Degradable compound

Abstract

The purpose of the present invention is to provide a degradable compound having high solubility in a solvent and not being susceptible to precipitation. The present invention relates to a degradable compound represented by formula (1). In formula (1): n ≥ 0, k ≥ 0, m ≥ 0, p1 ≥ 1, p2 ≥ 1, and p3 ≥ 1; R1, R2, and R3 are independently a hydrocarbon group, a group containing a siloxane structure, or a single bond; Z1 and Z2 are independently a hydrocarbon group or a group containing a siloxane structure; At least one item selected from the group consisting of R1, R2, and R3, and / or at least one molecular weight selected from the group consisting of Z1 and Z2 is 200 or more; Q1, Q2, and Q3 are independently a reactive functional group, or hydrogen or halogen; and A1 to A8 are independently a carbonyl group or a single bond, at least one of A1 and A2 is a carbonyl group, at least one of A3 and A4 is a carbonyl group, at least one of A5 and A6 is a carbonyl group, and at least one of A7 and A8 is a carbonyl group.)

Description

degradable compounds

[0001] The present invention relates to decomposable compounds.

[0002] Due to their moldability, durability, and light weight, plastic products are used in a variety of fields, including daily necessities, automobiles, and electronic devices. However, they are difficult to decompose after disposal. In recent years, efforts have been made to develop degradable polymers that can be easily decomposed in order to protect the global environment.

[0003] Patent Documents 1 to 3 disclose polymers having a diacylhydrazine structure as degradable polymers. Due to the diacylhydrazine structure, these polymers are stable in air, but are rapidly decomposed by reaction with an oxidizing agent such as sodium hypochlorite.

[0004] JP 2011-236381 A International Publication No. 2021 / 131003 JP 2011-052075 A

[0005] When a cured product is produced using a polymer having a diacylhydrazine structure as described in Patent Documents 1, 2, and 3, these polymers have low solubility in solvents, so that crystals tend to precipitate before curing, which can cause poor curing. Furthermore, even polymers with relatively high solubility in solvents are soluble only in high-boiling aprotic polar solvents or strong acids, and the process of removing the solvent to obtain a molded product requires a large amount of energy, which causes a problem of a large environmental load.

[0006] An object of the present invention is to provide a decomposable compound that is highly soluble in a solvent and is less likely to precipitate.

[0007] The present inventors have discovered that when a hydrazine derivative contains a specific structure, its solubility in a solvent can be increased and precipitation can be suppressed, and have completed the present invention.

[0008] That is, the present invention relates to a decomposable compound represented by the following formula (1): (In formula (1), n≧0, k≧0, m≧0, p1≧1, p2≧1, p3≧1. R １ , R ２ , R ３are each independently a hydrocarbon group, a group containing a siloxane structure, or a single bond. １ , Z ２ are each independently a hydrocarbon group or a group containing a siloxane structure. １ , R ２ , and R ３ and / or Z １ and Z ２ At least one selected from the group consisting of has a molecular weight of 200 or more. １ , Q ２ , Q ３ are each independently a reactive functional group, or hydrogen or halogen. １ ~A ８ are each independently a carbonyl group or a single bond, and A １ and A ２ At least one of A is a carbonyl group, ３ and A ４ At least one of A is a carbonyl group, ５ and A ６ At least one of A is a carbonyl group, ７ and A ８ At least one of the groups is a carbonyl group.

[0009] The decomposable compound is preferably decomposable upon contact with an oxidizing agent.

[0010] In the decomposable compound, Z １ or Z ２ Preferably, the molecular weight of the copolymer is 700 or more.

[0011] In the decomposable compound, it is preferable that n≧1 and k≧1.

[0012] In the decomposable compound, n≧1 and k≧1, and Z １ Preferably, the molecular weight of the copolymer is 200 or more.

[0013] The present invention also relates to a method for decomposing a decomposable compound, which comprises a step of contacting the decomposable compound with an aqueous solution containing an oxidizing agent at 100°C or lower.

[0014] The present invention also provides a decomposable crosslinking agent comprising the decomposable compound, wherein Q １ , Q ２ , Q ３ relate to a decomposable crosslinking agent in which each of the groups is independently one or more reactive functional groups selected from the group consisting of a hydroxyl group, an amino group, a thiol group, a hydrazide group, a carboxylic acid, an acid anhydride group, a vinyl group, an allyl group, an acrylate group, a methacrylate group, a crotonate group, an isoprenyl group, an acrylamide group, a methacrylamide group, a crotonamide group, an epoxy group, an oxetane group, an oxazoline group, an isocyanate group, a carbodiimide group, a methylol group, a silanol group, a hydroxysilyl group, and an alkoxysilyl group.

[0015] In the decomposable crosslinking agent, Q １ and Q ２ are the same reactive functional group, or Q １ and Q ３ are preferably the same reactive functional group.

[0016] In the decomposable crosslinking agent, it is preferable that p1=1, p2=1, or p3=1.

[0017] The decomposable crosslinking agent is preferably liquid at 30 to 60°C.

[0018] The present invention also relates to a composition comprising the decomposable crosslinking agent and one or more members selected from the group consisting of a curable resin, a polymerization initiator, and a solvent.

[0019] The present invention also relates to a degradable crosslinked product comprising the composition.

[0020] The decomposable crosslinked product is preferably decomposable upon contact with an oxidizing agent.

[0021] The present invention also relates to a method for decomposing a decomposable crosslinked product, which comprises a step of contacting the decomposable crosslinked product with an aqueous solution containing an oxidizing agent at 100°C or less.

[0022] The decomposable compound of the present invention is highly soluble in solvents and is less likely to precipitate.

[0023] <<Decomposable Compound>> The decomposable compound of the present invention is represented by the following formula (1). In formula (1), n, k, m, p1, p2, p3, R １ , R ２ , R ３ , Z １ , Z ２ , Q １ , Q ２ , Q ３ are as follows: n≧0, k≧0, m≧0, p1≧1, p2≧1, p3≧1. R １ , R ２ , R ３ are each independently a hydrocarbon group, a group containing a siloxane structure, or a single bond. １ , Z ２ are each independently a hydrocarbon group or a group containing a siloxane structure. １ , R ２ , and R ３ and / or Z １ and Z ２ At least one selected from the group consisting of has a molecular weight of 200 or more. １ , Q ２ , Q ３ are each independently a reactive functional group, or hydrogen or halogen. １ ~A ８ are each independently a carbonyl group or a single bond, and A １ and A ２ At least one of A is a carbonyl group, ３ and A ４ At least one of A is a carbonyl group, ５ and A ６ At least one of A is a carbonyl group, ７ and A ８ At least one of the groups is a carbonyl group.

[0024] <n, m, k in formula (1)> In formula (1), n ​​and m are all 0 or more, but each independently is preferably 1 or more, more preferably 2 or more. When n is 1 or more, the compound has two or more hydrazine-derived structures (-A-NH-NH-A-), thereby improving decomposition properties. There are no particular upper limits for n and m, but they can each be 50 or less.

[0025] In formula (1), k is 0 or more, preferably 1 or more, and more preferably 2 or more. When k is 1 or more, three-dimensional crosslinking can be achieved when the decomposable compound of the present invention is used as a crosslinking agent. The upper limit of k is not particularly limited, but can be 50 or less.

[0026] <R in formula (1) １ , R ２ , and R ３ > R １ , R ２ , and R ３ are each independently a hydrocarbon group, a group containing a siloxane structure, or a single bond.

[0027] The group containing a siloxane structure is preferably divalent or higher. The group containing a siloxane structure contains an —Si—O— bond as the main skeleton and may have a linear structure, a branched structure, or a cyclic structure. The number of silicon atoms in the group containing a siloxane structure is preferably 2 to 300, more preferably 4 to 100, and even more preferably 10 to 80.

[0028] The hydrogen atoms bonded to the silicon atoms may be substituted. Specific examples of the substituent include alkyl groups, alkoxy groups, phenoxy groups, halogen atoms, amino groups, sulfo groups, cyano groups, and nitro groups.

[0029] Specific examples of groups containing a siloxane structure include dimethyl silicone, diethyl silicone, ethyl methyl silicone, polymethyl silsesquioxane, and modified silicones obtained by modifying the hydrocarbon groups at the terminals and / or side chains of these groups to contain heteroatoms such as N, S, O, and P.

[0030] R １ , R ２ , and R ３ When is a hydrocarbon group, in order to adjust the decomposition rate and solvent solubility, the number of carbon atoms therein is preferably 1 to 600, more preferably 10 to 400, and even more preferably 20 to 300. The hydrocarbon group may be a saturated or unsaturated hydrocarbon group, and may have any of a linear structure, a branched structure, and a cyclic structure.

[0031] The hydrocarbon group may have a substituent, specific examples of which include an alkoxy group, a phenoxy group, a halogen atom, an amino group, a sulfo group, a cyano group, and a nitro group.

[0032] The hydrocarbon group may contain heteroatoms. When heteroatoms are contained, the number thereof is preferably 1 to 300. The heteroatoms may be present in the main chain of the hydrocarbon group or in the side chain. Examples of heteroatoms include N, S, O, and P. Examples of structures containing heteroatoms contained in the hydrocarbon group include: The hydrocarbon group may not contain a heteroatom.

[0033] Specific examples of the hydrocarbon group include linear hydrocarbons such as methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, ether, urethane, urea, ester, thioether, carbonate, and amide, branched hydrocarbons such as isopropylene, isobutylene, 2,2-dimethylpropylene, and 2-ethyl-2-methylpropylene, cyclic hydrocarbons such as cyclohexylene, cyclopentylene, norbornenylene, phenylene, and naphthylene, PEG chains, and trivalent or tetravalent groups formed from these groups. The hydrogen atoms of these hydrocarbon groups may be substituted with the aforementioned substituents.

