Method for producing dental composition, and dental composition

Abstract

To provide a dental composition that gives a cured body having high light-scattering properties, the dental composition having high operability.SOLUTION: The present invention discloses a method for producing a dental composition having a second component dispersed in a first component. The method comprises a step of mixing the first and second components, where the first component is a paste containing a first liquid polymerizable monomer and the second component contains a solvent in which the first polymerizable monomer is insoluble.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for producing a dental composition, and a dental composition. [Background technology]

[0002] In the field of dentistry, polymerizable compositions such as dental composite resins are used. Dental composite resins are widely used because they contain a photopolymerization initiator, which allows them to be polymerized and hardened in a timely manner by light irradiation (see, for example, Patent Documents 1 and 2).

[0003] It is also known that when light is irradiated onto natural teeth, a unique light scattering phenomenon (opal effect) is observed, and dental composite restorative materials have been disclosed for this purpose (see, for example, Patent Document 3).

[0004] Composite resins have high light scattering properties, and they absorb the color of the natural teeth surrounding the filling, resulting in good color compatibility and excellent aesthetics. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 6793106 [Patent Document 2] Patent No. 6793241 [Patent Document 3] Patent No. 5762405 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the conventional method using organic-inorganic composite fillers increases the amount of filler blended, which results in a problem of reduced operability (fluidity) as a composite resin.

[0007] An object of the present invention is to provide a dental composition which gives a cured product with high light scattering properties and which is easy to handle. [Means for solving the problem]

[0008] One aspect of the present invention is a method for producing a dental composition comprising a first component and a second component dispersed in the first component, the first component being a paste containing a liquid first polymerizable monomer, and the second component being: 2-(methacryloyloxy)ethyltrimethylammonium chloride or diallyldimethylammonium chloride as the second polymerizable monomer and a solvent in which the first polymerizable monomer is insoluble. 、 The method for producing a dental composition includes the step of mixing the first component and the second component. [Effects of the Invention]

[0009] According to one aspect of the present invention, a dental composition can be provided that provides a cured product with high light scattering properties and is easy to handle. [Brief explanation of the drawings]

[0010] [Figure 1] 1 is a schematic diagram showing a cross section of a dental composition according to an embodiment. [Figure 2] 1 is an optical microscope photograph of a dental composition according to an embodiment before hardening. [Figure 3] 1 is a photograph showing the appearance of a dental composition according to an embodiment after hardening. DETAILED DESCRIPTION OF THE INVENTION

[0011] Next, an embodiment of the present invention will be described.

[0012] <Method for producing dental composition> The method for producing a dental composition according to this embodiment is a method for producing a dental composition in which a second component is dispersed in a first component. The method for producing a dental composition according to this embodiment includes a step of mixing the first component and the second component (hereinafter referred to as a mixing step).

[0013] <First ingredient> The first component is a paste containing a liquid first polymerizable monomer. In this specification, the term "paste" refers to a pasty liquid.

[0014] <First polymerizable monomer> The first polymerizable monomer that is a liquid is, for example, a liquid at room temperature and normal pressure, and is insoluble in a first solvent described below.

[0015] The first polymerizable monomer is not particularly limited, but is preferably, for example, a (meth)acrylate, and more preferably a polyfunctional (meth)acrylate having two or more (meth)acryloyloxy groups.

[0016] Examples of the first polymerizable monomer include ethoxylated bisphenol A dimethacrylate, neopentyl glycol dimethacrylate, urethane dimethacrylate, glycerin dimethacrylate, triethylene glycol dimethacrylate, tricyclodecane dimethanol dimethacrylate, etc. These first polymerizable monomers may be used alone or in combination of two or more.

[0017] The content of the first polymerizable monomer in the dental composition is not particularly limited, but is preferably, for example, 1% by mass or more and 99.9% by mass or less, more preferably 1.5% by mass or more and 79% by mass or less, and even more preferably 2% by mass or more and 49% by mass or less.

[0018] When the content of the first polymerizable monomer in the dental composition is 1% by mass or more, the mechanical strength of the hardened dental composition is improved, and when the content is 99.9% by mass or less, the function or performance derived from the second polymerizable monomer of the hardened dental composition is improved.

[0019] The first component preferably further contains a hydrophobic filler.

[0020] Examples of hydrophobic fillers include silane-treated glass fillers. The silane-treated glass filler is, for example, barium glass treated with 3-methacryloyloxypropyltrimethoxysilane. These hydrophobic fillers may be used alone or in combination of two or more.

