JP6196493B2 - Resin tooth adhesive composition - Google Patents

Description

The present invention relates to a resin tooth adhesive composition capable of chemically bonding a denture base resin and a resin tooth during denture preparation.

In general, a denture is produced by a method called a gypsum embedding method shown below.
First, a model is created in which the shape of the mouth of a patient who has lost his teeth is made with an impression material such as alginate and the shape is reproduced with gypsum. Next, on this gypsum model, a dental prosthesis is prepared by using dental wax for the part corresponding to the gingiva and using the resin tooth for the part corresponding to the tooth. Further, this wax denture is buried in gypsum in a special frame called a flask and then dewaxed to remove the dental wax, and a gap is provided in the portion corresponding to the gum.
The denture is completed by replacing the gap provided in the denture mold with a denture base resin by various methods.
At present, various types of materials are used for denture base resins, including heat polymerization denture base resins, pressure injection type (pour-in type) denture base resins, and denture base resins made of thermoplastic resin. Etc.

The above-mentioned resin teeth have various forms from the viewpoints of the site and the occlusal pattern, and some of the layer structures are composed of a single layer or a plurality of layers from the viewpoint of aesthetics and physical characteristics. Furthermore, as for the resin tooth material, polymethyl methacrylate has been mainly used in the past, but a composite material of urethane resin and inorganic material called hard resin is also used from the viewpoint of improving strength and wear resistance. It has become like this. In recent years, from the viewpoint of aesthetics and physical properties, a composite material of urethane resin and inorganic material (hard resin) has been used for the layer called the buttock, which is the outermost layer of the resin tooth, Polymethylmethacrylate is still used for the layer called the base that contacts the denture base resin. Although this is mentioned later, it is because the adhesion | attachment with the denture base resin is taken into consideration.
This denture base resin is generally of a type such as a heat polymerization type or a pressure injection type (pour-in type), but these are mainly composed of polymethyl methacrylate as a powder material and methyl methacrylate as a liquid material. It is contained and used as a denture base resin by mixing and filling these powder materials and liquid materials and polymerizing and curing them.
When preparing dentures, when the denture base resin liquid and powder are mixed and filled in a mold in which resin teeth are arranged, methyl methacrylate, which is a component of the liquid material, is contained in the base of the resin tooth It has the function of chemically bonding the denture base resin and the resin teeth by penetrating and polymerizing inside the polymethyl methacrylate.

In the case of a heat-polymerized denture base resin, the powder material and the liquid material are first mixed at a ratio specified by the manufacturer. Next, the mixture is allowed to stand for a certain period of time, so that the mixture swells and becomes a state called a cage-like resin suitable for being inserted into a denture mold. This rod-shaped resin is filled in a denture mold and polymerized and cured by heating and pressing.
In the denture preparation method using these heat-polymerized denture base resins, it is important that the radical polymerizable monomer contained in the cage resin penetrates into the resin tooth base containing polymethylmethacrylate. Therefore, the concentration of the radical polymerizable monomer present on the surface of the rod-shaped resin changes depending on the ratio at the time of mixing the powder material and the liquid material, the degree of swelling of the rod-shaped resin, the surrounding environment at the time of denture preparation, etc. This is one of the factors that make the adhesion between the base of the resin tooth and the denture base resin unstable.
Further, in the case of a pressure injection type (pour-in type) denture base resin, a mixture of a powder material and a liquid material is pressure-injected (or poured) into a mold at a timing specified by the manufacturer. Then, it superposes | polymerizes and hardens by heating and pressurizing as needed.
In the denture preparation method using these pressure injection type (pour-in type) denture base resins, the temperature during polymerization is important. For this reason, the degree of polymerization of the radical polymerizable monomer that has penetrated into the base of the resin tooth changes depending on the surrounding environment during the preparation of the denture, which makes the adhesion between the base of the resin tooth and the denture base resin unstable. It is one of the factors.
Furthermore, in recent years, from the viewpoint of wearing feeling and aesthetics, there is an increasing demand for dentures made by injection molding a denture base resin made of a thermoplastic resin such as a polycarbonate resin called a non-clasp denture. When a denture is produced using a denture base resin made of these thermoplastic resins, the operation is performed according to the following procedure.
First, a denture base resin (pellet-shaped) made of a thermoplastic resin is melted at about 200 to 350 ° C., and then a plaster mold, which is a denture mold in which the resin teeth are arranged at a pressure of about 1 to 10 kgf / cm ^2. Eject. And after leaving a flask to room temperature, as a final process, an artificial tooth is indexed from the inside of a flask, and a denture is completed through finishing processes, such as grinding | polishing.
However, in a denture preparation method using a denture base resin made of a thermoplastic resin, the thermoplastic resin as a main component cannot penetrate into the resin tooth base containing polymethyl methacrylate. Therefore, chemical adhesion is not obtained between the resin tooth base and the denture base resin made of thermoplastic resin, and the resin teeth are maintained in the denture base resin only by mechanical fitting. Problems such as falling off of the resin teeth occurred.

