JPS63316710A - Photo-setting dental composition - Google Patents

Abstract

PURPOSE:To obtain a photo-setting dental prosthetic composition, readily polymerizable and curable by irradiation with visible rays and capable of providing cured products having high mechanical properties and excellent water resistance, by blending a high content of a specific organic filler as an inorganic substance with a monomer mixture and photopolymerization initiator. CONSTITUTION:A photo-setting dental composition consisting of (A) an organic composite filler obtained by polymerizing a monomer of a sulfonic acid or sulfonate thereof expressed by formula I (R1 is H, alkyl, etc.; X is CONH, etc.; R2 and R3 are H or alkyl; R4 is alkylene; Y is H, NH4, etc.) and a vinyl monomer in a system containing a dispersed inorganic compound, (B) a monomer mixture consisting of 2,2-bis[4-(methacryloxyethoxy)pheny]propane, a compound expressed by formula II (X is formula III (n is 1-10; R1 and R2 are H or methyl)] and a diluting ethylenic vinyl monomer and (C) an alpha-diketone compound and a reducing agent expressed by formula IV (R1-R4 are H or alkyl) as a polymerization initiator.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a dental prosthetic composition containing a high proportion of an organic composite filler as an inorganic substance. The present invention relates to a photopolymerizable dental prosthetic composition that cures and has high mechanical properties and excellent water resistance.

[Prior art]

It is important for dental prosthetic materials to have both physical properties such as mechanical strength, abrasion resistance, water resistance, and adhesiveness, as well as aesthetic properties such as transparency and abrasiveness in order to closely resemble natural teeth. As an alternative material for amalgam and amalgam, inorganic filler is added to the resin to improve these properties.
Many attempts have been made to develop so-called composite resins.

The main components constituting this composite resin include six components: (1) an inorganic filler, (2) an olefinic unsaturated compound, and (2) a polymerization initiator.

However, when simply blending an inorganic filler and an organic resin, the inorganic filler and organic resin lack compatibility and interfacial affinity such as adhesion, and optical composite performance cannot be obtained. In order to improve this point, dental materials have been proposed in which, for example, a filler treated with a silane coupling agent is added to the glass surface. It has the major disadvantage of being limited to glassy fillers on the surface and lacks versatility.Additionally, the siloxane bonds formed are susceptible to hydrolysis and have poor water resistance. Therefore, when applied to dental prosthetic compositions, quartz-based fillers, which are commonly used as fillers that provide high hardness and esthetics, are difficult to develop interfacial reinforcement properties, and furthermore, long-term clinical use in a moist oral cavity is difficult. On the other hand, it has clinical problems such as poor water resistance, which causes a decrease in mechanical strength over time.

Various studies have also been conducted on monomers constituting organic resins. For example, bisphenol A represented by bisphenol A diglycidyl methacrylate (hereinafter abbreviated as Bis-GMA) provides a composite with a low polymerization shrinkage rate. The hydrophobic monomer 2,2-bis[4-(methacryloxyethoxy)phenyl]propane (hereinafter abbreviated as Bis-MF, PP) is a polyfunctional monomer that provides excellent water resistance. ) and other monomers have been found. However, Bis-GM
Since A has a water group in its molecule, the resulting cured product has a high water absorption rate and poor water resistance; on the other hand, Bis-MI
When using PP'i, there are problems in that the curability is low, sufficient crosslinking density cannot be obtained, and mechanical strength is poor. Furthermore, in order to compensate for these shortcomings, for example, simply Bis-
Even if GMA and B10-MEPP were used in combination, a composite resin with excellent properties could not be obtained, so a very wide range of monomer composition studies were conducted to determine the monomer composition suitable for the purpose. The current situation is that it must be done.

[Problems to be Solved by the Invention] An object of the present invention is to provide a photopolymerizable dental composition that has excellent mechanical strength and good water resistance.