[0021] The amount of the hydrophobic filler in the dental composition is, for example, preferably 45% by mass or more and 75% by mass or less, more preferably 50% by mass or more and 70% by mass or less, and even more preferably 55% by mass or more and 65% by mass or less. When the amount of the hydrophobic filler in the dental composition is 45% by mass or more, the mechanical strength of the cured product of the dental composition is improved, and when it is 75% by mass or less, the dispersibility of the dental composition is improved, thereby improving the handleability of the dental composition.

[0022] The first component may contain, as other components, inorganic fillers other than the hydrophobic filler.

[0023] Examples of such inorganic fillers include silicic acid anhydride powder, fumed silica, alumina powder, and glass powder (e.g., barium glass powder and fluoroaluminosilicate glass powder). These inorganic fillers may be treated with a surface treatment agent such as a silane coupling agent. These inorganic fillers may be used alone or in combination of two or more.

[0024] The amount of inorganic filler in the dental composition is, for example, preferably 0.01% by mass or more and 30% by mass or less, more preferably 0.05% by mass or more and 20% by mass or less, and even more preferably 0.1% by mass or more and 10% by mass or less.

[0025] When the amount of inorganic filler in the dental composition is 0.01% by mass or more and 30% by mass or less, the viscosity of the dental composition containing the glass is reduced, and the handleability of the dental composition can be improved.

[0026] When the above-mentioned hydrophobic filler and / or inorganic filler is contained, it is preferable to use an automatic mortar for mixing in the production of the paste-like first component. in is already a filler but Since the material is in the form of a paste, an automatic mortar is not necessary, and a planetary centrifugal mixer or the like can be used.

[0027] <Second ingredient> The second component includes a first solvent in which the first polymerizable monomer is insoluble. In this specification, "insoluble" means that the amount of the first polymerizable monomer that dissolves in 100 g of the solvent at 25°C is less than 1 g.

[0028] <First solvent> The first solvent is a solvent in which the first polymerizable monomer is insoluble. In this specification, the first solvent is an example of a solvent in which the first polymerizable monomer is insoluble in the method for producing a dental composition of this embodiment.

[0029] The first solvent is not particularly limited as long as it is a solvent in which the first polymerizable monomer is insoluble, and examples thereof include water, glycerin, propylene glycol, ethylene glycol, polyethylene glycol having an average molecular weight of 1200 or less, butylene glycol, etc. These first solvents may be used alone or in combination of two or more.

[0030] The content of the first solvent in the dental composition is not particularly limited, but is preferably, for example, 0.01% by mass or more and 40% by mass or less, more preferably 0.02% by mass or more and 35% by mass or less, and even more preferably 0.03% by mass or more and 30% by mass or less.

[0031] When the content of the first solvent in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the hardened product of the dental composition is improved, and when the content is 40% by mass or less, the light scattering properties and operability of the hardened product of the dental composition are improved.

[0032] Preferably, the second component further comprises a second polymerizable monomer that is a solid.

[0033] <Second polymerizable monomer> The solid second polymerizable monomer is solid at room temperature and pressure and soluble in the first solvent. "Soluble" means that 10 g or more of the second polymerizable monomer dissolves in 100 g of the solvent at 25°C. Preferably, the second polymerizable monomer is insoluble in the first polymerizable monomer.

[0034] The second polymerizable monomer is preferably a (meth)acrylate, and more preferably a monofunctional (meth)acrylate having one (meth)acryloyloxy group.

[0035] The content of the second polymerizable monomer in the dental composition is not particularly limited, but is preferably, for example, 0.01% by mass or more and 99% by mass or less, more preferably 0.02% by mass or more and 79% by mass or less, and even more preferably 0.03% by mass or more and 49% by mass or less.

[0036] When the content of the second polymerizable monomer in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the hardened product of the dental composition is improved, and when the content is 99% by mass or less, the light scattering properties and operability of the hardened product of the dental composition are improved.

[0037] When the first solvent is water, the second polymerizable monomer may be allowed to absorb moisture from the atmosphere, thereby dissolving the second polymerizable monomer in water.

[0038] The content of the first solvent in the dental composition is not particularly limited, but is preferably, for example, 0.01% by mass or more and 40% by mass or less, more preferably 0.02% by mass or more and 35% by mass or less, and even more preferably 0.03% by mass or more and 30% by mass or less.

[0039] When the content of the first solvent in the dental composition is 0.01% by mass or more, the function or performance derived from the second polymerizable monomer of the hardened product of the dental composition is improved, and when the content is 40% by mass or less, the light scattering properties and operability of the hardened product of the dental composition are improved.

