Ascorbic acid derivative or salt thereof, additive for initiating polymerization, polymerization initiator, kit for preparing curable composition, curable composition, cured product and dental material

Abstract

An ascorbic acid derivative or a salt thereof that contains a structure in which at least one of hydroxyl groups contained in ascorbic acid has been substituted with an ether bond attached to a carbon atom.

Description

Ascorbic acid derivatives or salts thereof, polymerization initiation additives, polymerization initiators, kits for preparing hardenable compositions, hardenable compositions, hardened products, and dental materials

[0001] The present disclosure relates to an ascorbic acid derivative or a salt thereof, a polymerization initiation additive, a polymerization initiator, a kit for preparing a hardenable composition, a hardenable composition, a cured product, and a dental material.

[0002] In the field of dentistry, synthetic resin moldings are used to repair missing teeth. For example, hardenable compositions known as cements are used as tooth substitutes to repair large missing teeth. In recent years, the range of uses for cements has expanded.

[0003] Photopolymerization initiators, chemical polymerization initiators, etc. can be used for the polymerization of hardenable compositions for dental materials such as cement. For example, one common chemical polymerization initiator system is a redox polymerization initiator, which combines an oxidizing agent and a reducing agent. Known redox polymerization initiators include, for example, polymerization initiator systems that use an organic peroxide as an oxidizing agent and an aromatic amine compound as a reducing agent.

[0004] Patent Document 1 discloses a redox initiator system containing ascorbic acid or an ascorbic acid ester, a transition metal component, an organic peroxide, etc. [Patent Document 1] WO 2016 / 007453

[0005] However, the cured product obtained using ascorbic acid or an ascorbic acid ester as described in Patent Document 1 leaves room for improvement in terms of adhesiveness.

[0006] An object of one embodiment of the present disclosure is to provide an ascorbic acid derivative or a salt thereof that can improve the adhesiveness of the resulting cured product, as well as a polymerization initiation additive, a polymerization initiator, a kit for preparing a curable composition, a curable composition, a cured product, and a dental material that are obtained using the ascorbic acid derivative or a salt thereof.

[0007] Specific means for solving the above problems include the following aspects: <1> An ascorbic acid derivative or a salt thereof, which contains a structure in which at least one of the hydroxyl groups contained in ascorbic acid is substituted with an ether bond bonded to a carbon atom. <2> The ascorbic acid derivative or a salt thereof according to <1>, which contains a structure represented by the following general formula (A):

[0008]

[0009] In general formula (A), * indicates a bonding position to a carbon atom. <3> The ascorbic acid derivative or a salt thereof according to <1> or <2>, wherein the ascorbic acid derivative includes a compound represented by the following general formula (B):

[0010]

[0011] In general formula (B), R １Ｂ and R ２Ｂ <4> In the general formula (B), R １Ｂ or R ２Ｂ is a hydrogen atom, and R １Ｂ or R ２Ｂand the other is a monovalent organic group having 1 to 15 carbon atoms and is a calcium salt. <5> A polymerization initiator additive comprising the ascorbic acid derivative or salt thereof according to any one of <1> to <4>. <6> A polymerization initiator comprising the ascorbic acid derivative or salt thereof according to any one of <1> to <4>, a transition metal compound, and an organic peroxide. <7> A kit for preparing a curable composition, comprising: a first part containing a monomer (A); and a second part containing a monomer (B), wherein at least one of the first part and the second part independently contains the ascorbic acid derivative or salt thereof according to any one of <1> to <4>, a transition metal compound, and an organic peroxide. <8> The kit for preparing a curable composition according to <7>, wherein the first part contains the transition metal compound and the organic peroxide, and the second part contains the ascorbic acid derivative or salt thereof. <9> The curable composition preparation kit according to <7> or <8>, wherein either the monomer (A) in the first part or the monomer (B) in the second part contains an acidic group-containing monomer. <10> The curable composition preparation kit according to <9>, wherein the monomer (A) in the first part contains the acidic group-containing monomer, and the second part contains the ascorbic acid derivative or a salt thereof. <11> The curable composition preparation kit according to any one of <7> to <10>, wherein at least one of the first part and the second part contains at least one polymerization accelerator (1) selected from the group consisting of phosphonite compounds, phosphite compounds, and sulfite compounds. <12> The curable composition preparation kit according to any one of <7> to <11>, wherein the second part contains the ascorbic acid derivative or a salt thereof and the polymerization accelerator (1). <13> The curable composition preparation kit according to any one of <7> to <12>, wherein the first part and the second part contain a filler. <14> The kit for preparing a curable composition according to any one of <7> to <13>, wherein the total content of the ascorbic acid derivative or the salt thereof contained in the first agent and the second agent is 0.1% by mass to 5% by mass, based on the total mass of the curable composition to be prepared.<15> A hardenable composition comprising the ascorbic acid derivative or salt thereof according to any one of <1> to <4>, a transition metal compound, an organic peroxide, and a monomer. <16> A hardened product of the hardenable composition according to <15>. <17> A dental material comprising the hardened product according to <16>.

[0012] According to one embodiment of the present disclosure, it is possible to provide an ascorbic acid derivative or a salt thereof capable of improving the adhesiveness of the resulting cured product, as well as a polymerization initiation additive, a polymerization initiator, a kit for preparing a curable composition, a curable composition, a cured product, and a dental material obtained using the same.

[0013] In the present disclosure, a numerical range indicated using "to" means a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the Examples. In the present disclosure, a combination of two or more preferred embodiments is a more preferred embodiment. In the present disclosure, when multiple substances corresponding to each component are present, the amount of each component refers to the total amount of multiple substances unless otherwise specified. In the present disclosure, "(meth)acrylic" means acrylic and methacrylic, and "(meth)acryloyl" means acryloyl and methacryloyl. In the present disclosure, "A or B" means at least one of A and B, and may include both A and B (for example, a mixture of A and B).

[0014] Ascorbic Acid Derivative or Salt Thereof The ascorbic acid derivative or salt thereof of the present disclosure has a structure in which at least one hydroxyl group contained in ascorbic acid is substituted with an ether bond bonded to a carbon atom. Use of the ascorbic acid derivative or salt thereof of the present disclosure can improve the adhesiveness of the resulting cured product.

[0015] The ascorbic acid derivative or salt thereof according to the present disclosure may be an additive used in a polymerization initiator (an additive for a polymerization initiator), or may be used as a polymerization initiator in combination with other components (e.g., a transition metal compound, an organic peroxide, etc.).

[0016] Examples of the salt of the ascorbic acid derivative of the present disclosure include alkali metal salts of the ascorbic acid derivative and alkaline earth metal salts of the ascorbic acid derivative, and more specifically, sodium salts, potassium salts, magnesium salts, calcium salts of the ascorbic acid derivative, etc. Among these, calcium salts are preferred from the viewpoint of the balance between polymerizability and adhesiveness.

[0017] The ascorbic acid derivative or salt thereof of the present disclosure may contain a structure in which at least one of four hydroxyl groups contained in ascorbic acid is substituted with an ether bond bonded to a carbon atom, and preferably contains a structure in which two of four hydroxyl groups contained in ascorbic acid are substituted with ether bonds bonded to a carbon atom.

[0018] The ascorbic acid derivative of the present disclosure preferably includes a structure represented by the following general formula (A):

[0019]

[0020] In general formula (A), * indicates the bonding position to a carbon atom. Two * in general formula (A) may be bonded to the same carbon atom to form a 1,3-dioxolane skeleton.

[0021] The ascorbic acid derivative of the present disclosure preferably includes a compound represented by the following general formula (B):

[0022]

[0023] In general formula (B), R １Ｂ and R ２Ｂ R are each independently a hydrogen atom or a monovalent organic group. １Ｂ and R ２Ｂ At least one of R is preferably a monovalent organic group. １Ｂ and R ２ＢThe monovalent organic group in R is preferably an organic group having 1 to 12 carbon atoms, more preferably an organic group having 1 to 10 carbon atoms, and even more preferably an organic group having 3 to 10 carbon atoms. １Ｂ and R ２Ｂ The monovalent organic group in is preferably an organic group having 1 to 15 carbon atoms, more preferably an organic group having 3 to 14 carbon atoms, and even more preferably an organic group having 8 to 12 carbon atoms.

[0024] In general formula (B), R １Ｂ or R ２Ｂ is a hydrogen atom, and R １Ｂ or R ２Ｂ The other may be a monovalent organic group having 1 to 10 carbon atoms.

