Dental composition

Abstract

To obtain a dental composition capable of providing a cured product having excellent adhesive strength to a dental porcelain and a resin block even without carrying out a hydrofluoric acid treatment and further having excellent adhesive strength to dentin.SOLUTION: The dental composition includes a monomer (A) having an acidic group, a monomer (B) having no acidic group, a polymerization initiator (C), a silane coupling agent (D), and water (E). The silane coupling agent (D) contains a first silane coupling agent (D1) having a polymerizable group and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and a silanol group of the first silane coupling agent (D1), and the monomer (B) having no acidic group contains a monomer (B1) having an amide group without an acidic group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a dental composition. [Background technology]

[0002] Dental compositions used as dental bonding materials and dental primers are required to have high adhesion to tooth tissues such as enamel, dentin, and cementum, as well as to dental porcelain and resin blocks, which are used as restorative materials for crowns. Here, resin blocks are dental materials that constitute mill blanks, which are materials to be cut in CAD / CAM systems.

[0003] To meet this demand, for example, Patent Document 1 proposes a dental adhesive composition that exhibits good adhesion to the surface of a dental restorative material, and that contains a silane composition containing a (meth)acrylate-functional silane and an amino-functional silane. Patent Document 2 also describes a one-component dental composition used as an adhesive and primer, which contains a silane compound having a specific structure, a monomer having an acidic group, and water. Patent Document 3 also describes a dental pretreatment agent that contains a first silane compound having a functional group and a second silane compound not having the functional group. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Special Publication No. 2020-519674 [Patent Document 2] International Publication No. 2019 / 082855 [Patent Document 3] International Publication No. 2022 / 210010 Summary of the Invention [Problem to be solved by the invention]

[0005] In conventional dental compositions, in order to achieve sufficient adhesion to dental porcelain, the dental porcelain has been treated with hydrofluoric acid in advance. Hydrofluoric acid treatment involves etching the surface of the adherend with hydrofluoric acid to roughen it or form a retaining pattern, and the hydrofluoric acid treatment increases the adhesive strength. However, when a dental restorative material is treated with hydrofluoric acid, there is a risk that a strong acidic substance may be introduced into the oral cavity. Therefore, from the viewpoint of ensuring patient safety, there is a demand for a dental composition that does not require hydrofluoric acid treatment and that can produce a cured product having high adhesive strength to dental porcelain and resin blocks. Patent Documents 1 and 3 do not disclose specific examples of dental adhesive compositions or dental pretreatment agents that contain a monomer that has no acidic group but has an amide group. Patent Document 2 does not disclose specific examples of dental compositions that contain, as silane compounds having a specific structure, a silane coupling agent that has a polymerizable group and a silane coupling agent that has an amino group.

[0006] An object of the present invention is to provide a dental composition that can give a cured product having excellent adhesive strength to dental porcelain and resin blocks, and also having excellent adhesive strength to tooth structure, even without hydrofluoric acid treatment. [Means for solving the problem]

[0007] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by preparing a dental composition containing a monomer having an acidic group, a monomer having an amide group but no acidic group, and a specific number of types of silane coupling agents, and have arrived at the present invention. That is, the present invention encompasses the following inventions. [1] A dental composition comprising: a monomer (A) having an acidic group; a monomer (B) not having an acidic group; a polymerization initiator (C); a silane coupling agent (D); and water (E); The silane coupling agent (D) comprises a first silane coupling agent (D1) having a polymerizable group, and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group possessed by the first silane coupling agent (D1); A dental composition, wherein the monomer (B) having no acidic group comprises a monomer (B1) having no acidic group and an amide group. [2] The dental composition according to [1] above, wherein the hydrogen-bonding group possessed by the second silane coupling agent (D2) is at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group. [3] The dental composition according to the above [1] or [2], wherein the monomer (A) having an acidic group includes 10-methacryloyloxydecyl dihydrogen phosphate. [4] The dental composition according to any one of the above [1] to [3], wherein the monomer (B1) having no acidic group but having an amide group includes N-methacryloyloxyethyl acrylamide. [5] The dental composition according to any one of the above [1] to [4], wherein the monomer (B) having no acidic group further comprises a monomer (B2) having no acidic group or amide group. [6] The dental composition according to any one of the above [1] to [5], wherein the ratio MB1 / MD2 of the mass MB1 of the monomer (B1) having no acidic group but an amide group to the mass MD2 of the second silane coupling agent (D2) is 5 to 80. [7] The dental composition according to any one of the above [1] to [6], further comprising a filler (F). [8] The dental composition according to [7] above, wherein the filler (F) is surface-treated. [9] The dental composition according to any one of the above [1] to [8], which is a dental bonding material.

[10] The dental composition according to any one of the above [1] to [8], which is a dental primer. [Effects of the Invention]

[0008] The present invention provides a dental composition that can give a cured product having excellent adhesive strength to dental porcelain and resin blocks, and also having excellent adhesive strength to tooth structure, even without hydrofluoric acid treatment. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described in detail below using embodiments. In this specification, the upper and lower limits of the numerical ranges (contents of each component, values ​​calculated from each component, and each physical property) can be combined as appropriate. In addition, in this specification, the numerical values ​​of each symbol in the formula can also be combined as appropriate. In other words, in this specification, the lower and upper limits of numerical ranges described in stages can be independently combined. For example, the description of "preferably 10 to 90, more preferably 30 to 60" for the same item can be combined with the "preferable lower limit (10)" and the "more preferable upper limit (60)" to form "10 to 60." Furthermore, with regard to a numerical range, for example, based on the description "preferably 10 to 90, more preferably 30 to 60," the upper limit value may not be particularly specified and only the lower limit value may be specified as "10 or more" or "30 or more." Similarly, the lower limit value may not be particularly specified and only the upper limit value may be specified as "90 or less" or "60 or less." Unless otherwise specified, when a numerical range is simply stated as "10 to 90", it means a range of 10 or more and 90 or less. As above, for example, from the description of "preferably 10 or more, more preferably 30 or more" and the description of "preferably 90 or less, more preferably 60 or less" for the same item, the "preferable lower limit (10)" and the "more preferable upper limit (60)" can be combined to form "10 or more and 60 or less." Furthermore, as above, only the lower limit can be specified as "10 or more" or "30 or more," and similarly, only the lower limit can be specified as "90 or less" or "60 or less."

[0010] In this specification, the term "(meth)acrylic" is used to encompass both "methacrylic" and "acrylic." The same applies to similar terms such as "(meth)acrylate," "(meth)acrylic acid ester," "(meth)acrylamide," and "(meth)acryloyloxy."

[0011] [Dental composition] A dental composition according to an embodiment of the present invention is a dental composition comprising a monomer (A) having an acidic group, a monomer (B) not having an acidic group, a polymerization initiator (C), a silane coupling agent (D), and water (E), wherein the silane coupling agent (D) comprises a first silane coupling agent (D1) having a polymerizable group and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group possessed by the first silane coupling agent (D1), and the monomer (B) not having an acidic group comprises a monomer (B1) not having an acidic group but having an amide group.

[0012] The reason why the cured product of the dental composition has excellent adhesive strength to dental porcelain and resin blocks, and also to tooth structure, even without hydrofluoric acid treatment is presumed to be, but not limited to, the following. When the first silane coupling agent (D1) having a polymerizable group is used alone as a silane coupling agent, the alkoxy groups bonded to silicon in the molecule are hydrolyzed to form silanol groups. Subsequently, in a dental composition under acidic conditions, such as the dental composition according to the present invention, the monomer (A) having an acidic group rapidly dehydrates and condenses the silanol groups between the two molecules, reducing the number of reactive sites with the dental porcelain. Furthermore, the steric hindrance caused by the alkyl groups at the ends of the molecules and the acryloyl groups in the molecules approaching the hydroxyl groups that remain undehydrated and condensed further reduces the number of reactive sites with the resin block and the dental porcelain. As a result, it is believed that the cured product of the dental composition is less likely to exhibit sufficient adhesive strength to the substrate. Furthermore, when a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group of the first silane coupling agent (D1) is used alone as a silane coupling agent, the alkoxy group bonded to silicon in the molecule is hydrolyzed to form a silanol group, and then the hydrogen-bonding group in the molecule and the silanol group of the first silane coupling agent (D1) form a hydrogen bond to stabilize the compound, making it difficult for dehydration condensation to proceed.

[0013] On the other hand, in a dental composition according to an embodiment of the present invention, when a first silane coupling agent (D1) having a polymerizable group is used in combination with a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group of the first silane coupling agent (D1), each silane coupling agent hydrolyzes to form a silanol group, and then a portion of the first silane coupling agent (D1) and a portion of the second silane coupling agent (D2) undergo dehydration condensation. The hydrogen-bonding group derived from the dehydration condensation-induced second silane coupling agent (D2) then forms a hydrogen bond with an adjacent silanol group in the first silane coupling agent (D1), thereby suppressing the condensation of the silane coupling agents as a whole. As a result, a certain number of bonding points to the adherend are secured, and the cured product of the dental composition is thought to have high adhesive strength to dental porcelain.

[0014] On the other hand, the resin block is composed of an inorganic filler and a cured product of a monomer, and the cured product of the monomer is hydrophobic. Therefore, the coating ability of the dental composition on the resin block tends to be poorer than that of dental porcelain. The dental composition according to an embodiment of the present invention contains the second silane coupling agent (D2) having the highly hydrophilic hydrogen-bonding group and the monomer (B1) having an amide group but no acidic group, thereby enhancing the effect of modifying the resin block surface (imparting hydrophilicity). As a result, the dental composition is believed to have high adhesive strength not only to dental porcelain but also to the resin block.

[0015] <Monomer (A) Having an Acidic Group> The acidic group-containing monomer (A) contained in the dental composition according to an embodiment of the present invention has an acid etching effect and a priming effect, and is a component that provides demineralization and penetration. The acidic group-containing monomer (A) is also polymerizable and provides a curing effect. The inclusion of the acidic group-containing monomer (A) improves the adhesion and durability of the dental restoration material and tooth structure. Hereinafter, the monomer (A) having an acidic group may be simply referred to as "monomer (A)".

[0016] Examples of the monomer (A) having an acidic group include a monomer having at least one acidic group such as a phosphate group, pyrophosphate group, thiophosphate group, phosphonate group, sulfonate group, or carboxy group, and at least one polymerizable group such as a (meth)acryloyl group, vinyl group, or styrene group. From the viewpoint of adhesion to tooth tissue, a phosphate group-containing monomer is preferred. Specific examples of the monomer (A) having an acidic group are listed below.

