JP2008273889A - Dental composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a portion-pack type dental composition which scarcely drips down during coating, and can well be picked up from a container. <P>SOLUTION: This portion-pack type dental composition comprising a first paste (A) and a second paste (B) which each comprises a polymerizable monomer (a) having an aromatic ring and having a hydroxy group, a polymerizable monomer (b) having an aromatic ring and not having a hydroxy group, a polymerizable monomer (c) except the monomers (a) and (b), and an inorganic filler (d), wherein the contents of the polymerizable monomers (a), (b) and (c) in the mixture are 15 to 25 wt.%, 55 to 65 wt.% and 15 to 25 wt.%, respectively, in the total polymerizable monomers, when the first paste (A) and the second paste (B) are mixed in a weight ratio of 1:1; the content of the inorganic filler (d) is 150 to 300 pts.wt. per 100 pts.wt. of the total polymerizable monomers; and one of the pastes contains an oxidizing agent and the other contains a reducing agent. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a dental composition that can replace part or all of a natural tooth in the field of dentistry.

  In a dental material composed of a polymerizable monomer, an inorganic filler, and a polymerization initiator, the polymerizable monomer having an aromatic ring represented by Bis-GMA, having a hydroxyl group, and an aromatic ring represented by 3G Those containing a polymerizable monomer that does not contain slag are the most frequently used materials today, such as dental cements, abutment building materials, and filling composite resins. Many techniques for improving the physical properties of these materials, such as adhesion to teeth and mechanical strength, have been disclosed.

  In Patent Document 1, a cured product having excellent mechanical strength and color resistance is obtained by curing an acrylate monomer using an α-aminoacetophenone photoinitiator.

  Further, paying attention to the curing reaction catalyst amount of the composite resin, Patent Document 2 discloses a curing time adjusting agent containing a specific amount of amine in addition to a catalyst paste containing an organic peroxide and a universal paste containing an amine. Curing time is adjusted with a three-paste dental composite resin using

Further, paying attention to the handleability of the composite resin, in Patent Document 3, a) filler, b) polymerizable resin, and c) dispersed at 25 ° C. in the polymerizable resin, the molecular weight is about 500-100. A dental resin cement material is disclosed which includes 1,000,000 polymer handleability improvers and d) a polymerization initiator.
JP-A-6-345614 JP-A-5-148118 JP 2001-510146 A

  When the polymerization initiation reaction is an oxidation-reduction reaction, dental materials such as dental cement, abutment building material, and filling composite resin are composed of two pastes, a paste containing an oxidizing agent and a paste containing a reducing agent. It has been provided to dentists as a package. Moreover, according to the prior art, it is possible to improve the adhesiveness of a dental composition single-piece | unit. However, since it is difficult to adjust the viscosity and adhesiveness after mixing the two pastes in the packaging type, there are problems such as dripping at the time of application and adhesion to a container. In consideration of handleability, the packaging composition is also required to have little resistance to collecting the mixed paste from the container.

  An object of the present invention is to provide a package-type dental composition that is less likely to sag during application and has good collection properties from a container.

  As a result of diligent studies to solve the above problems, the present inventors have blended a specific polymerizable monomer and an inorganic filler at a specific ratio, so that dripping at the time of application is small, and from the container. The present inventors have found that a package-type dental composition having a good collection property can be obtained and completed the present invention.

  That is, the present invention comprises a first paste (A) and a second paste (B), both of which have an aromatic ring and a hydroxyl group-containing polymerizable monomer (a), aromatic Package containing a polymerizable monomer (b) having a ring and no hydroxyl group, a polymerizable monomer (c) other than (a) and (b), and an inorganic filler (d) When the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1 in the mold, the polymerizable monomer ( The contents of a), (b) and (c) are 15 to 25% by weight, 55 to 65% by weight and 15 to 25% by weight in the total polymerizable monomer, and the inorganic filler (d ) Is 150 to 300 parts by weight with respect to 100 parts by weight of the total polymerizable monomer, and one of the pastes contains an oxidizing agent and the other contains a reducing agent. And comprising, dental compositions of the packing type relates.