[0025] R １Ｂ and R ２Ｂ The monovalent organic group in may be an organic group containing an oxygen atom, a nitrogen atom, a sulfur atom, or the like, or may be a hydrocarbon group to which an oxygen atom, a nitrogen atom, a sulfur atom, or the like is bonded, or may be a hydrocarbon group.

[0026] The salt of the ascorbic acid derivative of the present disclosure may be a salt of a compound represented by general formula (B), or may be an alkali metal salt or alkaline earth metal salt of a compound represented by general formula (B). From the viewpoint of the balance between polymerizability and adhesiveness, a calcium salt of a compound represented by general formula (B) is preferred.

[0027] When the salt of the ascorbic acid derivative of the present disclosure is a salt of a compound represented by general formula (B), R １Ｂ and R ２Ｂ are preferably each independently a hydrogen atom or a monovalent organic group. １Ｂ or R ２Ｂ is a hydrogen atom, and R １Ｂ or R ２Ｂ The other is a monovalent organic group having 1 to 10 carbon atoms, or R １Ｂ and R ２Ｂ are preferably each independently a monovalent organic group having 1 to 10 carbon atoms. １Ｂ or R ２Ｂis a hydrogen atom, and R １Ｂ or R ２Ｂ and the other is a monovalent organic group having 1 to 10 carbon atoms, R １Ｂ or R ２Ｂ The other of R is preferably a monovalent organic group having 1 to 5 carbon atoms, more preferably a monovalent organic group having 1 to 3 carbon atoms, further preferably a methyl group, ethyl group, propyl group or isopropyl group, and particularly preferably an isopropyl group. １Ｂ and R ２Ｂ are each independently a monovalent organic group having 1 to 10 carbon atoms, R １Ｂ and R ２Ｂ are each independently preferably a monovalent organic group having 1 to 5 carbon atoms, more preferably a monovalent organic group having 1 to 3 carbon atoms, further preferably a methyl group, ethyl group, propyl group, or isopropyl group, and particularly preferably a methyl group.

[0028] An example of a method for producing an ascorbic acid derivative is described in detail below. In this method, ascorbic acid represented by the following general formula (C) is acetalized with an aldehyde compound represented by the following general formula (D) or a ketone compound represented by the following general formula (E) (see dashed line).

[0029]

[0030] R in the general formula (D) is R in the general formula (B) １Ｂ or R ２Ｂ The two R in the general formula (E) are the same as the R in the general formula (B) １Ｂ and R ２Ｂ The two R's in the general formula (E) may be the same or different. Examples of the aldehyde compound represented by the general formula (D) include butanal, isobutanal, hexanal, octanal, and dodecanal. Examples of the ketone compound represented by the general formula (E) include acetone, methyl ethyl ketone, and methyl isobutyl ketone. These compounds may be used alone or in combination of two or more.

[0031] The lower limit of the reaction temperature of the acetalization reaction is not particularly limited, and is, for example, preferably 40° C. or higher, more preferably 50° C. or higher, and even more preferably 60° C. or higher. The upper limit of the reaction temperature of the acetalization reaction is not particularly limited, and is, for example, preferably 90° C. or lower, more preferably 80° C. or lower, and even more preferably 70° C. or lower.

[0032] The lower limit of the reaction time of the acetalization reaction is not particularly limited, and is, for example, preferably 5 hours or more, more preferably 10 hours or more, and even more preferably 20 hours or more. The upper limit of the reaction time of the acetalization reaction is not particularly limited, and is, for example, preferably 100 hours or less, more preferably 80 hours or less, and even more preferably 60 hours or less.

[0033] In the acetalization reaction, a solvent, an acetalization catalyst, etc. may be added as necessary.

[0034] Examples of the solvent include amides such as dimethylacetamide and dimethylformamide. These solvents may be used alone or in combination of two or more. The blending ratio of the solvents is not particularly limited and may be appropriately determined depending on the purpose and application.

[0035] Examples of the acetalization catalyst include known acetalization catalysts such as acids such as p-toluenesulfonic acid. These acetalization catalysts may be used alone or in combination of two or more. The proportion of the esterification catalyst added is appropriately determined depending on the purpose and application.

[0036] An example of a method for producing the alkali metal salt or alkaline earth metal salt of an ascorbic acid derivative, which is the salt of the ascorbic acid derivative, will be described in detail below.

[0037] In this method, an ascorbic acid derivative represented by the following general formula (B) is reacted with an alkali metal salt or alkaline earth metal salt represented by the following general formula (F).

[0038]

[0039] In general formula (F), X represents an alkali metal element or an alkaline earth metal element, and R represents, for example, a carbonate group or a hydroxyl group. Examples of the alkali metal salt or alkaline earth metal salt represented by general formula (F) include sodium hydroxide, sodium bicarbonate, sodium carbonate, calcium hydroxide, calcium carbonate, etc. These may be used alone or in combination of two or more.

[0040] The lower limit of the reaction temperature for the reaction with an alkali metal salt or alkaline earth metal salt (hereinafter also referred to as "alkali metalation reaction") is not particularly limited, and is, for example, preferably 0° C. or higher, more preferably 10° C. or higher, and even more preferably 20° C. or higher. The upper limit of the reaction temperature for the alkali metalation reaction is not particularly limited, and is, for example, preferably 100° C. or lower, more preferably 90° C. or lower, and even more preferably 80° C. or lower.

[0041] The lower limit of the reaction temperature for the alkali metalation reaction is not particularly limited, but is preferably, for example, 0.1 hours or more, more preferably 0.5 hours or more, and even more preferably 1 hour or more. The upper limit of the reaction temperature for the alkali metalation reaction is not particularly limited, but is, for example, preferably 10 hours or less, more preferably 8 hours or less, and even more preferably 6 hours or less.

[0042] In the alkali metalation reaction, a solvent or the like may be added, if necessary.

[0043] Examples of the solvent include alcohols such as methanol, ethanol, 2-propanol, butanol, and hexanol; furans such as tetrahydrofuran; and ketones such as acetone and methyl ethyl ketone. These solvents may be used alone or in combination of two or more. The blending ratio of the solvents is not particularly limited and may be appropriately set depending on the purpose and application.

[0044] <Polymerization Initiating Additive> The polymerization initiating additive of the present disclosure includes the ascorbic acid derivative or a salt thereof of the present disclosure. A combination of the polymerization initiating additive of the present disclosure and other components (e.g., a transition metal compound, an organic peroxide, etc.) can be used as a polymerization initiator.

[0045] The polymerization initiator additive of the present disclosure may be an additive consisting solely of the ascorbic acid derivative or salt thereof of the present disclosure, or may be an additive consisting of the ascorbic acid derivative or salt thereof of the present disclosure and other components.

[0046] <Polymerization Initiator> The polymerization initiator of the present disclosure contains the ascorbic acid derivative or a salt thereof of the present disclosure, a transition metal compound, and an organic peroxide.

[0047] In the polymerization initiator of the present disclosure, the total content of the ascorbic acid derivative and its salt is preferably 10 parts by mass to 70 parts by mass, more preferably 15 parts by mass to 65 parts by mass, and even more preferably 20 parts by mass to 60 parts by mass, relative to 100 parts by mass of the polymerization initiator.

[0048] <Transition Metal Compound> The polymerization initiator of the present disclosure contains a transition metal compound. As the transition metal compound, a compound soluble in the monomer components in the curable composition preparation kit described below is preferred.

[0049] Examples of the transition metal compound include copper compounds, vanadium compounds, molybdenum compounds, scandium compounds, titanium compounds, chromium compounds, manganese compounds, iron compounds, cobalt compounds, nickel compounds, etc. Among the above, the transition metal compound preferably contains at least one of a copper compound and a vanadium compound, and more preferably contains a copper compound.

[0050] Examples of copper compounds include copper carboxylates such as copper acetate, copper isobutyrate, copper gluconate, copper citrate, copper phthalate, copper tartrate, copper oleate, copper octoate, copper octenoate, copper naphthenate, copper methacrylate, and copper 4-cyclohexylbutyrate; β-diketone coppers such as copper acetylacetone, copper trifluoroacetylacetone, copper hexafluoroacetylacetone, copper 2,2,6,6-tetramethyl-3,5-heptanedionato, and copper benzoylacetone; β-ketoester coppers such as copper acetoacetate; copper alkoxides such as copper methoxide, copper ethoxide, copper isopropoxide, copper 2-(2-butoxyethoxy)ethoxide, and copper 2-(2-methoxyethoxy)ethoxide; copper dithiocarbamates such as copper dimethyldithiocarbamate; copper salts of copper and inorganic acids such as copper nitrate and copper chloride. These may be used alone or in combination of two or more. Among these, copper carboxylate, copper β-diketone, and copper β-ketoester are preferred, and copper acetate and copper acetylacetone are more preferred, from the viewpoint of solubility in and reactivity with the monomer.