[0017] Examples of the phosphate group-containing monomer include 2-(meth)acryloyloxyethyl dihydrogen phosphate, 3-(meth)acryloyloxypropyl dihydrogen phosphate, 4-(meth)acryloyloxybutyl dihydrogen phosphate, 5-(meth)acryloyloxypentyl dihydrogen phosphate, 6-(meth)acryloyloxyhexyl dihydrogen phosphate, 7-(meth)acryloyloxyheptyl dihydrogen phosphate, 8-(meth)acryloyloxyoctyl dihydrogen phosphate, 9-(meth)acryloyloxynonyl dihydrogen phosphate, 10-(meth)acryloyloxydecyl dihydrogen phosphate, 11-(meth)acryloyloxyundecyl dihydrogen phosphate, 12-(meth)acryloyloxydodecyl dihydrogen phosphate, 16-(meth)acryloyloxyhexadecyl dihydrogen phosphate, 20-(meth)acryloyl Examples of suitable hydrogen phosphates include acryloyloxycosyl dihydrogen phosphate, bis[2-(meth)acryloyloxyethyl]hydrogen phosphate, bis[4-(meth)acryloyloxybutyl]hydrogen phosphate, bis[6-(meth)acryloyloxyhexyl]hydrogen phosphate, bis[8-(meth)acryloyloxyoctyl]hydrogen phosphate, bis[9-(meth)acryloyloxynonyl]hydrogen phosphate, bis[10-(meth)acryloyloxydecyl]hydrogen phosphate, 1,3-di(meth)acryloyloxypropyl dihydrogen phosphate, 2-(meth)acryloyloxyethylphenyl hydrogen phosphate, 2-(meth)acryloyloxyethyl-2-bromoethyl hydrogen phosphate, bis[2-(meth)acryloyloxy-(1-hydroxymethyl)ethyl]hydrogen phosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0018] Examples of pyrophosphate group-containing monomers include bis[2-(meth)acryloyloxyethyl] pyrophosphate, bis[4-(meth)acryloyloxybutyl] pyrophosphate, bis[6-(meth)acryloyloxyhexyl] pyrophosphate, bis[8-(meth)acryloyloxyoctyl] pyrophosphate, bis[10-(meth)acryloyloxydecyl] pyrophosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0019] Examples of the thiophosphate group-containing monomer include 2-(meth)acryloyloxyethyl dihydrogenthiophosphate, 3-(meth)acryloyloxypropyl dihydrogenthiophosphate, 4-(meth)acryloyloxybutyl dihydrogenthiophosphate, 5-(meth)acryloyloxypentyl dihydrogenthiophosphate, 6-(meth)acryloyloxyhexyl dihydrogenthiophosphate, 7-(meth)acryloyloxyheptyl dihydrogenthiophosphate, and 8-(meth)acryloyloxyoctyl dihydrogenthiophosphate. phosphate, 9-(meth)acryloyloxynonyl dihydrogen thiophosphate, 10-(meth)acryloyloxydecyl dihydrogen thiophosphate, 11-(meth)acryloyloxyundecyl dihydrogen thiophosphate, 12-(meth)acryloyloxydodecyl dihydrogen thiophosphate, 16-(meth)acryloyloxyhexadecyl dihydrogen thiophosphate, 20-(meth)acryloyloxyicosyl dihydrogen thiophosphate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0020] Examples of the phosphonic acid group-containing monomer include 2-(meth)acryloyloxyethyl phenylphosphonate, 5-(meth)acryloyloxypentyl-3-phosphonopropionate, 6-(meth)acryloyloxyhexyl-3-phosphonopropionate, 10-(meth)acryloyloxydecyl-3-phosphonopropionate, 6-(meth)acryloyloxyhexyl-3-phosphonoacetate, 10-(meth)acryloyloxydecyl-3-phosphonoacetate, and acid chlorides, alkali metal salts, and ammonium salts thereof.

[0021] Examples of sulfonic acid group-containing monomers include 2-(meth)acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, and 2-sulfoethyl(meth)acrylate.

[0022] Examples of the carboxy group-containing monomer include a monomer having one carboxy group in the molecule and a monomer having multiple carboxy groups in the molecule.

[0023] Examples of monomers having one carboxy group in the molecule include (meth)acrylic acid, N-(meth)acryloylglycine, N-(meth)acryloylaspartic acid, N-(meth)acryloyltyrosine, N-(meth)acryloyltyrosine, N-(meth)acryloylphenylalanine, N-(meth)acryloyl-p-aminobenzoic acid, N-(meth)acryloyl-o-aminobenzoic acid, p-vinylbenzoic acid, and 2-(meth)acryloyloxybenzoic acid. Acid, 3-(meth)acryloyloxybenzoic acid, 4-(meth)acryloyloxybenzoic acid, N-(meth)acryloyl-5-aminosalicylic acid, N-(meth)acryloyl-4-aminosalicylic acid, 2-(meth)acryloyloxyethyl hydrogen succinate, 2-(meth)acryloyloxyethyl hydrogen phthalate, and 2-(meth)acryloyloxyethyl hydrogen maleate, as well as acid halides thereof.

[0024] Examples of the monomer having a plurality of carboxy groups in the molecule include 6-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 9-(meth)acryloyloxynonane-1,1-dicarboxylic acid, 10-(meth)acryloyloxydecane-1,1-dicarboxylic acid, 11-(meth)acryloyloxyundecane-1,1-dicarboxylic acid, 12-(meth)acryloyloxydodecane-1,1-dicarboxylic acid, 13-(meth)acryloyloxytridecane-1,1-dicarboxylic acid, 4 ...4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 4-(meth)acryloyl Examples of the acid anhydrides include 4-(meth)acryloyloxyethyl trimellitate, 4-(meth)acryloyloxyethyl trimellitate anhydride, 4-(meth)acryloyloxybutyl trimellitate, 4-(meth)acryloyloxyhexyl trimellitate, 4-(meth)acryloyloxydecyl trimellitate, 2-(meth)acryloyloxyethyl-3'-(meth)acryloyloxy-2'-(3,4-dicarboxybenzoyloxy)propyl succinate, and acid anhydrides or acid halides thereof.

[0025] Among these monomers (A) having an acidic group, (meth)acrylic monomers containing a phosphate group or a pyrophosphate group are preferred because they exhibit superior adhesion to tooth structure, and (meth)acrylic monomers containing a phosphate group are more preferred. Among these, divalent (meth)acrylic monomers containing a phosphate group and an alkyl or alkylene group having 6 to 20 carbon atoms as the main chain in the molecule are more preferred because they exhibit high demineralization properties and high adhesion in the absence of organic solvents, and divalent (meth)acrylic monomers containing a phosphate group and an alkylene group having 8 to 12 carbon atoms as the main chain in the molecule, such as 10-methacryloyloxydecyl dihydrogen phosphate, are even more preferred, and it is particularly preferred that the monomer (A) having an acidic group includes 10-methacryloyloxydecyl dihydrogen phosphate.

[0026] The monomer (A) having an acidic group may be used alone or in combination of two or more. The content of the monomer (A) having an acidic group is preferably in the range of 1 to 50 mass %, more preferably 3 to 40 mass %, and even more preferably 5 to 30 mass %, based on 100 mass % of the total amount of the monomer components in the dental composition, from the viewpoint of easily preventing a decrease in adhesiveness.

[0027] The content of the monomer (A) having an acidic group in the dental composition is preferably 3 to 20 mass %, more preferably 4 to 18 mass %, and even more preferably 5 to 16 mass %, relative to 100 mass % of the dental composition, from the viewpoint of adhesion to tooth structure and crown restorative materials.

[0028] From the viewpoint of further enhancing adhesiveness, the content of 10-methacryloyloxydecyl dihydrogen phosphate in the monomer (A) having an acidic group is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more. There is no particular upper limit, and it may be 100% by mass, 99% by mass, or 98% by mass. In other words, the content of 10-methacryloyloxydecyl dihydrogen phosphate in the monomer (A) having an acidic group is preferably 50 to 100% by mass.

[0029] <Monomer (B) having no acidic group> Examples of the monomer (B) that does not have an acidic group and is contained in the dental composition according to an embodiment of the present invention include monomers that do not have an acidic group such as a phosphate group, a pyrophosphate group, a thiophosphate group, a phosphonate group, a sulfonic acid group, or a carboxy group, and that have at least one polymerizable group such as a (meth)acryloyl group, a vinyl group, or a styrene group. The monomer (B) having no acidic group is a component that imparts penetration properties to the dental composition according to an embodiment of the present invention and mechanical strength to the cured product. Furthermore, the monomer (B) having no acidic group is polymerizable and also imparts a curing property to the dental composition. The dental composition containing the monomer (B) having no acidic group improves adhesion to crown restorative materials and tooth structure and improves adhesion durability. As described above, the monomer (B) having no acidic group contains the monomer (B1) having no acidic group but an amide group. By including the monomer (B1) having no acidic group but an amide group, the dental composition according to the embodiment of the present invention is endowed with a penetrating effect and a modifying effect on the surface of the resin block. From the viewpoints of the mechanical strength of the cured product, adhesion to dental prosthetic restoration materials and tooth structure, etc., the monomer (B) having no acidic group is preferably a mixture of multiple types of compounds, and more preferably a mixture of a monomer (B1) having no acidic group but an amide group and a monomer (B2) having neither an acidic group nor an amide group, which will be described later. Hereinafter, the monomer (B) having no acidic group may be simply referred to as "monomer (B)". Also, the monomer (B1) having no acidic group but an amide group may be simply referred to as "monomer (B1)". Also, the monomer (B2) having no acidic group or amide group may be simply referred to as "monomer (B2)".

[0030] The content of the monomer (B) not having an acidic group in the dental composition is preferably 35 to 70 mass %, more preferably 40 to 65 mass %, and even more preferably 45 to 60 mass %, relative to 100 mass % of the dental composition, from the viewpoint of the mechanical strength and adhesiveness of the cured product.

[0031] The ratio MB1 / MB2 of the mass MB1 of the monomer (B1) having no acidic group but an amide group to the mass MB2 of the monomer (B2) having no acidic group or amide group is preferably 0.2 to 4.0, more preferably 0.3 to 3.0, and even more preferably 0.35 to 2.0, from the viewpoint of the mechanical strength and adhesiveness of the cured product.

[0032] (Monomer (B1) having no acidic group but having an amide group) As the monomer (B1) having an amide group but no acidic group, a known monomer having an amide group but no acidic group can be used, such as a hydrophobic monomer (B1a) having an amide group but no acidic group, or a hydrophilic monomer (B1b) having an amide group but no acidic group. The amide group includes a (meth)acrylamide group. The monomer (B1) may be used alone or in combination of two or more kinds. For example, a hydrophobic monomer (B1a) having no acidic group but an amide group may be used in combination with a hydrophilic monomer (B1b) having no acidic group but an amide group. The dental composition according to an embodiment of the present invention contains a monomer (B1) that does not have an acidic group but has an amide group, thereby improving the penetration into tooth structure and thereby improving adhesive strength.

[0033] (i) Hydrophobic monomer (B1a) having no acidic group but having an amide group The dental composition according to the embodiment of the present invention contains a hydrophobic monomer (B1a) that does not have an acidic group but has an amide group, thereby improving the mechanical strength, handleability, etc. of the cured product (a cured product obtained by curing the dental composition). The hydrophobic monomer (B1a) having no acidic group but an amide group preferably has no acidic group but a (meth)acrylamide group. The hydrophobic monomer (B1a) having no acidic group but an amide group may have a solubility in water at 25°C of less than 10% by mass, and examples thereof include aliphatic bifunctional monomers.

[0034] Examples of the aliphatic bifunctional monomer include N-methacryloyloxyethyl acrylamide, N-methacryloyloxypropyl acrylamide, N-methacryloyloxybutyl acrylamide, N-(1-ethyl-(2-methacryloyloxy)ethyl)acrylamide, and N-(2-(2-methacryloyloxyethoxy)ethyl)acrylamide. Among these, N-methacryloyloxyethyl acrylamide (commonly known as "MAEA") and N-methacryloyloxypropyl acrylamide are preferred.

