioned cured resin preferably has a bonding exchange temperature Tv. The bonding exchange temperature Tv of the above-mentioned cured resin product is preferably 50°C or higher, more preferably 55°C to 150°C, even more preferably 60°C to 140°C, even more preferably 65°C to 130°C, and even more preferably 65°C to 130°C, from the viewpoint of easy disassembly. The above-mentioned coupling exchange temperature Tv can be measured by the method described in the examples below.

[0099] The tensile shear adhesive strength of the above-mentioned cured resin, measured at a speed of 5 mm / min, is preferably 1 MPa or more, more preferably 1.5 MPa to 60.0 MPa, even more preferably 2.0 MPa to 50.0 MPa, even more preferably 2.0 MPa to 50.0 MPa, even more preferably 2.5 MPa to 40.0 MPa, even more preferably 3.0 MPa to 35.0 MPa, and even more preferably 3.5 MPa to 32.0 MPa. The tensile shear adhesive strength described above can be measured by the method described in the examples below.

[0100] The above-mentioned cured resin can be used as a liquid adhesive, but it is preferable to use an adhesive cured resin sheet. The thickness of the above-mentioned adhesive resin cured sheet is preferably 1 μm or more and 3000 μm or less, more preferably 5 μm or more and 2500 μm or less, even more preferably 10 μm or more and 2000 μm or less, even more preferably 20 μm or more and 1500 μm or less, even more preferably 20 μm or more and 1200 μm or less, even more preferably 20 μm or more and 1100 μm or less, and most preferably 20 μm or more and 1000 μm or less. [Examples]

[0101] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples.

[0102] The materials used in the examples and comparative examples are as follows: • Bifunctional polyol P2-1: Caprolactone polyol (Praxel 205UT, number-average molecular weight Mn 530) P2-2: Polycarbonate diol (Duranole T5650E, number average molecular weight Mn500) P2-3: Polyether polyol (PPG400, number average molecular weight Mn430) P2-4: Polyether polyol (PTMG250 (polytetramethylene ether glycol), number average molecular weight Mn225) • Trifunctional polyol P3-1: Caprolactone polyol (Praxel 303, number-average molecular weight Mn310) P3-2: TMP (Trimethylolpropane) P2-5: Aromatic polyol (bisphenol A ethylene oxide adduct (average number of moles added = approximately 4), Newport BPE-40, manufactured by Sanyo Chemical Industries) Polyisocyanate PI-3: XDI-based polyisocyanate (Takenate D131N (nurate type) (manufactured by Mitsui Chemicals, Inc.))

[0103] Synthesis of hardening agents (Synthesis Example 1) (Synthesis of polyisocyanate PI-1) A four-necked flask equipped with a stirrer, thermometer, and condenser was purged with nitrogen, and 1000 g of hexamethylene diisocyanate (HDI) was charged. The mixture was stirred at 60°C, and 0.11 g of tetramethylammonium caprylate was added as a catalyst. After 3.5 hours, the reaction endpoint was confirmed by measuring the refractive index of the reaction solution, and the reaction was stopped by adding 0.15 g of phosphoric acid. After filtering the reaction solution, unreacted HDI monomers were removed using a thin-film distillation apparatus to obtain isocyanurate-type polyisocyanate (PI-1). The isocyanate group content of the obtained polyisocyanate was 23.4% by mass, and the average number of isocyanate functional groups was 3.3.

[0104] (Synthesis Example 2) (Synthesis of polyisocyanate PI-2) A four-necked flask equipped with a thermometer, stirring blades, and reflux condenser was charged with 100 parts by mass of hexamethylene diisocyanate (HDI) under a nitrogen atmosphere. After raising the reactor temperature to 50°C, 8.0 parts by mass of trimethylolpropane were added while stirring. The reactor temperature was maintained at 66°C for 4.5 hours before the reaction was stopped. After filtering the reaction solution, unreacted HDI was removed using a thin-film distillation apparatus to obtain urethane adduct type polyisocyanate PI-2. The obtained polyisocyanate PI-2 had an NCO content of 17.3% by mass and an average isocyanate functional group count of 3.5. Furthermore, the presence of a urethane structure was confirmed by 1H-NMR analysis and IR spectral analysis of the obtained polyisocyanate PI-2.