[0040] The mass ratio of the first solvent to the second polymerizable monomer is preferably 0.01 or more and 5 or less, and more preferably 0.1 or more and 2 or less. When the mass ratio of the first solvent to the second polymerizable monomer is 0.01 or more, the stability of the second polymerizable monomer when dissolved in the first solvent is improved, and when the mass ratio is 5 or less, the mechanical strength of the cured product of the dental composition is improved.

[0041] The mass ratio of the first polymerizable monomer to the total amount of the second polymerizable monomer and the first solvent is preferably 0.1 or more and 100 or less, and more preferably 0.5 or more and 50 or less. When the mass ratio of the first polymerizable monomer to the total amount of the second polymerizable monomer and the first solvent is 0.1 or more, the mechanical strength of the cured product of the dental composition is improved, and when it is 100 or less, the performance derived from the second polymerizable monomer of the cured product of the dental composition is improved.

[0042] In the method for producing a dental composition according to this embodiment, as described above, a paste-like first component containing a liquid first polymerizable monomer is mixed with a second component containing a first solvent in which the first polymerizable monomer is insoluble, thereby controlling the dispersibility of the second component in the first component, thereby allowing the second component to be uniformly localized in the first component.

[0043] As a result, in the method for producing a dental composition of this embodiment, when the dental composition hardens, the first and second components become similar to a composite filler, thereby obtaining light-scattering properties. Therefore, according to this embodiment, a dental composition having excellent light-scattering properties in the cured form can be obtained.

[0044] Furthermore, in the method for producing a dental composition of the present embodiment, a cured product with high light scattering properties can be obtained without blending a conventional organic-inorganic composite filler, as described above. Therefore, according to the present embodiment, it is possible to prevent the deterioration of operability caused by adding a conventional organic-inorganic composite filler.

[0045] In this embodiment, as described above, the first component contains a hydrophobic filler, which improves the dispersibility of the first component, which is a paste. Furthermore, mixing the first component with the second component improves the dispersibility of the dental composition. Furthermore, the first component contains a hydrophobic filler, which improves the light scattering properties of the cured product without reducing operability.

[0046] In this embodiment, as described above, the second component contains the second polymerizable monomer which is a solid. When the first component and the second component are mixed, the first polymerizable monomer, the second polymerizable monomer, and the first solvent are mixed. and are mixed do.

[0047] In this case, if the first polymerizable monomer and the second polymerizable monomer are mixed without using the first solvent, it is difficult to control the particle size of the second polymerizable monomer, and therefore the second polymerizable monomer cannot be uniformly localized in the first polymerizable monomer, resulting in a deterioration in the appearance and strength of the cured dental composition.

[0048] Furthermore, if the first polymerizable monomer and the second polymerizable monomer are mixed without using the first solvent, the second polymerizable monomer functions as a filler with a different polarity from that of the first polymerizable monomer, resulting in a significant increase in viscosity of the dental composition and a decrease in the workability of the dental composition.

[0049] In contrast, in the present embodiment, by mixing a paste-like first polymerizable monomer insoluble in the first solvent, a second polymerizable monomer soluble in the first solvent, and the first solvent, the second polymerizable monomer can be uniformly localized in the dental composition. As a result, a dental composition can be obtained that has excellent light-scattering properties and is less likely to deteriorate in operability, while imparting functionality or performance derived from the second polymerizable monomer to a cured product of the dental composition.

[0050] In addition, in this embodiment, since the second component contains a second polymerizable monomer soluble in the first solvent, the second polymerizable monomer can function as a filler having a polarity different from that of the first polymerizable monomer in the dental composition. Therefore, in this embodiment, the presence of such a second polymerizable monomer can prevent the dental composition from changing during storage and from losing its light scattering properties.

[0051] The second polymerizable monomer preferably has a functional group exhibiting at least one of antibacterial and antiviral properties. Note that a functional group exhibiting at least one of antibacterial and antiviral properties refers to a case where one functional group exhibits both antibacterial and antiviral properties, or a case where one functional group exhibits either antibacterial or antiviral properties. Furthermore, a functional group exhibiting antibacterial and antiviral properties also includes a case where the functional group has both an antibacterial functional group and an antiviral functional group.

[0052] The functional group exhibiting at least one of antibacterial and antiviral properties is not particularly limited, but examples thereof include quaternary ammonium bases, etc. The quaternary ammonium bases can function as a functional group exhibiting antibacterial properties (hereinafter referred to as an antibacterial group) and also as a functional group exhibiting antiviral properties (hereinafter referred to as an antiviral group).