[0035] Among the above-mentioned hydrophobic monomers (B1a) having an amide group but no acidic group, the monomer (B1) having an amide group but no acidic group more preferably contains N-methacryloyloxyethyl acrylamide (commonly known as "MAEA") from the viewpoint of the mechanical strength and handling of the cured product. The hydrophobic monomers (B1a) having an amide group but no acidic group may be used alone or in combination of two or more.

[0036] From the viewpoint of improving the mechanical strength and handleability of the cured product, the content of the hydrophobic monomer (B1a) having no acidic group but an amide group in the dental composition according to an embodiment of the present invention is preferably 9% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, based on the mass of all monomers contained in the dental composition, and is preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, and particularly preferably 70% by mass or less. In other words, the content of the hydrophobic monomer (B1a) having no acidic group but an amide group in the dental composition is preferably 9 to 90% by mass.

[0037] (ii) Hydrophilic monomer (B1b) having no acidic group but having an amide group The dental composition according to an embodiment of the present invention contains a hydrophilic monomer (B1b) that does not have an acidic group but has an amide group, which can promote the penetration of the components in the dental composition into the tooth structure and also allow the dental composition itself to penetrate into the tooth structure and adhere to organic components (such as collagen) in the tooth structure. The hydrophilic monomer (B1b) having no acidic group but an amide group is preferably a radically polymerizable monomer having no acidic group but a polymerizable group. The polymerizable group is preferably a (meth)acryloyl group, since radical polymerization is easy. The hydrophilic monomer (B1b) having no acidic group but an amide group can be one having a solubility in water at 25°C of 10% by mass or more, preferably 30% by mass or more, and more preferably one that can be dissolved in water at any ratio at 25°C.

[0038] The hydrophilic monomer (B1b) having no acidic group but an amide group is preferably one having a hydrophilic group such as a hydroxy group, an oxymethylene group, an oxyethylene group, or an oxypropylene group in addition to the amide group, and examples thereof include monofunctional (meth)acrylamides such as N-methylol(meth)acrylamide, N-hydroxyethyl(meth)acrylamide, N-methoxymethyl(meth)acrylamide, N-ethoxymethyl(meth)acrylamide, diacetone(meth)acrylamide, 4-(meth)acryloylmorpholine, and disubstituted (meth)acrylamides represented by the following general formula (1):

[0039] [ka]

[0040] In the above general formula (1), R 10 and R 11 are each independently a linear or branched alkyl group having 1 to 3 carbon atoms which may have a substituent, and R 12 is a hydrogen atom or a methyl group.

[0041] R 10 and R 11 Examples of the alkyl group having 1 to 3 carbon atoms represented by the following formula include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group, and examples of the substituents that these groups may have include a hydroxy group.

[0042] Examples of disubstituted (meth)acrylamides represented by the above general formula (1) include N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, and N,N-di(hydroxyethyl)(meth)acrylamide. From the viewpoint of storage stability, N,N-dimethylacrylamide and N,N-diethylacrylamide are preferred, and N,N-diethylacrylamide is more preferred.

[0043] Among the above-mentioned hydrophilic monomers (B1b) having no acidic group but an amide group, from the viewpoint of adhesion to tooth structure, diacetone (meth)acrylamide and the disubstituted (meth)acrylamides represented by the above general formula (1) are more preferred, the disubstituted (meth)acrylamides represented by the above general formula (1) are even more preferred, and N,N-diethylacrylamide is particularly preferred. The hydrophilic monomers (B1b) having no acidic group but an amide group may be used alone or in combination of two or more.

[0044] The content of the hydrophilic monomer (B1b) having no acidic group but an amide group in the dental composition according to an embodiment of the present invention is preferably 9% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more, based on the mass of all monomers contained in the dental composition, from the viewpoint of improving adhesive strength, and is preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, and particularly preferably 70% by mass or less. In other words, the content of the hydrophilic monomer (B1b) having no acidic group but an amide group in the dental composition is preferably 9 to 90% by mass.

[0045] (Monomer (B2) having no acidic group or amide group) From the viewpoint of the mechanical strength and adhesiveness of the cured product, it is preferable that the monomer (B) having no acidic group further contains a monomer (B2) having no acidic group or amide group. The dental composition according to the embodiment of the present invention contains a monomer (B2) that does not have an acidic group or an amide group, and thus the mechanical strength, handleability, etc. of the cured product (a cured product obtained by curing the dental composition) can be improved. Examples of the monomer (B2) having neither an acidic group nor an amide group include a hydrophobic monomer (B2a) having neither an acidic group nor an amide group, and a hydrophilic monomer (B2b) having neither an acidic group nor an amide group.

[0046] (i) Hydrophobic monomer (B2a) having no acidic group or amide group The dental composition according to the embodiment of the present invention contains a hydrophobic monomer (B2a) that does not have an acidic group or an amide group, and thus the hardened product (the hardened product obtained by hardening the dental composition) can have improved mechanical strength, handleability, etc. The hydrophobic monomer (B2a) having no acidic group or amide group is preferably a radically polymerizable monomer having a polymerizable group but no acidic group. The polymerizable group is preferably a (meth)acryloyl group, since radical polymerization is easy. The hydrophobic monomer (B2a) having no acidic group or amide group may be one having a solubility in water at 25°C of less than 10% by mass, and examples thereof include crosslinkable monomers such as aromatic bifunctional monomers, aliphatic bifunctional monomers, and trifunctional or higher functional monomers.

[0047] Examples of aromatic bifunctional monomers include 2,2-bis((meth)acryloyloxyphenyl)propane, 2,2-bis[4-(3-(meth)acryloyloxy-2-hydroxypropoxy)phenyl]propane, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypolyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxytriethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxytetraethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypentaethoxyphenyl)propane, phenyl)propane, 2,2-bis(4-(meth)acryloyloxydipropoxyphenyl)propane, 2-(4-(meth)acryloyloxydiethoxyphenyl)-2-(4-(meth)acryloyloxyethoxyphenyl)propane, 2-(4-(meth)acryloyloxydiethoxyphenyl)-2-(4-(meth)acryloyloxytriethoxyphenyl)propane, 2-(4-(meth)acryloyloxydipropoxyphenyl)-2-(4-(meth)acryloyloxytriethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypropoxyphenyl)propane, and 2,2-bis(4-(meth)acryloyloxyisopropoxyphenyl)propane. Among these, 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane (commonly known as "Bis-GMA"), 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane (having an average number of ethoxy groups added of 2.6, commonly known as "D-2.6E"), 2,2-bis(4-(meth)acryloyloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxyto

[0033] Preferred are 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane (commonly known as "Bis-GMA") and 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane (having an average added mole number of ethoxy groups of 2.6, commonly known as "D-2.6E"), and more preferred are 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane (commonly known as "Bis-GMA") and 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane (having an average added mole number of ethoxy groups of 2.6, commonly known as "D-2.6E").

[0048] Examples of the aliphatic difunctional monomer include glycerol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,2-bis(3-methacryloyloxy-2-hydroxypropoxy)ethane, and 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)di(meth)acrylate. Among these, glycerol di(meth)acrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate (commonly known as "3G"), neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,2-bis(3-methacryloyloxy-2-hydroxypropoxy)ethane, and 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (commonly known as "UDMA") are preferred.

[0049] Examples of tri- or higher functional monomers include trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, N,N-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetra(meth)acrylate, and 1,7-diacryloyloxy-2,2,6,6-tetra(meth)acryloyloxymethyl-4-oxyheptane. Of these, N,N-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate is preferred.

[0050] Among the above-mentioned hydrophobic monomers (B2a) having no acidic group or amide group, aromatic bifunctional monomers and aliphatic bifunctional monomers are preferred from the viewpoint of the mechanical strength and handling of the cured product, and Bis-GMA, D-2.6E, 3G, and UDMA are more preferred from the viewpoint of adhesive strength and the mechanical strength of the cured product, with Bis-GMA, 3G, and UDMA being even more preferred. The hydrophobic monomers (B2a) having no acidic group or amide group may be used alone or in combination of two or more.

[0051] The content of the hydrophobic monomer (B2a) having no acidic group or amide group in the dental composition according to the embodiment of the present invention is preferably 9% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, based on the mass of all monomers contained in the dental composition, from the viewpoint of improving penetration into tooth structure and improving adhesive strength, and is preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, and particularly preferably 70% by mass or less. In other words, the content of the hydrophobic monomer (B2a) having no acidic group or amide group in the dental composition is preferably 9 to 90% by mass.

[0052] (ii) Hydrophilic monomer (B2b) having no acidic group or amide group The hydrophilic monomer (B2b) having no acidic group or amide group is preferably one having a hydrophilic group such as a hydroxy group, an oxymethylene group, an oxyethylene group, or an oxypropylene group, and examples thereof include (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1,3-dihydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-trimethylammoniumethyl (meth)acrylchloride, and polyethylene glycol di(meth)acrylate (having 9 or more oxyethylene groups).

[0053] Among the above-mentioned hydrophilic monomers (B2b) having no acidic group or amide group, from the viewpoint of adhesion to tooth substrate, 2-hydroxyethyl(meth)acrylate, 2,3-dihydroxypropyl(meth)acrylate, and monofunctional (meth)acrylamides are preferred, 2-hydroxyethyl(meth)acrylate and 2,3-dihydroxypropyl(meth)acrylate are more preferred, 2-hydroxyethyl(meth)acrylate is even more preferred, and 2-hydroxyethyl methacrylate is particularly preferred. The hydrophilic monomers (B2b) having no acidic group or amide group may be used alone or in combination of two or more.

[0054] The content of the hydrophilic monomer (B2b) having no acidic group or amide group in the dental composition according to the embodiment of the present invention is preferably 8% by mass or more, more preferably 9% by mass or more, and even more preferably 10% by mass or more, based on the mass of all monomers contained in the dental composition, from the viewpoint of improving adhesive strength, etc., and is preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, and particularly preferably 70% by mass or less. In other words, the content of the hydrophilic monomer (B2b) having no acidic group or amide group in the dental composition is preferably 8 to 90% by mass.

[0055] <Total content of monomers in dental composition> The total content of all monomers contained in the dental composition according to the embodiment of the present invention, such as the above-mentioned monomer (A) having an acidic group and monomer (B) having an acidic group, is preferably 20% by mass or more, more preferably 35% by mass or more, and is preferably 90% by mass or less, more preferably 80% by mass or less, based on the total mass of the dental composition, in order to further improve adhesion to both dental restorative materials such as dental porcelain and dental resin blocks and to tooth structure. In other words, the total content of all monomers contained in the dental composition is preferably 20 to 90% by mass.

[0056] <Polymerization initiator (C)> The polymerization initiator (C) can be selected from polymerization initiators commonly used in industry, and among these, polymerization initiators used in dental applications are preferred, with photopolymerization initiators being particularly preferred. The polymerization initiator (C) may be used alone or in combination of two or more kinds.

[0057] Preferred photopolymerization initiators include, for example, (bis)acylphosphine oxides, ketals, α-diketones, and coumarin compounds.