As a means for solving the above problem, a method of forming a denture by forming a maintenance structure such as a groove or a pore in advance on a resin tooth base using a technical carbide bar or the like is also performed. This is because the denture base resin made of the injected thermoplastic resin enters the grooves or pores formed in the base of the resin tooth to give an anchor effect, and the resin teeth are made from the thermoplastic resin only by physical fitting force. It is intended to maintain a denture base resin.

However, even in the above method, the denture base resin made of thermoplastic resin enters the maintenance structure formed in the base portion of the resin tooth, and the resin tooth is maintained by physical fitting. Chemical adhesion is not obtained between denture base resins made of a plastic resin. For this reason, a minute gap is formed between the resin tooth and the denture base resin made of thermoplastic resin.When a patient uses a denture for a long time, food residues and accompanying bacteria enter the gap and the In addition to being hygienic, the appearance looks dark, so there was also an aesthetic problem.
As means for solving the above problems, methods using an adhesive composition have been known so far (Patent Document 1, Patent Document 2, Patent Document 3).

In Patent Document 1, there is an adhesive composition for adhering a denture base resin made of a thermoplastic resin (polycarbonate resin) and a resin tooth made of a di (meth) acrylic acid resin containing a volatile solvent and bisphenol A. Proposed.
In Patent Document 1, a fine uneven surface is formed on the base portion of a resin tooth with a volatile solvent such as acetone, thereby providing a mechanical maintenance effect and di (meth) containing bisphenol A attached to the surface. It is described that the denture base resin made of a thermoplastic resin (polycarbonate resin) and the resin teeth are chemically bonded by the polymerization and curing of the acrylic resin.
However, in the adhesive composition of Patent Document 1, di (meth) acrylic resin containing bisphenol A does not penetrate into the fine uneven surface imparted to the resin tooth base, and the resin tooth base only. Since it is only cured on the surface layer of the part, the chemical adhesive force is low. Moreover, since the sufficient maintenance effect cannot be obtained only by dissolving the resin tooth base with a volatile solvent, there is a problem that the resin tooth is dropped and the practicality is lacking.

Patent Document 2 relates to a method of adhering a denture base resin and resin teeth made of a polysulfone resin, and proposed a 1 〜 20% carbon chloride solvent solution of polycarbonate resin as an adhesive composition to be used. ing.
In Patent Document 2, by forming a fine uneven surface on the resin tooth base with a carbon chloride solvent, a mechanical maintenance effect is given, and the polycarbonate resin adhering to the surface is softened and adhered by heat. Thus, it is described that the denture base resin made of polysulfone resin and the resin teeth are bonded.
However, the adhesive composition of Patent Document 2 can be said to be a method lacking versatility because the denture base resin is limited to polysulfone. Also, in the fine uneven surface formed on the resin tooth base, the polycarbonate resin does not penetrate and polymerize, it is present only on the surface layer of the artificial tooth base, and is only softened and adhered by heat, Chemical adhesion is low. Furthermore, since a sufficient maintenance effect cannot be obtained only by dissolving the resin tooth base with a carbon chloride solvent, the durability is inferior, and the resin tooth has fallen off.

