Two-component dental material

Abstract

To provide a two-component dental material that enables enhancement of bonding strength and bioactive properties.SOLUTION: The two-component dental material comprises an agent A containing a first acidic monomer and an agent B containing a basic material and a calcium salt of a second acidic monomer having a carboxyl group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a two-component dental material. [Background technology]

[0002] Conventionally, dental compositions containing a monomer having an acidic group and a calcium salt of a phosphate group-containing monomer have been known (see, for example, Patent Document 1). In the examples of Patent Document 1, a dental composition is disclosed that contains 10-methacryloyloxydecyl dihydrogen phosphate (MDP) as the monomer having an acidic group and a calcium salt of MDP as the calcium salt of the phosphate group-containing monomer. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2020-176089 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the dental composition described in Patent Document 1 has the drawback that the monomer having an acidic group reacts with the calcium salt of MDP, resulting in a decrease in adhesive strength and bioactivity. Note that bioactivity refers to the ability to promote or induce remineralization of hard tissues such as teeth.

[0005] The present invention provides a two-part dental material that can improve adhesive strength and bioactivity. [Means for solving the problem]

[0006] The present invention [1] includes a two-component dental material having a component A containing a first acidic monomer and a component B containing a basic material and a calcium salt of a second acidic monomer having a carboxy group.

[0007] The present invention [2] includes the two-component dental material according to the above [1], wherein the basic material is slightly water-soluble.

[0008] The present invention [3] includes the two-component dental material according to the above [1] or [2], wherein the basic material is a basic inorganic material.

[0009] The present invention [4] includes the two-component dental material according to the above [3], wherein the basic inorganic material is at least one of calcium hydroxide and calcium carbonate.

[0010] The present invention [5] includes the two-component dental material according to any one of the above [1] to [4], wherein at least one of the component A and the component B further contains an oxidizing agent.

[0011] The present invention [6] includes the two-component dental material according to any one of the above [1] to [5], wherein at least one of the agent A and the agent B further contains a reducing agent.

[0012] The present invention [7] includes the two-component dental material according to any one of the above [1] to [6], wherein at least one of the agent A and the agent B further contains a transition metal compound.

[0013] The present invention [8] includes the two-component dental material according to the above [7], wherein the transition metal compound is a fourth-period transition metal compound.

[0014] The present invention [9] includes the two-component dental material according to the above [7] or [8], wherein the transition metal compound is at least one selected from the group consisting of copper compounds, vanadium compounds, and iron compounds.

[0015] The present invention

[10] includes the two-component dental material according to any one of the above [1] to [9], wherein at least one of the agent A and the agent B further contains a filler.

[0016] The present invention

[11] includes the two-component dental material according to any one of the above [1] to

[10] , wherein the agent B further contains a basic filler.

[0017] The present invention

[12] includes the two-component dental material according to the above

[11] , wherein the basic filler is barium borosilicate glass.

[0018] The present invention

[13] includes the two-component dental material according to any one of [1] to

[12] above, wherein the agent B further contains a basic filler, the basic filler is barium borosilicate glass, and the basic material is calcium hydroxide.

[0019] The present invention

[14] includes the two-component dental material according to any one of the above [1] to

[13] , wherein the calcium salt of the second acidic monomer having a carboxy group is slightly water-soluble.

[0020] The present invention

[15] includes a two-component dental material according to any one of the above [1] to

[14] , wherein the calcium salt of the second acidic monomer having a carboxy group is a calcium salt of an aromatic carboxylic acid derivative.

[0021] The present invention

[16] includes the two-component dental material according to the above

[15] , wherein the calcium salt of an aromatic carboxylic acid derivative is a calcium salt of 4-methacryloyloxyethyltrimellitic acid. [Effects of the Invention]

[0022] In the two-component dental material of the present invention, component A contains a first acidic monomer, and component B contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. Therefore, the basic material can suppress a reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group, which occurs when components A and B are mixed or brought into contact with each other.

[0023] As a result, two-part dental materials can have improved adhesion and bioactivity. DETAILED DESCRIPTION OF THE INVENTION

[0024] <Two-component dental materials> The two-component dental material is provided with Agent A and Agent B separated (packaged). For example, the two-component dental material is used by mixing Agent A and Agent B immediately before use and applying the resulting mixture. For example, the two-component dental material is used by applying Agent A first, followed by Agent B.

[0025] The two-component dental material is packaged with a component A containing a first acidic monomer and a component B containing a basic material and a calcium salt of a second acidic monomer with a carboxyl group. This prevents neutralization and polymerization reactions during storage. Therefore, the two-component dental material maintains its improved adhesiveness and bioactivity even when stored for long periods.

[0026] A two-part dental self-adhesive resin cement will be described below as one embodiment of the two-part dental material. The two-part dental self-adhesive resin cement is used in dental treatment, for example, to bond a prosthesis to a tooth loss site.

[0027] When a two-component dental material has self-adhesive properties, such as a two-component dental self-adhesive resin cement, it can be applied directly to tooth structure. On the other hand, when a two-component dental material does not have self-adhesive properties, it can be used in combination with a pretreatment material.

[0028] The term "self-adhesive" means that the pretreatment material has sufficient adhesiveness to the tooth structure even without being applied to the tooth structure.

[0029] Furthermore, the pretreatment material is used in dental treatment, for example, to improve the adhesion between the two-component dental material and at least one of a prosthesis and a tooth structure.

[0030] (1) Agent A The component A contains a first acidic monomer. The component A optionally contains a non-acidic monomer, an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, and a filler. In this embodiment, the component A is in a liquid or paste form.

[0031] When component B does not contain a filler, component A preferably contains a filler. That is, at least one of components A and B contains a filler. More preferably, components A and B contain a filler.

[0032] When component B does not contain a photopolymerization initiator, component A preferably contains a photopolymerization initiator. That is, at least one of components A and B contains a photopolymerization initiator. More preferably, component A contains a photopolymerization initiator.

[0033] When component B does not contain an oxidizing agent, component A preferably contains an oxidizing agent. That is, at least one of components A and B contains an oxidizing agent. More preferably, component A contains an oxidizing agent.

[0034] (1-1) First Acidic Monomer The first acidic monomer is a polymerizable monomer having an acidic group. When the first acidic monomer contains a transition metal compound in the agent B, the first acidic monomer dissolves the transition metal compound in the agent B when the agents A and B are mixed or contacted with each other. The acidic group refers to a free acidic group and / or an acidic group that forms an acid anhydride (the same applies hereinafter).

[0035] The acidic group is located, for example, at one end of the molecule of the first acidic monomer. The number of functional groups of the acidic group is not particularly limited as long as it is 1 or more.

[0036] Examples of the acidic group include a carboxy group, a phosphate group, and a sulfo group. The molecule of the first acidic monomer may contain only one type of acidic group, or two or more types of acidic groups. In other words, the acidic group is preferably at least one functional group selected from the group consisting of a carboxy group, a phosphate group, and a sulfo group. The carboxy group refers to a free carboxy group and / or a carboxy group that forms an acid anhydride (the same applies hereinafter). The same applies to a phosphate group and a sulfo group.

[0037] Examples of the free acidic group include a free carboxy group, a free phosphate group, and a free sulfo group. The molecule of the first acidic monomer may contain only one type of free acidic group, or two or more types of free acidic groups in combination.

[0038] A free acidic group can form an acid anhydride. An acid anhydride is formed by dehydration condensation of two acidic groups. An acidic group forming an acid anhydride is referred to as an acid anhydride of the acidic group (the same applies hereinafter).

[0039] Examples of the acid anhydride of the acidic group include an acid anhydride of a carboxy group, an acid anhydride of a phosphoric acid group, and an acid anhydride of a sulfo group. The first acidic monomer molecule may contain only one type of acid anhydride, or two or more types of acid anhydrides in combination.

[0040] The acidic group preferably includes a carboxy group and a phosphate group, more preferably an acid anhydride of a carboxy group and a free phosphate group.

[0041] The first acidic monomer preferably further comprises a polymerizable group and a linking group.

[0042] The polymerizable group is located, for example, at the end opposite to the acidic group (the other end) in the molecule of the first acidic monomer.

[0043] The polymerizable group includes, for example, an ethylenically unsaturated group. Examples of the ethylenically unsaturated group include a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamide group, a vinyl group, and a vinyl cyanide group. A (meth)acryloyloxy group is preferred. That is, the acidic monomer preferably includes a (meth)acryloyloxy group. Note that, "(meth)acryloyl" includes methacryloyl and / or acryloyl (the same applies hereinafter).

[0044] The linking group links the polymerizable group and the acidic group, that is, the linking group preferably links the (meth)acryloyloxy group and the acidic group.

[0045] The linking group at least contains an alkylene group. The alkylene group has a carbon number of, for example, 1 to 30, preferably 2 to 30, or more preferably 4 to 18. That is, the linking group preferably contains an alkylene group having 4 to 18 carbon atoms.

[0046] When the number of carbon atoms in the alkylene group is within the above range, the adhesiveness of the two-component dental material can be improved. In particular, when the number of carbon atoms in the alkylene group is 4 to 18, the adhesiveness of the two-component dental material can be reliably improved compared to when the number of carbon atoms in the alkylene group is less than 4 (for example, 2).

[0047] The linking group may consist of only an alkylene group, or may contain other atomic groups in addition to the alkylene group.

[0048] Specifically, when the linking group is composed of only an alkylene group, one end of the alkylene group is directly bonded to the acidic group, and the other end of the alkylene group is directly bonded to the polymerizable group. In this case, the first acidic monomer preferably contains a free acidic group.