[0051] Examples of vanadium compounds include vanadyl acetylacetonate, vanadium naphthenate (III), vanadyl stearate, vanadium benzoylacetonate, bis(maltolato)oxovanadium (IV), and oxobis(1-phenyl-1,3-butanedionato)vanadium (IV).

[0052] In the polymerization initiator of the present disclosure, the content of the transition metal compound is preferably 0.1 parts by mass to 1.5 parts by mass, more preferably 0.2 parts by mass to 1 part by mass, and even more preferably 0.3 parts by mass to 1 part by mass, relative to 100 parts by mass of the polymerization initiator.

[0053] <Organic Peroxide> The polymerization initiator of the present disclosure includes an organic peroxide. The organic peroxide is not particularly limited and known organic peroxides can be used. Representative organic peroxides include hydroperoxides, peroxyesters, ketone peroxides, peroxyketals, dialkyl peroxides, diacyl peroxides, and peroxydicarbonates. Among these, hydroperoxides are preferred because they have little fluctuation in the usable time even when the curable composition is provided in a packaged form and stored for a long period of time. One type of organic peroxide may be used alone, or multiple types may be used in combination.

[0054] More specifically, examples of the hydroperoxide include cumene hydroperoxide, t-butyl hydroperoxide, t-hexyl hydroperoxide, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, and t-amyl hydroperoxide.

[0055] Any peroxyester can be used without any limitations as long as it contains an acyl group on one side of a peroxy group (-OO- group) and a hydrocarbon group (or a group similar thereto) on the other side. Specific examples include α,α-bis(neodecanoylperoxy)diisopropylbenzene, cumyl peroxy neodecanoate, 1,1,3,3-tetramethylbutyl peroxy neodecanoate, 1-cyclohexyl-1-methylethyl peroxy neodecanoate, t-hexyl peroxy neodecanoate, t-butyl peroxy neodecanoate, t-hexyl peroxy pivalate, t-butyl peroxy pivalate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1-cyclohexyl-1-methylethyl peroxy-2-ethylhexanoate, t-hexyl peroxy 2-ethylhexanoate, and t-butyl peroxy 2-ethylhexanoate. Examples include 2,5-dimethyl-2,5-bis(m-toluoylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, t-butylperoxymaleic acid, t-butylperoxy 3,5,5-trimethylhexanoate, t-butylperoxylaurate, 2,5-dimethyl-2,5-bis(m-toluoylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, t-butylperoxy 2-ethylhexyl monocarbonate, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butylperoxyacetate, t-butylperoxy-m-toluoyl benzoate, t-butylperoxybenzoate, bis(t-butylperoxy)isophthalate, etc. These can be used alone or in appropriate combinations of two or more.

[0056] Examples of the ketone peroxide include methyl ethyl ketone peroxide, cyclohexanoperoxide, methylcyclohexanone peroxide, methylacetoacetate peroxide, and acetylacetone peroxide.

[0057] Examples of peroxyketals include 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexanone, 1,1-bis(t-butylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)cyclodecane, 2,2-bis(t-butylperoxy)butane, n-butyl 4,4-bis(t-butylperoxy)valerate, and 2,2-bis(4,4-di-t-butylperoxycyclohexyl)propane.

[0058] Examples of dialkyl peroxides include α,α-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylcumyl peroxide, di-t-butyl peroxide, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane-3.

[0059] Examples of diacyl peroxides include isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearyl peroxide, succinic acid peroxide, m-toluoylbenzoyl peroxide, and benzoyl peroxides.

[0060] Examples of peroxydicarbonates include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-2-methoxybutyl peroxydicarbonate, and di(3-methyl-3-methoxybutyl) peroxydicarbonate.

[0061] In the polymerization initiator of the present disclosure, the content of the organic peroxide is preferably 20 parts by mass to 90 parts by mass, more preferably 30 parts by mass to 85 parts by mass, and even more preferably 40 parts by mass to 80 parts by mass, relative to 100 parts by mass of the polymerization initiator.

[0062] <Kit for Preparing Curable Composition> The kit for preparing a curable composition according to the present disclosure includes a first agent containing a monomer (A) and a second agent containing a monomer (B), and at least one of the first agent and the second agent independently contains the ascorbic acid derivative or a salt thereof according to the present disclosure, a transition metal compound, and an organic peroxide.

[0063] From the viewpoint of inhibiting the reaction between the ascorbic acid derivative or its salt and the transition metal compound or organic peroxide, it is preferable that the first agent contains a transition metal compound and an organic peroxide, and the second agent contains an ascorbic acid derivative or its salt.

[0064] <Monomer> In the kit for preparing a curable composition according to the present disclosure, the first part contains a monomer (A), and the second part contains a monomer (B). The monomer (A) and the monomer (B) may be the same monomer or different monomers. Known monomers can be used as the monomer (A) and the monomer (B). The monomer (A) and the monomer (B) may be monomers that do not contain an acidic group, or may be monomers that contain an acidic group (hereinafter also referred to as "acidic group-containing monomers"). It is preferable that the monomer (A) and the monomer (B) contain a monomer that does not contain an acidic group.

[0065] The monomer is a monomer that undergoes a radical polymerization reaction to be polymerized by the action of the ascorbic acid derivative or its salt, a transition metal compound, and an organic peroxide of the present disclosure. The monomer constituting the monomer of the present disclosure is not limited to one type, and may be two or more types. Examples of the monomer that does not contain an acidic group include a (meth)acrylate monomer that does not contain an acidic group. Examples of the (meth)acrylate monomer that does not contain an acidic group include a monofunctional monomer, a bifunctional monomer, and a trifunctional or higher functional monomer.

[0066] In the present disclosure, the content of the monomers (i.e., the total amount of the monomer (A) and the monomer (B) in the curable composition to be prepared) is preferably 10% by mass to 90% by mass, more preferably 20% by mass to 75% by mass, and even more preferably 30% by mass to 60% by mass, relative to the total mass of the curable composition to be prepared.

[0067] Examples of the monofunctional monomer include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1,3-dihydroxypropyl (meth)acrylate, and 2,3-dihydroxypropyl (meth)acrylate. Among these, 2-hydroxyethyl methacrylate (HEMA) is preferred.

[0068] Examples of aromatic compound-based bifunctional monomers include 2,2-bis((meth)acryloyloxyphenyl)propane, 2,2-bis[4-(3-(meth)acryloyloxy)-2-hydroxypropoxyphenyl]propane, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypolyethoxyphenyl)propane, and 2,2-bis(4-(meth)acryloyloxypolypropoxyphenyl)propane. Of these, 2,2-bis[4-(3-(methacryloyloxy)-2-hydroxypropoxyphenyl)propane (commonly known as "Bis-GMA") and 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane are preferred.

[0069] Examples of aliphatic compound-based bifunctional monomers include erythritol di(meth)acrylate, sorbitol di(meth)acrylate, mannitol di(meth)acrylate, pentaerythritol di(meth)acrylate, dipentaerythritol di(meth)acrylate, glycerol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and butylene glycol di(meth)acrylate. acrylate, neopentyl glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (UDMA), 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane, and the like. Among these, glycerol dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), 1,6-hexanediol dimethacrylate (HexDMA), neopentyl glycol dimethacrylate (NPG), 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (UDMA), and 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane are preferred.

[0070] Examples of tri- or higher functional monomers include trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, N,N-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate, and 1,7-diacryloyloxy-2,2,6,6-tetraacryloyloxymethyl-4-oxyheptane.

[0071] The above-mentioned monomers may be blended either individually or in combination.

[0072] The amount of the above-mentioned monomer not containing an acidic group is preferably in the range of 10 parts by mass to 100 parts by mass, more preferably 20 parts by mass to 100 parts by mass, and even more preferably 50 parts by mass to 100 parts by mass, relative to 100 parts by mass of the total amount of the monomer components in the curable composition preparation kit of the present disclosure. Furthermore, when the monomer components in the curable composition preparation kit of the present disclosure include an acidic group-containing monomer described below, the amount of the monomer not containing an acidic group is preferably 10 parts by mass to 99 parts by mass, more preferably 30 parts by mass to 97 parts by mass, and even more preferably 50 parts by mass to 95 parts by mass, relative to 100 parts by mass of the total amount of the monomer components in the curable composition preparation kit of the present disclosure.

[0073] Monomer (A) and monomer (B) preferably contain a (meth)acrylic monomer (C) having a molecular weight of 100 to 5000. The molecular weight of the (meth)acrylic monomer (C) is more preferably 120 to 3000, even more preferably 150 to 2000, and particularly preferably 200 to 1000.