[0058] Among the (bis)acylphosphine oxides, examples of the acylphosphine oxides include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylmethoxyphenylphosphine oxide, 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide, and benzoyldi(2,6-dimethylphenyl)phosphonate and salts thereof (such as sodium salt, potassium salt, and ammonium salt). Examples of bisacylphosphine oxides include bis(2,6-dichlorobenzoyl)phenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-1-naphthylphosphine oxide, bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-2,5-dimethylphenylphosphine oxide. phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and bis(2,5,6-trimethylbenzoyl)-2,4,4-trimethylpentylphosphine oxide and salts thereof (e.g., sodium salts, potassium salts, ammonium salts), sodium phenyl(2,4,6-trimethylbenzoyl)phosphinate, lithium phenyl(2,4,6-trimethylbenzoyl)phosphinate, sodium bis(2,4,6-trimethylbenzoyl)phosphinate, and lithium bis(2,4,6-trimethylbenzoyl)phosphinate.

[0059] Among these (bis)acylphosphine oxides, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylmethoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and the sodium salt of 2,4,6-trimethylbenzoylphenylphosphine oxide are particularly preferred. In some embodiments (dental bonding agents, dental primers), sodium bis(2,4,6-trimethylbenzoyl)phosphinate and lithium bis(2,4,6-trimethylbenzoyl)phosphinate are preferred from the viewpoint of adhesion to tooth structure.

[0060] Examples of ketals include benzyl dimethyl ketal and benzyl diethyl ketal.

[0061] Examples of α-diketones include diacetyl, benzyl, camphorquinone, 2,3-pentadione, 2,3-octadione, 9,10-phenanthrenequinone, 4,4′-oxybenzyl, and acenaphthenequinone. Among these, camphorquinone is particularly preferred because it has a maximum absorption wavelength in the visible light region.

[0062] Examples of coumarin compounds include 3,3'-carbonylbis(7-diethylaminocoumarin), 3-(4-methoxybenzoyl)coumarin, 3-thienylcoumarin, 3-benzoyl-5,7-dimethoxycoumarin, 3-benzoyl-7-methoxycoumarin, 3-benzoyl-6-methoxycoumarin, 3-benzoyl-8-methoxycoumarin, 3-benzoylcoumarin, 7-methoxy-3-(p-nitrobenzoyl)coumarin, 3-(p-nitrobenzoyl)coumarin, 3,5-carbonylbis(7-methoxycoumarin), 3-benzoyl-6-bromobenzoyl coumarin, 3,3'-carbonylbiscoumarin, 3-benzoyl-7-dimethylaminocoumarin, 3-benzoylbenzo[f]coumarin, 3-carboxycoumarin, 3-carboxy-7-methoxycoumarin, 3-ethoxycarbonyl-6-methoxycoumarin, 3-ethoxycarbonyl-8-methoxycoumarin, 3-acetylbenzo[f]coumarin, 3-benzoyl-6-nitrocoumarin, 3-benzoyl-7-diethylaminocoumarin, 7-dimethylamino-3-(4-methoxybenzoyl)coumarin, 7-diethylamino-3-(4-methoxybenzoyl)coumarin )coumarin, 7-diethylamino-3-(4-diethylamino)coumarin, 7-methoxy-3-(4-methoxybenzoyl)coumarin, 3-(4-nitrobenzoyl)benzo[f]coumarin, 3-(4-ethoxycinnamoyl)-7-methoxycoumarin, 3-(4-dimethylaminocinnamoyl)coumarin, 3-(4-diphenylaminocinnamoyl)coumarin, 3-[(3-dimethylbenzothiazol-2-ylidene)acetyl]coumarin, 3-[(1-methylnaphtho[1,2-d]thiazol-2-ylidene)acetyl]coumarin, 3,3'-carbo Nylbis(6-methoxycoumarin), 3,3'-carbonylbis(7-acetoxycoumarin), 3,3'-carbonylbis(7-dimethylaminocoumarin), 3-(2-benzothiazoyl)-7-(diethylamino)coumarin, 3-(2-benzothiazoyl)-7-(dibutylamino)coumarin, 3-(2-benzimidazoyl)-7-(diethylamino)coumarin, 3-(2-benzothiazoyl)-7-(dioctylamino)coumarin, 3-acetyl-7-(dimethylamino)coumarin, 3,3'-carbonylbis(7-dibutylaminocoumarin), 3,Examples of compounds include those described in JP-A-9-3109 and JP-A-10-245525, such as 3'-carbonyl-7-diethylaminocoumarin-7'-bis(butoxyethyl)aminocoumarin, 10-[3-[4-(dimethylamino)phenyl]-1-oxo-2-propenyl]-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one, and 10-(2-benzothiazoyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one.

[0063] Among the above-mentioned coumarin compounds, 3,3'-carbonylbis(7-diethylaminocoumarin) and 3,3'-carbonylbis(7-dibutylaminocoumarin) are particularly preferred.

[0064] Among the above photopolymerization initiators, (bis)acylphosphine oxides, α-diketones, and coumarin compounds have excellent photopolymerization initiation ability in the visible and near-ultraviolet regions, and therefore, polymerization can be initiated using a light source such as a halogen lamp, a light-emitting diode (LED), or a xenon lamp.

[0065] The dental composition may further contain a chemical polymerization initiator, and an organic peroxide is preferably used. The organic peroxide used in the chemical polymerization initiator is not particularly limited, and known organic peroxides can be used. Representative organic peroxides include, for example, ketone peroxides, hydroperoxides, diacyl peroxides, dialkyl peroxides, peroxyketals, peroxyesters, and peroxydicarbonates. Specific examples of these organic peroxides include those described in International Publication No. 2008 / 087977. A single chemical polymerization initiator may be used, or two or more may be used in combination. These chemical polymerization initiators undergo redox polymerization and hardening when combined with a polymerization accelerator for chemical polymerization. The polymerization accelerator to be combined is not particularly limited, but examples include amines, sulfinic acids and their salts, benzotriazole compounds, benzimidazole compounds, sulfur-containing reducing inorganic compounds, and thiourea compounds. A single polymerization accelerator may be used, or two or more may be used in combination. From the perspective of inducing chemical polymerization, the chemical polymerization initiator and the polymerization accelerator for chemical polymerization are preferably packaged separately, and a two-component paste is preferred, for example.

[0066] The amount of the polymerization initiator (C) used is not particularly limited, but from the viewpoint of the mechanical strength and adhesiveness of the dental composition, it is preferably 0.1 to 20 mass %, more preferably 0.5 to 15 mass %, and even more preferably 1.0 to 10 mass %, relative to 100 mass % of the total mass of the monomer (A) and the monomer (B) in the dental composition.

[0067] The content of the polymerization initiator (C) in the dental composition is preferably 0.1 to 15 mass %, more preferably 0.5 to 10 mass %, and even more preferably 1.0 to 8 mass %, relative to 100 mass % of the dental composition, from the viewpoint of facilitating hardening of the dental composition.

[0068] <Silane coupling agent (D)> As described above, the silane coupling agent (D) contained in the dental composition according to an embodiment of the present invention includes a first silane coupling agent (D1) which is a silane coupling agent having a polymerizable group, and a second silane coupling agent (D2) which is a silane coupling agent having a hydrogen-bonding group different from both the polymerizable group and the silanol group possessed by the first silane coupling agent (D1). From the viewpoint of ease of handling, the total content of the silane coupling agent (D) in the dental composition is preferably 0.1 to 15.0 mass %, more preferably 0.5 to 12.0 mass %, and even more preferably 1.0 to 10.0 mass %, based on the total mass of the dental composition.

[0069] (First silane coupling agent (D1)) The first silane coupling agent (D1) has a polymerizable group to bond to the surface of a dental restoration and bond the dental composition according to the embodiment of the present invention to the dental restoration. The first silane coupling agent (D1) does not have a "hydrogen-bonding group" (described below) other than the polymerizable group and silanol group. The silane coupling agent (D1) may be used alone or in combination of two or more.

[0070] The polymerizable group contained in the first silane coupling agent (D1) may be, for example, at least one group selected from the group consisting of a vinyl group, an acryloyl group, and a methacryloyl group.

[0071] As the first silane coupling agent (D1), for example, any known silane coupling agent satisfying the following general formula (2) can be used without any limitation.

[0072] [ka] (In formula (2), Y 1 represents an organic group having 1 to 20 carbon atoms and having at least one functional group selected from the group consisting of a (meth)acryloyl group and a vinyl group, or a functional group selected from the group consisting of an acryloyl group and a vinyl group; Y 2represents a group selected from the group consisting of a hydroxy group, an alkyl group having 1 to 5 carbon atoms, an aryl group, and an aralkyl group, or an alkoxy group having 1 to 5 carbon atoms; Y 3 , Y 4 are each a hydroxy group or an alkoxy group having 1 to 5 carbon atoms.

[0073] Y 1 The organic group of Y is not particularly limited, and examples thereof include saturated or unsaturated aliphatic, cycloaliphatic, or aromatic hydrocarbon groups. 1 Of these, the organic group Y is preferably an organic group having 1 to 20 carbon atoms and having two or less functional groups selected from the group consisting of (meth)acryloyl groups and vinyl groups, and is particularly preferably an alkylene group having 1 to 15 carbon atoms, more preferably an alkylene group having 2 to 14 carbon atoms, and even more preferably an alkylene group having 3 to 12 carbon atoms. 1 The organic group functions as a spacer moiety, resulting in superior adhesion to dental porcelain and resin blocks. Also, Y 1 The organic group Y does not have a substituent that does not contain a carbon atom, such as a halogen atom, a hydroxy group, an amino group, a mercapto group, a cyano group, or a nitro group. 1 The organic group does not contain any bond other than a carbon-carbon bond, such as an ether bond, an ester bond, an amide bond, a sulfonyl bond, a urethane bond, or a thioether bond, in its structure.

[0074] Y 2 The alkyl group may be linear, branched, or cyclic, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclobutyl group, an n-pentyl group, etc. An alkyl group having 1 to 5 carbon atoms is more preferred, and a methyl group is even more preferred. Y 2 There is no particular limitation on the type of aryl group represented by the formula, and examples thereof include aryl groups having 6 to 10 carbon atoms, more specifically, examples thereof include a phenyl group and a naphthyl group. Y 2There is no particular limitation on the type of aralkyl group represented by the formula: and examples thereof include aralkyl groups having 7 to 12 carbon atoms, and more specific examples thereof include a benzyl group. Y 2 , Y 3 , and Y 4 The alkoxy group of Y may be linear, branched, or cyclic, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group. 2 , Y 3 , and Y 4 The alkoxy group is more preferably an alkoxy group having 1 to 5 carbon atoms, and further preferably a methoxy group or an ethoxy group.