[0053] Examples of the second polymerizable monomer having a functional group exhibiting at least one of antibacterial and antiviral properties include monofunctional polymerizable monomers such as 2-(methacryloyloxy)ethyltrimethylammonium chloride, (3-acrylamidopropyl)trimethylammonium chloride, (2-(acryloyloxy)ethyl)trimethylammonium chloride, N-(2-acryloyloxyethyl)-N-benzyl-N,N-dimethylammonium chloride, dimethylaminopropylacrylamide methyl chloride quaternary salt, dimethylaminoethyl acrylate methyl chloride quaternary salt, and dimethylaminoethyl acrylate benzyl chloride quaternary salt; diallyl type quaternary ammonium salts such as diallyldimethylammonium chloride and diallyldiethylammonium chloride; and compounds represented by the following chemical formula:

[0054] [ka] These second polymerizable monomers having a functional group exhibiting at least one of antibacterial and antiviral properties may be used alone or in combination of two or more.

[0055] Examples of the second polymerizable monomer having neither an antibacterial group nor an antiviral group include phenoxyethylene glycol methacrylate and dimethylaminoethyl methacrylate.

[0056] The second polymerizable monomers having neither an antibacterial group nor an antiviral group may be used singly or in combination of two or more kinds.

[0057] In this embodiment, when the second polymerizable monomer has an antibacterial group, antibacterial properties can be imparted to the hardened dental composition as a function or performance derived from the second polymerizable monomer.Furthermore, when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to the hardened dental composition as a function or performance derived from the second polymerizable monomer.

[0058] In this embodiment, when the first polymerizable monomer, the second polymerizable monomer, and the first solvent are mixed, a surfactant may or may not be added.

[0059] The surfactant is not particularly limited as long as it can improve the dispersibility of the solution, and examples thereof include sodium lauryl sulfate, glycerin fatty acid esters, etc. These surfactants may be used alone or in combination of two or more.

[0060] In the present embodiment, in the mixing step, it is preferable to add and knead other components such as a photopolymerization initiator, a tertiary amine, and a polymerization inhibitor.

[0061] Examples of the photopolymerization initiator include camphorquinone, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzil ketal, diacetyl ketal, benzil dimethyl ketal, benzil diethyl ketal, benzil bis(2-methoxyethyl) ketal, 4,4'-dimethyl(benzyl dimethyl ketal), anthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 1,2-benzanthraquinone, 1-hydroxyanthraquinone, 1-methylanthraquinone, 2-ethylanthraquinone, and 1-bromoanthraquinone. Examples of photopolymerization initiators include thioxanthone, 2-isopropylthioxanthone, 2-nitrothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chloro-7-trifluoromethylthioxanthone, thioxanthone-10,10-dioxide, thioxanthone-10-oxide, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzophenone, bis(4-dimethylaminophenyl)ketone, 4,4'-bis(diethylamino)benzophenone, etc. These photopolymerization initiators may be used alone or in combination of two or more.

[0062] The tertiary amine may be either a tertiary aliphatic amine or a tertiary aromatic amine, but is preferably a tertiary aromatic amine, and more preferably an alkyl p-dialkylaminobenzoate.

[0063] Examples of tertiary aliphatic amines include N,N-dimethylaminoethyl methacrylate and triethanolamine.

[0064] Examples of alkyl p-dialkylaminobenzoates include methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, propyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, ethyl p-diethylaminobenzoate, and propyl p-diethylaminobenzoate.

[0065] Examples of tertiary aromatic amines other than alkyl p-dialkylaminobenzoates include 7-dimethylamino-4-methylcoumarin, N,N-dimethylaniline, N,N-dibenzylaniline, N,N-dimethyl-p-toluidine, N,N-diethyl-p-toluidine, N,N-bis(2-hydroxyethyl)-p-toluidine, N,N,2,4,6-pentamethylaniline, N,N,2,4-tetramethylaniline, and N,N-diethyl-2,4,6-trimethylaniline.

[0066] These tertiary amines may be used alone or in combination of two or more.

[0067] Examples of the polymerization inhibitor include dibutylhydroxytoluene (2,6-di-tert-butyl-p-cresol), 6-tert-butyl-2,4-xylenol, etc. These polymerization inhibitors may be used alone or in combination of two or more.

[0068] The other components may be added to the first polymerizable monomer, the second polymerizable monomer, and / or the first solvent before mixing in the mixing step, or may be added after mixing the first polymerizable monomer, the second polymerizable monomer, and the first solvent in the mixing step.

[0069] The mixing step may include a step of dissolving the second polymerizable monomer in the first solvent to obtain a solution, and a step of mixing the solution with the first component.