[0074] The content of the (meth)acrylic monomer (C) relative to the total content of the monomer (A) and the monomer (B) is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 90% by mass or more.

[0075] In the kit for preparing a curable composition according to the present disclosure, it is preferable that either the monomer (A) in the first agent or the monomer (B) in the second agent contains an acidic group-containing monomer. When at least one of the first agent and the second agent contains an acidic group-containing monomer, for example, when the kit for preparing a curable composition according to the present disclosure is used for dental purposes, it is possible to impart good tooth structure and high adhesion to dental prosthetic materials.

[0076] From the viewpoint of suppressing the reaction between the ascorbic acid derivative or its salt and the acidic group-containing monomer, it is preferable that the monomer (A) in the first agent contains an acidic group-containing monomer and the second agent contains an ascorbic acid derivative or its salt, and it is more preferable that the monomer (A) in the first agent contains an acidic group-containing monomer and the second agent does not contain an acidic group-containing monomer and contains an ascorbic acid derivative or its salt.

[0077] Examples of the acidic group-containing monomer include monomers having at least one acidic group such as a phosphate group, pyrophosphate group, thiophosphate group, phosphonate group, sulfonic acid group, or carboxylic acid group, and at least one polymerizable group such as an acryloyl group, methacryloyl group, vinyl group, or styrene group. The acidic group-containing monomer has affinity for the adherend and also has a demineralizing effect on tooth structure.

[0078] Examples of the phosphate group-containing monomer include (meth)acryloyloxyalkyl dihydrogen phosphates such as 10-(meth)acryloyloxydecyl dihydrogen phosphate (MDP), bis[2-(meth)acryloyloxyethyl]hydrogen phosphate, bis[4-(meth)acryloyloxybutyl]hydrogen phosphate, bis[6-(meth)acryloyloxyhexyl]hydrogen phosphate, bis[8-(meth)acryloyloxyoctyl]hydrogen phosphate, bis[9-(meth)acryloyloxy Examples of the alkyl acrylate include 2-(meth)acryloyloxyethylphenyl]hydrogenphosphate, bis[10-(meth)acryloyloxydecyl]hydrogenphosphate, 1,3-di(meth)acryloyloxypropyl dihydrogenphosphate, 2-(meth)acryloyloxyethylphenylhydrogenphosphate, 2-(meth)acryloyloxyethyl-2-bromoethylhydrogenphosphate, bis[2-(meth)acryloyloxy-(1-hydroxymethyl)ethyl]hydrogenphosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0079] Examples of pyrophosphate group-containing monomers include bis[2-(meth)acryloyloxyethyl]pyrophosphate, bis[4-(meth)acryloyloxybutyl]pyrophosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0080] Examples of thiophosphate group-containing monomers include 2-(meth)acryloyloxyethyl dihydrogenthiophosphate, 3-(meth)acryloyloxypropyl dihydrogenthiophosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0081] Examples of phosphonic acid group-containing monomers include 2-(meth)acryloyloxyethylphenylphosphonate, 5-(meth)acryloyloxypentyl-3-phosphonopropionate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0082] Examples of sulfonic acid group-containing monomers include 2-(meth)acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, and 2-sulfoethyl(meth)acrylate.

[0083] Carboxylic acid group-containing monomers include monomers containing one carboxy group in the molecule and monomers containing multiple carboxy groups in the molecule.

[0084] Examples of monomers containing one carboxy group in the molecule include (meth)acrylic acid, N-(meth)acryloylglycine, N-(meth)acryloylaspartic acid, O-(meth)acryloyltyrosine, N-(meth)acryloyltyrosine, N-(meth)acryloylphenylalanine, N-(meth)acryloyl-p-aminobenzoic acid, N-(meth)acryloyl-o-aminobenzoic acid, p-vinylbenzoic acid, and 2-(meth)acryloyloxybenzoic acid. Examples of the acryloyloxybenzoic acid include 3-(meth)acryloyloxybenzoic acid, 4-(meth)acryloyloxybenzoic acid, N-(meth)acryloyl-5-aminosalicylic acid, N-(meth)acryloyl-4-aminosalicylic acid, 2-(meth)acryloyloxyethyl hydrogen succinate, 2-(meth)acryloyloxyethyl hydrogen phthalate, 2-(meth)acryloyloxyethyl hydrogen maleate, and acid halides thereof.

[0085] Examples of monomers containing multiple carboxy groups in the molecule include 6-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 9-(meth)acryloyloxynonane-1,1-dicarboxylic acid, 10-(meth)acryloyloxydecane-1,1-dicarboxylic acid, 11-(meth)acryloyloxyundecane-1,1-dicarboxylic acid, 12-(meth)acryloyloxydodecane-1,1-dicarboxylic acid, 13-(meth)acryloyloxytridecane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyethyl trimellitate, Examples include 4-(meth)acryloyloxyethyl trimellitate anhydride, 4-(meth)acryloyloxybutyl trimellitate, 4-(meth)acryloyloxyhexyl trimellitate, 4-(meth)acryloyloxydecyl trimellitate, 2-(meth)acryloyloxyethyl-3'-(meth)acryloyloxy-2'-(3,4-dicarboxybenzoyloxy)propyl succinate, dihydroxyethyl methacrylate trimethylhexyl dicarbamate, and acid anhydrides or acid halides thereof.

[0086] Among the above-mentioned acidic group-containing monomers, 10-(meth)acryloyloxydecyl dihydrogen phosphate (MDP), 1,3-di(meth)acryloyloxypropyl dihydrogen phosphate, 2-(meth)acryloyloxyethyl dihydrogen phosphate, 4-(meth)acryloyloxyethyl trimellitate anhydride, 4-(meth)acryloyloxyethyl trimellitate, 2-(meth)acrylamido-2-methylpropanesulfonic acid, 11-(meth)acryloyloxyundecane-1,1-dicarboxylic acid, and dihydroxyethyl methacrylate trimethylhexyl dicarbamate are preferred in terms of their high adhesive strength to adherends. The above-mentioned acidic group-containing monomers may be used alone or in combination of two or more types.

[0087] The amount of the acidic group-containing monomer is preferably 1 to 50 parts by mass, more preferably 3 to 40 parts by mass, and even more preferably 5 to 30 parts by mass, relative to 100 parts by mass of the total amount of the monomer components in the curable composition preparation kit of the present disclosure. When the amount of the acidic group-containing monomer is 1 part by mass or more, it is easy to obtain high adhesion to various adherends. Furthermore, when the amount of the acidic group-containing monomer is 50 parts by mass or less, it is easy to maintain a balance between polymerizability and adhesiveness. Note that the total amount of the monomer components means the combined amount of the acidic group-containing monomer and the above-mentioned monomer not containing an acidic group.

[0088] As the monomer in the present disclosure, for example, monomers described in known documents such as WO 2012 / 157566, WO 2015 / 015220, WO 2015 / 015221, and JP 2016-094482 A can be used.

[0089] From the viewpoint of adhesiveness, the total content of the ascorbic acid derivative or a salt thereof contained in the first agent and the second agent is preferably 0.1% by mass to 5% by mass, more preferably 0.3% by mass to 3% by mass, and even more preferably 0.5% by mass to 2% by mass, relative to the total mass of the curable composition prepared.

[0090] From the viewpoint of curability, the total content of the transition metal compounds contained in the first agent and the second agent is preferably 0.00005 parts by mass to 0.1 parts by mass, more preferably 0.0001 parts by mass to 0.05 parts by mass, and even more preferably 0.001 parts by mass to 0.03 parts by mass, relative to 100 parts by mass of the total amount of the monomer components in the curable composition preparation kit of the present disclosure.

[0091] From the viewpoint of curability, the total content of the organic peroxides contained in the first agent and the second agent is preferably 0.01 parts by mass to 6 parts by mass, more preferably 0.01 parts by mass to 4 parts by mass, and even more preferably 0.05 parts by mass to 3 parts by mass, relative to 100 parts by mass of the total amount of the monomer components in the curable composition preparation kit of the present disclosure.

[0092] In the kit for preparing a curable composition according to the present disclosure, at least one of the first agent and the second agent may contain at least one polymerization accelerator (1) selected from the group consisting of a phosphonite compound, a phosphite compound, and a sulfite compound.

[0093] From the viewpoint that the polymerization accelerator (1) can function as a stabilizer for the ascorbic acid derivative or a salt thereof, the second agent preferably contains the ascorbic acid derivative or a salt thereof and the polymerization accelerator (1).