[0105] (Example 1) In a 300 mL two-necked flask, tert-butyl acetoacetate and P2-1 (caprolactone polyol) were added as starting materials. The amount of tert-butyl acetoacetate was 150 mol%, with the OH functional group content of the polyol set to 100 mol%, and the mixture was stirred with a stirring blade under N2 flow. The mixture was then heated in an oil bath to an ambient temperature of 125°C, and the pressure inside the system was gradually reduced to 50 hPa. After 4 hours of heating and reduced pressure, the unreacted tert-butyl acetoacetate was removed by distillation at an ambient temperature of 130°C and a reduced pressure of 5 hPa. After 2 hours of heating and reduced pressure, the mixture was allowed to cool to room temperature to obtain the caprolactone polyol-modified acetoacetate ester in the flask. To 100 mol% of the obtained caprolactone polyol-modified acetoacetate, 200 mol% of diaminoethanol was slowly added dropwise, and after nitrogen purging, the mixture was stirred at room temperature for 5 hours. Subsequently, a condensation reaction was carried out under reduced pressure at 80°C for 12 hours to obtain polymer A1 having vinylogous urethane groups as dynamic covalent bonds and hydroxyl groups as crosslinkable functional groups. To the obtained polymer A1, the synthesized polyisocyanate PI-1 (isocyanurate-type polyisocyanate PI-1) was weighed in such a ratio (moles of NCO / moles of OH) that it was 0.99, then mixed and stirred to obtain resin composition AC-1. Resin composition AC-1 was coated onto a release-treated PET film to a thickness of 50 μm, dried at 120°C for 30 minutes, and then cured at 23°C for 168 hours to obtain an adhesive resin-cured sheet AS-1 having dynamic covalent bonding.

[0106] (Examples 2-7) Except for replacing polyol P2-1 with P2-2, P3-1, and P2-4, and the curing agents with PI-2 and PI-3, the synthesis and manufacturing were carried out in the same manner as in Example 1 to obtain polymers A2 to A4, resin compositions AC-2 to AC-7, and adhesive resin curing sheets AS-2 to AS-7.

[0107] (Example 8) In a 300 mL two-necked flask, tert-butyl acetoacetate and a mixture of polyols P2-2 (polycarbonate diol) and P2-5 (aromatic polyol) (molar ratio = 90:10) were added as starting materials. The amount of tert-butyl acetoacetate was adjusted so that, when the mol% of the OH functional group of the polyol was set to 100 mol%, the molar amount of tert-butyl acetoacetate was 150 mol%. The mixture was then stirred with a stirring blade under N2 flow. Subsequently, the temperature was raised in an oil bath to an ambient temperature of 125°C, and the pressure inside the system was gradually reduced to 50 hPa. After 4 hours of heating and reduced pressure, the unreacted tert-butyl acetoacetate was removed by distillation at an ambient temperature of 130°C and a reduced pressure of 1 hPa. After 2 hours of heating and reduced pressure, the mixture was allowed to cool to room temperature to obtain modified acetoacetate esters of the polycarbonate diol and aromatic polyol in the flask. To 100 mol% of the modified acetoacetate ester of the obtained polycarbonate diol and aromatic polyol, 200 mol% of diaminoethanol was slowly added dropwise, and after nitrogen purging, the mixture was stirred at room temperature for 5 hours. Subsequently, a condensation reaction was carried out under reduced pressure at 80°C for 10 hours and at 100°C for 2 hours to obtain polymer A5 having vinylogous urethane groups as dynamic covalent bonds and hydroxyl groups as crosslinkable functional groups. To the obtained polymer A8, polyisocyanate PI-3 was weighed in such a ratio (moles of NCO / moles of OH) that it was 0.96, then mixed and stirred to obtain resin composition AC-8. Resin composition AC-8 was coated onto a release-treated PET film to a thickness of 50 μm, dried at 120°C for 30 minutes, and then cured at 23°C for 168 hours to obtain an adhesive resin-cured sheet AS-8 having dynamic covalent bonds.

[0108] (Comparative Examples 1-2) Comparative Example 1 was synthesized and manufactured in the same manner as in Example 1, except that polyol P2-1 was replaced with P2-3, to produce polymer B1. In Comparative Example 2, polyol P3-2 was used as is without synthesis to produce B2. Resin compositions BC-1 to BC-2 and adhesive resin curing sheets BS-1 to BS-2 were obtained for each.

[0109] [evaluation] The following measurements were performed on the resin compositions and adhesive resin cured sheets obtained in the examples and comparative examples.