[0070] By mixing a solution of the second polymerizable monomer dissolved in the first solvent with the first component containing the first polymerizable monomer, the second polymerizable monomer can be more uniformly localized in the dental composition, thereby imparting a function or performance derived from the second polymerizable monomer to the cured product of the dental composition and further improving the light scattering properties and operability of the cured product of the dental composition.

[0071] For example, when the second polymerizable monomer has an antibacterial group, antibacterial properties can be imparted to the cured product of the dental composition, and when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to the cured product of the dental composition.

[0072] Examples of methods for mixing a solution in which a second polymerizable monomer is dissolved in a first solvent with a first component containing a first polymerizable monomer include a method of kneading the solution with the first component using a mortar, a method of mixing the solution with the first component using a magnetic stirrer, and a method of mixing the solution with the first component using a stirrer with stirring blades.

[0073] Other components may be added to the solution and / or the first polymerizable monomer before mixing, or may be added after mixing the solution and the first component.

[0074] The mixing step may include a step of dissolving at least a portion of the first polymerizable monomer and the second polymerizable monomer in a second solvent to obtain a solution, a step of distilling off the second solvent from the solution to obtain a dispersion in which the second polymerizable monomer is dispersed in at least a portion of the first polymerizable monomer, and a step of mixing the dispersion with the first solvent.

[0075] <Second Solvent> The second solvent is not particularly limited, and examples thereof include organic solvents such as ethanol, acetone, hexane, etc. These second solvents may be used alone or in combination of two or more.

[0076] The content of the second solvent in the solution is not particularly limited, but is preferably, for example, 10% by mass or more and 99% by mass or less. When the content of the second solvent in the solution is 10% by mass or more, the dissolution stability of the polymerizable monomer is improved, and when it is 99% by mass or less, the second solvent can be easily removed by distillation from the solution.

[0077] In this embodiment, by mixing a dispersion liquid in which the second polymerizable monomer is dispersed in the first polymerizable monomer with the first solvent, the second polymerizable monomer can be more uniformly localized in the dental composition, which results in imparting functionality or performance derived from the second polymerizable monomer to the cured product of the dental composition, while further improving the appearance and strength of the cured product of the dental composition.

[0078] For example, when the second polymerizable monomer has an antibacterial group, antibacterial properties can be imparted to the cured product of the dental composition, and when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to the cured product of the dental composition.

[0079] Here, when a part of the first polymerizable monomer is used when obtaining the solution, the dispersion is obtained and then mixed with the remainder of the first polymerizable monomer. At this time, the timing of mixing the dispersion with the remainder of the first polymerizable monomer is not particularly limited, but it is preferable to mix the remainder of the first polymerizable monomer when mixing the dispersion with the first solvent.

[0080] When the solution is obtained, the mass ratio of the second polymerizable monomer to at least a portion of the first polymerizable monomer is preferably from 0.01 to 100, more preferably from 0.05 to 50. When the mass ratio of the first polymerizable monomer to the second polymerizable monomer is from 0.01 to 100, the dispersion state of the dispersion liquid obtained by distilling off the second solvent from the solution becomes good.

[0081] Examples of methods for mixing the dispersion liquid and the first solvent include a method of stirring the dispersion liquid and the first solvent, a method of mixing the dispersion liquid and the first solvent using a magnetic stirrer, and a method of mixing the dispersion liquid and the first solvent using a stirrer with stirring blades.

[0082] In this embodiment, when the dispersion liquid and the first solvent are mixed, a surfactant may or may not be added.

[0083] The surfactant is not particularly limited as long as it can improve the dispersibility of the solution, and examples thereof include sodium lauryl sulfate, glycerin fatty acid esters, etc. These surfactants may be used alone or in combination of two or more.

[0084] In the present embodiment, it is preferable to mix the dispersion liquid with the first solvent, and then add other components such as the hydrophobic filler, inorganic filler, photopolymerization initiator, tertiary amine, polymerization inhibitor, etc., and knead them.

[0085] Other components may be added to the dispersion liquid and / or the first solvent before mixing, or may be added when mixing the dispersion liquid and the first solvent.

[0086] <Dental composition> The dental composition of this embodiment has a second component dispersed in a first component, where the first component is a paste containing a liquid first polymerizable monomer, and the second component contains a solvent in which the first polymerizable monomer is insoluble.

[0087] The dental composition of this embodiment can be produced by the above-mentioned method for producing a dental composition. The first component used in the dental composition of this embodiment can be the same as the first component used in the above-mentioned method for producing a dental composition. Furthermore, the first polymerizable monomer can be the same as the first polymerizable monomer used in the above-mentioned method for producing a dental composition.