[0075] Specific examples of the first silane coupling agent (D1) include vinyl group-containing silane coupling agents such as vinyltriethoxysilane, vinyltris(β-methoxyethoxy)silane, vinyltrippropoxysilane, and vinyltributoxysilane; γ-(meth)acryloyloxypropyltriethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, γ-(meth)acryloyloxypropyltris(β-methoxyethoxy)silane, and 6-(meth)acryloyloxypropyltriethoxysilane. Examples of (meth)acryloyloxy group-containing silane coupling agents include oxyhexyltriethoxysilane, κ-methacryloyloxydecyltriethoxysilane, 11-(meth)acryloyloxyundecyltriethoxysilane, 11-(meth)acryloyloxyundecyltrimethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldiethoxysilane, and compounds represented by the following formula (3): Hydrolyzed versions of these compounds are also acceptable. Compound (A) may be used alone or in combination of two or more. [ka]

[0076] Of these, from the viewpoint of easily ensuring high adhesion, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldiethoxysilane, the compound represented by formula (3), and 3-(meth)acryloyloxypropyltrimethoxysilane are preferred, and 3-(meth)acryloyloxypropyltrimethoxysilane is more preferred.

[0077] (Second Silane Coupling Agent (D2)) The second silane coupling agent (D2) is a silane coupling agent having a hydrogen-bonding group. Because the second silane coupling agent (D2) has a hydrogen-bonding group different from the silanol group, hydrogen bonds are formed between the silanol group in the first silane coupling agent (D1) adjacent to the second silane coupling agent (D2) and the hydrogen-bonding group in the second silane coupling agent (D2), suppressing condensation of the silane coupling agent as a whole. As a result, a certain number of bonding points to the adherend are secured, and it is believed that the adhesive strength of the cured product of the dental composition to dental porcelain is increased. Generally, silane coupling agents contain silanol groups or alkoxy groups before they are hydrolyzed to generate silanol groups. However, by making the hydrogen-bonding groups in the second silane coupling agent (D2) different from silanol groups, it is possible to prevent the occurrence of a phenomenon in which condensation of two silanol groups, two silanol groups derived from alkoxy groups, or a silanol group and a silanol group derived from an alkoxy group contained in the second silane coupling agent (D2) occurs, and it becomes impossible to suppress condensation of the silane coupling agent as a whole. Furthermore, the inclusion of the monomer (B1) which does not have an acidic group but has an amide group enhances the effect of modifying the surface of the resin block (imparting hydrophilicity), resulting in increased adhesive strength not only to dental porcelain but also to the resin block. Here, the hydrogen-bonding group possessed by the second silane coupling agent (D2) is a group having at least one hydrogen atom directly bonded to a heteroatom, and is a group different from both the polymerizable group and the silanol group possessed by the first silane coupling agent (D1).

[0078] The hydrogen-bonding group of the second silane coupling agent (D2) is preferably at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group. From the viewpoint of storage stability in the dental composition, it is more preferably at least one group selected from the group consisting of an amino group and an amide group, and even more preferably an amino group. Here, the alcoholic hydroxy group is a hydroxy group bonded to an aliphatic hydrocarbon group.

[0079] The second silane coupling agent (D2) may or may not have the above-mentioned polymerizable group, but from the viewpoint of storage stability in the dental composition, it is preferable that it does not have the above-mentioned polymerizable group.

[0080] As the second silane coupling agent (D2), one that satisfies the following formula (4) is used.

[0081] [ka] (In formula (4), Y 11 represents an organic group having 1 to 20 carbon atoms and having at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group, or at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group; Y 12 represents a hydroxy group, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms; Y 13 , Y 14 represents a hydroxy group or an alkoxy group having 1 to 5 carbon atoms, and Y 12 ~Y 14 At least one of them is an alkoxy group having 1 to 5 carbon atoms.)

[0082] Y 11The organic group of Y is not particularly limited, and examples thereof include saturated or unsaturated aliphatic, cycloaliphatic, or aromatic hydrocarbon groups. 11 Of these, the organic group Y is preferably an organic group having 1 to 20 carbon atoms and having two or less groups selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group, and is particularly preferably an alkylene group having 3 to 15 carbon atoms, more preferably an alkylene group having 5 to 15 carbon atoms, and even more preferably an alkylene group having 6 to 14 carbon atoms. 11 The organic group functions as a spacer moiety with a long carbon chain length, resulting in superior hydrophobicity and superior adhesive durability to dental porcelain and resin blocks. Also, Y 11 The organic group Y may have a substituent that does not contain a carbon atom, such as a halogen atom, an amino group, a mercapto group, a cyano group, or a nitro group. 11 The organic group may contain, in its structure, a bond other than a carbon-carbon bond, such as an ether bond, an ester bond, an amide bond, a sulfonyl bond, a urethane bond, or a thioether bond.

[0083] Y 12 The alkyl group may be linear, branched, or cyclic, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclobutyl group, and an n-pentyl group. Y 12 , Y 13 , and Y 14 The alkoxy group may be linear, branched, or cyclic, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group.

[0084] Examples of the second silane coupling agent (D2) include 3-aminopropyltrimethoxysilane (commonly known as "APS"), 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, and 3-aminopropylmethyldiethoxysilane, with 3-aminopropyltrimethoxysilane being preferred.

[0085] The total content of the first silane coupling agent (1) and the second silane coupling agent (D2) in the silane coupling agent (D) is preferably 85% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on 100% by mass of the silane coupling agent (D), from the viewpoint of easily exhibiting the desired properties. There is no upper limit, and it may be 100% by mass.

[0086] The ratio MD1 / MD2 of the mass MD1 of the first silane coupling agent (D1) to the mass MD2 of the second silane coupling agent (D2) is preferably 0.2 to 3.0, more preferably 0.3 to 2.0, and even more preferably 0.35 to 1.5, from the viewpoints of adhesive strength to dental restorations and storage stability.

[0087] In the dental composition, the ratio MB1 / MD2 of the mass MB1 of the monomer (B1) that has no acidic group but has an amide group to the mass MD2 of the second silane coupling agent (D2) is preferably 5 to 80, more preferably 5.5 to 70, even more preferably 6 to 60, and still more preferably 6.5 to 50, from the viewpoint of adhesive strength to tooth structures and dental restorations.

[0088] Furthermore, from the viewpoint of increasing adhesive strength to the resin block, a particularly preferred combination is to use N-methacryloyloxyethyl acrylamide as the monomer (B1) that does not have an acidic group but has an amide group, and to use a silane coupling agent that has an amino group as the second silane coupling agent (D2).

[0089] <Water(E)> The dental composition contains water (E), which demineralizes the surface of tooth tissue to improve adhesion to the tooth tissue, and in the presence of a silane coupling agent, improves adhesion to prostheses containing inorganic fillers (e.g., CAD / CAM resin blocks, composite resins, zirconia, alumina, lithium disilicate glass, porcelain, and other ceramic materials, including dental ceramics).

[0090] The water (E) used is one that is substantially free of impurities that adversely affect adhesion, and is preferably distilled water or ion-exchanged water. From the viewpoint of ensuring the decalcification promoting effect, adhesion, and storage stability of the silane coupling agent, the content of water (E) is preferably in the range of 1 to 50% by mass, more preferably in the range of 2 to 30% by mass, and even more preferably in the range of 3 to 20% by mass, based on the total mass of the dental composition.

[0091] <Filler (F)> From the viewpoint of increasing the mechanical strength, the dental composition preferably further contains a filler (F). As the filler (F), any filler can be used as long as it does not impair the effects of the present invention, and examples thereof include inorganic fillers, organic fillers, and composite fillers of inorganic fillers and organic fillers. The filler (F) may be blended singly or in combination of two or more types. The average particle size of the filler (F) is preferably 0.001 to 10 μm, more preferably 0.002 to 5 μm, even more preferably 0.003 to 3 μm, still more preferably 0.004 to 1 μm, even more preferably 0.005 to 0.8 μm, and particularly preferably 0.01 to 0.5 μm. The average particle size of the filler (F) refers to the average primary particle size determined by a laser diffraction scattering method or by electron microscope observation of the particles, as described below.

[0092] Examples of inorganic fillers include amorphous inorganic particles and inorganic ultrafine particles. Examples of amorphous inorganic particles include various glasses (mainly composed of silica and optionally containing oxides of heavy metals, boron, aluminum, etc., such as dental glass powders, such as E-glass, barium glass (manufactured by Schott under the trade names "GM27884" and "GM8235"), and ESSTECH under the trade names "E2000" and "E3000"), and lanthanum glass ceramics (manufactured by Schott under the trade name "GM31684")), various ceramics, composite oxides such as silica-titania and silica-zirconia, kaolin, clay minerals (such as montmorillonite), mica, ytterbium fluoride, silica-coated ytterbium fluoride (manufactured by Sukgyung AT under the trade name "SG-YBF100WSCMP10"), and yttrium fluoride. Examples of inorganic ultrafine particles include inorganic oxide particles such as silica, alumina, titania, and zirconia, or composite oxide particles composed of these, as well as particles such as calcium phosphate, hydroxyapatite, yttrium fluoride, ytterbium fluoride, barium titanate, and potassium titanate. Preferred are particles of silica, alumina, titania, silica / alumina composite oxide, and silica / zirconia composite oxide prepared by flame pyrolysis, such as those manufactured by Nippon Aerosil Co., Ltd., under the trade names "Aerosil® 50," "Aerosil® 130," "Aerosil® 380," "Aerosil® R972," "Aerosil® OX50," "Aeroxide® AluC," "Aeroxide® TiO2P25," "VP Zirconium Oxide 3-YSZ," and "VP Zirconium Oxide 3-YSZPH." Inorganic ultrafine particles can also be used in the form of aggregated particles formed by aggregation of inorganic ultrafine particles. In this specification, even when the inorganic filler has been surface-treated as described below, the average particle size of the inorganic filler before the surface treatment is regarded as the average particle size after the surface treatment.

[0093] Examples of organic fillers include polymethyl methacrylate, polyethyl methacrylate, polyfunctional methacrylate polymers, polyamide, polystyrene, polyvinyl chloride, chloroprene rubber, nitrile rubber, and styrene-butadiene rubber.

[0094] Examples of composite fillers of inorganic and organic fillers include those in which inorganic fillers are dispersed in organic fillers, and inorganic / organic composite fillers in which inorganic fillers are coated with various polymers.

[0095] In order to improve curability, mechanical strength, and handling properties, the filler may be surface-treated in advance with a known surface treatment agent (e.g., a silane coupling agent) before use. Examples of the surface treatment agent include methacryloyloxymethyltrimethoxysilane, 2-methacryloyloxyethyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 4-methacryloyloxybutyltrimethoxysilane, 5-methacryloyloxypentyltrimethoxysilane, 6-methacryloyloxyhexyltrimethoxysilane, 1-methacryloyloxyoctyltrimethoxysilane, 9-methacryloyloxynonyltrimethoxysilane, and 10-methacryloyloxydecyltrimethoxysilane. Examples of silane coupling agents include 11-methacryloyloxyundecyltrimethoxysilane, 11-methacryloyloxyundecyldichloromethylsilane, 11-methacryloyloxyundecyltrichlorosilane, 11-methacryloyloxyundecyldimethoxymethylsilane, 12-methacryloyloxydodecyltrimethoxysilane, 13-methacryloyloxytridecyltrimethoxysilane, dimethyldichlorosilane, hexamethyldisilazane, and octylsilane.