  The sachet type dental composition of the present invention has an excellent effect that there is little dripping at the time of application and the collection property from the container is good.

  The package-type dental composition of the present invention comprises a first paste (A) and a second paste (B), all of which have an aromatic ring and a hydroxyl group. Polymer (a), polymerizable monomer (b) having an aromatic ring and no hydroxyl group, polymerizable monomer (c) other than (a) and (b), and inorganic filler (d) A dental composition containing selenium, wherein when the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1, the polymerization is performed in the mixture. One characteristic is that the contents of the functional monomers (a), (b) and (c) and the inorganic filler (d) are within a specific range.

  The polymerizable monomer (a) having an aromatic ring and having a hydroxyl group is not particularly limited as long as it is a polymerizable monomer having an aromatic ring and a hydroxyl group, and the number of aromatic rings and the number of hydroxyl groups are independent numbers. It is sufficient that each functional group has at least one. Examples of such a compound include a polymerizable monomer having a bisphenol A skeleton and a hydroxyl group, and more specifically 2,2-bis [4- [3- (meth) acryloyloxy-2 -Hydroxypropoxy] phenyl] propane (hereinafter sometimes referred to as Bis-GMA), 2- [4- [3- (meth) acryloyloxy-2-hydroxypropoxy] phenyl] -2- [4- [2 , 3-Di (meth) acryloyloxypropoxy] phenyl] propane (hereinafter sometimes referred to as Bis3), 2- [4- [3- (meth) acryloyloxy-2-hydroxypropoxy] phenyl] -2- [4- (meth) acryloyloxydiethoxyphenyl] propane, 2- [4- [3- (meth) acryloyloxy-2-hydroxypropoxy] phenyl] -2- [4- (meth) acryloyloxyditriethoxyphenyl] Prop 2- [4- [3- (meth) acryloyloxy-2-hydroxypropoxy] phenyl] -2- [4- (meth) acryloyloxydipropoxyphenyl] propane, etc., and these may be used alone or in combination The above can be used in appropriate combination. Among these, Bis-GMA is preferable from the viewpoint of increasing the adhesive strength with a tooth when used as a dental composition.

  The polymerizable monomer (b) having an aromatic ring and not having a hydroxyl group is not particularly limited as long as it is a polymerizable monomer having an aromatic ring and not having a hydroxyl group. What is necessary is just to have an aromatic ring. Examples of such a compound include a polymerizable monomer having a bisphenol A skeleton and having no hydroxyl group, and more specifically, a compound represented by formula (I):

(In the formula, m and n are 0 or a positive number indicating the average added mole number of the ethoxy group, and the sum of m and n is preferably 1 to 6, more preferably 2 to 4).
For example, 2,2-bis [4- (meth) acryloyloxypolyethoxyphenyl] propane (hereinafter sometimes referred to as D2.6E) in which m + n = 2.6, m + n = 6 2,2-bis [4- (meth) acryloyloxypolyethoxyphenyl] propane (hereinafter sometimes referred to as D6E), 2,2-bis [4- (meth) acryloyloxyphenyl] propane (m + n = 0) ), 2,2-bis [4- (meth) acryloyloxydiethoxyphenyl] propane (m + n = 2), 2,2-bis [4- (meth) acryloyloxytetraethoxyphenyl] propane (m + n = 4), 2,2-bis [4- (meth) acryloyloxypentaethoxyphenyl] propane (m + n = 5) and the like. In addition, 2,2-bis [(meth) acryloyloxyphenyl] propane, 2,2-bis [4- (meth) acryloyloxydipropoxyphenyl] propane, 2- [4- (meth) acryloyloxydiethoxyphenyl] -2- [4- (meth) acryloyloxyditriethoxyphenyl] propane, 2- [4- (meth) acryloyloxydipropoxyphenyl] -2- [4- (meth) acryloyloxytriethoxyphenyl] propane, 2, Examples thereof include 2-bis [4- (meth) acryloyloxypropoxyphenyl] propane, 2,2-bis [4- (meth) acryloyloxyisopropoxyphenyl] propane, and the like. These may be used alone or in combination of two or more. Of these, D2.6E and D6E are preferable from the viewpoint of the properties (precipitation, etc.) of the polymerizable monomer.

