KR20220148968A - Printable and Curable composition and Dental prosthesis - Google Patents

Abstract

Disclosed are: a curable composition for manufacturing a prosthesis which can be printed using a 3D printing technique, has excellent adhesion to tooth enamel, and can maintain the ability to inhibit the adhesion of contaminants in the oral cavity over a long period of time; and a dental prosthesis. The curable composition for manufacturing a prosthesis includes ceramic particles and a polymerizable organic compound.

Description

Printable and Curable composition and Dental prosthesis for manufacturing a dental prosthesis

The present invention relates to a dental prosthesis made of a cured material containing ceramic particles dispersed in a polymer matrix and a method for manufacturing the same, and more particularly, to a dental prosthesis having a structure similar to natural teeth and a three-dimensional printing method using the same It relates to a method for manufacturing using

US 6,955,776 relates to an example of manufacturing a dental part using three-dimensional printing techniques in the dental field, comprising: applying successive layers of powder to each other to form a dental element; A method comprising bonding the layers by means of a binder is disclosed.

In another example, US Pat. No. 6,322,728 discloses a method for manufacturing a dental restoration comprising the steps of depositing a layer of a ceramic or composite material; applying a bonding material on the ceramic or composite layer; repeating the above steps a plurality of times to produce a plurality of layers of ceramic or composite material bonded to each other to form a restoration shape of the tooth; and curing the molding to form a dental restoration.

On the other hand, EP 3 597 668 discloses a photocurable resin composition for 3D printing, which is described as being usable as a dental composition, a dental material such as an artificial tooth, and the like.

On the other hand, an aggregate having a zwitterionic group as a side chain is attracting attention as a raw material for pharmaceuticals and cosmetics. As an example of the application of the aggregate having a zwitterionic group as a side chain for dental purposes, a dental polymerizable composition containing the polymerizable monomer described in Japanese Patent Laid-Open No. 2007-217516 and an aggregate having a zwitterionic group as a side chain can be mentioned. have. Here, it has been shown that the use of an aggregate having a zwitterionic group as a side chain is effective in suppressing the adsorption of proteins, plaques, and the like.

In addition, Japanese Patent Laid-Open No. 2014-009219 discloses a dental adhesive composition in which an aggregate having a zwitterionic group as a side chain and water are used in combination, and the dental adhesive composition is a dental pretreatment material, an adhesive, and an adhesive composite. It is described as being useful as a resin.

In addition, the step of exposing a superhydrophilic titanium surface having bioactivity by removing the adsorbed and stabilized contaminants to the titanium oxide film, and a pH buffer and a mixture containing an organic amphoteric substance having a sulfonic group Mixing comprising i) an organic pH buffering material and/or an inorganic pH buffering material and ii) an organic amphiphilic material having a sulfone group on the rough surface pretreated to remove contaminants by applying a solution to form a uniform coating film A technique related to a dental implant made of titanium or a titanium alloy material in which a coating layer of a solution is formed is also disclosed (Korean Patent No. 10-1405859).

The present inventors have been continuously searching for a way to express the ability of the prosthesis itself to inhibit adhesion to oral contaminants in addition to the appearance and functional implementation of teeth in manufacturing a prosthesis by 3D printing technology.

An object of the present invention is to provide a curable composition for manufacturing a prosthesis that can be printed using a three-dimensional printing technique, has excellent adhesion to the teeth, and can maintain the ability to inhibit adhesion of contaminants in the oral cavity over a long period of time.

In addition, an object of the present invention is to provide a dental prosthesis that has excellent adhesion to the teeth and can maintain the ability to inhibit the adhesion of contaminants in the oral cavity over a long period of time by using a three-dimensional printing technique.

The present invention is a curable composition for manufacturing a dental prosthesis according to 3D printing comprising ceramic particles and a polymerizable organic compound,

The polymerizable organic compound provides a printable curable composition for manufacturing a dental prosthesis comprising at least one monomer selected from among zwitterionic polymerizable monomers represented by the following Chemical Formulas 1 to 4.

Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, a and b are each independently an integer of 1 to 10 to be.

Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, a and b are each independently 1 an integer from 10 to 10.

In the curable composition according to a preferred embodiment, the ceramic particles may be at least one selected from barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, leucite-based crystallized glass, alumina, zirconia, and vitreous.

In the curable composition according to an embodiment, the polymerizable organic compound is hydroxy ethyl methacrylate (HEMA), 2,2-bis [4-(2-hydroxy-3-methacryloxy propoxy) ) Phenyl] propane (2,2-bis [4- (2-hydroxy-3- methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), diurethane dimeth acrylate (diurethanedimethacrylate, UDMA), urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolyglycine-glycidylmethacrylate, NTGE), polyethylene glycol dimethacrylate (PEG-DMA), and oligocarbonate dimethacrylic esters may include at least one selected from the group consisting of.

In the curable composition according to an embodiment, it may include a thermal initiator or a photoinitiator.

Another embodiment of the present invention is a cured product according to three-dimensional printing comprising ceramic particles dispersed in a polymer matrix,

The polymer matrix provides a dental prosthesis comprising a zwitterionic group represented by the following Chemical Formulas 5 to 8 in a molecular chain.

Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.

In a preferred embodiment, the ceramic particles may be at least one selected from barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, leucite-based crystallized glass, alumina, zirconia, and vitreous.

In a preferred embodiment, the surface of the ceramic particles may be silane-treated.

In a preferred embodiment, the polymer matrix is hydroxy ethyl methacrylate (HEMA), 2,2-bis [4- (2-hydroxy-3-methacryloxy propoxy) phenyl] propane ( 2,2-bis [4-(2-hydroxy-3- methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), diurethanedimethacrylate, UDMA), urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolylglycine-glycidylmethacrylate (NTGE), polyethylene glycol at least one non-zwitterionic polymerizable organic compound selected from polyethylene glycol dimethacrylate (PEG-DMA) and oligocarbonate dimethacrylic esters;

It may be a cured product with at least one zwitterionic polymerizable organic compound selected from the compounds represented by the following Chemical Formulas 1 to 4.

Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, a and b are each independently an integer of 1 to 10 to be.

Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, a and b are each independently 1 an integer from 10 to 10.

In the dental prosthesis according to the embodiment, the cured product may be a cured product by photocuring or thermal curing.

Another example of the present invention is a laminate in which a plurality of ceramic particle layers and a polymer binder layer are laminated according to a three-dimensional printing technique,

The polymer binder layer provides a dental prosthesis comprising a polymer including a zwitterionic group represented by the following Chemical Formulas 5 to 8 in a molecular chain.

Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.

The curable composition according to the present invention is printable, so it is possible to easily implement a laminate by a three-dimensional printing technique, and has a high affinity for teeth and a restoration capable of continuously expressing the ability to inhibit the adhesion of contaminants in the oral cavity over a long period of time , dental replacements, inlays, onlays, veneers, full and partial crowns, bridges, implants, posts, and the like.

The present inventors, as part of maximally realizing natural teeth having such a double structure through a cured product containing ceramic particles dispersed in a polymer matrix, the content of ceramic particles is 70 to 90%, and the ceramic particles have an average particle diameter a first cured material layer having a thickness of 100 to 1,000 nm; Adjacent to the inner side of the first cured material layer, the content of ceramic particles is 40 to 60% by weight, and the ceramic particles have an average particle diameter of 10 to 500 μm to propose a dental prosthesis comprising a second cured material layer, A previous application has been filed (Patent Application No. 10-2020-0036682).

Here, it was identified that the microstructural and physical differences between enamel and dentin in natural teeth are the effects of the content and structure of inorganic and organic substances. A curable composition containing the composition was considered, and it was confirmed that the use of a three-dimensional printing technique (3D printing) using the curable composition was optimal in realizing the microstructure. In particular, it was confirmed that when two types of curable compositions in which the size and content of ceramic particles were controlled were used to implement the dual structure, a cured product close to enamel and dentin of natural teeth could be obtained in physical properties.