[0034] <Z in formula (1) １ and Z ２ > In formula (1), Z １ and Z ２ are each independently a hydrocarbon group or a group containing a siloxane structure.

[0035] The group containing a siloxane structure is divalent or higher. The group containing a siloxane structure contains an —Si—O— bond as a main skeleton and may have a linear structure, a branched structure, or a cyclic structure. The number of silicon atoms in the group containing a siloxane structure is preferably 2 to 300, more preferably 4 to 100, and even more preferably 10 to 80.

[0036] The hydrogen atoms bonded to the silicon atoms may be substituted. Specific examples of the substituent include alkyl groups, alkoxy groups, phenoxy groups, halogen atoms, amino groups, sulfo groups, cyano groups, and nitro groups.

[0037] Specific examples of groups containing a siloxane structure include dimethyl silicone, diethyl silicone, ethyl methyl silicone, polymethyl silsesquioxane, and modified silicones obtained by modifying the hydrocarbon groups at the terminals and / or side chains of these groups to contain heteroatoms such as N, S, O, and P.

[0038] Z １ and Z ２ When is a hydrocarbon group, in order to adjust the decomposition rate and solvent solubility, the number of carbon atoms is preferably 1 to 700, more preferably 15 to 500, and even more preferably 50 to 400. The hydrocarbon group has a saturated or unsaturated hydrocarbon group as the main skeleton, and may have a linear structure, a branched structure, or a cyclic structure.

[0039] The hydrocarbon group may have a substituent, specific examples of which include an alkoxy group, a phenoxy group, a halogen atom, an amino group, a sulfo group, a cyano group, and a nitro group.

[0040] The hydrocarbon group may contain heteroatoms such as N, S, O, and P. When heteroatoms are contained, the number thereof is preferably 1 to 350. The heteroatoms may be present in the main chain of the hydrocarbon group or in the side chain. Examples of structures containing heteroatoms contained in the hydrocarbon group include: The hydrocarbon group may not contain a heteroatom.

[0041] The hydrocarbon group may have a reactive functional group, such as a hydroxyl group, an amino group, a hydrazide group, a thiol group, an isoprenyl group, a crotonamide group, a crotonate group, a carboxylic acid, an acid anhydride group, a vinyl group, an allyl group, an acrylate group, a methacrylate group, an acrylamide group, a methacrylamide group, a hydroxysilyl group, an epoxy group, an oxetane group, an oxazoline group, an isocyanate group, a carbodiimide group, a methylol group, a silanol group, or an alkoxysilyl group.

[0042] Specific examples of the hydrocarbon group include linear hydrocarbons such as methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, ether, urethane, urea, ester, thioether, carbonate, and amide, branched hydrocarbons such as isopropylene, isobutylene, 2,2-dimethylpropylene, and 2-ethyl-2-methylpropylene, cyclic hydrocarbons such as cyclohexylene, cyclopentylene, norbornenylene, phenylene, and naphthylene, PEG chains, and trivalent or tetravalent groups formed from these groups. The hydrogen atoms of these hydrocarbon groups may be substituted with the aforementioned substituents.

[0043] Z １ and Z ２ The structures of are independent of each other and may be the same or different. When n≧2, or m≧2, or m≧1 and k≧2, Z １ and Z ２ There are multiple Z in the molecule. １ , Z ２ may be the same or different from each other. １ and Z ２ When the structures of Z are different from each other, the decomposition property and solvent solubility of the decomposable compound can be controlled by selecting a combination of the structures. １ and Z ２ The following are examples of cases where the structures of Z are different from each other: １ and Z ２ Contains one or more of each. １ Includes 2 or more Z ２ Includes: Z １ Contains one or more Z ２ Contains two or more. １ Contains two or more of Z ２The combination of two or more Z includes, for example, a combination of a Z having high water solubility in the decomposition product and a Z having low water solubility in the decomposition product. In addition, the characteristics before decomposition include a combination of a Z having a high molecular weight and a Z having a low molecular weight, a combination of a hydrophilic Z and a hydrophobic Z, a combination of a Z having a high polarity and a Z having a low polarity, and a combination of a Z having a flexible structure and a Z having a rigid structure.

[0044] The decomposable compound is Z １ or Z ２ It is preferable that the ring structure does not contain two or more ring structures. １ or Z ２ When the compound has a cyclic structure containing two or more of the following, the solvent solubility may decrease depending on the number of the cyclic structures. １ or Z ２ The cyclic structure containing two or more of R １ , R ２ , R ３ , Z １ , Z ２ Examples of the ring structure include a ring structure formed by bonding two or more of the following to each other.

[0045] <Molecular weight of R and Z> In formula (1), R １ , R ２ , and R ３ and / or Z １ and Z ２ At least one selected from the group consisting of has a molecular weight of 200 or more. By adjusting the molecular weights of R and Z in this manner, the solubility of the decomposable compound in a solvent can be improved. Furthermore, when a cured product is produced using the decomposable compound, precipitation is suppressed, and a molded product with uniform composition and physical properties can be obtained.

[0046] R １ , R ２ , R ３ When two or more of any of R are present, only one of them may have a molecular weight of 200 or more. １ If there is one R １ The molecular weight of R may be 200 or more. １ , R ２, and R ３ Preferably, the molecular weight of two or more selected from the group consisting of R １ , R ２ , and R ３ Preferably, the molecular weight of the copolymer is 200 or more.

[0047] Similarly, Z １ and Z ２ When two or more of any of Z are present, only one of them may have a molecular weight of 200 or more. １ and Z ２ It is preferable that the molecular weight of R is 200 or more. １ , R ２ , and R ３ and Z １ and Z ２ It is particularly preferred that at least one selected from the group consisting of has a molecular weight of 200 or more.

[0048] The molecular weight is 200 or more, preferably 300 or more, more preferably 700 or more, and even more preferably 900 or more. There is no particular upper limit to the molecular weight, but it is generally 1,000,000 or less. When the molecular weight is within this range, the solubility of the decomposable compound in a solvent can be improved, and the compound can be suitably used as a decomposable crosslinking agent. R １ , R ２ , R ３ , Z １ , Z ２ The molecular weight can be determined, for example, by contacting a decomposable compound with an oxidizing agent and determining the molecular weight from the resulting decomposition product by gel permeation chromatography (GPC), or by determining the molecular weight by NMR. When the molecular weight is determined by gel permeation chromatography (GPC), it is determined as a weight average molecular weight (Mw).

[0049] In formula (1), when n=0, R １ , and R ２ The molecular weight of at least one selected from the group consisting of is preferably 300 or more, more preferably 700 or more. In this case, the solubility in solvents is high, and crystal precipitation tends to be less likely to occur.

[0050] In formula (1), it is preferable that n ≥ 1 and k ≥ 1. In this case, the decomposable compound is branched, and when used as a decomposable crosslinking agent, for example, three-dimensional crosslinking becomes possible.

[0051] In addition, in formula (1), n ​​≧ 1 and k ≧ 1, and Z １ The molecular weight of Z is preferably 200 or more, more preferably 300 or more, and even more preferably 700 or more. １ as a main skeleton and having two or more hydrazine-derived structures (-A-NH-NH-A-) in the side chains. When this decomposable compound is used as a decomposable crosslinking agent, three-dimensional crosslinking becomes possible.

[0052] In order to complicate the structure of the decomposable compound, suppress crystallization, and improve solubility in a solvent, n≧2, m≧2, or m≧1 and k≧2 in formula (1), and Z １ or Z ２ It is preferable that a plurality of Z １ or Z ２ It is preferable that n≧2 and m≧2, and a plurality of Z １ or Z ２ It is more preferable that one or more of the Z groups have a molecular weight of 200 or more. １ or Z ２ It is even more preferable that the molecular weight of at least one of the above is 300 or more, and particularly preferably 700 or more.

[0053] <Q in formula (1) １ , Q ２ , and Q ３ In formula (1), Q １ , Q ２ , Q ３ are each independently a reactive functional group, or hydrogen or halogen. １ , Q ２ , Q ３ are R １ , R ２ , R ３It bonds to a hydrazine-derived structure (-A-NH-NH-A-) via

[0054] Examples of the reactive functional group include a hydroxyl group, an amino group, a thiol group, a hydrazide group, a carboxylic acid, an acid anhydride group, a vinyl group, an allyl group, an acrylate group, a methacrylate group, a crotonate group, an isoprenyl group, an acrylamide group, a methacrylamide group, a crotonamide group, an epoxy group, an oxetane group, an oxazoline group, an isocyanate group, a carbodiimide group, a methylol group, a silanol group, a hydroxysilyl group, and an alkoxysilyl group.

[0055] p1, p2, and p3 are Q contained in the decomposable compound. １ , Q ２ , Q ３ p1, p2, and p3 each represent a number of 1 or more, but each independently represents a number of 1 to 4, and more preferably 1 or 2. １ , Q ２ , Q ３ When p1 is a reactive functional group and p1, p2, and p3 are 2 or more, three-dimensional crosslinking becomes easy when a decomposable compound is used as a crosslinking agent, and the strength and reliability of the crosslinked product are improved. １ Comrade, Q ２ Peer or Q ３ When the reactive functional groups are different from each other, it becomes easy to select various types of curable resins and crosslinking processes when using a decomposable compound as a crosslinking agent. Furthermore, when only specific reactive functional groups are crosslinked, the reactive functional groups not used in the crosslinking reaction can contribute to improved adhesion, solubility, etc. When p1 = 1, p2 = 1, or p3 = 1, the decomposition rate is further improved.