[0094] <Phosphonite Compound> The phosphonite compound may be any trivalent organic phosphorus compound in which a carbon atom is bonded to a phosphorus atom. The phosphonite compound contained in the polymerization accelerator (1) of the present disclosure preferably has a structure represented by the following general formula (I):

[0095]

[0096] In general formula (I), * indicates the bonding position to a carbon atom. Three * are preferably bonding positions to carbon atoms contained in a hydrocarbon group, and more preferably bonding positions to carbon atoms contained in a benzene ring.

[0097] The phosphonite compound may contain one structure represented by general formula (I), or may contain two or more structures represented by general formula (I). The phosphonite compound preferably contains two structures represented by general formula (I), and more preferably contains a structure in which two structures represented by general formula (I) are bonded via a divalent linking group (preferably a biphenyl structure).

[0098] The phosphonite compound contained in the polymerization accelerator (1) of the present disclosure preferably includes a compound represented by the following general formula (II):

[0099]

[0100] In general formula (II), R Ｂ１ is an n-valent hydrocarbon group, and R Ｂ２ and R Ｂ３ are each independently a monovalent hydrocarbon group, and n is an integer of 1 or 2.

[0101] R Ｂ１Examples of the n-valent hydrocarbon group in the formula (I) include an n-valent aliphatic hydrocarbon group, an n-valent alicyclic hydrocarbon group, an n-valent aromatic hydrocarbon group, and a combination of two or more of these.

[0102] R Ｂ１ The monovalent hydrocarbon group in R is preferably an alkyl group, a phenyl group, a biphenyl group, or the like. Ｂ１ The hydrogen atoms of the phenyl group or biphenyl group in R may be substituted with a substituent such as an alkyl group. Ｂ１ The divalent hydrocarbon group in R is preferably an alkylene group, a phenylene group, or a biphenylene group such as a 4,4'-biphenylene group, a 4,3'-biphenylene group, or a 3,3'-biphenylene group. Ｂ１ The hydrogen atoms contained in the phenylene group or biphenylene group in the formula (I) may be substituted with a substituent such as an alkyl group.

[0103] R Ｂ２ and R Ｂ３ are each independently a monovalent hydrocarbon group, and an alkyl group, a phenyl group, or the like is preferred. Ｂ２ and R Ｂ３ The hydrogen atom contained in the phenyl group in the formula (I) may be substituted with an alkyl group such as a tert-butyl group or an n-butyl group.

[0104] n is an integer of 1 or 2, with 2 being preferred.

[0105] Specific examples of the phosphonite compound contained in the polymerization accelerator (1) of the present disclosure include, for example, tetrakis(2,4-di-tert-butylphenyl)4,4′-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butyl-5-methylphenyl)4,4′-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)4,3′-biphenylene-di-phosphonite, tetrakis(2,4-di-tert-butylphenyl)3,3′-biphenylene-di-phosphonite, tetrakis(2,6-di-tert-butylphenyl)-4,4′-biphenylene-di-phosphonite, tetrakis(2,6-di-t bis(2,4-di-tert-butylphenyl)-4,3'-biphenylene-di-phosphonite, tetrakis(2,6-di-tert-butylphenyl)-3,3'-biphenylene-di-phosphonite, bis(2,4-di-tert-butylphenyl)-4-phenyl-phenylphosphonite, bis(2,4-di-tert-butylphenyl)-3-phenyl-phenylphosphonite, bis(2,6-di-n-butylphenyl)-3-phenyl-phenylphosphonite, bis(2,6-di-tert-butylphenyl)-4-phenyl-phenylphosphonite, bis(2,6-di-tert-butylphenyl)-3-phenyl-phenylphosphonite, and the like.

[0106] Examples of the phosphite compound include triphenyl phosphite, trisnonylphenyl phosphite, tricresyl phosphite, diphenyl mono(2-ethylhexyl) phosphite, diphenyl monodecyl phosphite, diphenyl mono(tridecyl) phosphite, and tris(2,4-di-tert-butylphenyl) phosphite.

[0107] Examples of sulfite compounds include ethylene sulfite, propylene sulfite, dimethyl sulfite, diethyl sulfite, ethyl methyl sulfite, methyl-n-propyl sulfite, ethyl-n-propyl sulfite, di-n-propyl sulfite, diphenyl sulfite, methyl phenyl sulfite, ethyl sulfite, dibenzyl sulfite, benzyl methyl sulfite, and benzyl ethyl sulfite.

[0108] From the viewpoint of curability, the total content of the polymerization accelerator (1) contained in the first agent and the second agent is preferably 0.1 to 5 parts by mass, and more preferably 0.2 to 2 parts by mass, relative to 100 parts by mass of the total amount of the first agent and the second agent.

[0109] In the kit for preparing a curable composition according to the present disclosure, at least one of the first and second parts may contain a polymerization accelerator (2) other than the polymerization accelerator (1). The polymerization accelerator (2) according to the present disclosure is not particularly limited, and examples thereof include inorganic salts and thiourea.

[0110] Examples of inorganic salts include sodium sulfite, calcium sulfite, potassium sulfite, potassium nitrate, potassium chloride, potassium sulfate, and sodium chloride.

[0111] Examples of thioureas include acetylthiourea, phenylthiourea, triethylthiourea, tetramethylthiourea, dimethylthiourea, and diphenylthiourea.

[0112] From the viewpoint of curability, the total content of the polymerization accelerator (2) contained in the first agent and the second agent is preferably 0.0001 parts by mass to 1 part by mass, and more preferably 0.001 parts by mass to 0.1 parts by mass, relative to 100 parts by mass of the total amount of the first agent and the second agent.

[0113] From the viewpoint of curability, the total content of the inorganic salts contained in the first and second agents is preferably 0.0001 to 0.1 parts by mass, and more preferably 0.001 to 0.01 parts by mass, relative to 100 parts by mass of the total amount of the first and second agents.

[0114] From the viewpoint of curability, the total content of thiourea contained in the first agent and the second agent is preferably 0.001 part by mass to 1.0 part by mass, and more preferably 0.01 part by mass to 0.1 part by mass, relative to 100 parts by mass of the total amount of the first agent and the second agent.

[0115] <Filler> In the kit for preparing a curable composition according to the present disclosure, at least one of the first and second agents may contain a filler, and it is preferable that the first and second agents contain a filler. The filler may be a single type or a combination of multiple types. Examples of the filler include inorganic fillers, organic fillers, and composite fillers of inorganic and organic fillers.

[0116] Examples of inorganic fillers include silica; silica-based minerals such as kaolin, clay, mica, and mica; silica-based Al fillers; ２ O ３ , B ２ O ３ , TiO ２ , ZrO ２ , BaO, La ２ O ３ , SrO, ZnO, CaO, P ２ O ５ , Li ２ O, Na ２Examples of suitable glass include ceramics and glasses containing 0 and the like. Suitable glass materials include lanthanum glass, barium glass, strontium glass, soda glass, lithium borosilicate glass, zinc glass, fluoroaluminosilicate glass, borosilicate glass, and bioglass. Suitable materials include crystalline quartz, hydroxyapatite, alumina, titanium oxide, yttrium oxide, zirconia, calcium phosphate, barium sulfate, aluminum hydroxide, sodium fluoride, potassium fluoride, sodium monofluorophosphate, lithium fluoride, and ytterbium fluoride. Specifically, in terms of adhesive strength and ease of handling, finely divided silica particles having a primary particle size of 0.001 μm to 0.1 μm are preferably used. Commercially available products include "Aerosil OX50," "Aerosil 50," "Aerosil 200," "Aerosil 380," "Aerosil R972," and "Aerosil 130" (all manufactured by Nippon Aerosil Co., Ltd.).

[0117] Examples of organic fillers include polymethyl methacrylate, polyethyl methacrylate, polyfunctional methacrylate polymers, polyamide, polystyrene, polyvinyl chloride, chloroprene rubber, nitrile rubber, and styrene-butadiene rubber.

[0118] Examples of composite fillers of inorganic and organic fillers include those in which inorganic fillers are dispersed in organic fillers, and inorganic / organic composite fillers in which inorganic fillers are coated with various polymers.

[0119] To improve curability, mechanical strength, and handleability, the filler may be surface-treated in advance with a known surface treatment agent such as a silane coupling agent. Examples of surface treatment agents include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri(β-methoxyethoxy)silane, γ-methacryloyloxypropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, and γ-aminopropyltriethoxysilane.

[0120] The total content of the filler contained in the first agent and the second agent is preferably in the range of 10% by mass to 80% by mass, more preferably in the range of 30% by mass to 80% by mass, and even more preferably in the range of 50% by mass to 75% by mass, relative to the total mass of the curable composition to be prepared.