[Means for solving problems]

The gist of the present invention is that (A) the following general formula % formula % (1:] (wherein R1 is H1 an alkyl group having 1 to 20 carbon atoms, a phenyl group and its derivatives, or ha! logeno atom, X is -CONH-1-QONH-0-R4
-1Coo (CH2 cut or →CH2 treasure, R
2+R3 are each H or an alkyl group having 1 to 15 carbon atoms, R4 is an alkylene group having 1 to 15 carbon atoms, and m is 1 to 2
0 integer, n is an integer from 0 to 20, Y represents H, NH41, or an alkali metal atom) and at least one radically polymerizable vinyl. An organic composite filler obtained by polymerizing a monomer in a polymerization system in which inorganic compounds are completely dispersed, 03) 2.2-bis[:4-(methacryloxyethoxy)phenyl]propane and the following general formula [■ ] A monomer mixture consisting of at least one type of hexafunctional urethane (meth)acrylate represented by A photopolymerization initiator which is a diaminobenzophenone compound represented by the following general formula Cu1l] (wherein R1-R4 may be the same or different and are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, at least one is an alkyl group).

The organic composite filler constituting the composition of the present invention (Shu) contains a sulfonic acid monomer or a sulfonate monomer and one or more other polymerizable vinyl It can be obtained by polymerizing monomers,
There are no particular limitations on the manufacturing method. An example of a preferred production method is to suspend and disperse a vinyl monomer and an inorganic compound in an aqueous medium under temperature conditions that do not cause a thermal polymerization reaction, and then add a sulfonic acid monomer or a sulfonic acid salt. There are 9 methods in which a monomer is added and stirred to cause an aqueous heterogeneous polymerization reaction, and the polymerization is carried out for a predetermined period of time.

In addition, in the above polymerization, a radical polymerization initiator can be added depending on the purpose. For example, when a high grafting rate is required, or when using a mixture of various vinyl monomers, etc. A system in which a radical polymerization initiator is added is suitable.

The specific sulfonic acid monomer or sulfonate monomer represented by the general formula (I) used for forming the organic composite filler (A) has a sulfonic acid group as an active side that brings about polymerization activity. The presence of a double bond as an active side is essential for the formation of a strong bond between the polymer and the inorganic compound, and any compound having a structural formula containing these functional groups can be applied. Specific examples include 2-acrylamido-2-methylpropanesulfonic acid, sodium 2-methacrylethanesulfonate, 3-
Examples include sodium methacrylpropanesulfonate, sodium 2-propanesulfonate, sodium 2-methyl-2-propanesulfonate, and in particular, 2-acrylamido-2-methylpropanesulfonic acid containing an amide bond and containing an ester bond. Sodium 2-methacrylethanesulfonate and sodium 6-methacrylpropanesulfonate exhibit remarkable secondary flocculation performance,
Moreover, it is preferable because it has extremely high polymerization activity.

In addition, the inorganic compounds used in the production of the organic composite filler (A) include those listed in Periodic Rule 1. n, m, rv.

Examples include metals of the Group III and their oxides, hydroxides, chlorides, sulfates, sulfites, carbonates, phosphates, silicates, and mixtures and composite salts of these metals, among which sulfuric acid Glass fillers containing barium, barium fluoride, silicon dioxide, aluminum oxide, titanium oxide, quartz powder, glass powder, glass beads, glass fibers, barium salts, lead salts, or strontium salts, silica gel,
Zirconium oxide and stannic acid are preferred because they have a particularly remarkable effect of activating vinyl monomers and strongly integrating them with polymers. One of the major features of the present invention is that it can be applied to inorganic compounds for which ordinary coupling treatment is not effective, and the shape and size of the inorganic compound can be selected as appropriate.

Further, as the vinyl monomer used in the production of the organic composite filler (A) of the present invention, any ordinary vinyl monomer that can be radically polymerized can be used, and specific examples include, for example, methyl methacrylate. , (meth)acrylic acid alkyl esters such as butyl acrylate, aromatic vinyl monomers such as styrene and α-methylstyrene, vinyl cyanide monomers such as acrylonitrile and methacrylonitrile, and as described below. Examples include monomers used as the ethylenic vinyl monomer mixture (B) in the present invention, and can be arbitrarily selected depending on the purpose.