[0088] The second component used in the dental composition of this embodiment can be the second component used in the method for producing a dental composition described above.The solvent used in the dental composition of this embodiment can be the first solvent used in the method for producing a dental composition described above.

[0089] The content of the first polymerizable monomer in the dental composition is not particularly limited, but is preferably, for example, 1% by mass or more and 99.9% by mass or less, more preferably 1.5% by mass or more and 79% by mass or less, and even more preferably 2% by mass or more and 49% by mass or less.

[0090] The content of the first solvent in the dental composition is not particularly limited, but is preferably, for example, 0.01% by mass or more and 40% by mass or less, more preferably 0.02% by mass or more and 35% by mass or less, and even more preferably 0.03% by mass or more and 30% by mass or less.

[0091] The dental composition according to this embodiment includes a paste-like first component containing a liquid first polymerizable monomer and a second component containing a first solvent in which the first polymerizable monomer is insoluble, thereby achieving the same effects as the dental composition obtained by the above-described manufacturing method. Specifically, the dental composition according to this embodiment controls the dispersibility of the second component in the first component, allowing the second component to be uniformly localized within the first component.

[0092] Therefore, in this embodiment, when the dental composition hardens, the first and second components become similar to a composite filler, thereby providing light scattering properties, and the dental composition of this embodiment can have excellent light scattering properties after hardening.

[0093] Furthermore, in this embodiment, as described above, a cured product with high light scattering properties can be obtained without blending a conventional organic-inorganic composite filler, etc. Therefore, the dental composition of this embodiment can prevent the deterioration of operability caused by adding a conventional organic-inorganic composite filler.

[0094] In the dental composition of this embodiment, the second component preferably further includes a solid second polymerizable monomer. The second polymerizable monomer is preferably soluble in the first solvent. The second polymerizable monomer may be the same as the second polymerizable monomer used in the method for producing the dental composition.

[0095] The content of the second polymerizable monomer in the dental composition is not particularly limited, but is preferably, for example, 0.01% by mass or more and 99% by mass or less, more preferably 0.02% by mass or more and 79% by mass or less, and even more preferably 0.03% by mass or more and 49% by mass or less.

[0096] In the dental composition according to this embodiment, since the second polymerizable monomer is contained in the second component, the same effect as that of the dental composition obtained by the above-mentioned manufacturing method can be obtained. Specifically, in the dental composition according to this embodiment, when the first polymerizable monomer in a paste form insoluble in the first solvent, the second polymerizable monomer soluble in the first solvent, and the first solvent are mixed, the second polymerizable monomer can be uniformly localized in the dental composition.

[0097] Therefore, the dental composition of this embodiment can be a dental composition in which the hardened dental composition is endowed with the function or performance derived from the second polymerizable monomer, and which has excellent light-scattering properties and is less likely to be impaired in operability.

[0098] In the dental composition of this embodiment, the second polymerizable monomer preferably has a functional group exhibiting at least one of antibacterial and antiviral properties. The second polymerizable monomer having a functional group exhibiting at least one of antibacterial and antiviral properties may be the second polymerizable monomer having an antibacterial group and / or an antiviral group used in the above-mentioned method for producing a dental composition.

[0099] Specifically, the antibacterial group and / or antiviral group used in the second polymerizable monomer may be a quaternary ammonium base or the like used in the method for producing the dental composition described above.

[0100] In the dental composition according to this embodiment, the second polymerizable monomer has an antibacterial group and / or an antiviral group, and when the second polymerizable monomer has an antibacterial group, antibacterial properties can be imparted to a cured product of the dental composition as a function or performance derived from the second polymerizable monomer.Furthermore, when the second polymerizable monomer has an antiviral group, antiviral properties can be imparted to a cured product of the dental composition as a function or performance derived from the second polymerizable monomer.

[0101] The use of the dental composition of this embodiment is not particularly limited, and the dental composition of this embodiment can be used, for example, as a dental composite resin, a dental cement, a denture base resin, a general-purpose dental resin, etc.

[0102] In addition, as described above, the dental composition of this embodiment can be used preferably in dental composite resins, more preferably in flowable composite resins, from the viewpoint that it can be a dental composition that has excellent light scattering properties and is less susceptible to deterioration in operability. In addition, when the dental composition of this embodiment is used in a flowable composite resin, the flowable composite resin may be of a one-component type or a two-component type.

[0103] Furthermore, when the dental composition of this embodiment is a flowable composite resin, the extrusion hardness of the flowable composite resin can usually be set to 10 kgf or less, thereby improving the formability and operability of the flowable composite resin.