[0121] (Non-conductive filler) In the kit for preparing a curable composition according to the present disclosure, at least one of the first and second parts preferably contains a non-conductive filler. －４ The upper limit of the resistance value of the non-conductive filler is not particularly limited, and is, for example, 1.00 × 10 ２０ Examples of materials for the non-conductive filler include organic substances such as polyethylene, polystyrene, phenolic resin, epoxy resin, acrylic resin, and benzoguanamine resin, and inorganic substances such as silica (dimethyl silylated silica, etc.), silicates (borosilicate glass (barium borosilicate glass, etc.), aluminosilicate glass (boroaluminosilicate glass, strontium boroaluminosilicate glass, fluoroaluminosilicate glass, barium aluminosilicate glass, etc.)), ceramics, boron nitride, and barium nitride.

[0122] Among the above, silica and silicates are preferred as the material of the non-conductive filler, and dimethylsilyl silica and barium aluminosilicate are more preferred.

[0123] Preferably, the first agent contains a non-conductive filler, and the content of the non-conductive filler relative to the total mass of the first agent is 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more. When the non-conductive filler is contained in the second agent, the second agent contains a non-conductive filler, and the content of the non-conductive filler relative to the total mass of the second agent is 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more. In the kit for preparing a curable composition of the present disclosure, when the non-conductive filler is contained in the first agent, the content of the non-conductive filler relative to the total mass of the first agent is 10% by mass or more, and when the non-conductive filler is contained in the second agent, the content of the non-conductive filler relative to the total mass of the second agent is 10% by mass or more.

[0124] <Additives> In the curable composition preparation kit of the present disclosure, at least one of the first and second parts may independently contain additives such as a photopolymerization initiator, a stabilizer (polymerization inhibitor), a colorant, a fluorescent agent, and an ultraviolet absorber. As the photopolymerization initiator, known photopolymerization initiators can be used, such as camphorquinone (CQ) and ethyl dimethylaminobenzoate (EDB). Furthermore, antibacterial substances such as cetylpyridinium chloride, benzalkonium chloride, (meth)acryloyloxydodecylpyridinium bromide, (meth)acryloyloxyhexadecylpyridinium chloride, (meth)acryloyloxydecylammonium chloride, and triclosan may also be incorporated. Known dyes and pigments may also be incorporated into the curable composition preparation kit of the present disclosure.

[0125] The hardenable composition preparation kit of the present disclosure is preferably used for dental materials. Dental materials are not particularly limited, and examples thereof include dental adhesives, dental filling materials, dental sealants (dental fissure sealants), core builders, denture base resins, denture base lining materials, crown prosthetic resins (hard crown resins), and dental self-polymerizing resins. The hardenable composition preparation kit of the present disclosure is particularly preferably used as a dental adhesive. Examples of dental adhesives include dental adhesive resin cements, orthodontic adhesives, adhesives for fixing loose teeth, cavity adhesives, and dental bonding materials, with dental adhesive resin cements being preferred. Examples of dental filling materials include dental composite resins (including dental self-adhesive composite resins), root canal filling materials, temporary sealing materials, and lining materials.

[0126] <Curable Composition> The curable composition of the present disclosure comprises the ascorbic acid derivative or salt thereof of the present disclosure, a transition metal compound, an organic peroxide, and a monomer. When the curable composition of the present disclosure comprises the above-described components, polymerizability can be favorably improved. Specific examples, preferred aspects, etc. of the monomer in the curable composition are the same as those of the monomer described above. It is preferable that the curable composition of the present disclosure further comprises a non-conductive filler. Specific examples, preferred aspects, etc. of the non-conductive filler in the curable composition are the same as those of the non-conductive filler described above. The curable composition of the present disclosure may comprise the additives described above.

[0127] <Cured Product> The cured product of the present disclosure is a cured product of the curable composition of the present disclosure, or a cured product obtained using the kit for preparing a curable composition of the present disclosure. The cured product of the present disclosure can be suitably used as a dental material. That is, the dental material of the present disclosure preferably includes the cured product of the present disclosure.

[0128] Examples of the present disclosure will be shown below, but the present disclosure is not limited to the following examples.

[0129] The components used in this example are as follows: <Polymerization accelerator> PPP: tetrakis(2,4-di-tert-butylphenyl)[1,1'-biphenyl]-4,4'-diylbis(phosphonite) NaCl: sodium chloride ATH: acetylthiourea <Transition metal compound> Cu(OAc) ２monohydrate: copper acetate monohydrate <Filler> GM27884 UF1.5 Sil2.3%: GM27884 manufactured by Schott, 1.5 μm, silane coupling agent treatment amount 2.3% R812: AEROSIL® R812 manufactured by Evonik SG-YBF100WSCMP10: ytterbium filler, 0.1 μm <Ascorbic acid derivatives having ether bonds> C4AAA: 3,4-dihydroxy-5-(2-propyl-1,3-dioxolan-4-yl)furan-2(5H)-one C4isoAAA: 3,4-dihydroxy-5-(2-isopropyl-1,3-dioxolan-4-yl)furan-2(5H)-one C6AAA: 3,4-dihydroxy-5-(2-pentyl-1,3-dioxolan-4-yl)furan-2(5H)-one C12AAA: 3,4-dihydroxy-5-(2-undecyl-1,3-dioxolan-4-yl)furan-2(5H)-one IPDAA: 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxyfuran-2(5H)-one <Salts of ascorbic acid derivatives having an ether bond> C4AAANa: 4-hydroxy-5-oxo-2-(2-propyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-oleate sodium C4isoAAANa: sodium 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-olate C4isoAAACa: calcium 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-olate IPDAANa: sodium 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate IPDAACa: calcium 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate C6AAACa: 4-hydroxy-5-oxo-2-(2-pentyl-1,3-dioxolan-4-yl)-2,5-Dihydroxyfuran-3-calcium oleate C12AAACa: 4-hydroxy-5-oxo-2-(2-undecyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-calcium oleate <Other ascorbic acids> AS6P: Ascorbic acid palmitoyl ester AA: Ascorbic acid <Monomers not containing an acidic group> 2-HBMA: 2-hydroxybutyl methacrylate TEGDMA: Triethylene glycol dimethacrylate UDMA: Trimethylhexyl diurethane hydroxymethacrylate <Monomers containing an acidic group> MDP: 10-methacryloyloxydecyl dihydrogen phosphate <Organic peroxides> Luperox TAH: tert-amyl hydroperoxide <Photopolymerization initiator> BEDB: 2-butoxyethyl-4-(dimethylamino)benzoate CQ: Camphorquinone <Polymerization inhibitor> BHT: 2,6-di-tert-butyl-p-cresol,

[0130]

[0131] Synthesis Example 1 (Synthesis of C4AAA: 3,4-dihydroxy-5-(2-propyl-1,3-dioxolan-4-yl)furan-2(5H)-one) Ascorbic acid (10.0 g, 56.8 mmol) and dimethylacetamide (15 mL) as a solvent were placed in an apparatus connected to a 200 mL eggplant-bottom flask and a Dimroth condenser, and the temperature was raised to 60°C, and the solution was stirred uniformly. Next, n-butanal (4.04 g, 56.8 mmol) was added, and the solution was stirred uniformly. Furthermore, p-toluenesulfonic acid monohydrate (1.14 g, 5.7 mmol), an acid catalyst, was added, and the solution was stirred uniformly. Then, the reaction was stopped after 20 hours, and the solution was cooled to room temperature.

[0132] The resulting reaction product was then extracted. Specifically, an equal amount of distilled water was added to the reaction solution, followed by an equal amount of diethyl ether, and the mixture was extracted and washed in a separatory funnel. After repeating the above extraction three times, an equal amount of distilled water was added to the resulting organic layer, and the mixture was washed in a separatory funnel. After repeating the above washing three times, sodium sulfate was added to the resulting organic layer to dry it, and then the organic layer was concentrated under reduced pressure. The resulting crude product was washed with a hexane / ethyl acetate solvent and separated and purified by filtration.