The present invention was devised as a part of providing a high affinity to teeth and ability to inhibit the adhesion of contaminants in the oral cavity, focusing on the previously applied curable composition, and the present invention is a ceramic particle and a polymerizable organic compound It is a curable composition for manufacturing a dental prosthesis according to three-dimensional printing comprising a,

The polymerizable organic compound provides a printable curable composition for manufacturing a dental prosthesis comprising at least one monomer selected from among zwitterionic polymerizable monomers represented by the following Chemical Formulas 1 to 4.

Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, a and b are each independently an integer of 1 to 10 to be.

Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, a and b are each independently 1 an integer from 10 to 10.

The zwitterionic polymerizable monomer may be defined as a component each having at least one electrostatically charged atomic group, a negatively charged atomic group, and one or more polymerizable atomic groups in one molecule.

From this point of view, the zwitterionic polymerizable monomers represented by Chemical Formulas 1 to 4 are not limited thereto, but as an example, as a compound represented by Chemical Formula 1, dimethyl (3-sulfopropyl) (2- (meth) acryl loyloxyethyl) ammonium betaine, and the like, and examples of the compound represented by the formula (2) include dimethyl (2-carboxyethyl) (2-(meth)acryloyloxyethyl) ammonium betaine. and dimethyl(3-methoxyhoshopropyl)(2-(meth)acryloyloxyethyl)ammonium betaine etc. are mentioned as a compound represented by the said Formula (3). Further, examples of the compound represented by the formula (4) include 2-(meth)acryloyloxyethyl phosphorylcholine. Moreover, as a zwitterionic monomer, 2-(meth)acryloyloxy ethyl carboxyl betaine, 2-(meth)acryloyloxy ethyl sulfobetaine, etc. are mentioned. Among them, 2-(meth)acryloyloxyethyl phosphorylcholine may be particularly preferable because of its low protein adsorption properties, that is, a high effect of inhibiting the adhesion of contaminants in the oral cavity.

In the curable composition according to a preferred embodiment, the ceramic particles may be at least one selected from barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, leucite-based crystallized glass, alumina, zirconia, and vitreous.

In addition to the zwitterionic polymerizable monomers represented by the above formulas 1 to 4, the printable curable composition of the present invention may include a thermally polymerizable or photopolymerizable polymerizable organic compound well known in the art, the polymerizable organic compound Silver hydroxy ethyl methacrylate (HEMA), 2,2-bis [4- (2-hydroxy-3-methacryloxy propoxy) phenyl] propane (2,2-bis [4- ( 2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), diurethanedimethacrylate (UDMA), urethane dimethacrylate ( urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolyglycine-glycidylmethacrylate (NTGE), polyethylene glycol dimethacrylate, PEG-DMA) and at least one selected from oligocarbonate dimethacrylic esters.

Such curable compositions may include a thermal initiator or a photoinitiator.

In the present invention, in manufacturing a dental prosthesis with a cured product containing ceramic particles dispersed in such a polymer matrix, a prosthesis having a dual structure composed of enamel and dentin similar to natural teeth, for example, is manufactured using three-dimensional printing. can be manufactured.

Currently, in the manufacture of dental prostheses, 3D printing using metal and polymers is widely used in 3D printing, and 3D printing using metal is a method of manufacturing by laminating water by melting metal using a laser, and polymer is It is a method of laminating a polymer composition and curing the polymer using a light source.

In 3D printing, printing using only ceramics is still under research, and most of them use a method of hardening by mixing organic compounds. At this time, important variables include the content ratio of the ceramic to the polymer and the particle size of the ceramic, and through this, the physical properties after curing can also be controlled. In the present invention, as described above, the content ratio and particle size of the ceramic particles can be controlled, and the natural tooth structure can be reproduced using 3D printing.

As such, the present invention is a cured product according to 3D printing comprising ceramic particles dispersed in a polymer matrix, wherein the polymer matrix includes zwitterionic groups represented by the following Chemical Formulas 5 to 8 in the molecular chain. It provides a dental prosthesis.

Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.

According to the present invention, a double structure such as a natural tooth is realized using 3D printing, and changes in physical properties appearing after curing can be given according to the material constituting each structure, the content of each material, and the particle size of the material. The dental prosthesis of the present invention is suitable for use as a dental prosthetic material because it exhibits colors and properties very similar to those of teeth. Moreover, the affinity to the tooth quality is improved, so that the adhesion is improved, and the effect of suppressing the adhesion of plaque can be exerted by itself.

Among three-dimensional printing, methods such as Stereo Lithography Apparatus (SLA) and Digital Lighting Process (DLP) are suitable for manufacturing dental prostheses using ceramics that have a structure similar to natural teeth, and these methods are suitable for enamel and dentin of natural teeth. It is a method of printing each layer to have a structure and curing the polymerizable organic compound using a light source or heat source to polymerize it. In this case, an example of the light source may be a light source of 300 to 600 nm, but is not limited thereto.

In order to have similar physical properties of enamel and dentin of natural teeth, various physical properties can be secured by changing the ceramic particle size and controlling the ceramic and polymer content.

In the description above and below, the 'ceramic particles' may include various inorganic materials that can be used in the manufacture of dental prostheses, but are not limited thereto, but as a specific example, barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, and at least one selected from leucite-based crystallized glass, alumina, zirconia, and vitreous.

On the other hand, it goes without saying that silane-treating the surface of these ceramic particles may be preferable in terms of improving the bonding strength with the polymer matrix and ultimately improving the mechanical properties of the dental prosthesis. Examples of the silane coupling agent that can be used at this time include a silane coupling agent having a reactive functional group such as a (meth)acryl group, an epoxy group, a vinyl group, an amino group, and a mercapto group. It can be used, but is not limited thereto.

In a preferred embodiment, the polymer matrix is hydroxy ethyl methacrylate (HEMA), 2,2-bis [4- (2-hydroxy-3-methacryloxy propoxy) phenyl] propane ( 2,2-bis [4-(2-hydroxy-3- methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), diurethanedimethacrylate, UDMA), urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolylglycine-glycidylmethacrylate (NTGE), polyethylene glycol at least one non-zwitterionic polymerizable organic compound selected from polyethylene glycol dimethacrylate (PEG-DMA) and oligocarbonate dimethacrylic esters;

It may be a cured product with at least one zwitterionic polymerizable organic compound selected from the compounds represented by the following Chemical Formulas 1 to 4.

Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, a and b are each independently an integer of 1 to 10 to be.

Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, a and b are each independently 1 an integer from 10 to 10.

For example, ceramic particles treated with silane in the solution of the polymerizable organic compound are mixed according to the ceramic particle size and the content ratio of the ceramic particles, and each curable composition is put into a 3D printing equipment.

Lamination is carried out in a predetermined shape using each of these curable compositions, where the predetermined shape is, for example, a composition constituting the exterior of the tooth as the first curable composition. And, in the case of the second curable composition, the composition constituting the interior simulates the dentin of natural teeth, and lamination is carried out in a structure having pores, specifically, a structure having pores in a tubular shape, and hardening while proceeding with the lamination.

In this case, the curing may be photocuring or thermal curing. In the case of photocuring, photocuring is performed by irradiating a light source.

In the case of using a photocuring agent, curing may occur by supplying a necessary light source, and in the case of a thermosetting agent, curing may be progressed by supplying a necessary temperature.

As another example of the three-dimensional printing technique according to the present invention, it is a laminate in which a plurality of ceramic particle layers and a polymer binder layer are laminated according to a three-dimensional printing technique, and the polymer binder layer is a molecular chain represented by the following Chemical Formulas 5 to 8 It is possible to provide a dental prosthesis comprising a polymer including a zwitterionic group (group).

Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.

Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.

Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.

This is according to a method of forming a laminate so that interlayer bonding is achieved by first applying a powder composed of ceramic particles, applying a binder layer thereon, and then applying the powder and applying the binder a plurality of times according to the 3D printing technique. can

The dental prosthesis according to the present invention can exert the effect of suppressing the adhesion of plaque by itself, and the affinity with the tooth is increased, so that the adhesive force can be further improved.