Patent Document 3 relates to a resin tooth bonding method in which a denture base resin made of polysulfone resin and a resin tooth are bonded, and a method in which a thermoplastic resin such as polysulfone resin is fixed to a resin tooth base in advance. Has been proposed.
In Patent Document 3, a thermoplastic resin is fixed to the base portion of the resin tooth by an instantaneous polymerization resin to give a mechanical maintenance effect, and the fixed thermoplastic resin is softened / adhered by heat so that a polysulfone resin is obtained. It is described that the denture base resin and the resin teeth made of
However, the adhesive composition of Patent Document 3 is a method lacking versatility because the denture base resin is made of polysulfone resin. In addition, in the resin tooth base, the thermoplastic resin fixed by the immediate polymerization resin does not penetrate and polymerize, and is only welded by heat on the surface of the resin tooth base, so the chemical adhesive force is Low. Furthermore, it cannot be said that the adhesive force between the resin tooth base and the thermoplastic resin has sufficient durability, and the mechanical maintenance effect is low. For this reason, the resin teeth have fallen off.

JP-A-7-291816 Japanese Patent No. 6-24540 Patent 6-24542

Therefore, the present invention provides a strong chemical reaction between the denture base resin and the resin teeth at the time of denture preparation, regardless of the type of denture base resin and the filling method, and it is not necessary to add a maintenance structure to the base of the resin tooth. It is an object to provide a resin tooth adhesive composition to be bonded. Another object of the present invention is to provide a denture preparation method using the resin tooth adhesive composition.

As a result of intensive studies to solve the above problems, the present inventors have found that a radical polymerizable monomer having a specific solubility and a radical polymerization initiator for polymethyl methacrylate contained in the base portion of the resin tooth. When the denture base resin and resin teeth are chemically applied to the base of the resin tooth by applying the resin tooth adhesive composition to the base of the resin tooth during denture preparation, the resin tooth adhesive composition penetrates and polymerizes into the base of the resin tooth. It has been found that it adheres to this and has solved this problem.

That is, the present inventors, in the present application, in a method for preparing a denture by inserting a denture base resin into a denture mold in which resin teeth are arranged, a resin tooth adhesion for bonding the denture base resin and the resin teeth. The resin tooth adhesive composition includes a radical polymerizable monomer and a radical polymerization initiator, and the solubility of polymethyl methacrylate in the radical polymerizable monomer is 10% by weight or more. A resin tooth adhesive composition is provided.
The resin tooth adhesive composition is characterized in that the resin tooth adhesive composition includes 0.01 to 10 parts by weight of a radical polymerization initiator with respect to 100 parts by weight of the radical polymerizable monomer. .
Furthermore, in the preparation method of dentures using the above-mentioned resin-tooth adhesive composition, a denture preparation method is provided, wherein the denture base resin used is a denture base resin made of a thermoplastic resin.

In the conventional denture preparation method, since the adhesion between the resin tooth and the denture base resin was insufficient, there was a minute gap between them. Therefore, if a patient uses a denture for a long time, not only food residue and bacteria enter this minute gap, it becomes unsanitary but also emits a bad odor, which may interfere with the use of the denture. . In addition, it has been recognized that the food residue in the gap and the spoiled food discolored can adversely affect aesthetics, such as the appearance of the vicinity of the tooth neck being darkened.
Furthermore, in a denture preparation method using a denture base resin made of a thermoplastic resin, chemical adhesion cannot be obtained between the resin and the denture base resin made of a thermoplastic resin, and only a physical fitting force is obtained. Since both of them were maintained mechanically, there was a problem that the resin teeth dropped out. About these problems, it is the same also about the resin tooth by which the maintenance structure was previously provided to the base part of the resin tooth by the manufacturer, and the denture was not able to be utilized over a long period of time.