[0049] When the linking group contains other atomic groups in addition to the alkylene group, one end of the alkylene group is bonded to the acidic group via the other atomic group, and the other end of the alkylene group is bonded directly to the polymerizable group. In this case, the first acidic monomer preferably has two or more free acidic groups or one or more acid anhydrides of the acidic group.

[0050] Other atomic groups include, for example, aromatic rings and linking groups.

[0051] Two or more (preferably two) free acidic groups or one or more (preferably one) acid anhydrides of an acidic group are bonded to the aromatic ring. Examples of the aromatic ring include aromatic rings having 6 to 18 carbon atoms, such as a benzene ring, a naphthalene ring, an anthracene ring, and a biphenyl ring. A benzene ring is preferred.

[0052] The linking group connects one end of the alkylene group to the aromatic ring. Examples of the linking group include a carbonyl group and an amide group. A carbonyl group is preferred.

[0053] The molecular weight of the first acidic monomer is, for example, 70-600, or preferably 200-400.

[0054] The first acidic monomer can be classified according to the type of acidic group it contains. Examples of the first acidic monomer include a first acidic monomer having a carboxy group, a first acidic monomer having a phosphate group, and a first acidic monomer having a sulfo group. Preferred examples include a first acidic monomer having a carboxy group and a first acidic monomer having a phosphate group. More preferred examples include a first acidic monomer having a phosphate group.

[0055] The first acidic monomers can be used alone or in combination of two or more kinds, and are preferably used alone.

[0056] Examples of the first acidic monomer having a carboxyl group include the carboxyl group-containing polymerizable monomers exemplified in paragraph

[0043] of JP-A No. 2006-347943. The first acidic monomer having a carboxyl group can be used alone or in combination of two or more kinds.

[0057] Examples of the first acidic monomer having a carboxy group include aromatic carboxylic acid derivatives, aliphatic carboxylic acid derivatives, and amino acid derivatives. Preferably, aromatic carboxylic acid derivatives are used.

[0058] Examples of aromatic carboxylic acid derivatives include benzoic acid derivatives, salicylic acid derivatives, phthalic acid derivatives, trimellitic acid derivatives, pyromellitic acid derivatives, naphthalenetricarboxylic acid derivatives, benzophenonetetracarboxylic acid derivatives, and biphenyltetracarboxylic acid derivatives. Trimellitic acid derivatives are preferred.

[0059] Examples of trimellitic acid derivatives include 4-(meth)acryloyloxyethyl trimellitic acid and its anhydride, preferably 4-methacryloyloxyethyl trimellitic acid anhydride (4-MET).

[0060] 4-MET consists of a carboxyl anhydride group at one end of the molecule, a methacryloyloxy group (polymerizable group) at the other end of the molecule, a benzene ring (linking group) to which the carboxyl anhydride group is bonded, a carbonyl group (linking group) bonded to the benzene ring, and an ethylene group (linking group) that bonds the carbonyl group and the methacryloyloxy group.

[0061] The first acidic monomer having a carboxy group is preferably an aromatic carboxylic acid derivative, more preferably a trimellitic acid derivative, even more preferably a 4-(meth)acryloyloxyalkyltrimellitic acid, particularly preferably a 4-(meth)acryloyloxyethyltrimellitic acid, and most preferably 4-MET.

[0062] Examples of the first acidic monomer having a phosphoric acid group include the phosphoric acid group-containing polymerizable monomers exemplified in paragraph

[0045] of JP-A No. 2006-347943. The phosphoric acid type acidic monomers can be used alone or in combination of two or more.

[0063] Examples of the first acidic monomer having a phosphoric acid group include an aliphatic phosphoric acid ester and an aromatic phosphoric acid ester.

[0064] Examples of the aliphatic phosphate ester include (meth)acryloyloxyalkyl acid phosphate and bis[(meth)acryloyloxyalkyl] acid phosphate.

[0065] Examples of (meth)acryloyloxyalkyl acid phosphates include 2-(meth)acryloyloxyethyl acid phosphate and 10-(meth)acryloyloxydecyl acid phosphate. More preferred examples include 2-methacryloyloxyethyl acid phosphate (MEP) and 10-methacryloyloxydecyl acid phosphate (MDP). Even more preferred example is MDP.

[0066] MEP consists of a free phosphate group at one end of the molecule, a methacryloyloxy group (polymerizable group) at the other end of the molecule, and an ethylene group (linking group) that connects the phosphate group and the methacryloyloxy group.

[0067] MDP consists of a free phosphate group at one end of the molecule, a methacryloyloxy group (polymerizable group) at the other end of the molecule, and a decylene group (linking group) that connects the phosphate group and the methacryloyloxy group.

[0068] The first acidic monomer having a phosphoric acid group is preferably an aliphatic phosphoric acid ester, more preferably a (meth)acryloyloxyalkyl acid phosphate, even more preferably 10-(meth)acryloyloxydecyl acid phosphate, and particularly preferably MDP.

[0069] The content of the first acidic monomer in the agent A is, for example, 1 mass % or more, preferably 3 mass % or more, and for example, 30 mass % or less, preferably 10 mass % or less.

[0070] If the content of the first acidic monomer in agent A is within the above range, and agent B contains a transition metal compound, the transition metal compound in agent B can be sufficiently dissolved when agent A and agent B are mixed or contacted with each other. Here, "sufficiently" means "to the extent that the oxidation-reduction reaction between the oxidizing agent and the reducing agent can be promoted."

[0071] Furthermore, the monomer component of the agent A may contain a monomer (non-acidic monomer) other than the first acidic monomer, as will be described in detail later.

[0072] In the agent A, the content of the first acidic monomer in the monomer components (the total amount of the first acidic monomer and non-acidic monomer in the agent A) is, for example, 1 mass% or more, preferably 5 mass% or more, more preferably 10 mass% or more, and for example, 60 mass% or less, preferably 40 mass% or less, more preferably 20 mass% or less.

[0073] In the two-component dental material, the content of the first acidic monomer in all monomer components (the total amount of the first acidic monomer and non-acidic monomer in component A and the non-acidic monomer in component B) is, for example, 1 mass% or more, preferably 3 mass% or more, and for example, 30 mass% or less, preferably 15 mass% or less.

[0074] (1-2) Non-acidic Monomer The non-acidic monomer is a polymerizable monomer, and for example, does not have the above-mentioned acidic group but has the above-mentioned polymerizable group, preferably does not have the above-mentioned acidic group but has the above-mentioned ethylenically unsaturated group.

[0075] In the following description, (meth)acrylate includes acrylate and / or methacrylate.

[0076] The non-acidic monomers are monomers that do not have an acidic group and are classified into non-acidic monomers that have a hydroxyl group, non-acidic monomers that have a urethane bond, and non-acidic monomers that do not have a hydroxyl group or a urethane bond.

[0077] Examples of non-acidic monomers having a hydroxyl group include mono(meth)acrylates and di(meth)acrylates.

[0078] Examples of mono(meth)acrylates having a hydroxyl group include 2-hydroxyethyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, 6-hydroxyhexyl(meth)acrylate, and dihydroxypropyl mono(meth)acrylate. 2-hydroxyethyl(meth)acrylate is preferred. 2-hydroxyethyl methacrylate (HEMA) is more preferred.

[0079] Examples of di(meth)acrylates having a hydroxyl group include derivatives of bisphenol A. Examples of bisphenol A derivatives having a hydroxyl group include 2,2-bis[4-(3-(meth)acryloyloxy-2-hydroxypropoxy)phenyl]propane.

[0080] Examples of non-acidic monomers having a urethane bond include [2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)]di(meth)acrylate, and preferably [2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)]dimethacrylate (UDMA).

[0081] Examples of non-acidic monomers that do not have a hydroxyl group or a urethane bond include mono(meth)acrylates and di(meth)acrylates.

[0082] Examples of mono(meth)acrylates that do not have a hydroxyl group or a urethane bond include alkyl(meth)acrylates, such as methyl(meth)acrylate, ethyl(meth)acrylate, and butyl(meth)acrylate.

[0083] Examples of di(meth)acrylates that do not have a hydroxyl group or a urethane bond include alkanediol di(meth)acrylates, polyoxyalkylene group-containing di(meth)acrylates, and bisphenol A derivatives.

[0084] Examples of alkanediol di(meth)acrylates include ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate.

[0085] Examples of polyoxyalkylene group-containing di(meth)acrylates include polyoxyethylene group-containing di(meth)acrylates.

[0086] Examples of polyoxyethylene group-containing di(meth)acrylates include triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, and nonaethylene glycol di(meth)acrylate. Preferably, triethylene glycol dimethacrylate (TEGDMA) is used.

[0087] An example of a bisphenol A derivative that does not have a hydroxyl group or a urethane bond is ethoxylated bisphenol A di(meth)acrylate.

[0088] In the component A, the non-acidic monomers can be used alone or in combination of two or more, preferably in combination of two or more.

[0089] Component A preferably contains a non-acidic monomer having a hydroxyl group, a non-acidic monomer having a urethane bond, and a non-acidic monomer having no hydroxyl group or urethane bond, and more preferably contains HEMA, UDMA, and TEGDMA.

[0090] The content of non-acidic monomers in agent A is, for example, 5% by mass or more, preferably 15% by mass or more, more preferably 25% by mass or more, and for example, 95% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less.