  The polymerizable monomer (c) is not particularly limited as long as it is a polymerizable monomer other than (a) and (b). Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate , Isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, lauryl (meth) acrylate, 2,3-dibromopropyl (meth) acrylate, (meth) acrylamide, ethylene glycol di (meth) acrylate, tri Ethylene glycol di (meth) acrylate (hereinafter sometimes referred to as 3G), 1,2-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1,4-buta Diol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate (hereinafter sometimes referred to as DD), N, N ′-(2,2 , 4-Trimethylhexamethylene) bis [2- (aminocarboxy) ethane-1-ol] di (meth) acrylate (hereinafter sometimes referred to as UDMA), N, N ′-(2,2,4- Trimethylhexamethylene) bis [2- (aminocarboxy) propane-1,3-diol] tetra (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol tetra (meth) Acrylate, 1,7-diaacryloyloxy-2,2,6,6-tetraacryloyloxymethyl-4-oxyheptane. Among these, 3G and DD are preferable from the viewpoint of the properties of the polymerizable monomer.

  In addition, from the viewpoint of securing mechanical properties of the cured product by improving the polymerizability, the polymerizable monomers (a), (b) and (c) may be di (meth) acrylate polymerizable monomers. Preferably, each is an independent di (meth) acrylate-based polymerizable monomer. In the present specification, “(meth) acrylate” means acrylic ester and / or methacrylic ester.

  When the first paste and the second paste are mixed at a weight ratio of 1: 1, the content of the polymerizable monomer (a) in the mixture is 15 to 25 wt% in the total polymerizable monomers. %, Preferably 18 to 22% by weight.

  When the first paste and the second paste are mixed at a weight ratio of 1: 1, the content of the polymerizable monomer (b) in the mixture is 55 to 65 wt% in the total polymerizable monomers. %, Preferably 58-62% by weight.

  The ratio of the weight of the polymerizable monomer (a) to the weight of the polymerizable monomer (b) (polymerizable monomer (a) / polymerizable monomer (b)) is 1/4 to 1/1 /. 1 is preferable, and 1/4 to 1/2 is more preferable.

  When the first paste and the second paste are mixed at a weight ratio of 1: 1, the content of the polymerizable monomer (c) in the mixture is 15 to 25 wt% in the total polymerizable monomers. %, Preferably 18 to 22% by weight.

  In addition, the total polymerizable monomer in this invention means what combined the said monomer comprised by polymerizable monomer (a), (b) and (c).

  The contents of the polymerizable monomers (a), (b) and (c) in each paste are not particularly limited as long as the total content in the composition is within the above range, but the viscosity and extrusion stress of each paste. From the viewpoint of improving the handleability by equalizing the above, in the first paste (A), the polymerizable monomer (a), the polymerizable monomer (b) and the polymerizable monomer ( c) the respective contents are 15 to 25 wt%, 55 to 65 wt%, and 15 to 25 wt% in the total polymerizable monomer contained in the first paste (A), and In the paste (B) of 2, the contents of the polymerizable monomer (a), the polymerizable monomer (b) and the polymerizable monomer (c) are included in the second paste (B). It is preferable that they are 15-25 weight%, 55-65 weight%, and 15-25 weight% in all the polymerizable monomers.

  The polymerization of the polymerizable monomer can be performed according to a known method using an oxidizing agent and a reducing agent contained in each paste.

  The oxidizing agent is contained in one of the first paste and the second paste. Examples of the oxidizing agent include diacyl peroxides, peroxyesters, dialkyl peroxides, peroxyketals, and ketone peroxides. Organic peroxides such as hydroperoxides are effective.

  Specific examples of diacyl peroxides include benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, m-toluoyl peroxide, and the like. Examples of peroxyesters include t-butyl peroxybenzoate, bis-t-butylperoxyisophthalate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxy- Examples include 2-ethylhexanoate and t-butyl peroxyisopropyl carbonate.

  Examples of dialkyl peroxides include dicumyl peroxide, di-t-butyl peroxide, and lauroyl peroxide. Examples of peroxyketals include 1,1-bis (t-butylperoxy) 3,3,5-trimethylcyclohexane.