[0110] (Tensile shear adhesive strength) Resin compositions AC-1 to AC-8 and BC-1 to BC-2, which were obtained by mixing polyisocyanate and polymer according to the NCO / OH ratio in the table, were applied to electrodeposited coated plates and steel plates (SPCC) to an area of ​​12.5 mm (length direction) x 25 mm (width direction) using a 50 μm thick spacer, and two electrodeposited coated plates or steel plates were bonded together. After drying at 120°C for 30 minutes, the plates were cured at 23°C for 168 hours to obtain test specimens. The obtained test specimens were pulled in the shear direction at a speed of 5 mm / min, and the force (N) at which they broke was divided by the coated area to obtain the tensile shear adhesive strength (MPa). For steel plates (SPCC), all were delaminated at the substrate interface. (Tensile shear adhesive strength_evaluation 2) Resin compositions AC-1 to AC-8 and BC-1 to BC-2, obtained by mixing the polyisocyanate and polymer according to the NCO / OH ratio in the table, were applied to stainless steel plate SUS304BA and sandblasted aluminum plate A5052P to an area of ​​12.5 mm (length direction) x 25 mm (width direction) using a 50 μm thick spacer. Two electrodeposited plates, or two steel plates, were bonded together and pressed to the same thickness as the spacer. After drying at 120°C for 30 minutes, the plates were cured at 23°C for 168 hours to obtain test specimens. The obtained test specimens were pulled in the shear direction at a speed of 5 mm / min, and the force (N) at which they broke was divided by the coated area to obtain the tensile shear adhesive strength (MPa). For SUS304BA, all specimens peeled off at the substrate interface. (Tensile shear adhesion - Rating 3) Resin compositions AC-1 to AC-8 and BC-1 to BC-2, obtained by mixing the polyisocyanate and polymer according to the NCO / OH ratio in the table, were applied to PET (polyethylene terephthalate), PC (polycarbonate), and ABS plates, respectively, using a 50 μm thick spacer to cover an area of ​​12.5 mm (length direction) x 25 mm (width direction). Two PET, PC, or ABS plates were then bonded together and pressed to the same thickness as the spacer. The specimens were cured at 23°C / 50% RH for 168 hours to obtain test specimens. The obtained test specimens were pulled in the shear direction at a speed of 5 mm / min, and the force (N) at which they broke was divided by the coating area to obtain the tensile shear adhesive strength (MPa). All specimens except those that fractured were delaminated at the substrate interface.

[0111] (Tensile strength, elongation) Adhesive resin cured sheets AS-1 to AS-8 and BS-1 to BS-2, with a thickness of 50 μm, were cut into strips 10 mm wide and 40 mm long. These strips were then set on a tensile testing machine with a grip distance of 20 mm, and measured at a temperature of 23°C and a speed of 20 mm / min to obtain the maximum stress and elongation (%) values. The maximum stress was defined as the tensile strength (MPa).

[0112] (Storage modulus, Tg, Tv) Adhesive resin cured sheets AS-1 to AS-8 and BS-1 to BS-2, with a thickness of 300 μm and prepared using the same method as described above, were punched out to a size of 8 mm in diameter. These were then set up in a dynamic viscoelasticity measuring device (ARES (manufactured by TA Instruments)) and measured at a variable temperature from -50°C to 200°C under conditions of a frequency of 1 Hz and a strain of 0.2% to obtain the storage modulus G' and Tg (temperature at the peak of tanδ) (°C) at room temperature (23°C). The bond exchange temperature Tv (°C) was calculated by measuring the time (s) until the temperature became 1 / e under a 3.5% strain at three or more temperature levels, and then plotting Tv using an Arrhenius plot with ln(τ) on the vertical axis and 1 / T(K) on the horizontal axis.

[0113] (Gel fraction) Approximately 0.1 to 0.2 g of adhesive resin cured sheets were taken from adhesive resin cured sheets AS-1 to AS-8 and BS-1 to BS-2, wrapped in a mesh sheet, immersed in acetone for 24 hours, and then dried at 105°C for 1 hour. The gel fraction (%) was calculated as 100 × (weight of sample after drying) / (weight of sample before acetone immersion).

[0114] (Pot Life) For the obtained polymers A1-A5 and B1-B2, polyisocyanates PI-1, PI-2, and PI-3 were added as crosslinking agents. After weighing and stirring, the mixture was mixed so that the ratio of moles of NCO to moles of OH was as shown in the table (e.g., 0.99). After 10 minutes, the mixture was judged as ○ (good) if it was possible to coat or apply it and had a pot life of 10 minutes or more, and ◎ (excellent) if it had a pot life of 180 minutes or more. The mixture was judged as × (poor) if it was not possible to coat or apply it.