[0096] The average particle size (average primary particle size) can be determined by laser diffraction scattering or electron microscope observation of the particles. Specifically, laser diffraction scattering is convenient for measuring the particle size of particles with an average particle size of 0.1 μm or more, while electron microscope observation is convenient for measuring the particle size of ultrafine particles with an average particle size of less than 0.1 μm. For laser diffraction scattering, for example, measurements can be made on a volume basis using a laser diffraction particle size distribution analyzer (SALD-2300, manufactured by Shimadzu Corporation) using a 0.2% aqueous solution of sodium hexametaphosphate as a dispersion medium. For electron microscope observation, a scanning electron microscope (e.g., SU3800, S-4000, manufactured by Hitachi High-Technologies Corporation) can be used. For electron microscope observation, the particle size can be determined by taking an electron microscope photograph of the particles and measuring the particle size of particles (200 or more) observed within a unit field of view of the photograph using image analysis particle size distribution measurement software (Mac-View (Mountec Co., Ltd.)). In this case, the particle diameter is determined as the arithmetic mean value of the longest and shortest lengths of the particles, and the average primary particle diameter is calculated from the number of particles and their particle diameters.

[0097] From the viewpoint of paste operability and the mechanical strength of the cured product, the content of the filler (F) is preferably 0.1 to 20 mass%, more preferably 1 to 15 mass%, and even more preferably 2 to 10 mass%, of the total 100 mass% of the dental composition. From the viewpoint of paste workability and the mechanical strength of the cured product, the content of the filler (F) is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, and even more preferably 3 to 15% by mass, relative to 100% by mass of the total mass of the monomers (A) and (B) in the dental composition. Within these ranges, it is possible to obtain a cured product with good mechanical strength and surface hardness.

[0098] <Polymerization accelerator> The dental composition according to the embodiment of the present invention may contain a polymerization accelerator. Examples of the polymerization accelerator include amines, sulfinic acids (including salts), barbituric acid derivatives, triazine compounds, copper compounds, tin compounds, vanadium compounds, halogen compounds, aldehydes, thiol compounds, sulfites, hydrogen sulfites, and thiourea compounds. The polymerization accelerator may be used alone or in combination of two or more kinds.

[0099] The amines are divided into aliphatic amines and aromatic amines. The aliphatic amines include primary aliphatic amines, secondary aliphatic amines, and tertiary aliphatic amines. Examples of primary aliphatic amines include n-butylamine, n-hexylamine, and n-octylamine. Examples of secondary aliphatic amines include diisopropylamine, dibutylamine, and N-methylethanolamine. Examples of tertiary aliphatic amines include N-methyldiethanolamine, N-ethyldiethanolamine, Nn-butyldiethanolamine, N-lauryldiethanolamine, 2-(dimethylamino)ethyl methacrylate, N-methyldiethanolamine dimethacrylate, N-ethyldiethanolamine dimethacrylate, triethanolamine monomethacrylate, triethanolamine dimethacrylate, triethanolamine trimethacrylate, triethanolamine, trimethylamine, triethylamine, and tributylamine. Among these, from the viewpoint of the hardenability and storage stability of the dental composition, tertiary aliphatic amines are preferred, and N-methyldiethanolamine and triethanolamine are more preferred.

[0100] Examples of the aromatic amine include N,N-bis(2-hydroxyethyl)-3,5-dimethylaniline, N,N-bis(2-hydroxyethyl)-p-toluidine, N,N-bis(2-hydroxyethyl)-3,4-dimethylaniline, N,N-bis(2-hydroxyethyl)-4-ethylaniline, N,N-bis(2-hydroxyethyl)-4-isopropylaniline, N,N-bis(2-hydroxyethyl)-4-t-butylaniline, N,N-bis(2-hydroxyethyl)-3,5-diisopropylaniline, N,N-bis(2-hydroxyethyl)-3,5-di-t-butylaniline, N,N-dimethylaniline, N,N-dimethyl-p-toluidine, and N,N-dimethyl-m-toluidine. , N,N-diethyl-p-toluidine, N,N-dimethyl-3,5-dimethylaniline, N,N-dimethyl-3,4-dimethylaniline, N,N-dimethyl-4-ethylaniline, N,N-dimethyl-4-isopropylaniline, N,N-dimethyl-4-t-butylaniline, N,N-dimethyl-3,5-di-t-butylaniline, ethyl 4-(N,N-dimethylamino)benzoate, methyl 4-(N,N-dimethylamino)benzoate, 2-butoxyethyl 4-(N,N-dimethylamino)benzoate, 2-((meth)acryloyloxy)ethyl 4-(N,N-dimethylamino)benzoate, 4-(N,N-dimethylamino)benzophenone, and butyl 4-(N,N-dimethylamino)benzoate. Among these, N,N-bis(2-hydroxyethyl)-p-toluidine, ethyl 4-(N,N-dimethylamino)benzoate, 2-butoxyethyl 4-(N,N-dimethylamino)benzoate, and 4-(N,N-dimethylamino)benzophenone are preferred from the viewpoint of imparting excellent hardening properties to the dental composition.

[0101] Examples of the sulfinic acids include p-toluenesulfinic acid, sodium p-toluenesulfinate, potassium p-toluenesulfinate, lithium p-toluenesulfinate, calcium p-toluenesulfinate, benzenesulfinic acid, sodium benzenesulfinate, potassium benzenesulfinate, lithium benzenesulfinate, calcium benzenesulfinate, 2,4,6-trimethylbenzenesulfinic acid, sodium 2,4,6-trimethylbenzenesulfinate, potassium 2,4,6-trimethylbenzenesulfinate, lithium 2,4,6-trimethylbenzenesulfinate, and 2,4,6-trimethylbenzenesulfinate. Examples of suitable 2,4,6-triisopropylbenzenesulfinic acid include calcium 2,4,6-triethylbenzenesulfinate, 2,4,6-triethylbenzenesulfinic acid, sodium 2,4,6-triethylbenzenesulfinate, potassium 2,4,6-triethylbenzenesulfinate, lithium 2,4,6-triethylbenzenesulfinate, calcium 2,4,6-triethylbenzenesulfinate, 2,4,6-triisopropylbenzenesulfinic acid, sodium 2,4,6-triisopropylbenzenesulfinate, potassium 2,4,6-triisopropylbenzenesulfinate, lithium 2,4,6-triisopropylbenzenesulfinate, and calcium 2,4,6-triisopropylbenzenesulfinate. Among these, sodium benzenesulfinate, sodium p-toluenesulfinate, and sodium 2,4,6-triisopropylbenzenesulfinate are particularly preferred.

[0102] Examples of the barbituric acid derivatives include barbituric acid, 1,3-dimethylbarbituric acid, 1,3-diphenylbarbituric acid, 1,5-dimethylbarbituric acid, 5-butylbarbituric acid, 5-ethylbarbituric acid, 5-isopropylbarbituric acid, 5-cyclohexylbarbituric acid, 1,3,5-trimethylbarbituric acid, 1,3-dimethyl-5-ethylbarbituric acid, 1,3-dimethyl-5-n-butylbarbituric acid, 1,3-dimethyl-5-isobutylbarbituric acid, 1,3-dimethyl-5-cyclopentylbarbituric acid, 1,3-dimethyl-5-cyclohexylbarbituric acid, 1,3-dimethyl-5-phenylbarbituric acid, 1 ... Examples of barbituric acids include 1-cyclohexyl-1-ethylbarbituric acid, 1-benzyl-5-phenylbarbituric acid, 5-methylbarbituric acid, 5-propylbarbituric acid, 1,5-diethylbarbituric acid, 1-ethyl-5-methylbarbituric acid, 1-ethyl-5-isobutylbarbituric acid, 1,3-diethyl-5-butylbarbituric acid, 1-cyclohexyl-5-methylbarbituric acid, 1-cyclohexyl-5-ethylbarbituric acid, 1-cyclohexyl-5-octylbarbituric acid, 1-cyclohexyl-5-hexylbarbituric acid, 5-butyl-1-cyclohexylbarbituric acid, 1-benzyl-5-phenylbarbituric acid, thiobarbituric acids, and salts thereof. Salts of these barbituric acid derivatives include, for example, alkali metal salts and alkaline earth metal salts, and more specific examples include sodium 5-butylbarbiturate, sodium 1,3,5-trimethylbarbiturate, and sodium 1-cyclohexyl-5-ethylbarbiturate.

[0103] Particularly preferred barbituric acid derivatives are 5-butylbarbituric acid, 1,3,5-trimethylbarbituric acid, 1-cyclohexyl-5-ethylbarbituric acid, 1-benzyl-5-phenylbarbituric acid, and sodium salts thereof.

[0104] Examples of the triazine compound include 2,4,6-tris(trichloromethyl)-s-triazine, 2,4,6-tris(tribromomethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(tribromomethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(p-methylthiophenyl)-4,6-bis(trichloromethyl)-s-triazine. azine, 2-(p-chlorophenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2,4-dichlorophenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-bromophenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-n-propyl-4,6-bis(trichloromethyl)-s-triazine, 2-(α,α,β-trichloroethyl)-4,6-bis(trichloromethyl)-s-triazine, 2-styryl-4,6- Bis(trichloromethyl)-s-triazine, 2-[2-(p-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(o-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(p-butoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(3,4,5-trimethoxyphenyl)ethenyl]-4, 6-bis(trichloromethyl)-s-triazine, 2-(1-naphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-biphenylyl)-4,6-bis(trichloromethyl)-s-triazine, 2-[2-{N,N-bis(2-hydroxyethyl)amino}ethoxy]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-{N-hydroxyethyl-N-ethylamino}ethoxy]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-{N-hydroxyethyl-N-methylamino}ethoxy]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-{N-hydroxyethyl-N-methylamino}ethoxy]-4,Examples include 6-bis(trichloromethyl)-s-triazine and 2-[2-{N,N-diallylamino}ethoxy]-4,6-bis(trichloromethyl)-s-triazine.

[0105] Among these triazine compounds, 2,4,6-tris(trichloromethyl)-s-triazine is preferred in terms of polymerization activity, and 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-chlorophenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(4-biphenylyl)-4,6-bis(trichloromethyl)-s-triazine are preferred in terms of storage stability. The triazine compounds may be used alone or in combination of two or more.

[0106] Examples of the copper compound include copper acetylacetonate, copper (II) acetate, copper oleate, copper (II) chloride, and copper (II) bromide.

[0107] Examples of the tin compound include di-n-butyltin dimaleate, di-n-octyltin dimaleate, di-n-octyltin dilaurate, and di-n-butyltin dilaurate. Among these, di-n-octyltin dilaurate and di-n-butyltin dilaurate are preferred.

[0108] The vanadium compound is preferably a tetravalent or pentavalent vanadium compound, such as divanadium(IV) tetroxide, vanadium oxide acetylacetonate(IV), vanadyl oxalate(IV), vanadyl sulfate(IV), oxobis(1-phenyl-1,3-butanedionato)vanadium(IV), bis(maltolato)oxovanadium(IV), vanadium(V) pentoxide, sodium metavanadate(V), and ammonium metavanadate(V).

[0109] Examples of the halogen compounds include dilauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, benzyltrimethylammonium chloride, tetramethylammonium chloride, benzyldimethylcetylammonium chloride, and dilauryldimethylammonium bromide.

[0110] Examples of the aldehydes include terephthalaldehyde and benzaldehyde derivatives. Examples of the benzaldehyde derivatives include dimethylaminobenzaldehyde, p-methyloxybenzaldehyde, p-ethyloxybenzaldehyde, and pn-octyloxybenzaldehyde. Among these, pn-octyloxybenzaldehyde is preferred from the viewpoint of curability.