[0091] In the agent A, the content of the non-acidic monomer in the monomer components (the total amount of the first acidic monomer and the non-acidic monomer in the agent A) is, for example, 40% by mass or more, preferably 60% by mass or more, more preferably 80% by mass or more, and for example, 99% by mass or less, preferably 95% by mass or less, more preferably 90% by mass or less.

[0092] (1-3) Oxidizing agent The oxidizing agent oxidizes the reducing agent when component A and component B are mixed or contacted. In other words, the oxidizing agent is reduced by the reducing agent when component A and component B are mixed or contacted. This redox reaction generates radicals. When a transition metal compound is included, the transition metal compound functions as an accelerator of the redox reaction.

[0093] Oxidizing agents include, for example, organic peroxides and inorganic peroxides.

[0094] Examples of organic peroxides include peroxyesters, diacyl peroxides, dialkyl peroxides, peroxyketals, ketone peroxides, and hydroperoxides. Peroxyesters are preferred.

[0095] Examples of peroxyesters include t-butyl peroxybenzoate (BPB), bis-t-butylperoxyisophthalate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butylperoxy-2-ethylhexanoate, and t-butylperoxyisopropyl carbonate. BPB is preferred.

[0096] Examples of inorganic peroxides include persulfate compounds, perphosphate compounds, perchlorate compounds, and hydrogen peroxide derivatives. Preferably, persulfate compounds are used.

[0097] Examples of persulfate compounds include sodium persulfate, potassium persulfate, calcium persulfate, magnesium persulfate, and ammonium persulfate. Potassium persulfate is preferred. Examples of potassium persulfate include potassium peroxodisulfate (PSS).

[0098] The oxidizing agent can be used alone or in combination of two or more. Preferably, two or more are used in combination. Examples of the oxidizing agent include a combination of an organic peroxide and an inorganic peroxide. Preferably, a combination of a peroxyester and a persulfate compound is used. More preferably, a combination of BPB and PSS is used.

[0099] The content of the oxidizing agent in agent A is, for example, 1 mass % or more, preferably 3 mass % or more, and for example, 15 mass % or less, preferably 10 mass % or less.

[0100] (1-4) Reducing agent The reducing agent reduces the transition metal ions when agent A and agent B are mixed or when agent A and agent B are brought into contact with each other. In other words, the reducing agent is oxidized by the transition metal ions when agent A and agent B are mixed or when agent A and agent B are brought into contact with each other. The oxidation of the reducing agent by the transition metal ions generates radicals.

[0101] Examples of the reducing agent include aromatic amines, aromatic amino acids, sulfinic acids or salts thereof, thiourea compounds, phosphorous compounds, and sulfurous compounds. Preferably, aromatic amine sulfinic acids or salts thereof, and thiourea compounds are used.

[0102] Examples of aromatic amines include aromatic tertiary amines.

[0103] Examples of aromatic tertiary amines include N,N-dimethyl-p-toluidine (DMPT), N,N-diethyl-p-toluidine, N,N-bis(2-hydroxyethyl)-p-toluidine, N,N-bis(2-hydroxypropyl)-p-toluidine, N,N-dimethylaniline, N,N-diethylaniline, methyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate (EDAB), 2-butoxyethyl 4-(dimethylamino)benzoate, and isoamyl 4-(dimethylamino)benzoate.

[0104] The aromatic amines can be used alone or in combination of two or more kinds.

[0105] Examples of sulfinic acids and salts thereof include aromatic sulfinic acids and salts thereof. Examples of aromatic sulfinic acids include benzenesulfinic acid, o-toluenesulfinic acid, p-toluenesulfinic acid, ethylbenzenesulfinic acid, decylbenzenesulfinic acid, dodecylbenzenesulfinic acid, chlorobenzenesulfinic acid, fluorobenzenesulfinic acid, and naphthalenesulfinic acid. Examples of salts of aromatic sulfinic acids include lithium salts, sodium salts, potassium salts, magnesium salts, calcium salts, strontium salts, barium salts, amine salts, aniline salts, toluidine salts, ammonium salts, and pyridine salts of the above-mentioned aromatic sulfinic acids.

[0106] Examples of thiourea compounds include alkylthioureas. Examples of alkylthioureas include alkylthioureas having 1 to 12 carbon atoms and cycloalkylthioureas having 3 to 10 carbon atoms. Specific examples include methylthiourea, ethylthiourea, N,N'-dimethylthiourea, N,N'-diethylthiourea, N,N'-di-n-propylthiourea, trimethylthiourea (TMTU), triethylthiourea, tri-n-propylthiourea, tetramethylthiourea, tetraethylthiourea, tetra-n-propylthiourea, N,N'-dicyclohexylthiourea, and tricyclohexylthiourea.

[0107] (1-5) Imide compounds Examples of imide compounds include acyclic imides, cyclic imides, acyclic sulfonimides, cyclic sulfonimides, and alkali metal salts thereof. Preferred examples include cyclic sulfonimides and alkali metal salts thereof. Examples of alkali metal atoms include lithium, potassium, and sodium.

[0108] Examples of cyclic sulfonimides include saccharin, saccharin derivatives (e.g., methylsaccharin), and benzenedisulfonimide. Examples of alkali metal salts of cyclic sulfonimides include saccharin sodium hydrate.

[0109] That is, the imide compound preferably includes cyclic sulfonimide and alkali metal salts thereof. More preferably, saccharin, saccharin derivatives, and alkali metal salts thereof are used. Even more preferably, saccharin and saccharin sodium hydrate are used.

[0110] The content of the imide compound in the agent A is, for example, 0.01 mass % or more, preferably 0.1 mass % or more, and for example, 5 mass % or less, preferably 3 mass % or less.

[0111] (1-6) Azole compounds Examples of the azole compound include imidazole compounds and triazole compounds, and preferably imidazole compounds.

[0112] Examples of the imidazole compound include benzimidazole compounds, such as 1,2-dimethylbenzimidazole, 2-amino-1-methylbenzimidazole, 2-(4-bromophenyl)-1-phenylbenzimidazole, and 2-(2-n-propyl-4-methylbenzimidazol-6-yl)-1-methylbenzimidazole.

[0113] The azole compounds can be used alone or in combination of two or more.

[0114] The content of the azole compound in the agent A is, for example, 0.01 mass % or more, preferably 0.1 mass % or more, and for example, 5 mass % or less, preferably 3 mass % or less.

[0115] (1-7) Photopolymerization initiator The photopolymerization initiator generates radicals when exposed to light.

[0116] Examples of photopolymerization initiators include α-diketones, ketals, and thioxanthones. Examples of α-diketones include camphorquinone (CQ). Examples of ketals include benzyl dimethyl ketal and benzyl diethyl ketal. Examples of thioxanthones include 2-chlorothioxanthone and 2,4-diethylthioxanthone.

[0117] The photopolymerization initiator is preferably an α-diketone, more preferably CQ.

[0118] The content of the photopolymerization initiator in the agent A is, for example, 0.001 mass% or more, preferably 0.01 mass% or more, and for example, 5 mass% or less, preferably 1 mass% or less, more preferably 0.5 mass% or less.

[0119] (1-8)Transition metal compounds The transition metal compound preferably contains a transition metal atom belonging to the fourth period of the periodic table. That is, the transition metal compound is preferably a fourth period transition metal compound (a compound containing a transition metal atom belonging to the fourth period of the periodic table). The periodic table is the IUPAC Periodic Table of the Elements (version date 4 May 2022).

[0120] Specific examples of transition metal atoms include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), and gallium (Ga).Preferred examples include vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).

[0121] Examples of transition metal compounds include oxides, hydroxides, halides, carboxylates, sulfates, nitrates, carbonates, and complexes of transition metals. Examples of halides include chlorides and bromides. Examples of carboxylates include formates, acetates, oleates, acrylates, gluconates, phthalates, and citrates.

[0122] A transition metal complex has a transition metal atom as a central metal and a ligand coordinated to the transition metal atom.

[0123] Examples of the ligand include a diketone-based ligand, an amine-based ligand, a thiol-based ligand, a urea-based ligand, and a thiourea-based ligand.

[0124] Specific examples of the transition metal compound include copper compounds, iron compounds, cobalt compounds, chromium compounds, and vanadium compounds, and preferably copper compounds, vanadium compounds, and iron compounds.

[0125] Examples of copper compounds include copper(II) hydroxide, copper(I), copper(II) chloride, copper(II), copper(I) bromide, copper(II), copper(II) bromide, copper(II) formate, copper(I), copper(II) acetate, copper(II) acetate, copper(II) sulfate, copper(II) nitrate, copper(I) iodide, basic copper(II) carbonate, copper(I), copper(II) oxide, copper(II), metallic copper, copper(II) oleate, copper(II) acrylate, copper(II) gluconate, copper(II) phthalate, copper(II) citrate, copper(II) acetylacetonate, mercaptobenzothiazole copper, 2-mercaptobenzimidazole copper, benzoxazole copper, 1,3-propanediamine copper, indazole copper, imidazole copper, benzimidazole copper, benzothiazole copper, and thiourea copper. Preferably, copper(II) hydroxide is used.

[0126] Examples of vanadium compounds include vanadium(III) chloride, vanadium(III) bromide, metallic vanadium, vanadium(II) oxide, vanadium(III) oxide, vanadium(V) oxide, vanadium(IV) oxyacetylacetonate, vanadium(III) acetylacetonate, oxovanadium(IV) oxalate, vanadium(IV) stearate, vanadium(IV) oxide sulfate, ammonium vanadate(V), sodium orthovanadate(V), indazole vanadium, imidazole vanadium, and benzimidazole vanadium.