[0056] Q １ , Q ２ , Q ３ may be, independently of each other, hydrogen or a halogen, including fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0057] <A in formula (1) １ ~A ８ > In formula (1), A１ ~A ８ are each independently a carbonyl group or a single bond, and A １ and A ２ At least one of A is a carbonyl group, ３ and A ４ At least one of A is a carbonyl group, ５ and A ６ At least one of A is a carbonyl group, ７ and A ８ At least one of the two A's on either side of -NH-NH- is a carbonyl group. When one of the two A's is a carbonyl group, the decomposable compound has a monoacylhydrazine structure, and the decomposition rate by an oxidizing agent tends to be improved. When both are carbonyl groups, the decomposable compound has a diacylhydrazine structure, and the decomposition product tends to be more soluble in a solution containing an oxidizing agent.

[0058] <Physical Properties of Decomposable Compound> The decomposable compound preferably has a weight-average molecular weight of 300 to 1,000,000, and more preferably 400 to 500,000. When the molecular weight is within these ranges, it becomes easy to adjust the crosslink density and solvent solubility when used as a crosslinking agent.

[0059] The decomposable compound is preferably liquid at 30 to 60° C., more preferably liquid at 30 to 40° C. In this case, it has excellent miscibility with other components when preparing the composition, and can prevent precipitation of other components during molding.

[0060] The decomposable compound is preferably decomposable upon contact with an oxidizing agent. The oxidizing agent is not particularly limited as long as it is an oxidizing agent other than molecular oxygen, and examples include sodium hypochlorite, potassium hypochlorite, calcium hypochlorite, ammonium hypochlorite, hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, perbenzoic acid, ammonium hypobromite, calcium hypobromite, potassium hypobromite, sodium hypobromite, and ozone. These may be used alone or in combination of two or more. Among these, water-soluble salts such as sodium hypochlorite and sodium hypobromite, and ozone water are preferred. These oxidizing agents are preferably reacted as a decomposition solution mixed with an alkaline aqueous solution such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate, or tetramethylammonium hydroxide, or an organic solvent such as an alcohol such as ethanol, methanol, or isopropanol, or a surfactant. The concentration of the oxidizing agent in the aqueous solution is preferably 0.001 to 50% by weight, more preferably 0.01 to 3% by weight.

[0061] The temperature condition when the decomposable compound is brought into contact with the aqueous solution containing the oxidizing agent is preferably 100°C or less, more preferably 15 to 50°C. The time condition is preferably 60 minutes or less, more preferably 10 minutes or less. If necessary, the mixture may be shaken or stirred during the reaction with the oxidizing agent. The specific method for bringing the decomposable compound into contact with the aqueous solution containing the oxidizing agent is not particularly limited, and examples thereof include a method of immersing the decomposable compound in the aqueous solution containing the oxidizing agent, and a method of spraying or dropping the aqueous solution containing the oxidizing agent onto the decomposable compound.

[0062] The decomposable compounds are oxidized by contact with an oxidizing agent, and N ２ , H ２ It is preferable that the decomposition product be HO—CO—Z, or one or more of the decomposition products represented by the following formulas (2) to (8): １ (COOH) ｋ -COOH (2) H-Z １ (COOH) ｋ -COOH (3) HO-CO-Z １ (H) ｋ -COOH (4) H-Z １(H) ｋ -H (5) HO-CO-Z ２ -COOH (6) H-Z ２ -COOH (7) H-Z ２ —H (8) In formulas (2) to (8), Z and k are the same as in formula (1). H or a carboxyl group directly bonded to Z may be bonded to a heteroatom in Z.

[0063] Hydrazine-derived structure (-A-NH-NH-A-) is Z １ , Z ２ When A is a carbonyl group, the decomposition product contains a carboxyl group as represented by formulas (2) to (4) and (6) to (7). Specific examples of the carboxylic acids represented by formulas (2) to (4) and (6) to (7) include succinic acid, malonic acid, adipic acid, phthalic acid, trimellitic acid, and polyacrylic acid.

[0064] When the hydrazine-derived structure (-A-NH-NH-A-) bonds to the oxygen atom or nitrogen atom in Z and A is a carbonyl group, the decomposition product becomes an alcohol or amine represented by formula (5) or (8). Specific examples of the alcohol represented by formula (5) or (8) include ethylene glycol, diethylene glycol, triethylene glycol, hexanediol, pentitol, pentaerythritol, polyethylene glycol, polyvinyl alcohol, resorcinol, and phenol novolak. Specific examples of the amine represented by formula (3) include hexamethylenediamine, pentamethylenediamine, isophoronediamine, toluenediamine, and diaminodiphenylmethane.

[0065] The method for evaluating the decomposition of a decomposable compound by contact with an oxidizing agent is not particularly limited, and can be appropriately selected depending on the solvent solubility of the decomposable compound and the solvent solubility of the decomposition product. For example, a method can be used in which 2 mg of the decomposable compound is added with 2 ml of 20% aqueous sodium hypochlorite solution and allowed to react at room temperature for 30 minutes. Another method can be used in which 2 mg of the decomposable compound is mixed with 0.5 ml of a heavy solvent such as heavy water, heavy chloroform, heavy DMSO, or heavy methanol, and a few drops of 20% aqueous sodium hypochlorite solution are added, followed by reaction at room temperature for 5 minutes. After these treatments, it is preferable that the decomposable compound is completely decomposed. The decomposition product can be confirmed by NMR.

[0066] <Method for synthesizing decomposable compound> The method for synthesizing the decomposable compound is not particularly limited, and examples thereof include a reaction of a hydrazide compound, a semicarbazide compound, or a carbazate compound with a carbonate compound, an isocyanate compound, an acid anhydride, an acid halide, or a cyclic ester compound; a reaction of hydrazine with a carboxylic acid ester; a reaction of hydrazine with a carbonate compound; and a reaction of hydrazine with an isocyanate compound.

[0067] Examples of the hydrazide compound used in the above synthesis method include lactic acid hydrazide, acrylic acid hydrazide, methacrylic acid hydrazide, sebacic acid dihydrazide, adipic acid dihydrazide, phthalic acid dihydrazide, succinic acid monohydrazide, succinic acid dihydrazide, α-resorcylic acid hydrazide, salicylic acid dihydrazide, trimellitic acid trihydrazide, 4-hydroxybutyric acid hydrazide, 6-hydroxyhexanoic acid hydrazide, citric acid trihydrazide, 4-pentenoic acid hydrazide, 3-cyclohexene-1-carboxylic acid hydrazide, trimesic acid trihydrazide, 3-mercaptopropane hydrazide, allylacetohydrazide, and 4-hydroxybenzohydrazide. Examples of carbonate compounds include allyl N-succinimidyl carbonate and C,C'-(oxydi-2,1-ethanediyl)bisN-succinimidyl carbonate. Examples of isocyanate compounds include 2-isocyanatoethyl methacrylate, hexamethylene diisocyanate, toluene diisocyanate, and polymethylene polyphenyl polyisocyanate. Examples of semicarbazide compounds include N-allylhydrazinecarboxamide, N,N'-1,6-hexanediylbis[hydrazinecarboxamide], 4,4'-isophoronebis(semicarbazide), and 4,4'-(1,3-phenylenebismethylene)bis(semicarbazide). Examples of carbazate compounds include allyl carbazate and C,C'-(oxydi-2,1-ethanediyl)biscarbazate. Examples of acid anhydrides include methacrylic anhydride, succinic anhydride, and pyromellitic dianhydride. Examples of acid halides include acrylic acid chloride, sebacic acid dichloride, adipic acid dichloride, phthalic acid dichloride, salicylic acid dichloride, and trimesic acid trichloride. Examples of cyclic ester compounds include propiolactone, butyrolactone, and valerolactone. Examples of carboxylic acid esters include ethyl lactate, methylparaben, monomethyl succinate, diethyl adipate, and trimethyl trimellitate.

[0068] <<Decomposable Crosslinking Agent>> The decomposable crosslinking agent of the present invention is composed of the decomposable compound. １ , Q ２ , Q ３ are each independently one or more reactive functional groups selected from the group consisting of a hydroxyl group, an amino group, a thiol group, a hydrazide group, a carboxylic acid, an acid anhydride group, a vinyl group, an allyl group, an acrylate group, a methacrylate group, a crotonate group, an isoprenyl group, an acrylamide group, a methacrylamide group, a crotonamide group, an epoxy group, an oxetane group, an oxazoline group, an isocyanate group, a carbodiimide group, a methylol group, a silanol group, a hydroxysilyl group, and an alkoxysilyl group.

[0069] In a narrow sense, the term "crosslinking agent" can refer to a chemical substance that forms chemical bonds between polymers or within a polymer. In this specification, however, the term also refers to a chemical substance that can form chemical bonds between its own molecules, in addition to a chemical substance that forms chemical bonds between polymers or within a polymer.

[0070] In the decomposable crosslinking agent, p1≧2, p2≧2, or p3≧2, and a plurality of Q １ Comrade, Q ２ Peer or Q ３ When the reactive functional groups are different from each other, it becomes easy to select various types of curable resins and crosslinking processes. Furthermore, when only specific reactive functional groups are crosslinked, the reactive functional groups not used in the crosslinking reaction can contribute to improved adhesion and solubility. When p1 = 1, p2 = 1, or p3 = 1, the decomposition rate is further improved.