[0111] Examples of the thiol compound include 3-mercaptopropyltrimethoxysilane, 2-mercaptobenzoxazole, decanethiol, and thiobenzoic acid.

[0112] Examples of the sulfite include sodium sulfite, potassium sulfite, calcium sulfite, and ammonium sulfite.

[0113] Examples of the hydrogen sulfite include sodium hydrogen sulfite and potassium hydrogen sulfite.

[0114] Examples of the thiourea compound include 1-(2-pyridyl)-2-thiourea, thiourea, methylthiourea, ethylthiourea, N,N'-dimethylthiourea, N,N'-diethylthiourea, N,N'-di-n-propylthiourea, N,N'-dicyclohexylthiourea, trimethylthiourea, triethylthiourea, tri-n-propylthiourea, tricyclohexylthiourea, tetramethylthiourea, tetraethylthiourea, tetra-n-propylthiourea, and tetracyclohexylthiourea.

[0115] The content of the polymerization accelerator in the dental composition is not particularly limited, but from the viewpoint of the hardening property of the resulting dental composition, it is preferably 0.1 to 20 mass %, more preferably 0.5 to 15 mass %, and even more preferably 1.0 to 10 mass %, relative to 100 mass % of the total mass of the monomer (A) and the monomer (B) in the dental composition.

[0116] <Other ingredients> The dental composition according to the embodiment of the present invention may contain known additives within a range that does not lower the performance below a practically usable level. Examples of such additives include polymerization inhibitors, antioxidants, colorants (pigments, dyes), ultraviolet absorbers, solvents other than water (E) (e.g., volatile organic solvents), and thickeners. One type of additive may be used alone, or two or more types may be used in combination.

[0117] It is preferable that the dental composition according to the embodiment of the present invention further contains an organic solvent, since this can further improve adhesion to tooth tissue, application properties, and penetration into tooth tissue, and can further prevent separation of the components in the dental composition.

[0118] Examples of organic solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-2-propanol, acetone, methyl ethyl ketone, tetrahydrofuran, diethyl ether, diisopropyl ether, hexane, toluene, chloroform, ethyl acetate, and butyl acetate. Among these, taking into consideration both safety to living organisms and ease of removal based on volatility, water-soluble organic solvents are preferred, specifically, ethanol, 2-propanol, 2-methyl-2-propanol, acetone, and tetrahydrofuran are preferred, and ethanol, 2-propanol, 2-methyl-2-propanol, and tetrahydrofuran are more preferred. One type of organic solvent may be used alone, or two or more types may be used in combination.

[0119] The content of the organic solvent in the dental composition according to the embodiment of the present invention is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more. The content of the organic solvent is preferably 70% by mass or less, more preferably 50% by mass or less, and even more preferably 30% by mass or less. Depending on the embodiment, the organic solvent may not be contained.

[0120] Examples of the polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, dibutylhydroquinone, dibutylhydroquinone monomethyl ether, t-butylcatechol, 2-t-butyl-4,6-dimethylphenol, 2,6-di-t-butylphenol, and 3,5-di-t-butyl-4-hydroxytoluene. The content of the polymerization inhibitor is preferably 0.001 to 1.0% by mass relative to 100% by mass, which is the total mass of the monomer (A) and the monomer (B) in the dental composition.

[0121] The total mass of the other additives in the dental composition is not particularly limited as long as the effects of the present invention are exhibited, but from the viewpoint of more easily exhibiting the effects of the present invention, the total mass of the other additives in the dental composition is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, still more preferably 5% by mass or less, and still more preferably 2% by mass or less, based on 100% by mass of the dental composition. In other words, the mass of the other additives in the dental composition is preferably 0 to 20% by mass based on 100% by mass of the dental composition.

[0122] <Total content of ingredients (A) to (E)> The total mass of the monomer (A), monomer (B), polymerization initiator (C), silane coupling agent (D), and water (E) in the dental composition is preferably 65% ​​by mass or more, more preferably 70% by mass or more, even more preferably 75% by mass or more, still more preferably 78% by mass or more, and even more preferably 80% by mass or more, and may be 100% by mass, from the viewpoint of enabling the cured product to easily exhibit high adhesion to dental prosthetic materials and tooth structure, and the desired polymerization shrinkage stress and mechanical strength. In other words, the total mass of the monomer (A), monomer (B), polymerization initiator (C), silane coupling agent (D), and water (E) in the dental composition is preferably 65 to 100% by mass.

[0123] <Total content of ingredients (A) to (F)> The total mass of the monomer (A), monomer (B), polymerization initiator (C), silane coupling agent (D), water (E), and filler (F) in the dental composition is preferably 80% by mass or more, more preferably 85% by mass or more, even more preferably 90% by mass or more, still more preferably 95% by mass or more, and even more preferably 98% by mass or more, and may be 100% by mass, from the viewpoint of enabling the cured product to easily exhibit high adhesion to dental prosthetic materials and tooth structure, and the desired polymerization shrinkage stress and mechanical strength. In other words, the total mass of the monomer (A), monomer (B), polymerization initiator (C), silane coupling agent (D), water (E), and filler (F) in the dental composition is preferably 80 to 100% by mass.

[0124] [Method for producing dental composition] The dental composition can be produced by any method known to those skilled in the art without any particular limitations on the method for mixing the components. A preferred method is to mix the components other than the filler (F) and then add the filler (F) and mix them.

[0125] [Uses of dental compositions] In one embodiment, the dental composition is a dental bonding material. In another embodiment, the dental composition is a dental primer.

[0126] The dental filling and restorative material may be a one-component type or a two-component type. In the case of a two-component type, for example, specific components may be packaged separately in the first and second components to enhance storage stability.

[0127] <Physical properties of dental compositions> (Adhesion strength to dental porcelain) The dental composition preferably has a high adhesive strength to dental porcelain in order to facilitate the strong fixation of the crown restorative material to tooth structure. More specifically, the dental porcelain is polished to form a smooth surface, the dental composition is applied to a 5 mm diameter circle, dried, and then irradiated with light to harden the dental composition. The surface of the cured product is then coated with a dental filling composite resin, which is then irradiated with light to harden it. The end face of a stainless steel cylindrical rod (7 mm diameter) is bonded to the surface of the cured product using dental resin cement. The tensile strength measured with a universal testing machine at a head speed of 2 mm / min is preferably 17 GPa or more, more preferably 18 GPa or more, even more preferably 19 GPa or more, and even more preferably 20 GPa or more. While there is no particular upper limit, from the viewpoint of ease of production, it is, for example, 30 GPa or less. In other words, the adhesive strength of the dental filling and restorative material to dental porcelain is preferably 17 to 30 GPa. The adhesive strength to the dental porcelain is measured in detail by the method described in the Examples below. The adhesive strength to the dental porcelain can be set within the above range by selecting and adjusting at least one element selected from the group consisting of the types of monomer (A) and monomer (B), the amounts of monomer (A) and monomer (B), the type of polymerization initiator (C), the amount of polymerization initiator (C), the type of silane coupling agent (D), the amount of silane coupling agent (D), the amount of water (E), the type of filler (F), and the amount of filler (F).

[0128] (Adhesion strength to resin block) The dental composition preferably has a high adhesive strength to a resin block, which facilitates the strong fixation of the dental restoration material to tooth structure. More specifically, the resin block is polished to form a smooth surface, the dental composition is applied in a 5 mm diameter circle, dried, and then irradiated with light to harden the dental composition. The surface of the cured product is then coated with a dental filling composite resin, which is then cured by irradiating with light. The end face of a stainless steel cylindrical rod (7 mm diameter) is bonded to the surface of the cured product using dental resin cement. The tensile strength measured with a universal testing machine at a head speed of 2 mm / min is preferably 5.5 MPa or more, more preferably 5.8 MPa or more, even more preferably 6.0 MPa or more, even more preferably 7.0 MPa or more, even more preferably 8.0 MPa or more, and particularly preferably 9.0 MPa or more. While there is no particular lower limit, from the viewpoint of ease of manufacture, it is, for example, 15.0 MPa or less. In other words, the adhesive strength of the dental filling and restorative material to the resin block is preferably 5.5 to 15.0 MPa. The adhesive strength to the resin block is measured in detail by the method described in the Examples below. The adhesive strength to the resin block can be set within the above range by selecting and adjusting at least one element selected from the group consisting of the types of monomer (A) and monomer (B), the amounts of monomer (A) and monomer (B), the type of polymerization initiator (C), the amount of polymerization initiator (C), the type of silane coupling agent (D), the amount of silane coupling agent (D), the amount of water (E), the type of filler (F), and the amount of filler (F).

[0129] As described above, the dental composition according to the first embodiment (X-1) of the present invention is a dental composition including a monomer (A) having an acidic group, a monomer (B) not having an acidic group, a polymerization initiator (C), a silane coupling agent (D), and water (E), the silane coupling agent (D) comprises a first silane coupling agent (D) having a polymerizable group, and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group contained in the first silane coupling agent (D1); The monomer (B) having no acidic group includes a monomer (B1) having no acidic group but having an amide group.

[0130] Another embodiment (X-2) is the dental composition of the above embodiment (X-1), wherein, relative to 100% by mass of the dental composition, the content of the monomer (A) having an acidic group is 3 to 20% by mass, preferably 4 to 18% by mass, and more preferably 5 to 16% by mass; the content of the monomer (B) not having an acidic group is 35 to 70% by mass, preferably 40 to 65% by mass, and more preferably 45 to 60% by mass; the content of the polymerization initiator (C) is 0.1 to 15% by mass, preferably 0.5 to 10% by mass, and more preferably 1.0 to 8% by mass; the content of the silane coupling agent (D) is 0.5 to 15.0% by mass, preferably 1.0 to 12.0% by mass, and more preferably 1.5 to 10.0% by mass; and the content of water (E) is 1 to 50% by mass, preferably 2 to 30% by mass, and more preferably 3 to 20% by mass.

[0131] Another embodiment (X-3) includes the dental composition of the above embodiment (X-1) or (X-2), wherein the ratio MB1 / MD2 of the mass MB1 of the monomer (B1) that has no acidic group but has an amide group to the mass MD2 of the second silane coupling agent (D2) is 5 to 80, preferably 5.5 to 70, more preferably 6 to 60, and even more preferably 6.5 to 50.

[0132] A dental composition according to another embodiment (X-4) is a dental composition including a monomer (A) having an acidic group, a monomer (B) not having an acidic group, a polymerization initiator (C), a silane coupling agent (D), and water (E), the silane coupling agent (D) comprises a first silane coupling agent (D1) having a polymerizable group, and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group contained in the first silane coupling agent (D1); The monomer (B) having no acidic group includes a monomer (B1) having no acidic group but having an amide group, and a monomer (B2) having no acidic group or amide group.

[0133] A dental composition according to another embodiment (X-5) is a dental composition including a monomer (A) having an acidic group, a monomer (B) not having an acidic group, a polymerization initiator (C), a silane coupling agent (D), water (E), and a filler (F), the silane coupling agent (D) comprises a first silane coupling agent (D1) having a polymerizable group, and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group contained in the first silane coupling agent (D1); The monomer (B) having no acidic group includes a monomer (B1) having no acidic group but having an amide group.