  Examples of ketone peroxides include methyl ethyl ketone peroxide. Examples of hydroperoxides include t-butyl hydroperoxide.

  The said oxidizing agent can be used individually or in combination of 2 or more types as appropriate.

  The content of the oxidizing agent is such that when the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1, 100 parts by weight of the total polymerizable monomer in the mixture. 0.25 to 1.5 parts by weight, and more preferably 0.25 to 1.0 parts by weight.

  The reducing agent is contained in one of the first paste and the second paste that does not contain an oxidizing agent, such as an aromatic tertiary amine, an aliphatic tertiary amine, Sulfinic acid or a salt thereof is effective.

  Specifically, examples of the aromatic tertiary amine include diethanol-p-toluidine, N, N-dimethylaniline, N, N-dimethyl-p-toluidine, N, N-dimethyl-m-toluidine, N , N-diethyl-p-toluidine, N, N-dimethyl-3,5-dimethylaniline, N, N-dimethyl-3,4-dimethylaniline, N, N-dimethyl-4-ethylaniline, N, N- Dimethyl-4-i-propylaniline, N, N-dimethyl-4-t-butylaniline, N, N-dimethyl-3,5-di-t-butylaniline, N, N-bis (2-hydroxyethyl) -3,5-dimethylaniline, N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline, N, N-bis (2-hydroxyethyl) -4-ethylaniline, N, N-bis ( 2-hydroxyethyl) -4-i-propylaniline, N, N-bis (2-hydroxyethyl) -4-t-butylaniline, N, N- (2-hydroxyethyl) -3,5-di-i-propylaniline, N, N-bis (2-hydroxyethyl) -3,5-di-t-butylaniline, ethyl 4-dimethylaminobenzoate, Examples include n-butoxyethyl 4-dimethylaminobenzoate and (2-methacryloyloxy) ethyl 4-dimethylaminobenzoate.

  Examples of the aliphatic tertiary amine include trimethylamine, triethylamine, N-methyldiethanolamine, N-ethyldiethanolamine, N, N-butyldiethanolamine, N-lauryldiethanolamine, triethanolamine, (2-dimethylamino) ethyl methacrylate, Examples thereof include N-methyldiethanolamine dimethacrylate, N-ethyldiethanolamine dimethacrylate, triethanolamine monomethacrylate, triethanolamine dimethacrylate, and triethanolamine trimethacrylate.

  Examples of the sulfinic acid or a salt thereof include benzenesulfinic acid, sodium benzenesulfinate, potassium benzenesulfinate, calcium benzenesulfinate, lithium benzenesulfinate, toluenesulfinic acid, sodium toluenesulfinate, potassium toluenesulfinate, toluenesulfine. Acid calcium, lithium toluenesulfinate, 2,4,6-trimethylbenzenesulfinic acid, sodium 2,4,6-trimethylbenzenesulfinate, potassium 2,4,6-trimethylbenzenesulfinate, 2,4,6-trimethyl Calcium benzenesulfinate, lithium 2,4,6-trimethylbenzenesulfinate, 2,4,6-triethylbenzenesulfinate, sodium 2,4,6-triethylbenzenesulfinate, 2,4,6-triethylbenzenesulfinate Lithium, calcium 2,4,6-triethylbenzenesulfinate, 2,4,6-triisopropylbenzenesulfinate, sodium 2,4,6-triisopropylbenzenesulfinate, 2,4,6-triisopropylbenzenesulfinate Examples include potassium and calcium 2,4,6-triisopropylbenzenesulfinate.

  The above reducing agents can be used alone or in combination of two or more.

  The content of the reducing agent is such that when the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1, 100 parts by weight of the total polymerizable monomer in the mixture. 0.25 to 1.25 parts by weight, and more preferably 0.25 to 0.75 parts by weight.

  Further, the polymerization of the polymerizable monomer is performed by further using a known photopolymerization initiator in combination with the oxidizing agent and the reducing agent contained in each paste from the viewpoint of performing polymerization and curing with higher reactivity. be able to. In addition, a well-known photoinitiator can be used as a photoinitiator, Usually, it considers the polymerizability of a polymerizable monomer, and superposition | polymerization conditions.