[0071] The degradable crosslinking agent has excellent solubility in solvents and can be used for crosslinking various resins. Applications of crosslinked products using the degradable crosslinking agent of the present invention include adhesives, pressure-sensitive adhesives, water-absorbent resins, resins for three-dimensional modeling, photoresists, release agents, cell culture media, materials for fixing affected areas, and imprinted molded products.

[0072] <<Composition>> The composition of the present invention includes the decomposable crosslinking agent and one or more selected from the group consisting of a curable resin, a polymerization initiator, and a solvent. The amount of the decomposable crosslinking agent in the composition is preferably 0.1 to 99 wt %, more preferably 1 to 70 wt %, and even more preferably 2 to 50 wt %.

[0073] <Curable Resin> The curable resin is not particularly limited as long as it has a structure that reacts with the reactive functional group of the decomposable crosslinking agent to crosslink, and examples thereof include acrylic resins, phenolic resins, epoxy resins, melamine resins, urea resins, unsaturated polyester resins, alkyd resins, silicone resins, isocyanate compounds, and polyimides. The curable resin may be a thermosetting resin or a photocurable resin. The amount of the curable resin in the composition is preferably 0.1 to 95% by weight, and more preferably 1 to 50% by weight.

[0074] <Polymerization Initiator> The polymerization initiator is not particularly limited as long as it is a compound that can catalyze the polymerization of the curable resin, and either a thermal polymerization initiator or a photopolymerization initiator can be used. Examples of the polymerization initiator include radical generators such as alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, and phosphine compounds; base generators such as oxime ester compounds, ammonium compounds, benzoin compounds, dimethoxybenzyl urethane compounds, and orthonitrobenzyl urethane compounds; acid generators such as onium salts, halogen-containing compounds, diazomethane compounds, sulfone compounds, and sulfonic acid compounds; tin compounds such as dibutyltin dilaurate and dibutyltin diacetate; bismuth compounds such as bismuth octoate; titanium compounds such as tetraoctyl titanate and titanium ethyl acetoacetate; zirconium compounds such as zirconium monoacetylacetate and zirconium tetraacetylacetate; amines such as triethylenediamine and 1,4-diazabicyclo[2,2,2]octane (DABCO); platinum compounds such as chloroplatinic acid and alkenylsiloxane platinum complexes; iron complexes; and cobalt complexes. The amount of the polymerization initiator in the composition is preferably 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight, per 100 parts by weight of the curable resin.

[0075] <Solvent> Examples of the solvent include water and organic solvents, such as ether solvents, amide solvents, hydrocarbon solvents, alcohol solvents, ester solvents, aldehyde solvents, ketone solvents, and solvents containing carbon atoms, such as solvents containing carbon atoms and hetero atoms.

[0076] Examples of ether-based solvents include propylene glycol monomethyl ether, anisole, 4-methylanisole, diisopropyl ether, diethyl ether, dibutyl ether, tetrahydrofuran, dimethoxyethane, cyclopentyl methyl ether, and tert-butyl methyl ether. Examples of amide-based solvents include dimethylformamide, dimethylacetamide, and N-methylpyrrolidone. Examples of hydrocarbon-based solvents include aliphatic hydrocarbon solvents such as pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, and cyclohexane, and aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, ethylbenzene, tert-butylbenzene, trifluoromethylbenzene, nitrobenzene, and chlorobenzene. Examples of alcohol-based solvents include methanol, ethanol, propanol, butanol, ethylene glycol, and propylene glycol monomethyl ether. Examples of ester-based solvents include ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate. Examples of aldehyde-based solvents include formaldehyde and acetaldehyde. Examples of ketone solvents include acetone, methyl ethyl ketone, and methyl isobutyl ketone. Examples of solvents containing carbon atoms and heteroatoms include acetonitrile and dimethyl sulfoxide. The amount of the solvent in the composition is preferably 5 to 99% by weight, and more preferably 20 to 80% by weight.

[0077] The solvents listed above may be used alone or in combination of two or more. The boiling point of the solvent is preferably 150°C or lower, more preferably 130°C or lower, and even more preferably 110°C or lower. When the boiling point is within these ranges, the solvent can be removed by heating for a relatively short period of time. The amount of solvents with a boiling point higher than 150°C in the composition is preferably less than 1% by weight.

[0078] <<Degradable Crosslinked Product>> The degradable crosslinked product of the present invention is a cured product of a composition containing a degradable crosslinking agent and one or more selected from the group consisting of a curable resin, a polymerization initiator, and a solvent. The method for producing the degradable crosslinked product from the composition is not particularly limited as long as it can promote polymerization and crosslinking of the curable resin, and those skilled in the art can appropriately select light irradiation conditions, heating conditions, etc. depending on the types of degradable crosslinking agent, curable resin, and polymerization initiator contained in the composition. For example, when the degradable crosslinked product is made into a three-dimensional molded product, methods such as injection molding, compression molding, transfer molding, three-dimensional printing, and photolithography can be used.

[0079] Furthermore, when forming a coating film made of a decomposable crosslinked material, the composition can be applied to a substrate to form a coating film, and the coating film can then be irradiated with light or heated. The material and shape of the substrate are not particularly limited, and examples thereof include resins, inorganic materials, paper, and cloth. Examples of resins include polyesters such as polyethylene terephthalate, polyethylene naphthalate, polylactic acid, polyhydroxybutyric acid, and polybutylene succinate; polyolefins such as polyethylene, polypropylene, and polymethylpentene; cycloolefins; polystyrene, polytetrafluoroethylene, PMMA, polyamides such as nylon 6 and nylon 66; polycarbonates; polyvinyl acetate, polyvinyl alcohol, polyimides, ABS resins, cellulose, cellulose acetate, fibroin, and keratin. Examples of inorganic materials include glass, metals such as Ni, Cu, Cr, Fe, and Si, and oxides and composite materials thereof.

[0080] Examples of methods for applying the composition onto a substrate include bar coating, spin coating, spray coating, dip coating, nozzle coating, gravure coating, reverse roll coating, die coating, air doctor coating, blade coating, rod coating, curtain coating, knife coating, transfer roll coating, squeeze coating, impregnation coating, kiss coating, calendar coating, and extrusion coating.

[0081] The curing conditions for the composition applied to the substrate are not particularly limited. When the composition is cured by light irradiation, the curing conditions are 100 to 2000 mJ / cm. ２ When curing is performed by heating, the heating temperature is preferably 40 to 300° C., and more preferably 80 to 120° C. The heating time is preferably 0.5 to 180 minutes, and more preferably 0.5 to 10 minutes.

[0082] The thickness of the cured coating film is not particularly limited, but is preferably 0.01 to 30 μm, and more preferably 0.05 to 10 μm, within which the strength of the coating film and adhesion to the substrate can be maintained.

[0083] The decomposable crosslinked product is preferably decomposable upon contact with an oxidizing agent. Furthermore, the method for decomposing a decomposable compound preferably includes a step of contacting the decomposable crosslinked product with an aqueous solution containing an oxidizing agent at 100°C or lower. The criteria for decomposability upon contact with an oxidizing agent and the conditions for decomposition are as described above for the decomposable compound. An organic solvent for dissolving the decomposition product or additives may be mixed into the aqueous solution containing the oxidizing agent.

[0084] The present invention will be described below with reference to examples, but is not limited to the following examples. Hereinafter, "parts" and "%" mean "parts by weight" and "% by weight", respectively, unless otherwise specified.

[0085] Example 1: 11.1 g of poly(acrylic acid hydrazide) having a molecular weight of approximately 1,000 and 138 g of dimethyl sulfoxide were mixed in a 300 ml recovery flask, and 5.0 g of 2-isocyanatoethyl methacrylate was added dropwise at room temperature and stirred for 4 hours. After that, 10.6 g of succinic anhydride was added and stirred for an additional 2 hours. The reaction solution was added dropwise to 1,651 g of methyl isobutyl ketone, and the resulting solid was dried in a vacuum dryer at 50°C, yielding a decomposable compound having the structure of formula (A1) in a 60% yield.

[0086] 1 H-NMR (DMSO, δppm) 1.55 (20H, br, main chain CH ２ ), 2.11 (10H, br, main chain CH), 1.88 (9H, s, CH ３), 2.46 (28H, br, COCH ２ CH ２ CO), 3.47-3.51 (6H, m, NCH ２ ), 4.04-4.08 (6H, m, OCH ２ ), 5.67 (3H, d, C=CH ２ ), 6.06 (3H, d, C=CH ２ ), 6.43 to 6.52 (3H, m, CONHC), 9.82 (20H, br, NHNH), 12.12 (7H, br, COOH)

[0087] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A1), foaming occurred, and the formation of polyacrylic acid as a decomposition product was confirmed by 1 H-NMR.

[0088] 0.3 g of the decomposable compound of formula (A1) and 12 mg of a photopolymerization initiator (Omnirad 907, manufactured by IGM Resin Incorporated) were dissolved in 1.5 g of a mixed solvent of methanol and propylene glycol monomethyl ether (weight ratio 1:1) to prepare a composition for preparing a decomposable crosslinked product. The composition was applied to a glass plate to a dry film thickness of 10 μm, dried for 5 minutes in a 150°C air dryer, and then irradiated with ultraviolet light at 500 mJ / cm using an ultraviolet irradiation device (Unicur UVH-1500M, manufactured by Ushio Inc.). ２ The resulting decomposable crosslinked product was then irradiated with ultraviolet light for 10 seconds, yielding a decomposable crosslinked product. No precipitates were formed on the coating film after drying. The resulting decomposable crosslinked product was insoluble in ion-exchanged water, but when immersed in a 5% aqueous solution of sodium hypochlorite at 20°C, it foamed and was completely removed from the substrate and dissolved within 1 minute.