Claims (10)

It is a curable composition for manufacturing a dental prosthesis according to 3D printing comprising ceramic particles and a polymerizable organic compound,
The polymerizable organic compound comprises at least one monomer selected from among zwitterionic polymerizable monomers represented by the following Chemical Formulas 1 to 4, a printable curable composition for manufacturing a dental prosthesis.
Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10 to be.
Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently 1 an integer from 10 to 10.
According to claim 1, wherein the ceramic particles are at least one selected from barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, leucite-based crystallized glass, alumina, zirconia and vitreous, printable curability for manufacturing a dental prosthesis composition.
The method of claim 1, wherein the polymerizable organic compound is hydroxy ethyl methacrylate (HEMA), 2,2-bis [4- (2-hydroxy-3-methacryloxy propoxy) phenyl] propane (2,2-bis [4- (2-hydroxy-3- methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), diurethanedimethacrylate , UDMA), urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolyglycine-glycidylmethacrylate (NTGE), polyethylene A printable curable composition for manufacturing a dental prosthesis, comprising at least one selected from glycol dimethacrylate (PEG-DMA) and oligocarbonate dimethacrylic esters.
The printable curable composition of claim 1 comprising a thermal initiator or a photoinitiator.
It is a cured product according to 3D printing containing ceramic particles dispersed in a polymer matrix,
The polymer matrix is to include a zwitterionic group (group) represented by the following formulas 5 to 8 in the molecular chain,
dental prosthesis.
Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.
Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.
Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.
The dental prosthesis according to claim 5, wherein the ceramic particles are at least one selected from barium silicate-based crystallized glass, lithium disilicate-based crystallized glass, leucite-based crystallized glass, alumina, zirconia and vitreous.
The dental prosthesis according to claim 5 or 6, characterized in that the surface of the ceramic particles is silane-treated.
6. The method of claim 5, wherein the polymer matrix is hydroxy ethyl methacrylate (HEMA), 2,2-bis [4- (2-hydroxy-3-methacryloxy propoxy) phenyl] propane (2 ,2-bis [4-(2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane, Bis-GMA), triethylene glycoldimethacrylate (TEGDMA), diurethanedimethacrylate (UDMA) ), urethane dimethacrylate (UDM), biphenyldimethacrylate (BPDM), n-tolylglycine-glycidylmethacrylate (NTGE), polyethylene glycol di at least one non-zwitterionic polymerizable organic compound selected from methacrylate (polyethylene glycol dimethacrylate, PEG-DMA) and oligocarbonate dimethacrylic esters;
A dental prosthesis, characterized in that it is a cured product with at least one zwitterionic polymerizable organic compound selected from the compounds represented by the following Chemical Formulas 1 to 4.
Formula 1

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 2

In the above formula, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 3

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, a and b are each independently an integer of 1 to 10 to be.
Formula 4

In the above formula, R ¹ is a hydrogen atom or a linear or pulverized alkyl group having 1 to 4 carbon atoms, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, a and b are each independently 1 an integer from 10 to 10.
The dental prosthesis according to claim 5, wherein the cured product is a cured product by photocuring or thermal curing.
It is a laminate in which a plurality of ceramic particle layers and a polymer binder layer are laminated according to a three-dimensional printing technique,
The polymer binder layer comprises a polymer including a zwitterionic group (group) represented by the following formulas 5 to 8 in the molecular chain,
dental prosthesis.
Formula 5

In the above formula, a and b are each independently an integer of 1 to 10.
Formula 6

In the above formula, a and b are each independently an integer of 1 to 10.
Formula 7

In the above formula, R ² is a linear or pulverized alkyl group having 1 to 6 carbon atoms, and a and b are each independently an integer of 1 to 10.
Formula 8

In the above formula, R ³ , R ⁴ and R ⁵ are each independently an alkyl group having 1 to 2 carbon atoms, and a and b are each independently an integer of 1 to 10.