[0127] Examples of iron compounds include iron(II) hydroxide, iron(III) oxide hydroxide, iron(II) chloride, iron(III) chloride, iron(I) bromide, iron(II) bromide, iron(II) acetate, iron(III) acetate, iron(II) carbonate, iron(II) oxide, iron(III) oxide, iron(II, III) oxide, metallic iron, iron(II) sulfate, iron(III) sulfate, iron(III) acetylacetonate, iron(III) citrate, and iron(II) gluconate.

[0128] The transition metal compounds can be used alone or in combination of two or more.

[0129] (1-9) Filler The filler in agent A is not particularly limited as long as it is a conventionally known filler that can be used in dental materials. Specific examples of fillers include silica, silica alumina, alumina, alumina quartz, glass, titania, zirconia, and ytterbium fluoride. Preferred examples include silica and ytterbium fluoride. Examples of silica include fumed silica. Examples of glass include barium glass. The filler may be surface-treated with a coupling agent or the like to be hydrophobic or hydrophilic.

[0130] The filler content in agent A is, for example, 5% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, and for example, 97% by mass or less, preferably 90% by mass or less, more preferably 80% by mass or less.

[0131] (1-10) Other additives Component A may contain a polymerization inhibitor, a thickener, a coupling agent, an ultraviolet absorber, a fluorescent agent, a pigment, and a solvent, as necessary.

[0132] Examples of the polymerization inhibitor include dibutylhydroxytoluene (BHT) and 4-methoxyphenol, and preferably BHT.

[0133] The content of the polymerization inhibitor in the agent A is, for example, 0.001 mass% or more, preferably 0.01 mass% or more, and for example, 5 mass% or less, preferably 1 mass% or less, more preferably 0.5 mass% or less.

[0134] (2) Agent B Component B contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. Component B optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, and a filler. In this embodiment, component B is in the form of a powder or paste.

[0135] When agent A does not contain a reducing agent, agent B preferably contains a reducing agent. That is, at least one of agent A and agent B contains a reducing agent. More preferably, agent B contains a reducing agent.

[0136] When the agent A does not contain a transition metal compound, the agent B preferably contains a transition metal compound. That is, at least one of the agent A and the agent B contains a transition metal compound. More preferably, the agent B contains a transition metal compound.

[0137] (2-1) Basic materials A basic material is a material that exhibits basicity. "Basic" means that the pH is greater than 7. Note that the basic material does not include a basic filler, which will be described later.

[0138] Because component B contains a basic material, when components A and B are mixed or brought into contact with each other, it is possible to suppress the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described below), thereby improving adhesive strength and bioactivity.

[0139] The pH of the basic material is defined as the pH of a liquid obtained by dispersing the basic material in purified water at 4% by mass at 25° C. The pH of the basic material is, for example, 7 or more, preferably 7.5 or more, more preferably 8 or more, and is, for example, 14 or less.

[0140] That is, the basic material is preferably a strongly basic material. The term "strongly basic material" refers to a basic material having a pH of, for example, 10 or more and 14 or less. If component B contains a strongly basic material, even a small amount of the strongly basic material can be added to inhibit the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described later) when components A and B are mixed or brought into contact with each other. This, in turn, can improve adhesive strength and bioactivity.

[0141] The solubility of the basic material in 100 g of water is, for example, 0.01 g or more, preferably 0.05 g or more, more preferably 0.1 g or more, and for example, 1.5 g or less, preferably 1.2 g or less, more preferably 1.0 g or less.

[0142] In other words, the basic material is preferably slightly water-soluble. "Slightly water-soluble" refers to the solubility of the basic material in 100 g of water being within the above-mentioned range (specifically, 0.01 g or more and 1.5 g or less). If the basic material is slightly water-soluble, the basic material can be dispersed as a solid when component A and component B are mixed or brought into contact with each other. Therefore, inhibition of the hardening reaction due to changes in pH can be suppressed. Furthermore, when the two-component dental composition is applied to a tooth, it dissolves in the water contained in the tooth, reducing the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group, thereby achieving high bioactivity.

[0143] Examples of basic materials include basic inorganic materials.

[0144] Examples of basic inorganic materials include ammonia, ammonia salts, alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates, and alkali metal hydrogen carbonates. Preferred are alkaline earth metal hydroxides and alkaline earth metal carbonates. More preferred are alkaline earth metal hydroxides.

[0145] Examples of the hydroxides of alkali metals or alkaline earth metals include sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide, with calcium hydroxide being preferred.

[0146] Examples of carbonates of alkali metals or alkaline earth metals include sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, and calcium carbonate. Calcium carbonate is preferred.

[0147] Alkali metal bicarbonates include, for example, sodium bicarbonate and potassium bicarbonate.

[0148] The basic material preferably contains at least one of an alkaline earth metal hydroxide and an alkaline earth metal carbonate, more preferably contains at least one of calcium hydroxide and calcium carbonate, and even more preferably contains calcium hydroxide.

[0149] The basic inorganic materials can be used alone or in combination of two or more kinds.

[0150] The content of the basic material in Agent B is, for example, 0.01% by mass to 10% by mass, preferably 0.05% by mass to 5% by mass, more preferably 0.1% by mass to 1% by mass, and even more preferably 0.1% by mass to 0.5% by mass.

[0151] The content of the basic material in Agent B is, for example, 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and for example, 10% by mass or less, preferably 5% by mass or less, more preferably 1% by mass or less, and even more preferably 0.5% by mass or less.

[0152] If the content of the basic material in Agent B is equal to or greater than the lower limit, when Agent A and Agent B are mixed or contacted, the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described below) can be suppressed. Consequently, adhesive strength and bioactivity can be improved. If the content of the basic material in Agent B is equal to or less than the upper limit, adhesion inhibition due to excess basic material can be suppressed.

[0153] The amount of the basic material mixed relative to 100 parts by mass of the first acidic monomer is, for example, 0.5 to 20 parts by mass, preferably 1.0 to 10 parts by mass, and more preferably 2.0 to 7.0 parts by mass.

[0154] The amount of the basic material mixed relative to 100 parts by mass of the first acidic monomer is, for example, 0.5 parts by mass or more, preferably 1.0 parts by mass or more, more preferably 2.0 parts by mass or more, and for example, 20 parts by mass or less, preferably 10 parts by mass or less, more preferably 7.0 parts by mass or less.

[0155] If the amount of basic material blended relative to 100 parts by mass of the first acidic monomer is equal to or greater than the lower limit, when the A and B components are mixed or brought into contact with each other, the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described below) can be suppressed. Consequently, adhesive strength and bioactivity can be improved. If the amount of basic material blended relative to 100 parts by mass of the first acidic monomer is equal to or less than the upper limit, adhesion inhibition due to excess basic material can be suppressed.

[0156] (2-2) Calcium salt of second acidic monomer having a carboxy group The calcium salt of the second acidic monomer having a carboxy group is a bioactive material. A bioactive material is a material that has the ability (bioactivity) to promote or induce remineralization of hard tissues such as teeth.

[0157] The second acidic monomer has a carboxy group. Specific examples of the second acidic monomer having a carboxy group include those described above as the first acidic monomer having a carboxy group in the agent A.

[0158] The second acidic monomer having a carboxy group is preferably an aromatic carboxylic acid derivative, more preferably a trimellitic acid derivative, even more preferably a 4-(meth)acryloyloxyalkyltrimellitic acid, particularly preferably a 4-(meth)acryloyloxyethyltrimellitic acid, and most preferably 4-MET.

[0159] That is, the calcium salt of the second acidic monomer having a carboxy group is preferably a calcium salt of an aromatic carboxylic acid derivative. More preferably, a calcium salt of a trimellitic acid derivative. Still more preferably, a calcium salt of a 4-(meth)acryloyloxyalkyltrimellitic acid. Particularly preferably, a calcium salt of a 4-(meth)acryloyloxyethyltrimellitic acid. Most preferably, a calcium salt of 4-MET (C-MET) is used.

[0160] The solubility of the calcium salt of the second acidic monomer having a carboxy group in 100 g of water is, for example, 0.01 g or more, preferably 0.05 g or more, more preferably 0.1 g or more, and for example, 1.5 g or less, preferably 1.2 g or less, more preferably 1.0 g or less.

[0161] In other words, the calcium salt of the second acidic monomer having a carboxy group is preferably slightly water-soluble. "Slightly water-soluble" refers to the solubility of the calcium salt of the second acidic monomer having a carboxy group in 100 g of water being within the above-mentioned range (specifically, 0.01 g or more and 1.5 g or less). If the calcium salt of the second acidic monomer having a carboxy group is slightly water-soluble, the calcium salt of the second acidic monomer having a carboxy group can be dispersed as a solid when component A and component B are mixed or contacted. Furthermore, when the two-component dental composition is applied to a tooth, only a small amount of the calcium salt dissolves in the moisture contained in the tooth, enabling the promotion or development of remineralization in the tooth. However, if the calcium salt of the second acidic monomer having a carboxy group is too highly soluble, it will dissolve excessively in the moisture contained in the tooth, preventing the promotion or development of remineralization over the long term. Furthermore, if the solubility of the calcium salt of the second acidic monomer having a carboxy group is excessively low, it will not be able to dissolve in the water contained in the tooth substance, and will not be able to promote or induce remineralization.