[0133] As a result of the above, 3,4-dihydroxy-5-(2-propyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C4AAA, 2.2 g, 9.56 mmol, yield 16.8%) was obtained. １ H-NMR (CD ３ The assignments by OD are shown below. １ H-NMR: δ0.91 (t, 3H, J=7.3Hz), 1.39 (td, 2H, J=15.1Hz, 7.5Hz), 1.55 (tt, 2H, J=9. 0Hz, 2.6Hz), 3.89-4.30 (m, 3H), 4.67 (dd, 1H, J=12.6Hz, 3.0Hz), 4.86-4,90 (m, 1H)

[0134] Synthesis Example 2 (Synthesis of C4isoAAA: 3,4-dihydroxy-5-(2-isopropyl-1,3-dioxolan-4-yl)furan-2(5H)-one) Ascorbic acid (50.0 g, 284 mmol) and dimethylacetamide (105 mL) as a solvent were placed in an apparatus connected to a 300 mL eggplant-bottom flask and a Dimroth condenser, and the temperature was raised to 60°C, and the solution was stirred uniformly. Next, isobutanal (20.2 g, 284 mmol) was added, and the solution was stirred uniformly. Furthermore, p-toluenesulfonic acid monohydrate (5.7 g, 28 mmol), an acid catalyst, was added, and the solution was stirred uniformly. Then, the reaction was stopped after 20 hours, and the solution was cooled to room temperature.

[0135] Thereafter, the resulting reaction product was extracted in the same manner as in Synthesis Example 1. As a result, 3,4-dihydroxy-5-(2-isopropyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C4isoAAA, 16 g, 70 mmol, yield 24.6%) was obtained. １ H-NMR (CD ３ The assignments by OD are shown below. １ H-NMR: δ0.39 (td, 6H, J = 4.5Hz, 2.2Hz), 1.19-1.30 (m, 1H), 3.39-3.79 (m, 3H), 4.10-4.19 (m, 2H)

[0136] Synthesis Example 3 (Synthesis of C6AAA: 3,4-dihydroxy-5-(2-pentyl-1,3-dioxolan-4-yl)furan-2(5H)-one) Ascorbic acid (10.0 g, 56.8 mmol) and dimethylacetamide (15 mL) as a solvent were placed in an apparatus connected to a 300 mL eggplant-bottom flask and a Dimroth condenser, and the temperature was raised to 60°C, and the solution was stirred uniformly. Next, n-hexanal (5.69 g, 56.8 mmol) was added, and the solution was stirred uniformly. Furthermore, p-toluenesulfonic acid monohydrate (1.14 g, 5.7 mmol), an acid catalyst, was added, and the solution was stirred uniformly. Then, the reaction was stopped after 20 hours, and the solution was cooled to room temperature.

[0137] Thereafter, the resulting reaction product was extracted in the same manner as in Synthesis Example 1. As a result, 3,4-dihydroxy-5-(2-pentyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C6AAA, 4.73 g, 18.3 mmol, yield 32.2%) was obtained. １ H-NMR (CD ３ The assignments by OD are shown below. １ H-NMR: δ0.40 (m, 3H), 0.76-0.92 (m, 6H), 1.09 (ddd, 2H, J = 17.1Hz , 8.5Hz, 4.4Hz), 3.40-3.50 (m, 4H), 3.59 (dd, 1H, J=8.5Hz, 4.6Hz)

[0138] Synthesis Example 4 (Synthesis of C12AAA: 3,4-dihydroxy-5-(2-undecyl-1,3-dioxolan-4-yl)furan-2(5H)-one) Ascorbic acid (13.8 g, 78 mmol) and dimethylacetamide (60 mL) as a solvent were placed in an apparatus equipped with a 300 mL recovery flask and a Dimroth condenser, and the temperature was raised to 60°C, followed by stirring the solution uniformly. Next, n-dodecanal (14.4 g, 78 mmol) was added, and the solution was stirred uniformly. Furthermore, p-toluenesulfonic acid monohydrate (1.2 g, 7 mmol), an acid catalyst, was added, and the solution was stirred uniformly. After 20 hours, the reaction was stopped, and the solution was cooled to room temperature.

[0139] Thereafter, the resulting reaction product was extracted in the same manner as in Synthesis Example 1. As a result, 3,4-dihydroxy-5-(2-undecyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C12AAA, 3.8 g, 11.1 mmol, yield 14.2%) was obtained. １ H-NMR (CD ３ The assignments by OD are shown below. １ H-NMR: δ0.90 (t, 3H, J = 6.9Hz), 1.21-1.41 (m, 10H), 1.54-1.62 (m, 3H) , 3.90-4.31 (m, 3H), 4.66 (dd, 1H, J=12.1Hz, 3.3Hz), 4.87-4.90 (m, 1H)

[0140] Synthesis Example 5 (Synthesis of C4AAANa: 4-hydroxy-5-oxo-2-(2-propyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-olate sodium) 3,4-Dihydroxy-5-(2-propyl-1,3-dioxolan-4-yl)furan-2(5H)-one (0.92 g, 4 mmol) and methanol (5 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. An aqueous sodium bicarbonate solution (4 mmol, 5 mL) was then added, and the mixture was stirred and reacted. After 30 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure. The resulting crude product was washed with methanol and separated and purified by filtration.

[0141] As a result of the above, sodium 4-hydroxy-5-oxo-2-(2-propyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-olate (C4AAANa, 1.0 g, 4 mmol, yield 99%, white solid) was obtained. １ H-NMR (D ２ O) assignments are shown below. １ H-NMR: δ0.77 (td, 3H, J=7.4Hz, 2.0Hz), 1.18-1.30 (m, 2H), 1.47-1.52 (m, 2H), 3.70-4.38 (m, 4H), 4.85-4.89 (m, 1H)

[0142] Synthesis Example 6 (Synthesis of C4isoAAANa: 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-olate sodium) 3,4-Dihydroxy-5-(2-isopropyl-1,3-dioxolan-4-yl)furan-2(5H)-one (0.92 g, 4 mmol) and methanol (5 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. An aqueous sodium bicarbonate solution (4 mmol, 5 mL) was then added, and the mixture was stirred and reacted. After 30 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure. The resulting crude product was washed with methanol and separated and purified by filtration.

[0143] As a result of the above, sodium 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-olate (C4isoAAANa, 1.0 g, 4 mmol, yield 99%, white solid) was obtained. １ H-NMR (D ２ O) assignments are shown below. １ H-NMR: δ0.24-0.30 (m, 6H), 1.13-1.26 (m, 1H), 3.36-3.90 (m, 4H), 4.11-4.12 (m, 1H)

[0144] Synthesis Example 7 (Synthesis of C4isoAAACa: 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-calcium oleate) 3,4-Dihydroxy-5-(2-isopropyl-1,3-dioxolan-4-yl)furan-2(5H)-one (2.3 g, 10 mmol) and methanol (50 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. 20 mM aqueous calcium hydroxide solution (5 mmol, 250 mL) was added, and the mixture was stirred and reacted. After 30 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure. The resulting crude product was washed with methanol and separated and purified by filtration.

[0145] As a result of the above, 4-hydroxy-2-(2-isopropyl-1,3-dioxolan-4-yl)-5-oxo-2,5-dihydrofuran-3-olate calcium (C4isoAAACa, 1.8 g, 7.2 mmol, yield 72.2%, white solid) was obtained. １ H-NMR (D ２ O) assignments are shown below. １ H-NMR: δ0.72-0.77 (m, 6H), 1.60-1.72 (m, 1H), 3.85-4.35 (m, 4H), 4.58-4.60 (m, 1H)

[0146] Synthesis Example 8 (Synthesis of IPDAANa: sodium 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate) 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxyfuran-2(5H)-one (0.86 g, 4 mmol) and methanol (50 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. An aqueous sodium hydrogencarbonate solution (4 mmol, 5 mL) was then added, and the mixture was stirred and reacted. After 30 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure. The resulting crude product was washed with methanol and separated and purified by filtration.

[0147] As a result of the above, sodium 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (IPDAANa, 0.95 g, 4 mmol, yield 99%, white solid) was obtained. １ H-NMR (D ２ O) assignments are shown below. １ H-NMR: δ1.25 (s, 3H), 1.27 (s, 3H), 4.07 (ddd, 2H, J = 58.1Hz, 8.8Hz, 6.5Hz), 4.33-4.38 (m, 2H)

[0148] Synthesis Example 9 (Synthesis of IPDAACa: 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-calcium oleate) 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxyfuran-2(5H)-one (2.16 g, 10 mmol) and methanol (10 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. A 20 mM aqueous calcium hydroxide solution (5 mmol, 250 mL) was added, and the mixture was stirred to react. After 30 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure. The resulting crude product was then freeze-dried to sublimate the water.