Incidentally, as the radical polymerization initiator used in the production of the organic composite filler (A), all usual peroxides and azo compounds can be used, but preferably at 40 °C to 1
Particularly effective are radical polymerization initiators that can be decomposed in the temperature range of 00°C.

Among them, peroxides such as benzoyl peroxide, azobisinbutyronitrile, and potassium persulfate, and azo compounds are particularly effective and preferred from the viewpoint of the grafting rate of the organic composite filler produced.

The concentration of the sulfonic acid monomer or sulfonate monomer when obtaining the organic composite filler is about 10% to 100% by weight, preferably 01 to 5ON, based on the total weight of the inorganic compound and vinyl monomer. Amount ratio, particularly preferably α5-60 weight: 1%
used in amounts of In many cases, it is preferred to increase the amount of sulfonic acid or sulfonate monomer as the vinyl monomer content increases. The weight ratio of vinyl monomer or mixture thereof to mechanical compound used can vary within a wide range and is from about 500:1 to 1:5, preferably from about 50:1 to about 1:1. In addition, when polymerizing in an aqueous medium, the water content is about 1% to several hundred times, preferably about 10% to several hundred times, based on the total weight of the inorganic compound and vinyl monomer.
It is 10 times more.

The reaction is preferably carried out under an atmosphere of an inert gas, such as nitrogen, at a temperature of about 10 to 100°C, preferably at a temperature of about 40 to 100°C, which allows the radical polymerization initiator to decompose. The specific reaction temperature here is selected as appropriate depending on the vinyl monomer used, but it is important to carry out the reaction at a temperature at which thermal polymerization is suppressed to a negligible level. When carried out at
It takes about 15 hours. The organic composite filler produced is approximately 10-3
Drying can be carried out at a temperature range of 00°C, preferably about 50-200°C. Note that the interaction between the surface of the inorganic compound and the polymer applied by the method of the present invention goes beyond adhesion in a physical sense due to simple adsorption or van der Waals forces, and this fact This is clear from the fact that a large amount of unextracted polymer is observed even after extraction with a good solvent for vinyl polymer.

The above-mentioned organic composite filler (A) has a strong combination of various inorganic compounds and M-careful combination, so the inorganic compounds in the composite resin and M-careful combination have high compatibility, and therefore, it is suitable for the purpose. By appropriately selecting the inorganic compounds necessary for the dental composition, it is possible to obtain the dental composition targeted by the present invention.

The ethylenic vinyl monomer mixture (B
) must contain Bie-MKPP and a hexafunctional urethane (meth)acrylate represented by the general formula (II).

By combining the above two types of monomers, surprisingly, when the composition of the present invention is cured, it is possible to obtain a composite resin with excellent mechanical strength and good water resistance.

Among the monomers represented by the general formula (II), from the viewpoint of curability, n is 6, R1 is hydrogen, and R2 is a methyl group, hexafunctional urethane acrylate (hereinafter abbreviated as U-6HA) and n
is 6, and R1 and R2 are methyl groups, hexafunctional urethane methacrylate (hereinafter abbreviated as U-6H) is preferred, and U-6HA is most preferred.

In the present invention, Bis in the monomer mixture (B)
- The blending ratio of MKPF, hexafunctional urethane (meth)acrylate, and ethylenic monomer for dilution is not particularly limited, but from the viewpoint of workability of the obtained composition of the present invention, the composition of the present invention The viscosity of the substance is 1000 to 500,000 (25℃
) It is preferable to mix them so that they become voids. Usually, the amount of Bie-MFiPP and hexafunctional urethane (meth)acrylate in the monomer mixture (B) is 40% each.
~70 weight scale, weight ~40 weight scale. In addition, from the viewpoint of water resistance and mechanical strength, the blending ratio (X amount ratio) of hexafunctional urethane (meth)acrylate and Bis-MKPP is α05:1 to 1:1, preferably R1:1.
~ α8:1, preferably R2:1 ~ α5:1 is usually used.