[0104] The manner in which the flowable composite resin is provided is not particularly limited, and for example, it may be provided as a package having a syringe filled with the flowable composite resin, a plunger fitted into the syringe from the rear end side, and a needle tip attached to the front end of the syringe.

[0105] When the flowable composite resin has such a needle tip, the inner diameter of the needle of the needle tip can be 0.3 mm or more and 0.9 mm or less.

[0106] Also, when the flowable composite resin is a two-component type, the package may have, for example, two syringes connected in parallel and two plungers connected in parallel, and static mixers may be provided at the tips of both syringes.

[0107] As described above, the dental composition of this embodiment can impart antibacterial and / or antiviral properties to a hardened product of the dental composition as a function or performance derived from the second polymerizable monomer, and is therefore suitable for use in products in the dental field that require antibacterial, antiviral, and other properties. [Example]

[0108] The present embodiment will be further described below using examples. In the following, numerical values ​​without units or "%" are based on mass (% by mass) unless otherwise specified.

[0109] <Preparation of the original solution> As polymerizable monomer components, 120g of bisphenol A polyethoxy methacrylate (BPE-80N) and neopentyl glycol dimethacrylate (NPG )3 0 g, and 30 g of tricyclodecane dimethanol dimethacrylate (DCP), respectively, were weighed, followed by 1.5 g of camphorquinone (CQ), 3.0 g of ethyl p-dimethylaminobenzoate (EPA), and 6-tert-dibutyl-2,4-xylenol (BHT). )1 .2g of The mixture was added and kneaded uniformly using a stirrer to prepare a base liquid.

[0110] <Preparation of paste> destination 3.5 g of the original solution prepared in step 1 was weighed out, and 0.16 g of Aerosil R812 (fine particle silica surface-treated with hexamethyldisilazane, manufactured by Nippon Aerosil Co., Ltd., AEROSIL (registered trademark) R812) was weighed out and added. , and kneaded using an automatic mortar After mixing for 5 minutes, 8 g of silane-treated glass filler was weighed out and added in 8 batches and mixed. After adding the silane-treated glass filler, the mixture was mixed for a total mixing time of 30 minutes to obtain a uniform paste.

[0111] <Addition of subsequent ingredients> 7 g of the prepared paste was weighed out, and the post-added ingredients were added according to Table 1 below and mixed with a spatula. Then, the mixture was kneaded for 3 minutes at 800 rpm using a planetary centrifugal mixer to obtain a flowable composite resin (Figures 1 to 4).

[0112] The preparation of the base solution and the production of the paste were carried out in the same manner in all Examples and Comparative Examples. The blending composition was changed when adding the subsequent components. The blending compositions of the Examples and Comparative Examples are shown in Table 2.

[0113] [Table 1]

[0114] [Table 2]

[0115] In Tables 1 and 2, the abbreviations have the following meanings: BPE-80N: Bisphenol A polyethoxymethacrylate NPG: Neopentyl glycol dimethacrylate DCP: Tricyclodecane dimethanol dimethacrylate CQ: Camphorquinone EPA: Ethyl p-dimethylaminobenzoate BHT: 6-tert-dibutyl-2,4-xylenol MTMAC: 2-(methacryloyloxy)ethyltrimethylammonium chloride DADMAC: Diallyldimethylammonium chloride UDMA: Di-2-methacryloyloxyethyl-2,2,4-trimethylhexamethylene dicarbamate

[0116] The refractive index of each component in the original solution is 1.543 for BPE-80N, 1.452 for NPG, 1.500 for DCP, 1.460 for MTMAC, 1.480 for DADMAC, 1.333 for water, 1.53 for barium glass (SCHOTT, G018-053), and 1.457 for silicon dioxide (SiO2).

[0117] In Table 2, the silane-treated glass filler was obtained by silanizing barium glass powder (G018-053 UF 0.4 μm, manufactured by SCHOTT) with 3-methacryloyloxypropyltrimethoxysilane at a glass weight ratio of 8 w / w%. The silane treatment method was performed with reference to Patent Document 2 (Japanese Patent No. 6793241), a prior art document.

[0118] In Table 2, the organic filler is an organic-inorganic composite filler prepared with reference to JP 2011-68596 A. Specifically, this organic-inorganic composite filler is prepared by mixing a (meth)acrylate compound with glass powder containing, as main components, SiO, SrO, BO, BaO, AlO, NaO, CaO, ZnO, LaO, WO, ZrO, TiO, NbO, F, etc., and then pulverizing the cured product obtained by polymerizing and curing the mixture.