[0089] 0.3 g of the compound of formula (A1), 0.1 g of acryloylmorpholine (ACMO manufactured by KJ Chemicals), and 12 mg of a photopolymerization initiator (Omnirad 907 manufactured by IGM Resin Corporation) were dissolved in 1.5 g of a mixed solvent of methanol and propylene glycol monomethyl ether (weight ratio 1:1) to prepare a composition for preparing a degradable crosslinked product. The composition was applied to a glass plate to a dry film thickness of 10 μm, dried for 5 minutes in a 150°C air dryer, and then irradiated with ultraviolet light at 500 mJ / cm using an ultraviolet irradiation device (Uniqure UVH-1500M manufactured by Ushio Inc.). ２The resulting decomposable crosslinked product was then irradiated with ultraviolet light for 10 seconds, yielding a decomposable crosslinked product. No precipitates were formed on the coating film after drying. The resulting decomposable crosslinked product was insoluble in ion-exchanged water, but when immersed in a 5% aqueous solution of sodium hypochlorite at 20°C, foaming occurred, and it was confirmed that the resin was being removed from the substrate.

[0090] Example 2: 10 g of triol-type polypropylene glycol (Fujifilm Wako Pure Chemical Industries, Ltd.) with a molecular weight of approximately 1500, 40 g of acetonitrile, and 18.2 g of triethylamine were mixed in a 100 ml recovery flask, and 15.3 g of di(N-succinimidyl) carbonate was added and stirred overnight at room temperature. After removing the precipitated solids by filtration, 54 g of chloroform and 100 g of pure water were added to the filtrate, and a separation operation was performed. After removing the aqueous layer, the solvent was distilled off to a concentration of 80%. 72 g of methanol was added, followed by 0.22 g of succinic acid monohydrazide, and the mixture was stirred at room temperature for 4 hours. The completion of the reaction was confirmed by NMR, and then 0.58 g of α-resorcylic acid hydrazide was added and the mixture was stirred overnight. The reaction solution was concentrated using an evaporator, and then 60 g of ethyl acetate was added. This solution was washed three times with 85 g of pure water, and the organic solvent was then distilled off to obtain a decomposable compound having the structure of formula (A2) in a yield of 70%.

[0091] 1 H-NMR (DMSO, δppm) 1.04 (73H, d, CH ３ ), 2.60 (4H, br, CH ２ CH ２ ), 3.3 to 3.6 (75H, m, CHCH ２ ), 4.76 (3H, br, COOCH), 6.38 (2H, t, benzene ring), 6.67 (4H, d, benzene ring), 9.05 (3H, br, NHNH), 9.49 (4H, br, OH), 10.00 (3H, br, NHNH), 12.00 (1H, br, COOH)

[0092] The resulting decomposable compound of formula (A2) was liquid at 30°C.

[0093] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A2), foaming occurred, and the formation of α-resorcylic acid and succinic acid as decomposition products was confirmed by 1 H-NMR.

[0094] A crosslinking composition was obtained by stirring and mixing 3 g of the decomposable compound of formula (A2), 0.8 g of polyethylene glycol diglycidyl ether (Denacol EX-821, manufactured by Nagase ChemteX Corporation), and 0.05 g of 1,8-diazabicyclo(5,4,0)-undecene-7. The composition was impregnated into 80 μm-thick water-disintegrable paper, the surface was lightly squeezed, and the paper was heated in a 130°C air dryer for 20 minutes to obtain a decomposable crosslinked product. No precipitates were formed on the decomposable crosslinked product. The obtained decomposable crosslinked product was insoluble in ion-exchanged water and ethanol, but when immersed in a mixed solution of 20% aqueous sodium hypochlorite solution and ethanol (weight ratio 1:1) and stirred at room temperature, foaming occurred, and decomposition of the resin and crushing of the fibers were confirmed.

[0095] Example 3: 10 g of a carbinol-modified polydimethylsiloxane (KF-6000 manufactured by Shin-Etsu Chemical Co., Ltd.) having a molecular weight of approximately 1000, 16 g of acetone, and 6.5 g of triethylamine were mixed in a 100 ml recovery flask, and 6.0 g of di(N-succinimidyl) carbonate was added and stirred at room temperature overnight. 47 g of chloroform and 3.1 g of 4-pentenoic acid hydrazide were added to the reaction solution, and the mixture was stirred overnight at room temperature. This reaction solution was transferred to a separatory funnel, and 140 g of chloroform was added. The organic layer was then washed three times with 140 g of pure water. After washing, the organic layer was distilled off, yielding a decomposable compound having the structure of formula (A3) in a yield of 98%. In the formula, R represents a hydrocarbon group.

[0096] 1H-NMR (CDCl ３ , δppm) 0.06 (76H, br, CH ３ ), 2.29-2.46 (8H, m, CH ２ CH ２ ), 4.96-5.10 (4H, m, CH=CH ２ ), 5.76-5.94 (2H, m, CH=CH ２ ), 7.74 (2H, br, NHNH), 8.41 (2H, br, NHNH)

[0097] The resulting decomposable compound of formula (A3) was liquid at 30°C.

[0098] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A3), foaming occurred, and the formation of 4-pentenoic acid as a decomposition product was confirmed by 1 H-NMR.

[0099] To 30 g of ethyl acetate, 0.3 g of the decomposable compound of formula (A3), 0.03 g of poly(methylhydrosiloxane), and 4.0 mg of a platinum-based catalyst (product name: CAT-PL-50T, manufactured by Shin-Etsu Chemical Co., Ltd.) were added and mixed to obtain a crosslinking composition solution. The solution was applied to a PET film substrate so that the film thickness after curing would be 0.1 μm, and then dried and cured at 130°C for 2 minutes to obtain a decomposable crosslinked product. No precipitates were formed on the coating film. The decomposable crosslinked product was insoluble in water and ethyl acetate, but when immersed in a 10% aqueous solution of sodium hypochlorite, foaming and decomposition were observed. Subsequent immersion in ethyl acetate removed the entire coating film.

[0100] Example 4: 10 g of a carbinol-modified polydimethylsiloxane (KF-6000 manufactured by Shin-Etsu Chemical Co., Ltd.) having a molecular weight of approximately 1000, 16 g of acetone, and 6.5 g of triethylamine were mixed in a 100 ml recovery flask, and 6.0 g of di(N-succinimidyl) carbonate was added and stirred at room temperature overnight. 47 g of chloroform and 3.3 g of 3-cyclohexene-1-carboxylic acid hydrazide were added to the reaction solution, and the mixture was stirred overnight at room temperature. This reaction solution was transferred to a separatory funnel, and 140 g of chloroform was added. The organic layer was then washed three times with 140 g of pure water. After washing, the organic layer was distilled off, yielding a decomposable compound having the structure of formula (A4) in a 97% yield. In the formula, R represents a hydrocarbon group.

[0101] 1H-NMR (CDCl ３ , δppm) 0.06 (76H, br, CH ３ ), 1.71 to 1.77 (2H, m, CH ２ ), 1.87 to 1.97 (2H, m, CH ２ ), 2.05-2.34 (8H, m, CH ２), 2.35 to 2.52 (2H, m, CH), 5.69 to 5.72 (4H, m, CH=CH), 7.57 (2H, br, NHNH), 8.22 (2H, br, NHNH)

[0102] The resulting decomposable compound of formula (A4) was liquid at 50°C.

[0103] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A4), foaming occurred, and the formation of 3-cyclohexene-1-carboxylic acid as a decomposition product was confirmed by 1 H-NMR.

[0104] Example 5: In a 100 ml recovery flask, 10 g of polymethyl acrylate (UMM-1001, manufactured by Soken Chemical & Engineering Co., Ltd.) having a molecular weight of approximately 1000 and a hydroxyl group at one end, 13 g of acetonitrile, and 5.1 g of triethylamine were mixed, and 4.7 g of di(N-succinimidyl) carbonate was added and stirred at room temperature overnight. Next, 1.4 g of trimesic acid trihydrazide and 80 g of dimethyl sulfoxide were added, and the mixture was stirred at 60°C for 4 hours. The reaction solution was transferred to a separatory funnel, and 210 g of ethyl acetate and 210 g of pure water were added, and the aqueous layer was removed. The organic layer was further washed four times with 90 g of pure water, and the organic solvent was then distilled off to obtain a decomposable compound having the structure of formula (A5) in a 79% yield. In the formula, R represents a hydrocarbon group.

[0105] 1 H-NMR (DMSO, δppm) 1.4-1.9 (69H, m, CH ２ ), 2.19-2.41 (34H, m, CH), 3.58 (103H, br, OCH ３ ), 8.48 (3H, s, benzene ring), 9.42 (3H, br, NHNH), 10.59 (3H, br, NHNH)

[0106] The resulting decomposable compound of formula (A5) was liquid at 30°C.

[0107] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A5), foaming occurred, and the formation of trimesic acid as a decomposition product was confirmed by 1 H-NMR.

[0108] Example 6: 10 g of polymethyl acrylate (UMM-1001, manufactured by Soken Chemical & Engineering Co., Ltd.) having a hydroxyl group at one end and a molecular weight of approximately 1000, 13 g of acetonitrile, and 3.5 g of triethylamine were mixed in a 100 ml recovery flask, and 4.7 g of di(N-succinimidyl)carbonate was added and stirred overnight at room temperature. Next, 1.8 g of methacrylic acid hydrazide was added and stirred for another overnight at room temperature. The reaction solution was washed four times with 50 g of pure water, after which 70 g of ethanol was added and the solvent and residual water were distilled off to obtain a decomposable compound having the structure of formula (A6) in a 77% yield. In the formula, R represents a hydrocarbon group.