  When performing photopolymerization by irradiation with visible light, oxidation-reduction initiators such as α-diketone / tertiary amine, α-diketone / aldehyde, α-diketone / mercaptan are preferable. Examples of the photopolymerization initiator include α-diketone / reducing agent, ketal / reducing agent, and thioxanthone / reducing agent. Examples of α-diketones include camphorquinone, benzyl, 2,3-pentanedione and the like. Examples of ketals include benzyl dimethyl ketal and benzyl diethyl ketal. Examples of thioxanthone include 2-chlorothioxanthone and 2,4-diethylthioxanthone. Examples of the reducing agent include Michler's ketone and the like; 2- (dimethylamino) ethyl methacrylate, N, N-bis [(meth) acryloyloxyethyl] -N-methylamine, ethyl N, N-dimethylaminobenzoate, 4- Such as butyl dimethylaminobenzoate, butoxyethyl 4-dimethylaminobenzoate, N-methyldiethanolamine, 4-dimethylaminobenzophenone, N, N-di (2-hydroxyethyl) -p-toluidine, dimethylaminophenanthol Tertiary amines; aldehydes such as citronellal, lauryl aldehyde, phthaldialdehyde, dimethylaminobenzaldehyde, terephthalaldehyde; thiosalicylic acid such as 2-mercaptobenzoxazole, decanethiol, 3-mercaptopropyltrimethoxysilane, 4-mercaptoacetophenone, Thio repose Examples thereof include compounds having a thiol group such as perfume acid. An α-diketone / organic peroxide / reducing agent system obtained by adding an organic peroxide to these oxidation-reduction systems is also preferably used.

  In the case of performing photopolymerization by ultraviolet irradiation, benzoin alkyl ether, benzyl dimethyl ketal and the like are preferable. Furthermore, an acylphosphine oxide photopolymerization initiator is also preferably used. Examples of the acylphosphine oxide include benzoyl methyl ether, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,3, Examples include 5,6-tetramethylbenzoyldiphenylphosphine oxide, benzoyldi- (2,6-dimethylphenyl) phosphonate, and 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide. These acylphosphine oxide photopolymerization initiators can be used alone or in combination with reducing agents such as various amines, aldehydes or mercaptans, and sulfinates. The above visible light photopolymerization initiator can also be suitably used in combination.

  The photopolymerization initiator can be used alone or in combination of two or more, and the content of the photopolymerization initiator is 1: 1 for the first paste (A) and the second paste (B). When mixed at a weight ratio, 0.1 to 10 parts by weight is preferable and 0.2 to 5.0 parts by weight is more preferable with respect to 100 parts by weight of all polymerizable monomers in the mixture. The photopolymerization initiator may be contained in either one of the first paste and the second paste or in both, and is not limited by the oxidizing agent and the reducing agent.

  Examples of the inorganic filler (d) in the present invention include oxides such as silicon, calcium, titanium, iron, zinc, strontium, zirconia, tin, barium, lanthanum, cerium, hafnium, tungsten, and the like. Or two or more kinds can be used in appropriate combination.

  The inorganic filler (d) is preferably 95% by volume or more, more preferably 97% by volume of particles having a particle size of 0.5 to 30 μm from the viewpoint of imparting an appropriate viscosity to the paste and improving the handleability. The inorganic particles having a volume median particle size of preferably 0.7 to 10 μm, more preferably 0.7 to 5 μm are desirable. In the present specification, the volume-median particle size and the ratio of the number of particles of the inorganic filler are measured by the method described in the examples described later.

  The inorganic filler (d) can be easily produced by a known pulverization method or a precipitation generation method by solution reaction, and the shape thereof may be any of a crushed shape, a spherical shape, a scale shape, etc., and is not particularly limited. .

