KR102643312B1 - Dental self-adhesive resin cement composition - Google Patents

Abstract

The present invention facilitates storage and improves color stability by including a hydroperoxide compound and a thiourea derivative as a self-polymerization initiator for dental resin, and is a two-component type divided into a first paste and a second paste depending on the composition. It relates to a dental self-adhesive resin cement composition capable of light curing and self-curing by mixing a paste and a second paste.

Description

Dental self-adhesive resin cement composition}

The present invention facilitates storage and improves color stability by including a hydroperoxide compound and a thiourea derivative as self-polymerization initiators for dental resin, and is a two-component type divided into a first paste and a second paste depending on the composition. It relates to a dental self-adhesive resin cement composition capable of light-curing and self-curing by mixing a paste and a second paste.

Dental composites are widely used as restorative materials (composite for filling) or cement (resin cement) in the dental prosthetics field. In general, composites are hydrophobic in nature and contain as major parts of the blend composition an inorganic filler, a (meth)acrylate-based resin matrix, and an initiator for radical polymerization.

Redox initiation systems are generally known in the field of dental composites and have been used in a variety of self-curing and dual-curing materials, such as crown and bridge materials, abutment materials, and resin cement. .

Recently, the category of materials for indirect restoration of lost tooth structure has been expanded to include ceramics that are not supported by metal, due to their excellent aesthetics. Accordingly, the need for resin cement that bonds to the tooth structure and achieves adhesion is increasing. Resin cement has been difficult to use because it is sensitive to pre-stage surface treatment and binder treatment in the adhesion process, but self-adhesive resin cement with fewer additional adhesion steps has recently been developed and applied.

Resin cement has excellent physical properties such as high compressive and tensile strength and low abrasion, and has a high water absorption, so it is used in aesthetic restorative materials, especially ceramic veneers, where water-soluble cement cannot be used because it absorbs water and expands after bonding, causing fracture. ) and ceramic crowns, etc., it is mainly used as an adhesive, and the use of aesthetic resin cement, which has various shades for aesthetics, is increasing.

In this regard, U.S. Patent No. 5,501,727 discloses a curable dental composition in which the incorporation of metal-complexed ascorbic acid exhibits improved color stability and includes an ethylenically unsaturated moiety, an oxidizing agent, and metal-complexed ascorbic acid. there is.

In addition, U.S. Patent No. 6,953,535 discloses a redox initiator system that hardens dental preparations in an acidic medium through free radical polymerization and ensures high adhesion of the polymerized composition to the hard materials of teeth, that is, enamel and especially dentin. It is disclosed about.

However, self-adhesive resin cement has a high initial acidity after hardening, so there is a risk of hydrolysis, which may delay the polymerization rate in the early stages of polymerization. Dental self-adhesive resin cement with improved physical and mechanical properties is It is being demanded.

US Patent No. 5,501,727 US Patent No. 6,953,535

The present invention facilitates storage and improves color stability by including a hydroperoxide compound and a thiourea derivative as a self-polymerization initiator for dental resin, and is a two-component type divided into a first paste and a second paste depending on the composition. The object is to provide a dental self-adhesive resin cement composition capable of light curing and self-curing by mixing a paste and a second paste.

In order to solve the above problems,

In one embodiment, the present invention includes: a first paste consisting of a first polymerizable monomer, a self-polymerization initiator for polymerizing the first polymerizable monomer, and a first inorganic filler; And a dental self-adhesive resin cement composition comprising a second paste consisting of a second polymerizable monomer, an adhesive monomer, a tertiary amine catalyst, a photopolymerization initiator, a reducing agent that reacts with the self-polymerization initiator, a second inorganic filler, and an inorganic pigment. provides.

The dental self-adhesive resin cement composition includes a first paste consisting of 45 to 60 wt% of a first polymerizable monomer, 0.1 to 0.5 wt% of a self-polymerization initiator, and 35 to 45 wt% of a first inorganic filler; and 45 to 60 wt% of a second polymerizable monomer, 5 to 10 wt% of an adhesive monomer, 0.1 to 0.5 wt% of a tertiary amine catalyst, 0.1 to 0.5 wt% of a photopolymerization initiator, 0.5 to 1.0 wt% of a reducing agent, and 35 to 35 wt% of a second inorganic filler. It may include a second paste consisting of 45 wt% and 0.005 to 0.01 wt% of inorganic pigment.

The self-polymerization initiator is t-butyl hydroperoxide, t-amyl hydroperoxide, p-diisopropylbenzene hydroperoxide, and cumene hydroperoxide. oxide (cumene hydroperoxide), pinane hydroperoxide, p-methane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide (1,1,3,3 -tetramethylbutyl hydroperoxide) and combinations thereof.

The second paste may contain a thiourea derivative capable of self-polymerization in combination with the self-polymerization initiator.

The first polymerizable monomer and the second polymerizable monomer are 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane (Bis-GMA), ethoxylate bisphenol A Dimethacrylate (Bis-EMA), methacrylate, diurethane dimethacrylate, 2-hydroxyethyl methacrylate, trifunctional methacrylate prepolymer ( It may include one or more selected from the group consisting of Tri-GMA) and combinations thereof. The first inorganic filler and the second inorganic filler are quartz, barium glass, quartz/barium mixture glass, silanized glass, silicon dioxide, silica, zirconia/silica mixture, barium glass/silica mixture, alumino silicate, barium alumino. It may include one or more selected from the group consisting of silicate, lithium alumino silicate, and combinations thereof.

The first paste and the second paste may contain a polymerization inhibitor and an antioxidant, respectively.