[0109] 1 H-NMR (DMSO, δppm) 1.4-1.9 (22H, m, CH ２ ), 1.86 (3H, s, CH ３ ), 2.19-2.41 (11H, m, CH), 3.58 (33H, br, OCH ３ ), 5.44 (1H, br, C=CH ２ ), 5.72 (1H, br, C=CH ２ ), 9.09 (1H, br, NHNH), 9.87 (1H, br, NHNH)

[0110] The resulting decomposable compound of formula (A6) was liquid at 30°C.

[0111] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A6), foaming occurred, and the production of methacrylic acid as a decomposition product was confirmed by 1 H-NMR.

[0112] A photocurable composition was obtained by mixing 3.0 g of the decomposable compound of formula (A6), 0.3 g of N-(2-hydroxyethyl)acrylamide (HEAA manufactured by KJ Chemicals), and 0.1 g of a photopolymerization initiator (Omnirad 907 manufactured by IGM Resin Corporation). The composition was applied to a glass plate so as to give a dry film thickness of 20 μm, and then irradiated with an ultraviolet ray from a UV irradiator (UniCure UVH-1500M manufactured by Ushio Inc.) at 500 mJ / cm. ２The resulting decomposable crosslinked product was then irradiated with ultraviolet light for 10 seconds, yielding a decomposable crosslinked product. No precipitates were formed on the coating film. The resulting decomposable crosslinked product was insoluble in ion-exchanged water, but when immersed in a mixed solution of 20% aqueous sodium hypochlorite solution and propylene glycol monomethyl ether (weight ratio 1:1), foaming occurred and the coating film was removed from the substrate.

[0113] Example 7: 2.0 g of 3-mercaptopropanehydrazide was dissolved in 26 g of THF in a 100 ml recovery flask, and 3.0 g of poly(hexamethylene diisocyanate) (Sigma-Aldrich) was added dropwise thereto, followed by stirring overnight at room temperature. The precipitated white solid was collected by decantation and dried in a vacuum dryer, yielding a decomposable compound having the structure of formula (A7) in a yield of 94%.

[0114] 1H-NMR (DMSO, δppm) 1.24-1.50 (24H, m, CH ２ ), 2.41 (6H, t, C=OCH ２ ), 2.67 (6H, t, SCH ２ ), 2.97-3.10 (12H, m, NCH ２ ), 6.26 (3H, s, NH), 7.67 (3H, s, NH), 8.21 (2H, br, NH), 9.50 (3H, s, NH)

[0115] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A7), foaming occurred, and the formation of 3-mercaptopropanoic acid as a decomposition product was confirmed by 1 H-NMR.

[0116] 1.2 g of the decomposable compound of formula (A7), 2.3 g of dimethyl silicone having acrylate groups at both ends (X-22-2445 manufactured by Shin-Etsu Silicones Co., Ltd.), 0.2 g of a photopolymerization initiator (Omnirad 907 manufactured by IGM Resinside), and 0.2 g of a photopolymerization initiator (Omnirad TPO-L manufactured by IGM Resinside) were dissolved in 20 g of N-methylpyrrolidone, and 4 g of toluene and 10 g of methyl ethyl ketone were added to obtain a photocurable composition. The composition was applied to a glass plate to a dry film thickness of 0.8 μm, dried at 120°C for 10 minutes, and then irradiated with an ultraviolet ray from a UV irradiator (Uniqure UVH-1500M manufactured by Ushio Inc.) at 500 mJ / cm.２ The resulting decomposable crosslinked product was then irradiated with ultraviolet light for 10 seconds, yielding a decomposable crosslinked product. No precipitates were formed on the coating film. The resulting decomposable crosslinked product was insoluble in ion-exchanged water, but when immersed in a mixed solution of 10% aqueous sodium hypochlorite and 5% aqueous sodium hydroxide (weight ratio 1:1), foaming occurred and the coating film was removed from the substrate.

[0117] Example 8 In a 500 ml recovery flask, 4 g of the compound of formula (A5) obtained by the method described in Example 5 was dissolved in 168 g of ethanol and 100 g of acetonitrile, and 38 g of hydrazine monohydrate was added in four portions, followed by stirring at room temperature for 4 days. The reaction solution was added dropwise to 140 g of ice-cooled isopropanol to precipitate a solid.

[0118] The resulting solid was washed with 40 g of acetonitrile and then dried for 3 hours in a vacuum dryer at 50°C. 1.0 g of the dried solid was transferred to a 30 ml recovery flask and dissolved in 11.1 g of DMSO. 2.3 g of N-allyloxycarbonyloxysuccinimide was added and stirred at room temperature overnight. The reaction solution was added dropwise to 87 g of ion-exchanged water to precipitate a solid. The resulting solid was dissolved in 6 g of ethanol and added dropwise to 60 g of methyl isobutyl ketone to precipitate a solid again. The resulting solid was dried overnight in a vacuum dryer at 30°C to obtain 0.5 g of the compound of formula (A8). In the formula, R represents a hydrocarbon group.

[0119] 1 H-NMR (DMSO, δppm) 1.4-1.9 (75H, m, CH ２ ), 1.95-2.41 (37H, m, CH), 4.55 (71H, d, OCH ２ ), 5.21 (35H, t, C=CH ２ ), 5.32 (35H, d, C=CH ２ ), 5.91 (35H, br, C=CH), 8.48 (3H, s, benzene ring), 9.30 (72H, br, NHNH), 10.61 (3H, br, NHNH)

[0120] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A8), foaming occurred, and the formation of trimesic acid and allyl alcohol as decomposition products was confirmed by 1 H-NMR.

[0121] The compound of formula (A8), pentaerythritol tetrakis(mercaptoacetate), and 4-acryloylmorpholine were mixed in a weight ratio of 3:2:2 and diluted with methanol to a concentration of 15% by weight. To this solution were added 0.2 parts by weight of a photopolymerization initiator (Omnirad 907, manufactured by IGM ResinS), 0.2 parts by weight of a photopolymerization initiator (Omnirad TPO-N, manufactured by IGM ResinS), and 1 part by weight of citric acid pigment blue 15:3, to obtain a photocurable composition solution. The composition was applied to a glass substrate so that the film thickness after curing would be 2 μm, dried at 120° C. for 1 minute, and then irradiated with 200 mJ / cm using an ultraviolet irradiation device (UniCure UVH-1500M, manufactured by Ushio Inc.). ２ The resulting decomposable crosslinked material was then irradiated with ultraviolet light for 10 seconds, yielding a decomposable crosslinked material. No precipitates were formed on the coating film. The resulting decomposable crosslinked material was insoluble in ion-exchanged water, but when immersed in a 1% aqueous solution of sodium hypochlorite, it was observed that the material foamed and was removed from the substrate.

[0122] Example 9: 10 g of triol-type polypropylene glycol (Fujifilm Wako Pure Chemical Industries, Ltd.) with a molecular weight of approximately 1500, 40 g of acetonitrile, and 18.2 g of triethylamine were mixed in a 100 ml recovery flask, and 15.3 g of di(N-succinimidyl) carbonate was added and stirred overnight at room temperature. After removing the precipitated solids by filtration, 54 g of chloroform and 100 g of pure water were added to the filtrate, and a separation operation was performed. After removing the aqueous layer, the solvent was distilled off to a concentration of 80%. 11 g of acetonitrile and 2.8 g of triethylamine were added, followed by 0.22 g of 2-hydroxyethyl carbazate, and the mixture was stirred at room temperature for 4 hours. The completion of the reaction was confirmed by NMR, and then 1.9 g of α-resorcylic acid hydrazide was added and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated using an evaporator, and then 103 g of chloroform was added and the mixture was transferred again to a separatory funnel. The organic layer was washed twice with 70 g of ion-exchanged water, and the solvent was removed using an evaporator to obtain a decomposable compound having the structure of formula (A9) in a yield of 61%. The obtained decomposable compound of formula (A9) was liquid at 30°C.

[0123] 1H-NMR (DMSO, δppm) 1.05 (77H, d, CH ３ ), 3.32 to 3.67 (80H, m, CH, CH ２ ), 4.00 (6H, t, O=COCH ２ ), 4.75 (3H, t, OH), 8.97 (3H, br, NHNH), 8.99 (3H, br, NHNH)

[0124] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A9), foaming occurred, and the formation of ethylene glycol as a decomposition product was confirmed by 1 H-NMR.

[0125] A curable composition solution was obtained by mixing 1.0 g of polymethylene polyphenyl polyisocyanate (Millionate MR-200, manufactured by Tosoh Corporation), 5.0 g of the compound of formula (A9), and 60 mg of a dibutyltin-based curing catalyst (Neostan U-810, manufactured by Nitto Kasei Co., Ltd.). The composition was applied to nylon 66 woven fabric to a dry film thickness of 200 μm, heated at 60°C for 10 minutes, and then heated at 40°C for 6 hours to obtain a decomposable crosslinked product. No precipitates were formed on the coating film. The decomposable crosslinked product did not dissolve in isopropanol or ion-exchanged water, but when immersed in a solution obtained by diluting a 5% aqueous solution of sodium dichloroisocyanurate two-fold with isopropanol, foaming and removal from the substrate were observed.