As the diluting ethylenic vinyl monomer used in the present invention, conventionally known monomers used in dental composite resins can be used. Acrylate, 1.
6- H *+ Alkanediol (meth)acrylates such as methylene glycol dimethacrylate, polyalkylene glycol di(meth)acrylates such as triethylene glycol dimethacrylate (hereinafter abbreviated as 3G), tetraethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, etc. (Meth)acrylic acid alkyl esters such as methylolpropane tri(meth)acrylate, glycidyl (meth)acrylate, methyl methacrylate, butyl acrylate, aromatic hydrocarbons such as styrene and α-methylstyrene, cyanide of acrylonitrile, methacrylatetrile, etc. Examples include vinyl compounds. In the present invention, the radical-capable vinyl monomer used in the organic composite filler (4) and the monomer mixture (B) may be the same.

The blending amounts of the organic composite filler (A) and the monomer mixture (B) can be arbitrarily selected depending on the type and purpose of use of the inorganic compound and monomer mixture (B) used in the filler (A). Usually, 20 to 90 parts by weight of organic composite filler,
Monomer mixture (B) is used in an amount of 10 to 80 Ni parts.

α used in the photopolymerization initiator (0) used in the present invention
- The diketone compound is not particularly limited, but
Since it is used for dentistry, it is desirable to use visible light with a wavelength of 400 to 800 nm, excluding the near ultraviolet region, in consideration of its toxicity in the oral cavity.

Furthermore, clinically, it is desirable to perform hard fc within about 30 seconds.

From the above points, preferable compounds include α-
Mention may be made of diketone compounds or mixtures thereof. or,
The α-diketone compound is used in combination with a reducing agent, and in the composition of the present invention, a diaminobenzophenone compound represented by the following general formula CI [1] is particularly required as a reducing agent in terms of high curability. It is.

(In the formula, R1-R4 may be the same or different and are a hydrogen atom or an argyl group having 1 to 5 carbon atoms, and at least one is an alkyl group.) Especially, R1-R4
4,4'-bis(dimethylamino)benzophenone (hereinafter abbreviated as AB) in which all of the methyl groups are represented by methyl groups is preferred from the viewpoint of curability.

The amount of the photopolymerization initiator (0) to be added may be arbitrarily selected in consideration of the curability, storage stability, and color tone of the composition, but usually, the amount of α-diketone added to the monomer mixture (B) is The compound is used in an amount of α01 to 151, preferably 005 to 5, preferably 01 to 2i [i%], and the diaminobenzophenone compound is used in a weight range of α01 to 15.

In the composition (C) of the present invention, a filler is further added to the above-mentioned components as necessary.The filler components include Periodic Law No. 1. Il, I[1, IV.

Group III, transition metals, and their oxides, hydroxides, chlorides, sulfates, sulfites, carbonates, phosphates, silicates, and mixtures and composite salts thereof, among which silicon dioxide , quartz powder, aluminum oxide, barium sulfate, titanium oxide, Merck, glass powder, glass beads, glass fiber, barium salt, glass filler containing lead salt, silica gel, colloidal silica, carbon fiber, zirconium oxide, tin oxide , other ceramic powders, etc. are preferred. The above-mentioned filler may be any of an untreated filler, a surface-treated filler using a silane coupling agent, etc., and an organic composite filler composited with a polymer and pulverized.

The amount of the filler blended can be changed as appropriate depending on the purpose of use of the photopolymerizable dental composition, but is usually 01 to 103% by weight, preferably α5 to 103% by weight, based on the monomer mixture (B). 5×10”3 [quantity factor, particularly preferably 1 to 102
It is used as a paste-like composition by blending in the range of x amount ratio.