Since the present invention can chemically bond the resin tooth and the denture base resin simply by applying the resin tooth adhesive composition of the present invention to the base of the resin tooth when preparing the denture, Can be solved, and the service life of the denture can be extended. In addition, the resin tooth adhesive composition of the present invention can use all the resin teeth that can be used in the conventional denture preparation method, and the usage method is very simple. The feature that the burden can be reduced is also recognized.
In other words, the denture prepared using the resin tooth adhesive composition of the present invention has a resin tooth and a denture base resin that are firmly bonded, so the denture has features such as form, color, and physical properties of the resin tooth. It can be used for a long period of time while maintaining the color tone, physical properties, and compatibility of the floor resin.

Examples of denture base resins that can be used in denture preparation using the resin tooth adhesive composition of the present invention include heat-polymerized denture base resins, pressure injection type (pour-in type) denture base resins, and heat. Examples include denture base resins made of a plastic resin. Among these denture base resins, denture base resins made of a thermoplastic resin are preferable, and specific examples thereof include denture base resins made of a polycarbonate resin, an acrylic resin, a polyamide resin, and a polyethylene terephthalate resin. Further preferred denture base resins are denture base resins made of polycarbonate resin and acrylic resin.

The resin tooth adhesive composition of the present invention is characterized by containing a radically polymerizable monomer having a polymethyl methacrylate solubility of 10% by weight or more.
Here, the radical polymerizable monomer used in the resin tooth adhesive composition of the present invention is a monomer having a solubility in polymethyl methacrylate of 10% by weight or more and having at least one radical polymerizable group. There is no particular limitation. Among these, a radical polymerizable monomer having an acryloyl group and / or a methacryloyl group is preferable. In the present invention, both (acryloyl group-containing radical polymerizable monomers) and (methacryloyl group-containing radical polymerizable monomers) are comprehensively described as having (meth) acrylate or (meth) acryloyl groups.

Specific examples of the radical polymerizable monomer used in the present invention include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, t-butyl (meth) acrylate, styrene, 2-hydroxyethyl (meth) acrylate, glycerol dimethacrylate, 2,3-dihydroxypropyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate , 6-hydroxyhexyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 3- (meth) acryloyloxyhexyltriethoxysilane, γ- (meth) acryloyloxypropylmethoxysilane, [2,2,4-trimethyl Hexamethylenebis (2-cal Bamoyloxyethyl)] di (meth) acrylate, ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipentaerythritol di (meth) acrylate, 1,6-hexanedi (meth) acrylate, pentaerythritol Examples thereof include tetra (meth) acrylate and trimethylolpropane tri (meth) acrylate.
Among these radical polymerizable monomers, methyl (meth) acrylate and ethylene glycol di (meth) acrylate are preferable, and ethylene glycol di (meth) acrylate is more preferable. These radical polymerizable monomers can be used alone or in combination of two or more.
In the present invention, the radical polymerizable monomer having a solubility of polymethyl methacrylate of 10% by weight or more is obtained by stirring and mixing for 24 hours at 30 ° C. with respect to 100 parts by weight of the radical polymerizable monomer. It is a radically polymerizable monomer in which 10 parts by weight of polymethyl methacrylate can be uniformly dissolved.
Furthermore, there is no restriction | limiting in particular in content of the radically polymerizable monomer used for the resin tooth | gear adhesive composition of this invention, What is necessary is just to select suitably according to operativity or a use use. Generally, it is in the range of 0.1 to 99.9 parts by weight, preferably in the range of 50 to 99 parts by weight, more preferably in the range of 80 to 97 parts by weight with respect to the entire resin tooth adhesive composition. is there.
When the content of the radical polymerizable monomer is more than 99.9 parts by weight, the ratio of the radical polymerizable monomer to the radical polymerization initiator is increased, so that the polymerization rate of the radical polymerizable monomer is reduced and sufficient adhesion is achieved. The problem that power cannot be obtained occurs.
In addition, when the content of the radical polymerizable monomer is less than 0.1 parts by weight, the amount of the radical polymerizable monomer that penetrates and polymerizes inside the resin tooth base decreases, so that sufficient adhesive strength cannot be obtained. The problem occurs.