  Further, the inorganic filler (d) may be subjected to an appropriate surface treatment, and may be blended with other components after the surface treatment. For example, when inorganic particles having a volume median particle size of 0.7 to 10 μm as a surface treatment and a small amount of inorganic particles having a primary average particle size of 100 nm or less are used in combination, the paste properties are improved and long-term This is preferable in that the separation of the paste during storage is suppressed. The content of inorganic particles having a primary average particle size of 100 nm or less is preferably 1 to 10 parts by weight with respect to 100 parts by weight of the inorganic filler. Examples of the surface treatment agent include known coupling agents, for example, γ-mercaptopropyltrimethoxysilane, and the addition amount is preferably 0.5 to 3.0 parts by weight with respect to 100 parts by weight of the inorganic filler. .

  The content of the inorganic filler (d) is such that when the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1, the total polymerizable monomer 100 in the mixture is 100%. It is 150-300 weight part with respect to a weight part, Preferably it is 200-300 weight part, More preferably, it is 220-260 weight part. Further, from the viewpoint of improving the handleability by equalizing the viscosity and extrusion stress of each paste, the content of the inorganic filler (d) in the first paste (A) is the first paste ( The amount of the inorganic filler (d) in the second paste (B) is 150 to 300 parts by weight with respect to 100 parts by weight of the total polymerizable monomer contained in A), and the second paste It is preferable that it is 150-300 weight part with respect to 100 weight part of all the polymerizable monomers contained in (B).

  In the present invention, in addition to the polymerizable monomers (a), (b) and (c), the inorganic filler (d), the oxidizing agent, and the reducing agent, a polymerization inhibitor, a pigment and the like are blended as raw materials. Also good.

  In the composition of the present invention, each paste contains the polymerizable monomers (a), (b) and (c), and the inorganic filler (d) in a predetermined content, and any one of the pastes There is no particular limitation as long as the oxidizing agent and the other each contain a reducing agent, and they can be easily produced by methods known to those skilled in the art.

  The paste of the composition of the present invention is usually easily used in a static mixer mounted on the tip of the double syringe by filling the first paste and the second paste into a double syringe or the like and pressing the piston at the time of use. Can be mixed.

  The paste of the composition of the present invention thus obtained has an excellent effect that the adhesiveness to the tooth surface is good, the dripping at the time of application is small, and the sampling property from the container is good. .

  The composition of the present invention can further enhance the adhesion to the tooth surface when used in combination with known tooth surface treating agents, bonding agents, metal primers, and the like.

[Ratio of volume median particle size and number of particles of inorganic filler]
The volume median particle size means a particle size at which the cumulative volume frequency calculated by the volume fraction is 50% calculated from the smaller particle size.
Measuring machine: Particle size distribution analyzer SALD-2100 (manufactured by Shimadzu Corporation)
Analysis software: WingSALD
Dispersion: 0.2% sodium hexametaphosphate Dispersion condition: 15 mg of a sample is added to 20 mL of the dispersion, and dispersed for 30 minutes with an ultrasonic disperser to prepare a sample dispersion.
Measurement conditions: The sample dispersion is measured, and the ratio of the number of particles having a volume-median particle size and a particle size of 0.5 to 30 μm is determined.

Production example 1 of inorganic filler
Barium glass ceramics “GM27884” (manufactured by Schott) was pulverized with a vibration ball mill to obtain fine inorganic particle powders having a volume median particle size of 3.5 μm and a ratio of the number of particles having a particle size of 0.5 to 30 μm of 99% by volume. . To 100 parts by weight of the obtained inorganic particle fine powder, 1 part by weight of γ-mercaptopropyltrimethoxysilane was added and mixed to obtain surface-treated inorganic particles.

  1 part by weight of AEROSIL 380 (primary average particle diameter: about 7 nm, manufactured by Nippon Aerosil Co., Ltd.) is added to and mixed with 69 parts by weight of the obtained surface-treated inorganic fine particle powder, and has a particle diameter of 0.5 to 30 μm. Inorganic fine particles B-1 having a particle ratio of 97 vol% and a volume median particle diameter of 2.1 μm were obtained.

Examples 1-6 and Comparative Examples 1-6
The raw material shown in Table 1 was mixed for every paste, and the 1st paste and the 2nd paste of Examples 1-6 and Comparative Examples 1-6 were prepared. The following Test Examples 1 and 2 were performed using the obtained pastes. The results are shown in Table 1.