[0162] The content of the calcium salt of the second acidic monomer having a carboxy group in agent B is, for example, 0.01% by mass to 10% by mass, preferably 0.02% by mass to 9% by mass, more preferably 0.03% by mass to 8% by mass, and even more preferably 0.05% by mass to 7% by mass.

[0163] The content of the calcium salt of the second acidic monomer having a carboxy group in component B is, for example, 0.01 mass% or more, preferably 0.02 mass% or more, more preferably 0.03 mass% or more, even more preferably 0.05 mass% or more, and for example, 10 mass% or less, preferably 9 mass% or less, more preferably 8 mass% or less, even more preferably 7 mass% or less.

[0164] When the content of the calcium salt of the second acidic monomer having a carboxy group in Component B is equal to or greater than the lower limit, bioactivity can be improved. When the content of the calcium salt of the second acidic monomer having a carboxy group in Component B is equal to or less than the upper limit, adhesiveness can be improved.

[0165] The amount of the calcium salt of the second acidic monomer having a carboxy group per 100 parts by mass of the basic material is, for example, 10 parts by mass or more, preferably 100 parts by mass or more, more preferably 500 parts by mass or more, even more preferably 1000 parts by mass or more, and for example, 8000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 4000 parts by mass or less, even more preferably 3000 parts by mass or less.

[0166] The amount of the calcium salt of the second acidic monomer having a carboxy group relative to 100 parts by mass of the first acidic monomer is, for example, 0.1 parts by mass or more, preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and for example, 100 parts by mass or less, preferably 95 parts by mass or less, more preferably 90 parts by mass or less.

[0167] (2-3) Non-acidic Monomers Examples of the non-acidic monomer in component B include the same non-acidic monomers as those described for component A. The explanation for the non-acidic monomer in component B is the same as the explanation for the non-acidic monomer in component A.

[0168] In the agent B, the non-acidic monomers can be used alone or in combination of two or more, preferably in combination of two or more.

[0169] The component B contains, for example, a non-acidic monomer having no hydroxyl group or urethane bond. Preferably, it contains a di(meth)acrylate having no hydroxyl group or urethane bond. More preferably, it contains an alkanediol di(meth)acrylate and a bisphenol A derivative. Even more preferably, it contains neopentyl glycol di(meth)acrylate and ethoxylated bisphenol A di(meth)acrylate. Particularly preferably, it contains neopentyl glycol dimethacrylate (NPGDMA) and ethoxylated bisphenol A dimethacrylate (EBPADMA).

[0170] There are no particular limitations on the proportion of non-acidic monomers in component B. The proportion of non-acidic monomers in component B is, for example, 5% by mass or more, preferably 15% by mass or more, more preferably 20% by mass or more, and for example, 99% by mass or less, preferably 90% by mass or less, more preferably 80% by mass or less.

[0171] (2-4) Reducing agent Examples of the reducing agent in agent B include the same reducing agents as those described for agent A. The explanation for the reducing agent in agent B is the same as the explanation for the reducing agent in agent A.

[0172] The reducing agent in agent B can be used alone or in combination of two or more kinds, preferably in combination of two or more kinds.

[0173] The reducing agent in agent B is preferably a combination of an aromatic amine, a sulfinic acid or its salt, and a thiourea compound. More preferably, it is a combination of an aromatic tertiary amine, an aromatic sulfinic acid or its salt, and an alkylthiourea. Even more preferably, it is a combination of DMPT, EDAB, STS, and TMTU.

[0174] The content of the reducing agent in agent B is, for example, 0.01 mass% or more, preferably 0.1 mass% or more, more preferably 0.5 mass% or more, and for example, 30 mass% or less, preferably 20 mass% or less, more preferably 10 mass% or less.

[0175] (2-5) Oxidizing agent Examples of the oxidizing agent in agent B include the same oxidizing agents as those described for agent A. The explanation for the oxidizing agent in agent B is the same as the explanation for the oxidizing agent in agent A.

[0176] The reducing agents in agent B can be used alone or in combination of two or more.

[0177] (2-6)Transition metal compounds Examples of the transition metal compound in agent B include the same transition metal compounds as those described for agent A. The explanation for the transition metal compound in agent B is the same as the explanation for the transition metal compound in agent A.

[0178] When a transition metal compound is contained in Agent B, the transition metal compound is solid in Agent B. That is, Agent B contains the components in Agent B and a water-insoluble transition metal compound powder that may be obtained by moisture absorption during storage. The amount of the transition metal compound dissolved in 100 g of water at 20°C and 1 atmosphere is, for example, 5 g or less, preferably 4 g or less, and more preferably 3 g or less. The average particle size of the transition metal compound powder is not particularly limited, but if it is too large, it will tend to settle, and if it is too small, the specific surface area will be too large and the amount that can be dispersed will decrease. Therefore, the average particle size of the transition metal compound is, for example, 0.01 μm to 500 μm, preferably 0.1 μm to 100 μm, and more preferably 1 μm to 50 μm.

[0179] When component B contains a transition metal compound, the transition metal compound preferably dissolves in the first acidic monomer when components A and B are mixed or brought into contact with each other. The dissolution of the transition metal compound in the first acidic monomer generates transition metal ions. The transition metal ions chemically react with a reducing agent, dissolved oxygen, or an oxidizing agent to generate radicals. The generated radicals polymerize each monomer.

[0180] In Agent B, the transition metal compounds can be used alone or in combination of two or more.

[0181] The content of the transition metal compound in agent B is, for example, 0.001 mass% or more, preferably 0.01 mass% or more, more preferably 0.03 mass% or more, and for example, 1 mass% or less, preferably 0.5 mass% or less, more preferably 0.3 mass% or less.

[0182] (2-7) Filler The filler in Agent B is not particularly limited as long as it is a conventionally known filler that can be used in dental materials. Specific examples of the filler in Agent B include basic fillers and non-basic fillers. A basic filler is a filler that exhibits basicity. "Basic" refers to a pH greater than 7.

[0183] Examples of basic fillers include basic glasses. Examples of basic glasses include barium borosilicate glasses (e.g., "E-3000" (manufactured by Esstech), "GM8235", "GM27884", and "GM39923" (manufactured by Schott)), strontium boroaluminosilicate glasses (e.g., "E-4000" (manufactured by Esstech), "G018-093", and "GM32087" (manufactured by Schott)), lanthanum glasses (e.g., "GM31684" (manufactured by Schott)), and fluoroaluminosilicate glasses (e.g., "G01 Examples of suitable glass include glasses containing zirconia (e.g., "G018-310" and "G018-159" (manufactured by Schott)), glasses containing strontium (e.g., "G018-163", "G018-093", and "GM32087" (manufactured by Schott)), glasses containing zinc oxide (e.g., "G018-161" (manufactured by Schott)), and glasses containing calcium (e.g., "G018-309" (manufactured by Schott)). Preferred examples include glasses containing alkaline earth metals (e.g., barium borosilicate glass, strontium boroaluminosilicate glass, strontium-containing glass, and calcium-containing glass). More preferred examples include barium borosilicate glass.

[0184] The pH of the basic filler is defined as the pH of a liquid obtained by dispersing the basic filler in purified water at 4% by mass at 25° C. The pH of the basic filler is, for example, 7 or more, preferably 7.5 or more, more preferably 8 or more, and for example, 14 or less, preferably 13.5 or less, more preferably 13 or less.

[0185] That is, the basic filler is preferably a weakly basic filler. The term "weakly basic filler" refers to a basic filler having a pH of, for example, 7 or more and 14 or less, preferably 10 or less, more preferably less than 10, and even more preferably 9.5 or less.

[0186] The pH of the non-basic filler is defined as the pH of a liquid obtained by dispersing the non-basic filler in purified water at 4% by mass at 25°C. Examples of non-basic fillers include silica, silica alumina, alumina, alumina quartz, glass (excluding the basic glass described above), titania, zirconia, and ytterbium fluoride. Preferred examples include silica and ytterbium fluoride silica. Examples of silica include fumed silica.

[0187] The pH of the non-basic filler is, for example, 1 or more, preferably 1.5 or more, more preferably 2 or more, and for example, less than 7, preferably 6.5 or less, more preferably 6 or less.

[0188] The filler may be surface-treated with a coupling agent or the like to be made hydrophobic or hydrophilic.

[0189] Component B preferably contains a basic filler, more preferably contains a glass containing an alkaline earth metal, and even more preferably contains barium borosilicate glass.

[0190] The filler in component B can be used alone or in combination of two or more. Preferably, a basic filler and a non-basic filler are used in combination. Specifically, a barium borosilicate glass and fumed silica are used in combination. Alternatively, the filler in component B may be only a non-basic filler. Specifically, a fumed silica and ytterbium fluoride are used in combination.

[0191] If component B contains a basic filler, even if the amount of basic material is reduced, the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described later) can be suppressed when components A and B are mixed or brought into contact with each other, thereby improving adhesive strength and bioactivity.

[0192] The solubility of the filler in 100 g of water is, for example, less than 0.1 g, preferably 0.01 g or less, more preferably less than 0.01 g, and even more preferably 0.005 g or less.

[0193] The filler content in agent B is, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, and for example, 95% by mass or less, preferably 85% by mass or less, more preferably 80% by mass or less.

[0194] When component B contains a basic filler, the content of the basic filler in all fillers in component B (total amount of basic filler and non-basic filler) is, for example, 10% by mass or more, preferably 30% by mass or more, more preferably 50% by mass or more, even more preferably 70% by mass or more, particularly preferably 90% by mass or more, or, for example, less than 100% by mass.