[0134] Another embodiment (X-6) is the same as the embodiment (X-5) above, wherein the content of the monomer (A) having an acidic group is 3 to 20% by mass, preferably 4 to 18% by mass, and more preferably 5 to 16% by mass, the content of the monomer (B) not having an acidic group is 35 to 70% by mass, preferably 40 to 65% by mass, and more preferably 45 to 60% by mass, relative to 100% by mass of the dental composition, and the content of the polymerization initiator (C) is 0.1 to 15% by mass, preferably 0.5 to 10% by mass. % by mass, preferably 1.0 to 8% by mass, the content of the silane coupling agent (D) is 0.5 to 15.0% by mass, preferably 1.0 to 12.0% by mass, more preferably 1.5 to 10.0% by mass, the content of the water (E) is 1 to 50% by mass, preferably 2 to 30% by mass, more preferably 3 to 20% by mass, and the content of the filler (F) is 1 to 20% by mass, preferably 2 to 15% by mass, more preferably 3 to 10% by mass.

[0135] Another embodiment (X-7) is a dental composition according to any one of the above embodiments (X-1) to (X-6), wherein the hydrogen-bonding group possessed by the second silane coupling agent (D2) is at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group, preferably at least one group selected from the group consisting of an amino group and an amide group, and more preferably an amino group.

[0136] Another embodiment (X-8) is a dental composition in any one of the above embodiments (X-1) to (X-7), wherein the polymerizable group is at least one group selected from the group consisting of vinyl groups, acryloyl groups, and methacryloyl groups, preferably at least one group selected from the group consisting of vinyl groups, acryloyl groups, and methacryloyl groups, and more preferably at least one group selected from the group consisting of acryloyl groups and methacryloyl groups.

[0137] Another embodiment (X-9) includes a dental composition in any of the above embodiments (X-1) to (X-8), which has an adhesive strength to dental porcelain of 17 to 30 GPa, preferably 18 to 30 GPa, more preferably 19 to 30 GPa, and even more preferably 20 to 30 GPa, when measured under the conditions described above, and an adhesive strength to a resin block of 5.5 to 15.0 MPa, preferably 5.8 to 15.0 MPa, more preferably 6.0 to 15.0 MPa, even more preferably 7.0 to 15.0 MPa, still more preferably 8.0 to 15.0 MPa, and particularly preferably 9.0 to 15.0 MPa, when measured under the conditions described above. [Example]

[0138] Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples in any way.

[0139] Each component used in the examples and comparative examples will be explained below together with its abbreviation.

[0140] [Monomer (A) having an acidic group] MDP: 10-methacryloyloxydecyl dihydrogen phosphate [Monomer (B) without an acidic group] <Monomer (B1) Having No Acidic Group but Having an Amide Group> DEAA: N,N-diethylacrylamide MAEA: N-methacryloyloxyethyl acrylamide <Monomer (B2) Having No Acidic Group or Amide Group> HEMA: 2-hydroxyethyl methacrylate Bis-GMA: 2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane UDMA: 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (Kyoeisha Chemical Co., Ltd.) [Polymerization initiator (C)] CQ: Camphorquinone BAPO: Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide [Polymerization accelerator] DABE: Ethyl 4-(N,N-dimethylamino)benzoate DEPT: N,N-dimethyl-p-toluidine [Silane coupling agent (D)] <Silane coupling agent having a polymerizable group (D1)> MPS: 3-methacryloxypropyltrimethoxysilane <Silane coupling agent (D2) having a hydrogen-bonding group but not a polymerizable group> APS: 3-aminopropyltrimethoxysilane [Water(E)] ·Purified water Filler Filler 1: Nippon Aerosil Co., Ltd., ultrafine silica particle "Aerosil (registered trademark) R972", average particle size: 16 nm [Volatile organic solvents] EtOH: Ethanol [others] <Polymerization inhibitor> BHT: 3,5-di-t-butyl-4-hydroxytoluene

[0141] [Examples 1 to 10 and Comparative Examples 1 to 2] The dental compositions of the Examples and Comparative Examples were prepared by mixing the components shown in Tables 1-1 and 1-2 below by the masses listed in the columns other than "water, filler (F), and volatile organic solvent" at room temperature (25°C), then adding the components listed in the "filler (F)" column by mass, mixing, and then further mixing with water and a volatile organic solvent. All of these were in paste form and had fluidity suitable for filling, sealing, or coating dental porcelain and resin blocks, as well as tooth structure. For each of the dental compositions of the Examples and Comparative Examples, the adhesive strength to a resin block, the adhesive strength to dental porcelain, the adhesive strength to enamel, and the adhesive strength to dentin were measured or evaluated according to the following procedures.

[0142] <Adhesion strength to dental porcelain> Dental porcelain "VITA Block Mark II" (manufactured by VITA Zahnfabrik) was polished with #1000 silicon carbide paper under running water and then dried. The resulting smooth surface was used to measure bond strength. This surface was not treated with hydrofluoric acid. Next, an adhesive tape having a thickness of about 150 μm and having a round hole with a diameter of 5 mm was stuck to the smooth surface, thereby defining the adhesive area of ​​the dental composition to be measured. Next, the dental compositions prepared in each Example and Comparative Example were applied to the round holes using a brush, left for 3 seconds, and then dried with an air blower until the fluidity of the applied dental compositions disappeared. After that, the applied dental compositions were irradiated with light for 10 seconds using a dental visible light irradiator (manufactured by Morita Corporation, product name "Pencure 2000") to harden the applied dental compositions.

[0143] A dental filling composite resin (manufactured by Kuraray Noritake Dental Co., Ltd., product name "Clearfil (registered trademark) AP-X") was applied to the surface of the cured dental composition and covered with a release film (polyester). A slide glass was then placed on top of the release film and pressed against it to smooth the surface coated with the dental filling composite resin. Furthermore, the dental filling composite resin was irradiated with light for 20 seconds using a dental visible light irradiator through the release film to cure the dental filling composite resin. Finally, one end (circular cross section) of a stainless steel cylindrical rod (diameter 7 mm, length 2.5 cm) was bonded to the surface of the cured product using a commercially available dental resin cement (manufactured by Kuraray Noritake Dental Co., Ltd., product name "Panavia (registered trademark) 21"). After bonding, the sample was left to stand at room temperature for 30 minutes and then immersed in distilled water to obtain a test sample for the adhesion test.

[0144] For each Example and Comparative Example, 10 test samples for the above adhesion test were prepared and left to stand for 24 hours in an incubator maintained at 37°C. Immediately after leaving the samples to stand for 24 hours, the tensile adhesive strength of the samples was measured and recorded as the initial adhesive strength. The tensile adhesive strength of the adhesive test sample was measured using a universal testing machine (Shimadzu Corporation, Autograph "AG-I 100kN") with a crosshead speed set to 2 mm / min, and was calculated as the arithmetic mean value of the measured values ​​of 10 samples.

[0145] <Adhesion strength to resin block> The adhesive strength to the resin block was measured using the same procedure as described above in "Adhesion strength to dental porcelain," except that a resin block (Katana (registered trademark) Avencia (registered trademark) block manufactured by Kuraray Noritake Dental Co., Ltd.) was used instead of dental porcelain.

[0146] <Bonding strength to dentin> The adhesive strength to dentin was measured in the same manner as described above in "Adhesion strength to dental porcelain," except that bovine dentin was used instead of dental porcelain, and adhesive tape approximately 150 μm thick with a round hole 3 mm in diameter was used.

[0147] The components and physical properties (measurement results of adhesive strength for each material) of the dental compositions of the Examples and Comparative Examples are shown in Tables 1-1 and 1-2 below. In Tables 1-1 and 1-2, a "-" in the "Components" column indicates that the corresponding component was not blended.

[0148] [Table 1-1] [Table 1-2]

[0149] As shown in Tables 1-1 and 1-2, the cured products obtained by curing the dental compositions of Examples 1 to 10 had high adhesive strength to resin blocks that had not been treated with hydrofluoric acid and dental porcelain that had not been treated with hydrofluoric acid. In particular, the dental compositions of Examples 3, 5, 6, and 10 produced cured products that had high adhesive strengths of 9 MPa or more to dental resin blocks. Furthermore, the hardened products obtained by hardening the dental compositions of Examples 1 to 10 generally had high adhesive strength to dentin.

[0150] On the other hand, as is clear from Tables 1-1 and 1-2, the dental composition of Comparative Example 1, which was composed of the same components as those of Example 3 except that it did not contain the second silane coupling agent (D2), had good adhesive strength to dentin, but its adhesive strength to the resin block and dental porcelain was significantly lower than that of the dental composition of Example 3. Furthermore, the dental composition of Comparative Example 2, which had the same components as those of Example 7 except that it did not contain the monomer (B1) having no acidic group but an amide group, had inferior adhesive strength to dentin, resin block, and dental porcelain compared to the dental composition of Example 7. Furthermore, the dental composition of Comparative Example 3, which had the same components as those of Example 3 except that it did not contain the first silane coupling agent (D1), had inferior adhesive strength to dentin, resin block, and dental porcelain compared to the dental composition of Example 3. [Industrial Applicability]

[0151] The dental composition of the present invention can be widely used for bonding dental porcelain to tooth structure, bonding a resin block to tooth structure, bonding dental porcelain to other materials, bonding a resin block to other materials, etc. Furthermore, the dental composition of the present invention can be cured to form a cured product with high adhesive strength without treating the surface of the adherend with hydrofluoric acid, and therefore can be suitably used in treatments within the oral cavity while ensuring high safety.

Claims

1. A dental composition comprising: a monomer (A) having an acidic group; a monomer (B) not having an acidic group; a polymerization initiator (C); a silane coupling agent (D); and water (E); The silane coupling agent (D) comprises a first silane coupling agent (D1) having a polymerizable group, and a second silane coupling agent (D2) having a hydrogen-bonding group different from both the polymerizable group and the silanol group contained in the first silane coupling agent (D1); A dental composition, wherein the monomer (B) having no acidic group comprises a monomer (B1) having no acidic group and an amide group.

2. 2. The dental composition according to claim 1, wherein the hydrogen-bonding group possessed by the second silane coupling agent (D2) is at least one group selected from the group consisting of an amino group, an amide group, an alcoholic hydroxy group, an epoxy group, a ketone group, and a carboxy group.

3. 3. The dental composition according to claim 1, wherein the monomer (A) having an acidic group includes 10-methacryloyloxydecyl dihydrogen phosphate.

4. 3. The dental composition according to claim 1, wherein the monomer (B1) having no acidic group but having an amide group comprises N-methacryloyloxyethyl acrylamide.

5. The dental composition according to claim 1 or 2, wherein the monomer (B) having no acidic group further comprises a monomer (B2) having no acidic group and no amide group.

6. 3. The dental composition according to claim 1, wherein the ratio MB1 / MD2 of the mass MB1 of the monomer (B1) having no acidic group but an amide group to the mass MD2 of the second silane coupling agent (D2) is 5 to 80.

7. The dental composition according to claim 1 or 2, further comprising a filler (F).

8. The dental composition according to claim 7 , wherein the filler (F) is surface-treated.

9. The dental composition according to claim 1 or 2, which is a dental bonding material.

10. The dental composition according to claim 1 or 2, which is a dental primer.

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