Furthermore, the composition of the present invention may optionally contain a colorant, a polymerization inhibitor (e.g., hydroquinone, methoxybenzophenone, methylphenol, hydroquinone monomethyl ether, etc.), an oxidation stabilizer, an ultraviolet absorber (e.g., benzophenone, etc.) , pigments (for example, iron oxide, titanium oxide, etc.), dyes, etc. can also be blended.

Next, the present invention will be explained in detail with reference to examples, but the present invention is not limited to the following examples. In the examples, parts indicate parts by weight.

Production of organic composite filler (Organic composite filler (1)) Add the compound as a free compound to a 500-meter rose bulb flask equipped with a cooling tube, nitrogen introduction tube, stirring rod, and thermocouple for internal temperature detection. Quartz fine powder (Tatsumori mA-2 with average particle size 1~
50 g of barium glass (7724 manufactured by Corning, ground to an average particle size of 1 to 2 μm) 50 ft: Suspended and dispersed in 290 ml of deionized water, and replaced with nitrogen for 30 minutes. Ta. Next, 50 tons of methyl methacrylate as a vinyl monomer was added and suspended and dispersed under a nitrogen atmosphere with vigorous stirring. Next, the temperature of the suspension was raised to 70°C in a hot water bath, and after confirming that the suspension was uniformly dispersed, sodium 2-methacrylethanesulfonate α5t was added as a sulfonate monomer. A solution dissolved in deionized water was gradually added, and a polymerization reaction was carried out at the same temperature for 8 hours.

After the reaction was completed, the entire product was filtered under reduced pressure, thoroughly washed with deionized water, and then dried with hot air at 100° C. to remove moisture, yielding about 1000% of organic composite filler (1). The obtained composite filler had a polymer content of 2.6% as measured by the calcination method, and a 50-hour Soxhlet extraction test using hot benzene as an extraction solvent revealed that the polymer content after the extraction process was 2.6%. It was found that the surface of the quartz fine powder and barium glass and most of the polymer composited by this method were extremely strongly integrated. In addition, quartz fine powder, barium glass and Q
Even when each 100f was polymerized individually with the same formulation, each showed almost the same polymer content as the mixed system, so the surfaces of the two types of inorganic fillers in the mixed system were uniformly composed of polymers. It is presumed that the

(Organic composite filler (2)) 2 instead of sodium 2-methacrylethanesulfonate
- Organic composite filler (2) is produced in the same manner as the method for producing organic composite filler (1) except for using acrylamide-2-methylpropanesulfonic acid, and filler (1) is
A similar evaluation was conducted. The obtained filler (2) showed the same results as filler (1), and is considered to be uniformly composited.

(Organic composite filler (3)) Quartz fine powder (Tatsumori MA- 2 to average particle size 1 to
50f (pulverized to 2 μm) and 50f of barium glass (made by Corning ÷7724i, crushed to an average particle size of 1 to 2 μm) were suspended and dispersed in 290 μm of deionized water.
Nitrogen substitution was performed for 30 minutes. Next, 2.5 f of methyl methacrylate was added as a vinyl monomer with vigorous stirring under a nitrogen atmosphere, and the mixture was suspended and dispersed. Next, the temperature of the suspension was raised to 70°C in a hot water bath, and after confirming that the suspension was uniformly dispersed, the sulfonate monomer was
- A solution of sodium methacrylethanesulfonate α5t dissolved in deionized water 10- and benzoyl peroxide α07t as a radical polymerization initiator and methyl methacrylate α
A solution dissolved in 5f was gradually added, and a polymerization reaction was carried out at the same temperature for 8 hours.