[0195] When agent B contains a basic filler, the amount of the basic filler mixed per 100 parts by mass of the basic material in agent B is, for example, 1,000 parts by mass or more, preferably 5,000 parts by mass or more, more preferably 10,000 parts by mass or more, even more preferably 15,000 parts by mass or more, and for example, 100,000 parts by mass or less, preferably 75,000 parts by mass or less, more preferably 50,000 parts by mass or less, even more preferably 30,000 parts by mass or less.

[0196] As long as the amount of basic filler per 100 parts by mass of basic material in Agent B is within the above range, even if the amount of basic material is reduced, when Agents A and B are mixed or contacted, the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group (described below) can be suppressed, thereby improving adhesive strength and bioactivity.

[0197] (2-8) Other additives Component B may contain a photopolymerization initiator, polymerization inhibitor, thickener, solvent, coupling agent, UV absorber, fluorescent agent, and pigment as needed. The explanations for the photopolymerization initiator, polymerization inhibitor, thickener, solvent, coupling agent, UV absorber, fluorescent agent, and pigment in component B are the same as those for the photopolymerization initiator, polymerization inhibitor, thickener, solvent, coupling agent, UV absorber, fluorescent agent, and pigment in component A. Note that when component A does not contain a photopolymerization initiator, component B preferably contains a photopolymerization initiator.

[0198] 2. Preparation method A method for preparing the above-mentioned two-component dental material will now be described.

[0199] To prepare a two-component dental material, first prepare the liquid components of component A and component B. Specifically, in component A, completely soluble materials (e.g., a first acidic monomer, a non-acidic monomer, an oxidizing agent, a photopolymerization initiator, and a stabilizer) are mixed and stirred at room temperature until completely dissolved. In component B, completely soluble materials (e.g., a non-acidic monomer, a reducing agent, and a stabilizer) are mixed and stirred at room temperature until completely dissolved.

[0200] Next, dispersion components for component A and dispersion components for component B are prepared. Specifically, materials that are not completely soluble in component A (e.g., an oxidizing agent and a filler) are prepared. Also, materials that are not completely soluble in component B (e.g., a reducing agent, a transition metal compound, a calcium salt of a second acidic monomer having a carboxy group, a basic material, and a filler) are prepared.

[0201] Next, Agent A can be prepared by mixing the dispersion components of Agent A with the liquid components of Agent A. Similarly, Agent B can be prepared by mixing the dispersion components of Agent B with the liquid components of Agent B. For example, a centrifugal stirring defoamer can be used for mixing.

[0202] A two-component dental material can be produced by filling a container for the two-component dental material with the obtained components A and B. The container for the two-component dental material is not particularly limited as long as it can separately package components A and B. It may be a single syringe-type container in which components A and B can be separately packaged, or they may be packaged in a syringe-type container and a bottle-type container, or they may be packaged in two bottle-type containers, or a kit configuration in which either component A or component B is supported on a brush.

[0203] 3.Reaction mechanism The reaction mechanism of the above-mentioned two-component dental material will be explained below.

[0204] To use a two-part dental material, parts A and B are mixed or applied one on top of the other.

[0205] When components A and B are mixed or brought into contact with each other, the transition metal compound in component B dissolves in the first acidic monomer in component A. The dissolution of the transition metal compound in the first acidic monomer generates transition metal ions. The transition metal ions chemically react with the reducing agent, dissolved oxygen, and oxidizing agent to generate radicals. The generated radicals polymerize each monomer. This reaction mechanism allows two-component dental materials to be used in dental treatments such as filling missing teeth and bonding prosthetic appliances to missing tooth sites.

[0206] 4. Effects In the two-component dental material of the present invention, the component B contains a basic material, which can inhibit the reaction between the first acidic monomer and the calcium salt of the second acidic monomer having a carboxy group that occurs when the components A and B are mixed or brought into contact with each other.

[0207] As a result, two-part dental materials can have improved adhesion and bioactivity.

[0208] 5. Other Embodiments Other embodiments of the two-component dental composition will be described below.

[0209] (1) The two-component dental composition may include a one-component dental pretreatment material and a one-component dental resin cement. The one-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion between the one-component dental resin cement and at least one of a prosthesis and a tooth. For example, after treating the surface of at least one of the tooth and a prosthesis with the one-component dental pretreatment material, the prosthesis is bonded to the tooth with the one-component dental resin cement.

[0210] Agent A may be a one-component dental pretreatment material. The one-component dental pretreatment material contains a first acidic monomer. The one-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0211] When Agent A is a one-component dental pretreatment material, Agent B is a one-component dental resin cement. The one-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives.

[0212] Alternatively, the agent A may be a one-component dental resin cement. The one-component dental resin cement contains a first acidic monomer, a non-acidic monomer, and a filler. The one-component dental resin cement may optionally contain an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, and other additives.

[0213] When Agent A is a one-component dental resin cement, Agent B is a one-component dental pretreatment material. The one-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental pretreatment material optionally contains a transition metal compound, a reducing agent, a non-acidic monomer, a photopolymerization initiator, a filler, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0214] (2) The two-component dental composition may contain a one-component dental pretreatment material and a two-component dental resin cement. The one-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion of the two-component dental resin cement to at least one of a prosthesis and a tooth. For example, after treating the surface of at least one of the tooth and a prosthesis with the one-component dental pretreatment material, the prosthesis is bonded to the tooth with the two-component dental resin cement. The two-component dental resin cement contains a first component and a second component. For example, the two-component dental resin cement may be prepared by mixing the first component and the second component immediately before use and applying the resulting mixture. Alternatively, the two-component dental resin cement may be prepared by applying the first component first and then the second component.

[0215] Agent A may be a one-component dental pretreatment material. In this case, the one-component dental pretreatment material contains a first acidic monomer. The one-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0216] When agent A is a one-component dental pretreatment material, agent B may be the first component of a two-component dental resin cement. In this case, the first component of the two-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The second component of the two-component dental resin cement contains an optional component. At least one of the first and second components of the two-component dental resin cement contains a filler. At least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer.

[0217] Alternatively, component A may be the first component of a two-component dental resin cement. In this case, the first component of the two-component dental resin cement contains a first acidic monomer. The first component of the two-component dental resin cement optionally contains a non-acidic monomer, an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. Either the first component or the second component of the two-component dental resin cement contains a non-acidic monomer. Either the first component or the second component of the two-component dental resin cement contains a filler.

[0218] When component A is the first component of a two-component dental resin cement, component B may be a one-component pretreatment material. In this case, the one-component pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0219] Furthermore, when component A is the first component of a two-component dental resin cement, component B may be the second component of the two-component dental resin cement. In this case, the second component of the two-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. At least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer. At least one of the first and second components of the two-component dental resin cement contains a filler. The one-component pretreatment material has optional components.

[0220] (3) The two-component dental composition may contain a two-component dental pretreatment material and a one-component dental resin cement. The two-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion between the dental resin cement and at least one of a prosthesis and a tooth. For example, the first and second components of the two-component dental pretreatment material are mixed, and the surface of at least one of the tooth and the prosthesis is treated with the resulting mixture. The prosthesis is then bonded to the tooth with the one-component dental resin cement. Alternatively, for example, the surface of at least one of the tooth and the prosthesis is treated with the first component of the two-component dental pretreatment material, and the surface of at least one of the tooth and the prosthesis is then treated with the second component of the two-component dental pretreatment material. The prosthesis is then bonded to the tooth with the one-component dental resin cement.

[0221] Agent A may be the first agent of a two-component dental pretreatment material. In this case, the first agent of the two-component dental pretreatment material contains a first acidic monomer. The first agent of the two-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0222] When component A is the first component of a two-component dental pretreatment material, component B may be the second component of the two-component dental pretreatment material. In this case, the second component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The first and second components of the two-component dental pretreatment material may not contain the non-acidic monomer and the filler. In this case, the one-component dental resin cement contains the non-acidic monomer and the filler.

[0223] Furthermore, when component A is the first component of a two-component dental pretreatment material, component B may be a one-component dental resin cement. The one-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental pretreatment material contains optional components.

[0224] Alternatively, the agent A may be a one-component dental resin cement. In this case, the one-component dental resin cement contains a first acidic monomer, a non-acidic monomer, and a filler. The one-component dental resin cement may optionally contain an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, and other additives.

[0225] When component A is a one-component dental resin cement, component B may be the first component of a two-component dental pretreatment material. In this case, the first component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental pretreatment material contains optional components. The first and second components of the two-component dental pretreatment material do not necessarily contain a non-acidic monomer.

[0226] (4) The two-component dental composition may be a kit consisting of a two-component dental pretreatment material and a two-component dental resin cement. The two-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion of the two-component dental resin cement to at least one of a prosthesis and a tooth. For example, the first and second parts of the two-component dental pretreatment material are mixed, and the surface of at least one of the tooth and the prosthesis is treated with the resulting mixture, and then the prosthesis is bonded to the tooth with the two-component dental resin cement. Alternatively, for example, the surface of at least one of the tooth and the prosthesis is treated with the first part of the two-component dental pretreatment material, and then the surface of at least one of the tooth and the prosthesis is treated with the second part of the two-component dental pretreatment material. Then, for example, the prosthesis is bonded to the tooth with the two-component dental resin cement. For example, the two-component dental resin cement may be prepared by mixing the first and second parts immediately before use and applying the resulting mixture. Furthermore, in the case of a two-component dental resin cement, for example, the first component may be applied first, and then the second component may be applied.