The abbreviations shown in Table 1 mean the following.
U4TH: N, N ′-(2,2,4-trimethylhexamethylene) bis [2- (aminocarboxy) propane-1,3-diol] tetramethacrylate BPO: benzoyl peroxide DEPT: diethanol-p-toluidine

[Test Example 1] (Dripability during application)
The first paste and the second paste of Examples 1 to 6 and Comparative Examples 1 to 6 were mixed at a weight ratio of 1: 1 (first paste: second paste) by a static mixer, and then on a kneaded paper ( 200 mg of the obtained paste was placed on 11.5 cm × 8.5 cm), and the length of paste dripping after 1 minute was measured after standing the kneaded paper vertically. In addition, the actual use level is a length of 7 mm or less.

[Test Example 2] (collectability from container)
A MIXPAC double syringe (product number: ML2.5-08-S) filled with the first paste and the second paste of Examples 1 to 6 and Comparative Examples 1 to 6, and a static mixer attached to the tip Then, the stress applied at the time of discharging the paste was measured using an autograph (AG-100 kN (manufactured by Shimadzu Corporation)) under the condition of a crosshead speed of 14 mm / min. Note that the actual use level is that with a discharge stress of 40 N or less.

  From the above results, it can be seen that the dental compositions of the examples are less drooping at the time of application and have a lower discharge stress and better sampling properties from the container than the dental compositions of the comparative examples. On the other hand, Comparative Examples 1 to 4 which contain only one of the polymerizable monomers (a) and (b) are suitable viscosity even if the discharge stress is too high or the discharge stress is moderate. Viscosity was too low or poor. Even if the content of the polymerizable monomers (a), (b) and (c) is 20 parts by weight, 60 parts by weight, and 20 parts by weight, respectively, the content of the inorganic filler can be reduced. In Comparative Examples 5 and 6 in which excess or deficiency occurred, it was difficult to achieve both the viscosity and adhesiveness and the ability to collect from the container.

  The dental composition of the present invention is suitably used in the field of dentistry as a substitute for a part or the whole of a natural tooth.

Claims (4)

  A first paste (A) and a second paste (B), both of which have an aromatic ring, a polymerizable monomer (a) having a hydroxyl group, an aromatic ring, and a hydroxyl group A polymerizable monomer (b), a polymerizable monomer (c) other than (a) and (b), and a packaged dental composition comprising an inorganic filler (d) When the first paste (A) and the second paste (B) are mixed at a weight ratio of 1: 1, the polymerizable monomer (a), (b) And (c) the respective contents are 15 to 25% by weight, 55 to 65% by weight, and 15 to 25% by weight in the total polymerizable monomer, and the content of the inorganic filler (d) is all 150-300 parts by weight with respect to 100 parts by weight of the polymerizable monomer, and any one of the pastes further contains an oxidizing agent and the other contains a reducing agent. Dental composition.   In the first paste (A), the contents of the polymerizable monomer (a), the polymerizable monomer (b), and the polymerizable monomer (c) are included in the first paste (A). 15 to 25% by weight, 55 to 65% by weight, and 15 to 25% by weight in the total polymerizable monomer, and the content of the inorganic filler (d) is included in the first paste (A) 150 to 300 parts by weight based on 100 parts by weight of the total polymerizable monomer, and in the second paste (B), the polymerizable monomer (a), the polymerizable monomer (b) and The content of each polymerizable monomer (c) is 15 to 25% by weight, 55 to 65% by weight, and 15 to 25% by weight in the total polymerizable monomer contained in the second paste (B). The content of the inorganic filler (d) is 150 to 300 parts by weight with respect to 100 parts by weight of the total polymerizable monomer contained in the second paste (B). Envelope dental composition .   The packaging according to claim 1 or 2, wherein the inorganic filler (d) is inorganic particles having a ratio of particles having a particle diameter of 0.5 to 30 µm of 95% by volume or more and a volume-median particle size of 0.7 to 10 µm. Mold dental composition.   The package-type dental composition according to any one of claims 1 to 3, wherein the polymerizable monomers (a), (b) and (c) are di (meth) acrylate polymerizable monomers.