The radical polymerization initiator used in the resin tooth adhesive composition of the present invention is not particularly limited, and a known radical polymerization initiator can be used without any limitation. Radical polymerization initiators generally start polymerization by mixing immediately before use (chemical polymerization initiator), start polymerization by heating or heating (thermal polymerization initiator), or start polymerization by light irradiation (Photopolymerization initiator)
Chemical polymerization initiators include organic peroxides / amine compounds or organic peroxides / amine compounds / sulfinates, redox type polymerization initiators composed of organic peroxides / amine compounds / borate compounds, oxygen and water. Organometallic type polymerization initiator systems that start polymerization by reacting with sulfinates, and sulfinates and borate compounds can also initiate polymerization by reaction with polymerizable monomers having acidic groups. it can.
Examples of the thermal polymerization initiator include organic peroxides, azo compounds, and organic boron compounds.
Photopolymerization initiators include α-diketone compounds / amines, α-diketone compounds / barbituric acids, and α-diketone compounds / organotin compounds combined with acid generators, or (bis) acylphosphine Examples include fin oxides.
These radical polymerization initiators can be used not only independently but also in combination of two or more, regardless of the polymerization mode or polymerization method. Moreover, there is no problem even if these radical polymerization initiators are subjected to a secondary treatment such as being encapsulated in microcapsules as necessary.

Among these radical polymerization initiators, thermal polymerization initiators are preferable, and organic peroxides are more preferable. A specific example of this organic peroxide is benzoyl peroxide, 1,1-di (t-butylperoxy) cyclohexane.
The content of the radical polymerization initiator used in the resin tooth adhesive composition of the present invention can be appropriately selected according to the intended use, but is 0.01 to 100 parts by weight with respect to 100 parts by weight of the radical polymerizable monomer. The range of 10 parts by weight is preferable, and the range of 1 to 5 parts by weight is more preferable.
When the content of the radical polymerization initiator is more than 10 parts by weight, the storage stability of the resin tooth-adhesive composition is lowered, which causes a problem that the expiration date is shortened.
On the other hand, when the content of the radical polymerization initiator is less than 0.01 parts by weight, the polymerization rate of the radical polymerizable monomer is lowered, which causes a problem that sufficient adhesive force cannot be obtained.

Furthermore, a thickener can be used in the resin tooth adhesive composition of the present invention to adjust operability. As the type of the thickener, inorganic particles or polymers (polymers) can be mentioned, but they can be used alone or in combination of two or more regardless of the type of the thickener, and the content ratio is also particularly limited. There is no.

Specific examples of the inorganic particle thickener include oxides such as silica, alumina, zirconia, diatomaceous earth, kaolin, clay minerals (montmorillonite, etc.), and the like. These inorganic particles may be subjected to various surface treatments such as various hydrophobization treatments in order to improve the affinity with the radical polymerizable monomer.

Specific examples of polymer (polymer) thickeners include monofunctional radical polymerizable (meth) such as polymethyl (meth) acrylate, polyethyl (meth) acrylate, polyisopropyl (meth) acrylate, and polybutyl (meth) acrylate. Acrylic homopolymer and at least two or more monofunctional radicals selected from methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and the like Polymerizable (meth) acrylate copolymers may be mentioned.
The content of the thickener used in the resin tooth adhesive composition of the present invention can be appropriately selected according to the intended use, but is 0.01 to 30 parts by weight based on the entire resin tooth adhesive composition. The range is preferably 0.1 to 10 parts by weight.

Furthermore, a diluent can be used in the resin tooth adhesive composition of the present invention to adjust operability. Examples of diluents include alcohols, ketones, and alkyl halides, but they can be used alone or in combination of two or more regardless of the type of diluent, and the content ratio is particularly limited. There is no.