[0227] Alternatively, the agent A may be the first agent of a two-component dental pretreatment material. The first agent of the two-component dental pretreatment material contains a first acidic monomer. The first agent of the two-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0228] When component A is the first component of a two-component dental pretreatment material, component B may be the second component of the two-component dental pretreatment material. The second component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The second component of the two-component dental pretreatment material may not contain a non-acidic monomer or a filler. In this case, at least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer. Furthermore, at least one of the first and second components of the two-component dental resin cement contains a filler.

[0229] Furthermore, when component A is the first component of a two-component dental pretreatment material, component B may be the first component of a two-component dental resin cement. In this case, the first component of the two-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The second component of the two-component dental pretreatment material and the second component of the two-component dental resin cement each contain an optional component. At least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer. At least one of the first and second components of the two-component dental resin cement contains a filler.

[0230] Alternatively, the component A may be the first component of a two-component dental resin cement. In this case, the first component of the two-component dental resin cement contains a first acidic monomer. The first component of the two-component dental resin cement optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0231] When component A is the first component of a two-component dental resin cement, component B may be the second component of the two-component dental resin cement. In this case, the second component of the two-component dental resin cement contains a transition metal compound and a reducing agent. The second component of the two-component dental resin cement optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. At least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer. Furthermore, at least one of the first and second components of the two-component dental resin cement contains a filler. In this case, the first and second components of the two-component dental pretreatment material contain optional components.

[0232] Furthermore, when component A is the first component of a two-component dental resin cement, component B may be the first component of a two-component dental pretreatment material. In this case, the first component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The first component of the two-component dental pretreatment material may not contain a non-acidic monomer or a filler. In this case, the second component of the two-component dental resin cement and the second component of the two-component dental pretreatment material may contain optional components. At least one of the first and second components of the two-component dental resin cement contains a non-acidic monomer. At least one of the first and second components of the two-component dental resin cement contains a filler.

[0233] (5) The two-component dental composition may be a two-component dental self-adhesive composite resin. Two-component dental self-adhesive composite resins are used in dental treatment, for example, to fill missing tooth sites. The definition of self-adhesive is the same as that of the two-component self-adhesive resin cement described above. The two-component dental self-adhesive composite resin includes component A and component B. The two-component dental self-adhesive composite resin may be prepared, for example, by mixing component A and component B immediately before use and applying the resulting mixture. Furthermore, the two-component dental self-adhesive composite resin may be prepared, for example, by applying component A first and then component B.

[0234] Component A contains a first acidic monomer. Component A optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. Component B contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. Component B optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. At least one of components A and B contains a non-acidic monomer. Furthermore, at least one of components A and B contains a filler.

[0235] (6) The two-component dental composition may contain a one-component dental pretreatment material and a one-component dental composite resin. The one-component dental pretreatment material is used in dental treatment, for example, to improve adhesion between the one-component dental composite resin and tooth structure. For example, after treating the tooth surface with the one-component dental pretreatment material, the one-component dental composite resin is filled into the tooth defect.

[0236] Agent A may be a one-component dental pretreatment material. In this case, the one-component dental pretreatment material contains a first acidic monomer. The one-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0237] When Agent A is a one-component dental pretreatment material, Agent B may be a one-component dental composite resin. In this case, the one-component dental composite resin contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives.

[0238] Alternatively, the agent A may be a one-part dental composite resin. The one-part dental composite resin contains a first acidic monomer, a non-acidic monomer, and a filler. The one-part dental composite resin may optionally contain an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, and other additives.

[0239] When component A is a one-component dental composite resin, component B may be a one-component dental pretreatment material. The one-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler.

[0240] (7) The two-component dental composition may be a kit consisting of a one-component dental pretreatment material and a two-component dental composite resin. The one-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion between the two-component dental composite resin and tooth structure. For example, after treating the tooth surface with the one-component dental pretreatment material, the two-component dental composite resin is filled into the tooth defect. The two-component dental composite resin may be prepared, for example, by mixing the first and second components immediately before use and applying the resulting mixture. Alternatively, the two-component dental composite resin may be prepared, for example, by applying the first component followed by the second component.

[0241] Agent A may be a one-component dental pretreatment material. The one-component dental pretreatment material contains a first acidic monomer. The one-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0242] When component A is a one-component dental pretreatment material, component B may be the first component of a two-component dental resin cement. The first component of the two-component dental resin cement contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental composite resin contains an optional ingredient. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler.

[0243] Alternatively, the component A may be the first component of a two-component dental composite resin. In this case, the first component of the two-component dental composite resin contains a first acidic monomer. The first component of the two-component dental resin cement optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0244] When component A is the first component of a two-component dental composite resin, component B may be a one-component dental pretreatment material. The one-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The one-component dental pretreatment material does not necessarily contain the non-acidic monomer or the filler. The second component of the two-component dental composite resin contains an optional ingredient. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. Furthermore, at least one of the first and second components of the two-component dental composite resin contains a filler.

[0245] Furthermore, when component A is the first component of a two-component dental composite resin, component B may be the second component of the two-component dental composite resin. The second component of the two-component dental composite resin contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler. In this case, the one-component pretreatment material may contain any optional components.

[0246] (8) The two-component dental composition may contain a two-component dental pretreatment material and a one-component dental composite resin. The two-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion between the one-component dental composite resin and tooth structure. For example, after treating the tooth surface with the two-component dental pretreatment material, the one-component dental composite resin is filled into the tooth defect. The two-component dental pretreatment material may be prepared, for example, by mixing the first and second components immediately before use and applying the resulting mixture. Alternatively, the two-component dental pretreatment material may be prepared, for example, by applying the first component followed by the second component.

[0247] Agent A may be the first agent of a two-component dental pretreatment material. In this case, the first agent of the two-component dental pretreatment material contains a first acidic monomer. The first agent of the two-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0248] When component A is the first component of a two-component dental pretreatment material, component B may be the second component of the two-component dental pretreatment material. The second component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The first and second components of the two-component dental pretreatment material may not contain a non-acidic monomer or a filler. The one-component dental composite resin contains a non-acidic monomer.

[0249] Furthermore, when component A is the first component of a two-component dental pretreatment material, component B may be a one-component dental composite resin. The one-component dental composite resin contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The one-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental pretreatment material contains optional components.

[0250] Alternatively, the component A may be a one-part dental composite resin. In this case, the one-part dental composite resin contains a first acidic monomer, a non-acidic monomer, and a filler. The one-part dental composite resin may optionally contain an oxidizing agent or a reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, and other additives.

[0251] When component A is a one-component dental composite resin, component B may be the first component of a two-component dental pretreatment material. The first component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental pretreatment material contains optional components. The first and second components of the two-component dental pretreatment material do not necessarily contain the non-acidic monomer or the filler.

[0252] (9) The two-component dental composition may contain a two-component dental pretreatment material and a two-component dental composite resin. The two-component dental pretreatment material is used in dental treatment, for example, to improve the adhesion between the two-component dental composite resin and tooth structure. For example, after treating the tooth surface with the two-component dental pretreatment material, the two-component dental composite resin is filled into the tooth defect. The two-component dental pretreatment material may be prepared, for example, by mixing the first and second components immediately before use and applying the resulting mixture. Alternatively, the two-component dental pretreatment material may be prepared, for example, by applying the first component and then the second component. Alternatively, the two-component dental composite resin may be prepared, for example, by mixing the first and second components immediately before use and applying the resulting mixture. Alternatively, the two-component dental composite resin may be prepared, for example, by applying the first component and then the second component.

[0253] The agent A may be the first agent of a two-component dental pretreatment material. The first agent of the two-component dental pretreatment material contains a first acidic monomer. The first agent of the two-component dental pretreatment material optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0254] When component A is the first component of a two-component dental pretreatment material, component B may be the second component of the two-component dental pretreatment material. The second component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The first and second components of the two-component dental pretreatment material may not contain the non-acidic monomer or the filler. In this case, the first and second components of the two-component dental composite resin may contain optional components. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler.

[0255] Furthermore, when component A is the first component of a two-component dental pretreatment material, component B may be the first component of a two-component dental composite resin. The first component of the two-component dental composite resin contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. In this case, the second component of the two-component dental pretreatment material and the second component of the two-component dental composite resin contain optional ingredients. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler.

[0256] Alternatively, the component A may be the first component of a two-component dental composite resin. In this case, the first component of the two-component dental composite resin contains a first acidic monomer. The first component of the two-component dental composite resin optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives.

[0257] When component A is the first component of a two-component dental composite resin, component B is the first component of a two-component dental pretreatment material. The first component of the two-component dental pretreatment material contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The first component of the two-component dental pretreatment material optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The second component of the two-component dental pretreatment material and the second component of the two-component dental composite resin contain optional ingredients. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler.

[0258] Furthermore, when component A is the first component of a two-component dental composite resin, component B may be the second component of the two-component dental composite resin. The second component of the two-component dental composite resin contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. The second component of the two-component dental composite resin optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. The first and second components of the two-component dental pretreatment material may contain optional ingredients. At least one of the first and second components of the two-component dental composite resin contains a non-acidic monomer. At least one of the first and second components of the two-component dental composite resin contains a filler.

[0259] (10) The two-component dental composition may be a two-component dental coating agent. Two-component dental coating agents are used in dental treatment, for example, to coat the surface of tooth structure. The two-component dental coating agent includes agent A and agent B. The two-component dental coating agent may be prepared, for example, by mixing agent A and agent B immediately before use and applying the resulting mixture. Alternatively, the two-component dental coating agent may be prepared by applying agent A first and then agent B second.