[0126] Example 10 In a 100 ml recovery flask, 10 g of a 4-branched polyethylene glycol (4arm-PEG40K-Succinimidyl Carboxymethyl Ester manufactured by Aldrich) having a molecular weight of approximately 40,000 and having terminally active esters was mixed with 21 g of chloroform and 0.24 g of triethylamine, and then 0.11 g of methacrylic acid hydrazide was added and stirred at room temperature for 3 hours. The reaction solution and 21 g of ion-exchanged water were placed in a separatory funnel and a separation operation was carried out. The lower layer was washed again with 21 g of ion-exchanged water, and the solvent was then removed using an evaporator. The remaining solid was dried overnight in a vacuum dryer to obtain a decomposable compound having the structure of formula (A10) in a yield of 71%.

[0127] 1H-NMR (CDCl ３, δppm) 2.01 (12H, br, CH ３ ), 2.19-2.41 (11H, m, CH), 3.64 (4800H, br, OCH ２ ), 4.15 (8H, br, O=CCH ２ ) 5.45 (4H, s, C=CH ２ ), 5.90 (4H, s, C=CH ２ ), 8.57 (8H, br, NHNH)

[0128] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A10), foaming occurred, and the production of methacrylic acid as a decomposition product was confirmed by 1 H-NMR.

[0129] A photocurable composition was obtained by mixing 0.7 g of the decomposable compound of formula (A10), 0.3 g of 4-acryloylmorpholine, 0.05 g of a photopolymerization initiator (Omnirad 127 manufactured by IGM ResinS), 0.05 g of a photopolymerization initiator (Omnirad 754 manufactured by IGM ResinS), 0.03 g of a silicone-based leveling agent (BYK-348 manufactured by BYK), 3 g of methanol, and 1 g of ion-exchanged water. The composition was applied to a glass plate to a dry film thickness of 10 μm, dried on a hot plate at 100°C for 1 minute, and then irradiated with an ultraviolet ray irradiation device (Uniqure UVH-1500M manufactured by Ushio Inc.) at 200 mJ / cm. ２ The resulting decomposable crosslinked material was insoluble in ion-exchanged water, but when immersed in a solution prepared by diluting a 5% aqueous solution of sodium dichloroisocyanurate twice with a 2% aqueous solution of sodium hydroxide, it was observed that the material foamed and was removed from the substrate.

[0130] Example 11: 200 g of polyglycerol polyglycidyl ether (Green Denacol GEX-521, manufactured by Nagase ChemteX Corporation) having a molecular weight of approximately 710, 200 g of toluene, and 1.8 g of tetrabutylammonium bromide were mixed in a 500 ml separable flask equipped with a reflux condenser, and the mixture was stirred at 100 °C for 170 hours under a carbon dioxide gas atmosphere. The reaction solution was transferred to a 1000 ml recovery flask, and the toluene was removed using an evaporator. 300 g of chloroform, 200 g of methanol, and 47 g of hydrazine monohydrate were added, and the mixture was stirred overnight at room temperature. The solvent was then removed again using an evaporator. 9.6 g of the resulting viscous liquid was collected and dissolved in 200 g of methanol in a 500 ml recovery flask. To this was added 6.0 g of N-allyloxycarbonyloxysuccinimide, and the mixture was stirred for 3 hours. The solvent was then distilled off, and 100 g of acetonitrile was added and the mixture was allowed to stand overnight. The separated acetonitrile layer was removed by decantation, and the remaining viscous liquid was dried overnight in a vacuum dryer, yielding a decomposable compound having the structure of formula (A11) in 86% yield. The obtained decomposable compound of formula (A11) was liquid at 60°C.

[0131] 1 H-NMR (DMSO, δppm) 3.49 (46H, br, OCH), 3.90 (9H, br, O=COCH), 3.99 (4H, br, NH ２ ), 4.52 (6H, s, C=C-CH ２ ) 4.82 (8H, br, OH), 5.20 (3H, d, C=CH ２ ), 5.30 (3H, d, C=CH ２ ), 5.86-5.96 (3H, m, CH=C), 8.14 (2H, br, NH), 9.10 (3H, br, NHNH), 9.13 (3H, br, NHNH)

[0132] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A11), foaming occurred, and the formation of allyl alcohol as a decomposition product was confirmed by 1 H-NMR.

[0133] 2 g of the compound of formula (A11), 0.3 g of pentaerythritol tetrakis(mercaptoacetate), 0.5 g of 4-acryloylmorpholine, and 0.4 g of polymethylene polyphenyl polyisocyanate (Millionate MR-200 manufactured by Tosoh Corporation) were dissolved in 5.5 g of N-methylpyrrolidone, and 0.1 g of a photopolymerization initiator (Omnirad 907 manufactured by IGM ResinS), 0.1 g of a photopolymerization initiator (Omnirad TPO-N manufactured by IGM ResinS), and 0.03 g of dibutyltin dilaurate were added to obtain a curable composition solution. The composition was applied to a glass substrate so that the film thickness after curing would be 1 μm, and then heated at 120°C for 5 minutes to obtain a semi-cured film. After that, the film was exposed to 500 mJ / cm using an ultraviolet irradiation device (UniCure UVH-1500M manufactured by Ushio Inc.). ２ The resulting decomposable crosslinked material was insoluble in ion-exchanged water, but when immersed in a 3% aqueous solution of sodium hypochlorite, it was observed that the material foamed and was removed from the substrate.

[0134] Example 12 30 g of bisphenol A epoxy resin (jER828 manufactured by Mitsubishi Chemical Corporation), 0.12 g of tetramethylammonium chloride, and 28.5 g of ethylparaben were mixed in a 300 ml separable flask and stirred overnight at 100°C. The mixture was then returned to room temperature and 93 g of chloroform and 30 g of ion-exchanged water were added for separation. The lower layer was returned to the flask and concentrated under reduced pressure at 75°C. 42 g of methanol and 10.1 g of hydrazine monohydrate were added and stirred at 70°C for 3 hours. 20.2 g of hydrazine monohydrate was then added and stirred overnight. The mixture was concentrated using an evaporator to obtain 52 g of the compound of formula (A12).

[0135] In a separate 100 ml recovery flask, 10 g of an allyl polyether (Sanicol H-0725, manufactured by Sanyo Chemical Industries, Ltd.) with a molecular weight of 1650 and a hydroxyl group at one end and 2.7 g of triethylamine were dissolved in 33 g of acetonitrile, and 1.84 g of di(N-succinimidyl) carbonate was added. After stirring at room temperature for 1 hour, the solvent was removed using an evaporator. 20 g of dimethylformamide, 2.7 g of triethylamine, and 2.15 g of the compound of formula (A12) were added and stirred overnight. 200 g of ion-exchanged water was added to this reaction solution, followed by stirring. After allowing to stand for 1 hour, the aqueous layer was removed by decantation. 20 g of isopropanol was added to the remaining viscous liquid, the solvent was removed using an evaporator, and the mixture was dried overnight in a vacuum dryer to obtain 6.8 g of a decomposable compound having the structure of formula (A13). The resulting decomposable compound of formula (A13) was liquid at 50°C.

[0136] 1H-NMR (DMSO, δppm) 1.04 (150H, d, CH ３ ), 1.58 (6H, s, CH ３ ), 3.21-3.69 (206H, m, OCH), 3.95 (4H, d, C=C-CH ２ ), 4.00-4.16 (10H, m, OCH), 4.76 (2H, br, OH), 5.12 (2H, dd, C=CH ２ ), 5.24 (2H, dd, C=CH ２ ), 5.82-5.92 (2H, m, CH═C), 6.85 (4H, d, benzene ring), 7.03 (4H, d, benzene ring), 7.10 (4H, d, benzene ring), 7.83 (4H, d, benzene ring), 9.00 (2H, br, NHNH), 10.11 (2H, br, NHNH)

[0137] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A13), foaming occurred, and the formation of allyl polyether as a decomposition product was confirmed by 1 H-NMR.

[0138] The compound of formula (A13), pentaerythritol tetrakis(3-mercaptobutyrate), and 4-acryloylmorpholine were mixed in a weight ratio of 10:1:4, and then 0.2 parts by weight of a photopolymerization initiator (Omnirad 907, manufactured by IGM ResinS), 0.2 parts by weight of a photopolymerization initiator (Omnirad TPO-N, manufactured by IGM ResinS), and 1 part by weight of Pigment Blue 15:3 were added to obtain a photocurable composition solution. The composition was applied to a PET film substrate so that the film thickness after curing would be 10 μm, and then the composition was irradiated with 200 mJ / cm using an ultraviolet irradiation device (UniCure UVH-1500M, manufactured by Ushio Inc.). ２ The resulting degradable crosslinked material was then irradiated with ultraviolet light for 10 seconds, yielding a degradable crosslinked material. No precipitates were formed on the coating film. The resulting degradable crosslinked material was insoluble in ion-exchanged water, but when immersed in a solution containing sodium hypochlorite, a surfactant, and sodium hydroxide (Kitchen Foam Haiter, manufactured by Kao Corporation) diluted three times with tap water, it was observed that the material foamed and was removed from the substrate.

[0139] Example 13: 7.8 g of dehydrated acetonitrile, 0.7 g of triethylamine, and 0.28 g of 2-hydroxyethyl carbazate were mixed in a 20 ml recovery flask, and 0.36 g of methacrylic anhydride was added dropwise while cooling on ice. After stirring at room temperature for 2 hours, the solvent was removed using an evaporator. The residue was transferred to a 200 ml recovery flask, and 29 g of ethyl acetate, 30 g of butyl acrylate, 8.6 g of 2-ethylhexyl acrylate, and 2.98 g of diethylacrylamide were added and mixed. The mixture was heated to 75°C, and 0.12 g of azobis(isobutyronitrile) was added in small portions. After stirring overnight, 71 g of an ethyl acetate solution containing the compound of formula (A14) was obtained. 30 g of this ethyl acetate solution was transferred to a 50 ml recovery flask and concentrated using an evaporator, yielding 17 g of the compound of formula (A14). GPC confirmed that the average molecular weight was 400,000.