[0115] (Easy disassembly) Test specimens were prepared using the same method as described above for shear adhesion strength. Each test specimen was heated at Tv+10°C for 10 minutes, and the shear adhesion strength was measured at that temperature. Specimens that were 1 / 15 or less of the tensile shear adhesion strength at 23°C were rated ◎ (excellent), those that were 1 / 10 or less but greater than 1 / 15 of the shear adhesion strength at 23°C were rated ○ (good), those that were 1 / 2 or less but greater than 1 / 10 of the shear adhesion strength at 23°C were rated △, and those that were greater than 1 / 2 of the shear adhesion strength at 23°C and could not be peeled off by hand were rated × (poor).

[0116] [Table 1]

Claims

1. The oligomer or polymer comprises a structure having a dynamic covalent bond and at least one crosslinkable functional group, and having a structure derived from a polyol selected from the group consisting of polyester polyols, polycarbonate polyols, polyolefin polyols, polyamide polyols, polyamide polyester polyols, silicone polyols, polyether polyols with 4 or more carbon atoms in the repeating unit, acrylic polyols, and polyurethane polyols. A resin composition characterized by the following features.

2. The resin composition according to claim 1, wherein the at least one crosslinkable functional group is a crosslinkable functional group selected from the group consisting of a hydroxyl group, a carboxyl group, a carbonyl group, a thiol group, an amino group, an epoxy group, an oxetane group, an isocyanate group, and a vinyl group.

3. The resin composition according to claim 1, wherein the number-average molecular weight of the polyol is 200 or more.

4. The resin composition according to claim 1, wherein the dynamic covalent bond is at least one selected from the group consisting of vinylogous urethane type, imine type, cyclic acetal type, urethane type, carbonate type, diketoenamine type, silyl ether type, and disulfide type.

5. The resin composition according to claim 1, wherein the weight-average molecular weight Mw of the oligomer or polymer is 300 or more.

6. The resin composition according to claim 1, wherein the polyester polyol is a polycaprolactone polyol.

7. The resin composition according to claim 1, wherein the crosslinkable functional group is at least one selected from the group consisting of a hydroxyl group, a carboxyl group, a carbonyl group, an epoxy group, an oxetane group, an isocyanate group, and a vinyl group.

8. The resin composition according to claim 1, wherein the dynamic covalent bond is at least one selected from the group consisting of vinylogous urethane type, imine type, diketoenamine type, and disulfide type.

9. The resin composition according to claim 1, wherein the polyol comprises a polycaprolactone polyol, a polycarbonate polyol, and / or a polyether polyol having four or more carbon atoms in its repeating units.

10. The resin composition according to claim 1, wherein the Tg of the resin composition is -10°C or higher.

11. Furthermore, the resin composition according to claim 1 comprises a curing agent containing a functional group B that can react with the crosslinkable functional group in the oligomer or polymer.

12. The resin composition according to claim 11, wherein the molar ratio of the functional group B to the crosslinkable functional group (number of moles of functional group B / number of moles of crosslinkable functional group) is 0.05 or more and 2.0 or less.

13. The resin composition according to claim 11, wherein the pot life from immediately after mixing the oligomer or polymer with the curing agent is 10 minutes or more.

14. The resin composition according to claim 11, wherein after mixing the oligomer or polymer with the curing agent, the mixture is heated at a temperature of 50°C to 180°C, and the gel fraction after 168 hours at 23°C is 60% to 100%.

15. A cured resin product obtained by curing the resin composition according to claim 11.

16. The resin cured product according to claim 15, wherein the elongation measured in a tensile test at 23°C is 10% or more.

17. The storage modulus G' at 23°C, as measured by dynamic viscoelasticity, is 5.0 × 10⁻⁶. ５ The resin cured product according to claim 15, wherein the pressure is Pa or higher.

18. The resin cured product according to claim 15, wherein the maximum stress measured in a tensile test at 23°C is 1 MPa or more.

19. The resin cured product according to claim 15, wherein the bonding exchange temperature Tv is 50°C or higher.

20. The resin cured product according to claim 16, wherein the tensile shear adhesive strength measured at a speed of 5 mm / min is 1 MPa or more.

21. The resin cured product according to claim 15, which is an adhesive resin cured sheet.

22. The resin cured product according to claim 15, which is an adhesive resin cured sheet having a thickness of 1 μm or more and 3000 μm or less.

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