After the reaction was completed, the product was filtered under reduced pressure, thoroughly washed with deionized water, and then dried with hot air at 100° C. to remove water to obtain about 100 f of organic composite filler (3). This composite filler has a polymer content of 53% as measured by a calcination method.
When a 50-hour Soxhlet extraction test was conducted using hot benzene as an extraction solvent, the polymer content after extraction treatment was as high as 51%. It was found that most of the composite polymers were extremely strongly integrated. Separately, even when 100 tons of quartz fine powder and barium glass were individually polymerized using the same recipe, each showed almost the same polymer content as the mixed system, so the two types of inorganic fillers in the mixed system were It is thought that all the surfaces are uniformly composited with polymer.

(Organic composite filler (4) to (6)) 2 instead of sodium 2-methacrylethanesulfonate
- When using acrylamide-2-methylpropanesulfonic acid, when using butyl acrylate instead of methyl methacrylate, and when using azobisin butyronitrile instead of benzoyl peroxide, the other Organic composite fillers (4) to (6) were produced using the same method as organic composite filler (3), and the same evaluations as for filler (3) were performed. The obtained filler (4
) to (6) showed similar results to filler (3) and are considered to be uniformly composited.

Organic composite fillers (1) to (6) obtained by the above method
Aerosil R- as a viscosity adjusting filler at 90F
972 (Hydrophobized amorphous silica manufactured by Degutsusa) 10
Each of the fillers added with f was used as a filler (ml-(F')).

[Examples 1 to 6. Comparative Example 1.2 Various photopolymerizable dental compositions prepared with the compositions shown in Table 1 were filled into a stainless steel mold with an inner diameter of 4 m and a height of 6 m, and molds with a thickness of approximately α1 mm were placed on both the upper and lower surfaces. After adhering the cover glass, use a visible light irradiator (manufactured by 3M, "0ptil").
ux') to set the distance between the cover glass and the irradiation port to 1.
A cured product was obtained by irradiating cod for 30 seconds from both the top and bottom surfaces.

The obtained cured product was stored in water at 37° C. for 24 hours, and then its compressive strength was evaluated. Furthermore, the compressive strength after storing the cured product in water at 37° C. for one week was evaluated as the water resistance strength. The strength was measured using Tensilon (Takashi Seisakusho M5-500) i at a crosshead speed of 1. It was carried out using Owm/win.

In addition, using a stainless steel mold with an inner diameter of 20 goI and a height of 1 inch, a cured product obtained in the same manner was stored in water at 37°C for one week, and then the weight increase per unit surface area of the cured product was measured. The water absorption rate was evaluated.

For comparison, instead of the composite filler according to the present invention, a mixed filler of 50 g of quartz fine powder and 50 g of barium glass was used as a silane coupling agent (KBM-4 manufactured by Shin-Etsu Silicone).
503: When Aerosil R-972, 10f is mixed and prepared with silane-treated filler 909 treated with 3% of 3-methacryloxypropyltrimethoxysilane (a), untreated quartz fine powder and barium glass are each mixed with 45 grams of untreated quartz fine powder and barium glass. Similar evaluations were also conducted for the untreated filler (1) prepared by mixing Aerosil R-9'72,109.

As is clear from Table 1, the composite filler (A) of the present invention
(Dental materials using F5 (Examples 1 to 6) are all silanized fillers that have been used conventionally (Comparative Example 1)
It can be seen that a cured product having superior mechanical strength and water resistance can be obtained as compared to a compound containing an untreated filler (Comparative Example 2).

Moreover, the composite filler used in the present invention is a monomer mixture (E
), it was easy to combine with the compound, and the appearance of the cured product was significantly better than that of the comparative example.

[Example 7. Comparative Examples 3 and 4] Aluminum oxide powder (reagent special grade) 1 as an inorganic compound
An aqueous heterogeneous polymerization reaction was carried out in the same manner as in Example 1, except for using 00F, to obtain an organic composite filler (G). The resulting composite filler had a polymer content of 2.6%,
The polymer content after the extraction process was 2.2. This is 4! ! A dental composition was mixed and prepared using the quality composite filler (G) according to the composition shown in Table 2, and the various physical properties of the cured product were evaluated in the same manner as in Example 1. The results obtained are shown in Table 2.