[0149] As a result of the above, 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate calcium (IPDAACa, 2.35 g, 10 mmol, yield 99%, white solid) was obtained. １ H-NMR (D ２ O) assignments are shown below. １ H-NMR: δ1.24 (s, 3H), 1.26 (s, 3H), 3.99 (dd, 1H, J=8.9Hz, 5.7Hz), 4. 14 (dd, 1H, J = 8.8Hz, 7.1Hz), 4.32 (d, 1H, J = 2.7Hz), 4.34-4.38 (m, 1H)

[0150] Synthesis Example 10 (Synthesis of C6AAACa: 4-hydroxy-5-oxo-2-(2-pentyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-calcium oleate) 3,4-Dihydroxy-5-(2-pentyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C6AAA, 2.58 g, 10 mmol) and methanol (25 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. A 20 mM aqueous calcium hydroxide solution (5 mmol, 250 mL) was added, and the mixture was stirred to allow the reaction to proceed. After 180 minutes, the reaction was stopped, and the mixture was concentrated under reduced pressure.

[0151] As a result of the above, 4-hydroxy-5-oxo-2-(2-pentyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-olate calcium (C6AAACa, 1.66 g, 6 mmol, yield 60%, white solid) was obtained.

[0152] Synthesis Example 11 (Synthesis of C12AAACa: 4-hydroxy-5-oxo-2-(2-undecyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-olate calcium) 3,4-Dihydroxy-5-(2-undecyl-1,3-dioxolan-4-yl)furan-2(5H)-one (C12AAA, 3.42 g, 10 mmol) and methanol (25 mL) as a solvent were placed in a 500 mL recovery flask, and the solution was stirred uniformly at room temperature. A 20 mM aqueous calcium hydroxide solution (5 mmol, 250 mL) was added, and the mixture was stirred to allow the reaction to proceed. After 300 minutes, the reaction was stopped, and the precipitated solid was filtered using filter paper. The resulting solid was washed three times with methanol (25 mL), and then dried under reduced pressure.

[0153] As a result of the above, 4-hydroxy-5-oxo-2-(2-undecyl-1,3-dioxolan-4-yl)-2,5-dihydroxyfuran-3-olate calcium (C12AAACa, 2.17 g, 6 mmol, yield 60%, white solid) was obtained.

[0154] Examples 1 to 14 and Comparative Examples 1 to 3 First and second agents of Examples 1 to 14 and Comparative Examples 1 to 3 were prepared using the respective components as shown in Tables 1 to 4. The numbers in the columns for each composition or component shown in Tables 1 to 4 indicate the amount (parts by mass) of each composition or component in the first or second agent.

[0155] <Evaluation of Adhesion> Bovine mandibular anterior teeth were subjected to root amputation and pulp removal, then placed in a plastic cylindrical container with a diameter of 25 mm and a depth of 25 mm and embedded in acrylic resin. This was used as a bovine tooth adherend. Immediately before use, the bovine tooth adherend was polished with waterproof emery paper (P400) to remove a smooth surface of the bovine tooth dentin. Using the first and second agents of each Example and Comparative Example, which were separately prepared, as test specimens for measuring adhesive strength, adhesiveness was evaluated in accordance with ISO 16506.

[0156] Specifically, the surface of the bovine tooth adherend was wiped to remove excess water with a Kimwipe, and a drop of water was dropped onto it. Next, an appropriate amount of the first and second parts listed in Tables 1 to 4, mixed for 20 seconds, was applied to the surface of a cylindrical cured filler composition (Vinus Diamond, manufactured by Kulzer, the surface of which had been previously polished with waterproof emery paper P180), and the filler composition was then placed vertically on the bovine tooth adherend. The cylindrical cured filler composition was then pressed against the bovine tooth adherend with a force of 5 N using a dedicated jig. After removing the excess composition, the specimen was left at 37°C for 40 minutes while attached to the dedicated jig, then at 37°C for 60 minutes without the jig, and then left to stand in a constant temperature bath at 37°C for 24 hours, after which the adhesive strength was measured. Adhesion strength was determined by applying a shear load parallel to and in contact with the surface of the bovine tooth adherend at a crosshead speed of 1.0 mm / min, and measuring the shear load when the cylindrical cured product adhered to the bovine tooth adherend peeled from the surface. Adhesion was evaluated according to the following Criterion 1 for Examples 1 to 12 and Comparative Examples 1 to 3, while Examples 13 and 14 were evaluated according to the following Criterion 2, which further refines Criterion 1's A and B. Criterion 1 is the evaluation criterion for Examples and Comparative Examples in which the ascorbic acid content was the same. Criterion 2 is the evaluation criterion for Examples in which the number of moles of ascorbic acids was the same. (Criterion 1) A: Adhesion strength is 15 MPa or more and less than 23 MPa. B: Adhesion strength is 13 MPa or more and less than 15 MPa. C: Adhesion strength is 10 MPa or more and less than 13 MPa. D: Adhesion strength is less than 10 MPa. E: All adherends detached before the test, making it impossible to evaluate adhesion. (Criteria 2) A1: The adhesive strength is 17 MPa or more and less than 23 MPa. A2: The adhesive strength is 15 MPa or more and less than 17 MPa. B1: The adhesive strength is 14 MPa or more and less than 15 MPa. B2: The adhesive strength is 13 MPa or more and less than 14 MPa.

[0157]

[0158]

[0159]

[0160]

[0161] As shown in Tables 1 to 3, in Examples 1 to 12, the adhesiveness of the cured product was improved compared to Comparative Examples 1 and 2 by using a specific ascorbic acid derivative or a salt thereof.

[0162] As shown in Table 4, when the adhesive properties of the cured products of Examples 13 and 14 were compared after the molar number of the calcium salt of the ascorbic acid derivative was made the same, Example 14 (using C12AAACa as the calcium salt of the ascorbic acid derivative) had better adhesive properties than Example 13 (using C6AAACa as the calcium salt of the ascorbic acid derivative).

[0163] The disclosure of Japanese Patent Application No. 2022-050804, filed on March 25, 2022, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. An ascorbic acid derivative or a salt thereof, which has a structure in which at least one of the hydroxyl groups contained in ascorbic acid is substituted with an ether bond bonded to a carbon atom.

2. The ascorbic acid derivative or a salt thereof according to claim 1 , wherein the ascorbic acid derivative comprises a structure represented by the following general formula (A): 【Chemistry 1】 In formula (A), * indicates the bonding position to a carbon atom.

3. The ascorbic acid derivative or a salt thereof according to claim 1 or 2, wherein the ascorbic acid derivative comprises a compound represented by the following general formula (B): 【Chemistry 2】 In general formula (B), R １Ｂ and R ２Ｂ each independently represents a hydrogen atom or a monovalent organic group.

4. In the general formula (B), R １Ｂ Or R ２Ｂ is a hydrogen atom, and R １Ｂ Or R ２Ｂ The ascorbic acid derivative or a salt thereof according to claim 3, wherein the other of said groups is a monovalent organic group having 1 to 15 carbon atoms and is a calcium salt.

5. A polymerization initiator additive comprising the ascorbic acid derivative or a salt thereof according to claim 1 or 2.

6. A polymerization initiator comprising the ascorbic acid derivative or a salt thereof according to claim 1 or 2, a transition metal compound, and an organic peroxide.

7. A first agent containing a monomer (A); A second agent containing a monomer (B), A kit for preparing a curable composition, wherein at least one of the first agent and the second agent independently contains the ascorbic acid derivative or a salt thereof according to claim 1 or 2, a transition metal compound, and an organic peroxide.

8. the first agent contains the transition metal compound and the organic peroxide, The kit for preparing a curable composition according to claim 7 , wherein the second agent comprises the ascorbic acid derivative or a salt thereof.

9. The kit for preparing a curable composition according to claim 7 , wherein either the monomer (A) in the first agent or the monomer (B) in the second agent contains an acidic group-containing monomer.

10. The monomer (A) in the first agent contains the acidic group-containing monomer, The kit for preparing a curable composition according to claim 9 , wherein the second agent comprises the ascorbic acid derivative or a salt thereof.

11. The kit for preparing a curable composition according to claim 7, wherein at least one of the first agent and the second agent contains at least one polymerization accelerator (1) selected from the group consisting of a phosphonite compound, a phosphite compound, and a sulfite compound.

12. The kit for preparing a curable composition according to claim 7 , wherein the second agent comprises the ascorbic acid derivative or a salt thereof and the polymerization accelerator (1).

13. The kit for preparing a curable composition according to claim 7 , wherein the first agent and the second agent contain a filler.

14. The kit for preparing a curable composition according to claim 7, wherein a total content of the ascorbic acid derivative or a salt thereof contained in the first agent and the second agent is 0.1% by mass to 5% by mass with respect to a total mass of the curable composition to be prepared.

15. A curable composition comprising the ascorbic acid derivative or a salt thereof according to claim 1 or 2, a transition metal compound, an organic peroxide, and a monomer.

16. A cured product of the curable composition according to claim 15.

17. A dental material comprising the hardened product according to claim 16.

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