Specific examples of alcohol diluents include methanol, ethanol, isopropyl alcohol, and isobutyl alcohol.
Specific examples of the diluent for ketones include methyl ethyl ketone and acetone.
Illustrative examples of diluents of alkyl halides include dichloromethane, chloroform, carbon tetrachloride and the like.
The content of the diluent that can be used in the resin tooth adhesive composition of the present invention can be appropriately selected according to the intended use, but is 5 to 95 parts by weight based on the entire resin tooth adhesive composition. A range is preferable, More preferably, it is the range of 10-90 weight part.

In addition, the resin tooth adhesive composition of the present invention includes, as necessary, a polymerization inhibitor, an ultraviolet absorber, an antioxidant, a chain transfer material, a coloring material, in order to adjust storage stability, polymerization characteristics, and color tone. Materials, antibacterial materials, fluorescent materials and the like can be used alone or in combination.

Specific examples of the polymerization inhibitor include 2,6-di-butylhydroxytoluene, hydroquinone, dibutylhydroquinone, dibutylhydroquinone monomethyl ether, and 2,6-t-butylphenol.

The packaging form of the resin-tooth-adhesive composition of the present invention is not particularly limited, and can be either a 1-pack packaging form, a 2-pack packaging form, or any other form depending on the type of polymerization initiator and the purpose of use. Yes, it can be selected appropriately according to the application.

The resin-tooth-adhesive composition of the present invention is used for bonding a resin tooth and a denture base resin in a method for preparing a denture by filling a denture base resin into a denture mold in which resin teeth are arranged. A specific denture preparation method using the resin tooth adhesive composition of the present invention is shown below, but is not limited thereto.
The mouth of the patient who lost his teeth is cast with an impression material such as alginate, and a model is created in which the shape is reproduced with gypsum. On this gypsum model, a wax denture is produced using a dental wax corresponding to the gingiva and a resin tooth corresponding to the tooth. This wax denture is buried in gypsum in a special frame called a flask. At this time, a sprue serving as a passage for the injected denture base resin and a vent for allowing internal air to escape during injection are provided. The flask in which the wax denture is embedded is heated and dewaxed to remove the wax, and a gap is provided in a portion corresponding to the gum. The flask is opened, and the resin tooth adhesive composition of the present invention is applied to the base of the resin tooth placed in the denture mold. Close the flask and inject the molten denture base resin. After the flask is allowed to reach room temperature, the denture is indexed from the flask, and the denture is completed through a finishing process such as polishing.
As described above, the resin tooth adhesive composition of the present invention may be composed of not only a one-pack type packaging form but also a two-pack or more packaging form. In that case, the first liquid is applied to the base of the resin tooth and dried, and then the second liquid and the subsequent liquids are sequentially applied. However, there is no limitation on any of the techniques.
Moreover, when the resin-tooth adhesive composition contains a diluent such as alcohol, it is a technique of moving to the next step after air drying after application.
Furthermore, when the resin tooth adhesive composition includes a radical polymerization initiator that decomposes by light, the resin tooth base after application is irradiated with light under predetermined conditions.
When the dentures of the present invention are produced, there is no particular limitation even if the resin tooth adhesive composition of the present invention is used in combination with other adhesive systems and adhesive primers used in the dental field.

The present invention will be described in more detail and specifically below, but the present invention is not limited to these examples.
The test method for evaluating the performance of the resin tooth adhesive compositions prepared in Examples, Comparative Examples, and Target Examples is as follows.
1. Resin tooth bond strength test (Japanese Industrial Standard JIS T 6506 (2005))
Purpose of evaluation :
Evaluate the binding force between resin teeth and denture base resins.
Evaluation method :
Using Endura Anterio (Matsukaze), which is a hard resin tooth, a test body (wax) was prepared according to a resin tooth binding force test described in Japanese Industrial Standard JIS T 6506 (2005). In accordance with the denture preparation method of Cosmos Denture System (Sankyo Co., Ltd.), the prepared test specimen is opened after plaster embedding and dewaxing, and the resin tooth adhesive composition of the present invention is applied to the resin tooth base. The flask was closed, the flask temperature was 60 ° C., the resin softening temperature was 320 ° C., and a denture base reinforced polycarbonate resin (Toshin Yoko) was injection molded to obtain a test piece.