[0140] 1H-NMR (DMSO, δppm) 0.83-0.93 (420H, m, CH ３ ), 1.02-1.13 (60H, m, CH ３), 1.25-1.41 (360H, m, OCH), 1.42-1.88 (490H, m, CH, CH ２ , C.H. ３ ), 2.19-2.42 (130H, m, CH), 3.29-3.43 (40H, m, NCH ２ ), 3.57 (2H, dd, C=CH ２ ), 5.24 (2H, dd, C=CH ２ ), 5.82-5.92 (2H, br, HOCH ２ ), 3.99-4.43 (242H, m, O=COCH ２ ), 9.02 (1H, br, NH), 9.77 (1H, br, NH)

[0141] When a small amount of 20% aqueous sodium hypochlorite solution was added to the obtained decomposable compound of formula (A14), foaming occurred, and the formation of ethylene glycol as a decomposition product was confirmed by 1 H-NMR.

[0142] A thermosetting composition solution was obtained by mixing 30 g of an ethyl acetate solution containing 57% of the compound of formula (A14), 0.16 g of 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazinane-2,4,6-trione, and 3 mg of dioctyltin dilaurate. The composition was applied to a PET film substrate so that the cured film thickness was 20 μm, and then dried and cured at 110°C for 2 minutes to obtain a decomposable crosslinked product. No precipitates were formed on the coating film. The resulting decomposable crosslinked product possessed tackiness and was capable of adhering to alkali-free glass with a strength of 5 N / 25 mm (in accordance with JIS-Z0237). The decomposable crosslinked product was insoluble in a 50% aqueous isopropanol solution, but when immersed in a mixed solution of 2% aqueous sodium hypochlorite solution and isopropanol (1:1 by weight), foaming occurred and the coating film was removed from the substrate.

[0143] Comparative Example 1: 1.4 g of pyridine, 10.3 g of acetonitrile, and 0.86 g of allylacetohydrazide were mixed in a 30 ml two-neck flask, and 0.82 g of sebacoyl chloride dissolved in 6.2 g of acetonitrile was added dropwise at 5° C. or below, followed by stirring at room temperature for 3 hours. The obtained white solid was washed with 30 g of acetonitrile and dried in a vacuum dryer at 40° C., obtaining a decomposable compound of formula (B1) in a yield of 95%.

[0144] 1 H-NMR (DMSO, δppm) 1.25 (8H, S, C8H16), 1.50 (4H, t, C8H16), 2.09 (4H, t, C8H16), 2.17 to 2.18 (8H, m, C2H4), 4 96 (2H, d, CH=CH2), 5.05 (2H, d, CH=CH2), 5.76-5.87 (2H, m, CH=CH2), 9.66 (2H, S, NHNH), 9.69 (2H, S, NHNH)

[0145] The solvent solubility of the obtained decomposable compound of formula (B1) was evaluated, and the results are shown in Table 2. When a 20% aqueous solution of sodium hypochlorite was added to the powdery decomposable compound of formula (B1), foaming and decomposition were observed.

[0146] A crosslinking composition solution was obtained by adding 0.3 g of the decomposable compound of formula (B1), 0.1 g of poly(methylhydrosiloxane), and 4.0 mg of a platinum catalyst (product name: CAT-PL-50T, manufactured by Shin-Etsu Chemical Co., Ltd.) to 40 g of a mixed solvent of dimethyl sulfoxide and dimethylformamide (weight ratio 2:1). The solution was applied to a glass substrate so that the film thickness after curing would be 0.1 μm, and then dried and cured at 150°C for 10 minutes to obtain a decomposable crosslinked product. A small amount of precipitate was observed on the dried coating film. The obtained decomposable crosslinked product was insoluble in water, but when immersed in a 10% aqueous sodium hypochlorite solution, foaming and removal from the substrate were observed.

[0147] Comparative Example 2: 3.30 g of 1,12-bis(2,5-dioxy-1-pyrrolidinyl)2,5,8,11-tetraoxadodecanedioic acid, 26 g of dimethylformamide, and 1.6 g of triethylamine were mixed in a 100 ml recovery flask, and 0.88 g of succinic acid dihydrazide was added and stirred at room temperature overnight. Next, 0.31 g of 4-hydroxybenzohydrazide was added, and the mixture was stirred at room temperature for an additional 6 hours. 37 g of ethyl acetate was added to the reaction solution, and the mixture was allowed to stand overnight at -10°C to form a precipitate. The organic solvent was removed by decantation, and the precipitate was washed twice with 35 g of ethyl acetate. Finally, the solvent was distilled off, yielding a decomposable compound having the structure of formula (B2) as a white solid in a 79% yield.

[0148] 1H-NMR (DMSO, δppm) 2.34 (36H, br, CH ２ CO), 3.54 (40H, br, CH ２ O), 3.59 (40H, br, CH ２ O), 4.10 (40H, br, CH ２ OCO), 6.81 (4H, d, benzene ring), 7.72 (4H, d, benzene ring), 9.07 (20H, br, NHNH), 9.67 (20H, br, NHNH), 10.02 (2H, br, OH)

[0149] The solvent solubility of the obtained decomposable compound of formula (B2) was evaluated, and the results are shown in Table 2. When a small amount of 20% aqueous sodium hypochlorite solution was added to the powdery decomposable compound of formula (B2), foaming occurred, and the production of succinic acid and 4-hydroxybenzoic acid as decomposition products was confirmed by 1 H-NMR.

[0150] (Evaluation of Solvent Solubility) 0.5 ml of a solvent shown in Tables 1 and 2 was added to 2 mg of the decomposable compound of Examples 1 to 13 and Comparative Examples 1 and 2, and the mixture was stirred, and dissolution was confirmed visually. If any residue remained after stirring at room temperature for 2 minutes, the mixture was heated with a heat gun while stirring for 2 minutes, and then visually checked again. A compound that was completely dissolved at room temperature was given a score of 3, a compound that remained partially dissolved at room temperature but was completely dissolved after heating was given a score of 2, a compound that remained slightly dissolved after heating was given a score of 1, and a compound that remained largely dissolved after heating was given a score of 0. The results are shown in Tables 1 and 2.

[0151]

[0152]

[0153] The decomposable compounds of Comparative Examples 1 and 2 had low solubility in any solvent, whereas the decomposable compounds of Examples 1 to 13 showed high solubility in multiple solvents.

Claims

1. A degradable compound represented by the following formula (1). 【Chemistry 1】 (In formula (1), n≧0, k≧0, m≧0, p1≧1, p2≧1, p3≧1. ・R １ , R ２ , R ３ These are, independently of each other, hydrocarbon groups, groups containing siloxane structures, or single bonds. ・Z １ Z ２ These are groups that independently contain a hydrocarbon group or a siloxane structure. ・R １ 、R ２ 、and R ３ selected from the group consisting of at least one, and / or, Z １ and Z ２ has a molecular weight of 200 or more and is selected from the group consisting of at least one. Q １ Q ２ Q ３ These are, independently of each other, reactive functional groups, or hydrogen or halogens. A １ ~A ８ These are independently carbonyl groups or single bonds, A １ and A ２ At least one of them is a carbonyl group, A ３ and A ４ At least one of them is a carbonyl group, A ５ and A ６ At least one of them is a carbonyl group, A ７ and A ８ At least one of them is a carbonyl group.

2. A degradable compound according to claim 1, which can be degraded by contact with an oxidizing agent.

3. Z １ or Z ２ The degradable compound according to claim 1 or 2, wherein the molecular weight is 700 or more.

4. A degradable compound according to claim 1 or 2, wherein n ≥ 1 and k ≥ 1.

5. n≧1 and k≧1, Z １ The degradable compound according to claim 1 or 2, wherein the molecular weight of is 200 or more.

6. A method for decomposing a decomposable compound, comprising the step of contacting the decomposable compound according to claim 1 or 2 with an aqueous solution containing an oxidizing agent at a temperature of 100°C or lower.

7. A degradable crosslinking agent comprising the degradable compound described in claim 1 or 2, Q １ Q ２ Q ３ A degradable crosslinking agent in which each is independently one or more reactive functional groups selected from the group consisting of hydroxyl groups, amino groups, thiol groups, hydrazide groups, carboxylic acids, acid anhydride groups, vinyl groups, allyl groups, acrylate groups, methacrylate groups, crotonate groups, isoprenyl groups, acrylamide groups, methacrylamide groups, crotonamide groups, epoxy groups, oxetane groups, oxazoline groups, isocyanate groups, carbodiimide groups, methylol groups, silanol groups, hydroxysilyl groups, and alkoxysilyl groups.

8. Q １ and Q ２ Are they the same reactive functional group, or Q １ and Q ３ The same reactive functional group The degradable crosslinking agent according to claim 7.

9. The degradable crosslinking agent according to claim 7, wherein p1=1, p2=1, or p3=1.

10. The degradable crosslinking agent according to claim 7, which is liquid at 30 to 60°C.

11. A composition comprising the degradable crosslinking agent described in claim 7 and one or more selected from the group consisting of a curable resin, a polymerization initiator, and a solvent.

12. A degradable crosslinked product comprising the composition described in claim 11.

13. A degradable crosslinked product according to claim 12, which can be degraded by contact with an oxidizing agent.

14. A method for decomposing a decomposable crosslinked product, comprising the step of bringing the decomposable crosslinked product described in claim 12 into contact with an aqueous solution containing an oxidizing agent at a temperature of 100°C or lower.

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