[0119] The examples and comparative examples were evaluated for light scattering properties, transparency, paste fluidity, and aesthetics as follows. The evaluation results are shown in Table 3.

[0120] <Light scattering characteristics> The obtained flowable composite resin paste was evenly applied to the surface of an acrylic plate to create a disk-shaped test piece with a diameter of 15 mm and a thickness of 1 mm (Figures 1 and 2). Using a light irradiator (GC Corporation, G-Light Prima II Plus), the front and back of the test piece were irradiated for 10 seconds each 9 times to create a hardened body, which was used as the test piece (Figure 3). Using a variable angle photometer (Murakami Color Research Laboratory), ±90 ° Under the measurement range conditions, light scattering characteristics (light scattering) The evaluation criteria are as follows: Good: The measurement angle at which the transmitted light intensity first becomes 10% or less -90° to -30° or +30° to +90° in the case of Unacceptable: The measurement angle at which the transmitted light intensity first becomes 10% or less Over -30° and under +30° in the case of

[0121] <Transparency> The total light transmittance (TT) of the specimens obtained in the above-mentioned light scattering property test (Figure 3) was measured using a haze meter (manufactured by Nippon Denshoku Industries Co., Ltd.) to evaluate transparency. A total light transmittance (TT) of 35% or more was judged to be good (transparent).

[0122] <Paste fluidity> The resulting flowable composite resin paste was applied to the surface of an acrylic plate under the same conditions as in the light scattering property test described above (Fig. 1, Fig. 2), and its appearance was checked to evaluate its fluidity. The evaluation criteria were as follows: Good: Flowable properties (fluidity) Unacceptable: Putty-like properties (no fluidity)

[0123] <Aesthetics> The test specimens obtained in the light scattering property test (Fig. 3) were subjected to an appearance evaluation. In the appearance evaluation, visually observable irregularities and obvious opacity were confirmed for the prepared cured body (Fig. 3). The aesthetic evaluation criteria were as follows. Note that even if the aesthetic evaluation was not possible, the dental composition was evaluated as being good if the transparency evaluation described above was good. Good: No irregularities or cloudiness Not acceptable: If there are irregularities and / or cloudiness

[0124] [Table 3]

[0125] As can be seen from Table 3, Examples 1 to 6 had good light scattering properties, transparency, and paste fluidity, and Examples 1 to 3 among these also had good aesthetic properties.

[0126] In contrast, Comparative Example 1 had poor light scattering properties, and Comparative Example 2 had poor paste fluidity.

[0127] In Example 1, in the uncured flowable composite resin 20 fixed to the acrylic plate (subject) 10, it is considered that the solution 40 in which the second polymerizable monomer is dissolved in the first solvent is uniformly dispersed in the first polymerizable monomer 30 (the droplet diameter of the solution 40 in which the second polymerizable monomer is dissolved in the first solvent is small) (see Figures 1 and 2).

[0128] Although the embodiments of the present invention have been described above, the present invention is not limited to the specific embodiments, and various modifications and changes are possible within the scope of the invention described in the claims. [Explanation of symbols]

[0129] 10 Acrylic plate (object) 20 Flowable composite resin 30 First polymerizable monomer 40 Solution in which the second polymerizable monomer is dissolved in the first solvent

Claims

1. 1. A method for producing a dental composition comprising a first component and a second component dispersed in the first component, comprising: the first component is a paste containing a liquid first polymerizable monomer; the second component includes 2-(methacryloyloxy)ethyltrimethylammonium chloride or diallyldimethylammonium chloride as a second polymerizable monomer, and a solvent in which the first polymerizable monomer is insoluble; Mixing the first component and the second component, A method for producing a dental composition.

2. The first component further comprises a hydrophobic filler. A method for producing the dental composition according to claim 1.

3. the second polymerizable monomer is soluble in the solvent; A method for producing the dental composition according to claim 1 or 2.

4. the step of dissolving the second polymerizable monomer in the solvent to obtain a solution; mixing the solution with the first component; A method for producing the dental composition according to claim 3 .

5. The dental composition is a flowable composite resin. A method for producing the dental composition according to any one of claims 1 to 4.

6. A dental composition comprising a first component and a second component dispersed therein, the first component is a paste containing a liquid first polymerizable monomer; the second component contains 2-(methacryloyloxy)ethyltrimethylammonium chloride or diallyldimethylammonium chloride as a second polymerizable monomer, and a solvent in which the first polymerizable monomer is insoluble; Dental compositions.

7. the second polymerizable monomer is soluble in the solvent; The dental composition of claim 6 .

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