The resin tooth binding strength test was performed using an Instron universal testing machine (Instron 5567, manufactured by Instron) at a crosshead speed of 0.5 mm / min. The test was conducted with 10 specimens, and the average value was evaluated.

The raw materials used for the preparation of the resin tooth adhesive composition are as follows.
MMA: methyl methacrylate EM-1: ethylene glycol dimethacrylate Bis-MEPPE: 2,2-bis (4-methacryloxypolyethoxyphenyl) propane BPO: benzoyl peroxide

The solubility of the radical polymerizable monomer used in the resin tooth adhesive composition in polymethyl methacrylate was evaluated by the following test method.
In a sealable reagent bottle having a capacity of 300 mL, 100 parts by weight of an arbitrary radical polymerizable monomer and 10 parts by weight of polymethyl methacrylate (weight average molecular weight: 300,000, 50% average particle size: 30 μm) are added and sealed. The reagent bottle is mixed with a tumbler mixer at a temperature of 30 ° C. for 24 hours. After mixing, the mixture was allowed to stand at room temperature for 24 hours, and the dissolved state of polymethyl methacrylate was visually confirmed. The evaluation results are shown in Table 1.

Example 1, Example 2 and Comparative Example Resin tooth adhesive composition 1 〜 3 (resin tooth adhesive compositions 1 and 2: Examples 1 and 2, according to the composition shown in Table 2. Resin tooth adhesive composition 3: comparative example) was prepared.
Using the prepared resin tooth adhesive composition 1 〜 3, a resin tooth binding force test was performed according to the evaluation method described above. The test results are shown in Table 3.

As shown in Table 3, using resin tooth adhesive compositions 1 and 2 (Examples 1 and 2) containing a radical polymerizable monomer having a polymethyl methacrylate solubility of 10% by weight or more and a radical polymerization initiator, It was confirmed that the denture base resin made of a thermoplastic resin (polycarbonate resin) and the resin teeth had high bonding strength and were firmly bonded.

On the other hand, when a resin tooth adhesive composition 3 (comparative example) containing a radical polymerizable monomer having a solubility of polymethyl methacrylate of less than 10% by weight and a radical polymerization initiator is used as a comparative example, a thermoplastic resin (polycarbonate resin) is used. It was confirmed that the binding force between the denture base resin and the resin teeth composed of

Subject example Resin tooth binding force test was carried out according to the evaluation method described above, taking the case where no resin tooth adhesive composition was used at the time of denture preparation as a subject example. The test results are shown in Table 3. As shown in Table 3, in the comparison with Examples 1 and 2 and Comparative Example 1, when a resin tooth adhesive composition is not used (target example), a denture base composed of resin teeth and a thermoplastic resin (polycarbonate resin) There was no binding force with the resin for use, and it was found that the resin teeth dropped out.

Claims (3)

A denture base resin and a resin tooth are bonded in a method for preparing a denture by inserting a denture base resin made of a thermoplastic resin into a denture mold in which a base portion of a resin tooth containing polymethyl methacrylate is arranged. A resin tooth adhesive composition, the resin tooth adhesive composition includes a radical polymerizable monomer and a radical polymerization initiator, and the radical polymerizable monomer has at least one of an acryloyl group or a methacryloyl group, and Resin tooth adhesive composition, wherein the solubility of polymethyl methacrylate in the radical polymerizable monomer is 10% by weight or more. 2. The resin tooth adhesive composition according to claim 1, comprising 0.01 to 10 parts by weight of a radical polymerization initiator with respect to 100 parts by weight of the radical polymerizable monomer. The method for manufacturing a denture using a resin teeth adhesive composition according to claim 1 or claim 2.