For comparison purposes, silane-treated filler (0)'e in which aluminum oxide powder was treated with 3% silane coupling agent was used instead of the composite filler according to the present invention, and untreated aluminum oxide powder ( The same evaluation as in Example 1 was conducted also in the case of using d).

[Example 8] Aluminum oxide powder (reagent special grade) 1 as an inorganic compound
An aqueous heterogeneous polymerization reaction was carried out in the same manner as in Example 3 except that 009 was used to obtain an organic composite filler@. The resulting composite filler had a polymer content of 53%, and the polymer content after extraction was 50%. A dental composition was mixed and prepared using this organic composite filler @ with the composition shown in Table 2, and the various physical properties of the cured product were evaluated in the same manner as in Example 3. The results obtained are shown in Table 2.

As is clear from Table 2, similar to the results in Table 1, the dental composition of the present invention showed superior results compared to conventional silane-treated fillers and untreated fillers. It can be seen that it has certain characteristics.

[Examples 9-11. Comparative Examples 5 to 7] Dental compositions were prepared in the same manner as in Example 1 except for the composition of the monomer mixture (B) shown in Table 3, and
Similarly, various physical properties of the obtained cured product were evaluated. The obtained results are shown in Table 3.

[Examples 12-16. Comparative Examples 8 to 12 Dental compositions were prepared in the same manner as in Example 3, except that the composition of the monomer mixture (B) shown in Table 3 was used. Various physical properties of the cured product were evaluated. The results obtained in the third
Shown in the table.

As is clear from Table 3, by including the specific monomer throughout the monomer mixture (B), a cured product for dental materials having excellent mechanical strength and water resistance can be obtained.

〔Effect of the invention〕

As detailed above, since the composition of the present invention has excellent mechanical strength and water resistance, it can exhibit excellent effects when used as a dental material composition or a suction.

Claims (1)

[Claims] 1. (A) The following general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [I] (In the formula, R_1 is H, an alkyl group having 1 to 20 carbon atoms, a phenyl group and its derivatives or halogen atom, X is -
CONH-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -C
OO(CH_2)-_m, or -(CH_2)-_n
and R_2 and R_3 are each H or carbon number 1 to
15 alkyl group, R_4 is an alkylene group having 1 to 15 carbon atoms, m is an integer of 1 to 20, n is an integer of 0 to 20, Y is H, NH_4, or an alkali metal atom). an organic composite filler obtained by polymerizing a polymer or sulfonate monomer and at least one radically polymerizable vinyl monomer in a polymerization system in which an inorganic compound is dispersed; (B) 2,2 -Bis[4-(methacryloxyethoxy)
phenyl]propane, at least one type of hexafunctional urethane (meth)acrylate represented by the following general formula [II], and a monomer mixture consisting of an ethylenic vinyl monomer for dilution; ▼[II] (In the formula, ) (C) Photopolymerization initiator consisting of an α-diketone compound and a reducing agent, where the reducing agent is a diaminobenzophenone compound represented by the following general formula [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( III) (In the formula, R_1 to R_4 may be the same or different and are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and at least one is an alkyl group.) thing. 2. The sulfonic acid monomer or sulfonate monomer is 2-
Acrylamido-2-methylpropanesulfonic acid, 2-
The photopolymerizable dental composition according to claim 1, which is sodium methacrylethanesulfonate or sodium 3-methacrylpropanesulfonate. 3. Inorganic compounds include barium sulfate, barium fluoride, silicon dioxide, aluminum oxide, titanium oxide, quartz powder,
glass powder, glass beads, glass fiber, barium salt,
The photopolymerizable dental composition according to claim 1, which is at least one selected from glass filler, silica gel, zirconium oxide, and tin oxide containing lead salt or strontium salt. thing. 4. The photopolymerizable dental composition according to claim 1, wherein the α-diketone compound is at least one selected from camphorquinone, benzyl, and diacetyl.