[0260] Component A contains a first acidic monomer. Component A optionally contains a non-acidic monomer, an oxidizing agent or reducing agent, an imide compound, an azole compound, a photopolymerization initiator, a transition metal compound, a filler, and other additives. Component B contains a basic material and a calcium salt of a second acidic monomer having a carboxy group. Component B optionally contains a non-acidic monomer, a reducing agent or oxidizing agent, a transition metal compound, a filler, a photopolymerization initiator, and other additives. At least one of components A and B contains a non-acidic monomer. Component A and component B may not contain a filler. [Example]

[0261] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited thereto. Specific numerical values ​​of the blending ratios (content ratios), physical property values, parameters, etc. used in the following description can be replaced with the upper limit values ​​(defined numerical values ​​for "not more than" and "less than") or lower limit values ​​(defined numerical values ​​for "not less than" and "exceeding") of the corresponding blending ratios (content ratios), physical property values, parameters, etc. described in the above "Modes for Carrying Out the Invention."

[0262] The components used in the examples and comparative examples are shown below.

[0263] MDP: 10-methacryloyloxydecyl acid phosphate 4-MET: 4-methacryloyloxyethyl trimellitic acid UDMA: [2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)]dimethacrylate EBPADMA: Ethoxylated bisphenol A dimethacrylate NPGDMA: Neopentyl glycol dimethacrylate HEMA: 2-hydroxyethyl methacrylate TEGDMA: Triethylene glycol dimethacrylate BPB: t-butyl peroxybenzoate DMPT: N,N-dimethyl-p-toluidine EDAB: Ethyl 4-(dimethylamino)benzoate TMTU: Trimethylthiourea SA: Saccharin DMI: 1,2-dimethylbenzimidazole CQ: Camphorquinone BHT: Dibutylhydroxytoluene STS: Sodium p-toluenesulfinate (powder, particle size 63 μm or less) CuH: Copper (II) hydroxide (powder, particle size 20 μm or less) PSS: Potassium peroxodisulfate C-MET: Calcium salt of 4-MET C-MDP: Calcium salt of MDP CH: Calcium hydroxide CC: Calcium carbonate BG: Barium borosilicate glass (silane-treated), trade name "GM8235", manufactured by Shot Co., Ltd. R812 (trade name): Fumed silica, manufactured by Aerosil Co., Ltd. YbF3: Ytterbium fluoride

[0264] Example 1 <Preparation of Agent A and Agent B> According to the formulation of Preparation Example a shown in Table 1, the liquid component of Agent A was stirred at room temperature until completely dissolved. Also, the liquid component of Agent B was similarly stirred at room temperature until completely dissolved.

[0265] According to the formulation of Preparation Example 1 shown in Table 2, the dispersion components of Agent A and Agent B were prepared.

[0266] Next, as shown in Table 3, the dispersion component of Agent A in Preparation Example 1 was mixed with the liquid component of Agent A in Preparation Example a above using a centrifugal stirring defoamer to obtain Agent A. Similarly, the dispersion component of Agent B in Preparation Example 1 was mixed with the liquid component of Agent B in Preparation Example a above using a centrifugal stirring defoamer to obtain Agent B. Agent A and Agent B were uniform paste-like compositions.

[0267] The obtained Agent A and Agent B were filled into a 2-paste syringe manufactured by Medmix Co., Ltd. In this way, a two-agent type dental material of Example 1 was produced.

[0268] The two-agent type dental material of Example 1 (syringe filled with Agent A and Agent B) was used for the following evaluation.

[0269] Examples 2, 3 and Comparative Examples 1 - 9 Except for the following changes, two-agent type dental materials of Examples 2, 3 and Comparative Examples 1 - 9 were produced in the same manner as in Example 1 and used for the following evaluation.

[0270] Dispersion components of agent A and dispersion components of agent B were prepared according to the formulations of Preparation Examples 2 and 3 and Comparative Preparation Examples 1 to 9 shown in Tables 2 and 3. Then, as shown in Table 4, each dispersion component was mixed with the liquid component of Preparation Example a. Note that the dispersion components of Examples 2 and 3 and Comparative Preparation Examples 1 to 9 correspond to Preparation Examples 2 and 3 and Comparative Preparation Examples 1 to 9, respectively.

[0271] Comparative Examples 10 and 11 Two-component dental materials of Comparative Examples 10 and 11 were prepared in the same manner as in Example 1, except for the following changes, and used in the following evaluations.

[0272] Liquid components for agent A and agent B were prepared according to the formulation of Preparation Example b shown in Table 1. Dispersion components for agent A and agent B were prepared according to the formulations of Comparative Preparation Examples 10 and 11 shown in Table 3. Then, as shown in Table 4, each dispersion component was mixed with the liquid component of Preparation Example b. The dispersion components of Comparative Examples 10 and 11 correspond to those of Comparative Preparation Examples 10 and 11.

[0273] <Evaluation> [Adhesiveness] Bovine dentin was scraped to a smooth surface using waterproof abrasive paper, and then Agents A and B from each Example and Comparative Example were mixed and applied. A 50 μm-thick cellophane film was then placed over the surface and pressed against a glass plate to flatten the mixture to approximately 1 mm. The mixture was allowed to stand at room temperature for 30 minutes to harden, and an adhesion evaluation sample was prepared. After the hardening, the adhesion evaluation sample was immersed in purified water at 37°C for 24 hours. The removed adhesion evaluation sample was sliced ​​to a thickness of 1 mm and immersed in 6 mol / L hydrochloric acid for 35 seconds to decalcify the dentin surface. The adhesion evaluation sample was then immersed in approximately 2% sodium hypochlorite aqueous solution for 12 minutes and then subjected to ultrasonic irradiation for 60 seconds to remove organic matter from the dentin. The adhesion evaluation sample was then dried in a desiccator at 37°C for 24 hours, and the adhesive interface between the hardened mixture and bovine dentin was observed using a scanning electron microscope and evaluated according to the following criteria. The results are shown in Table 3. {standard} ○: No cracks were observed at the adhesive interface. △: Slight cracks observed at the adhesive interface. ×: Large cracks were observed at the adhesive interface, or the interface could not be observed due to detachment.

[0274] [Bioactive] Simulated body fluid (SBF) was prepared in accordance with ISO29022:2013. After 24 hours of storage, agent A and agent B from each Example and Comparative Example were mixed in SBF at 37°C, and the mixture was left at room temperature for 30 minutes to obtain a hardened body having a diameter of 10 mm and a thickness of 2 mm. This was then immersed for 120 hours. The formation of crystals on the surface of the hardened body after immersion was evaluated using a scanning electron microscope (SEM) and energy dispersive X-ray analysis (EDS) according to the following criteria. The results are shown in Table 3. {standard} ○: Apatite-like crystals consisting of phosphorus and calcium were formed on the entire surface of the hardened body. Δ: Crystals consisting of phosphorus and calcium were formed on at least a part of the surface of the hardened body. ×: No crystals made of phosphorus and calcium were formed on the surface of the hardened body.

[0275] [Table 1]

[0276] [Table 2]

[0277] [Table 3]

[0278] [Table 4]

[0279] <Consideration> The results in Table 4 show that the two-component dental materials comprising Parts A and B of Examples 1 to 3 can improve adhesion and bioactivity. Therefore, the two-component dental materials of the present invention are effective as dental materials.

Claims

1. an agent A containing a first acidic monomer; a component B containing a basic material and a calcium salt of a second acidic monomer having a carboxy group; A two-component dental material comprising:

2. The two-part dental material according to claim 1 , wherein the basic material is slightly water-soluble.

3. The two-part dental material according to claim 2 , wherein the basic material is a basic inorganic material.

4. The two-component dental material according to claim 3 , wherein the basic inorganic material is at least one of calcium hydroxide and calcium carbonate.

5. The two-component dental material according to claim 1 , wherein at least one of the A-component and the B-component further contains an oxidizing agent.

6. The two-component dental material according to claim 1 , wherein at least one of the A component and the B component further contains a reducing agent.

7. The two-component dental material according to claim 1 , wherein at least one of the A and B components further contains a transition metal compound.

8. The two-component dental material according to claim 7 , wherein the transition metal compound is a fourth-period transition metal compound.

9. 9. The two-component dental material according to claim 8, wherein the transition metal compound is at least one selected from the group consisting of a copper compound, a vanadium compound, and an iron compound.

10. The two-component dental material according to claim 1 , wherein at least one of the A-component and the B-component further contains a filler.

11. The two-component dental material according to claim 10 , wherein the part B further contains a basic filler.

12. 12. The two-part dental material of claim 11, wherein the basic filler is barium borosilicate glass.

13. The agent B further contains a basic filler, the basic filler is barium borosilicate glass; The two-part dental material of claim 1 , wherein the basic material is calcium hydroxide.

14. The two-component dental material according to any one of claims 1 to 13, wherein the calcium salt of the second acidic monomer having a carboxy group is slightly water-soluble.

15. The two-component dental material according to claim 14, wherein the calcium salt of the second acidic monomer having a carboxy group is a calcium salt of an aromatic carboxylic acid derivative.

16. 16. The two-component dental material according to claim 15, wherein the calcium salt of an aromatic carboxylic acid derivative is a calcium salt of 4-methacryloyloxyethyltrimellitic acid.

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