The dental self-adhesive resin cement composition includes 5 to 10 wt% of methacrylate, 35 to 40 wt% of diurethane dimethacrylate, and 2-hydroxyethyl methacrylate. 5 to 10 wt%, hydroperoxide compound 0.1 to 0.5 wt%, benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertbutyl)-4-methylphenol (2,6-di A first paste consisting of 0.01 to 0.05 wt% of (tertiary butyl)-4-methylphenol), 35 to 40 wt% of silanized glass, and 1 to 5 wt% of silicon dioxide; and 5 to 10 wt% of methacrylate, 35 to 40 wt% of diurethane dimethacrylate, and 5 to 10 wt% of 10-methacryloyloxydecyl dihydrogen phosphate. , benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertiary butyl)-4-methylphenol (2,6-Di(tertiary butyl)-4-methylphenol) 0.01 to 0.05 wt%, ethyl 4 -Dimethylaminobenzoate (ethyl 4-dimethylaminobenzoate) 0.1 to 0.5 wt%, camphorquinone (camphorquinone) 0.1 to 0.5 wt%, thiourea derivative 0.5 to 1.0 wt%, N,N-dimethyl-para-toluidine ( A second paste consisting of 0.5 to 1.0 wt% of N,N-dimethyl-para-toluidine), 35 to 40 wt% of silanized glass, 1 to 5 wt% of silicon dioxide, and 0.005 to 0.01 wt% of iron oxide. It may include.

The thiourea derivatives include 1-(2-pyridyl)-2-thiourea [1-(2-pyridyl)-2-thiourea], 1-acetyl-2-thiourea, 1-(2-tetrahydrofurfuryl)-2-thiourea [1-(2-tetrahydrofurfuryl)-2-thiourea], 1-benzoylthiourea (1-benzoylthiourea), 1-benzoyl-3-phenylthiourea ( It may include one or more selected from the group consisting of 1-benzoyl-3-phenylthiourea), 1,1,3,3-tetramethylthiourea (1,1,3,3-tetramethylthiourea), and combinations thereof. .

The dental self-adhesive resin cement composition may be photopolymerized and self-polymerized by mixing the first paste and the second paste.

The first paste and the second paste may be mixed in a 1:1 ratio.

The dental self-adhesive resin cement composition may maintain a curing time of 2 to 5 minutes for more than 2 years.

Benzoyl peroxide/tertiary aromatic amine, which is used as a self-polymerization initiator for conventional dental resins, is deactivated due to the low thermal stability of benzoyl peroxide, discoloration of the amine, and acid/base reaction in an acidic environment. However, the dental self-adhesive resin cement composition according to the present invention can improve the stability problems of existing initiators by applying a hydroperoxide compound and a thiourea derivative, and is easy to store, even in an acidic environment. It has stable characteristics.

In addition, the dental self-adhesive resin cement composition according to the present invention not only allows long-term storage, but also has excellent physical strengths such as compressive strength and flexural strength.

Figure 1 shows the results of measuring the curing time every 3 months based on the accelerated aging time (365 days) according to the accelerated aging calculation formula in one embodiment of the present invention.

Since the present invention can make various changes and have various embodiments, specific embodiments will be illustrated in the drawings and described in detail in the detailed description.

However, this is not intended to limit the present invention to specific embodiments, and should be understood to include all changes, equivalents, and substitutes included in the spirit and technical scope of the present invention.

In the present invention, terms such as "comprise" or "have" are intended to designate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, but are not intended to indicate the presence of one or more other features. It should be understood that this does not exclude in advance the possibility of the existence or addition of elements, numbers, steps, operations, components, parts, or combinations thereof.

Hereinafter, the present invention will be described in detail.

Benzoyl peroxide/tertiary aromatic amine, which is used as a self-polymerization initiator for conventional dental resins, is deactivated due to the low thermal stability of benzoyl peroxide, discoloration of the amine, and acid/base reaction in an acidic environment. However, the dental self-adhesive resin cement composition according to the present invention contains a hydroperoxide compound as a self-polymerization initiator, and by applying a thiourea derivative, the stability problem of the existing initiator can be improved and storage. It is easy to use and has stable properties even in acidic environments.

The dental self-adhesive resin cement composition of the present invention includes a first paste consisting of a first polymerizable monomer, a self-polymerization initiator for polymerizing the first polymerizable monomer, and a first inorganic filler; And a dental self-adhesive resin cement composition comprising a second paste consisting of a second polymerizable monomer, an adhesive monomer, a tertiary amine catalyst, a photopolymerization initiator, a reducing agent that reacts with the self-polymerization initiator, a second inorganic filler, and an inorganic pigment. Includes.

Specifically, the dental self-adhesive resin cement composition includes a first paste consisting of 45 to 60 wt% of a first polymerizable monomer, 0.1 to 0.5 wt% of a self-polymerization initiator, and 35 to 45 wt% of a first inorganic filler; and 45 to 60 wt% of a second polymerizable monomer, 5 to 10 wt% of an adhesive monomer, 0.1 to 0.5 wt% of a tertiary amine catalyst, 0.1 to 0.5 wt% of a photopolymerization initiator, 0.5 to 1.0 wt% of a reducing agent, and 35 to 35 wt% of a second inorganic filler. It may include a second paste consisting of 45 wt% and 0.005 to 0.01 wt% of inorganic pigment.

The first polymerizable monomer and the second polymerizable monomer are 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane (Bis-GMA), ethoxylate bisphenol A Dimethacrylate (Bis-EMA), methacrylate, diurethane dimethacrylate, 2-hydroxyethyl methacrylate, trifunctional methacrylate prepolymer ( It may include one or more selected from the group consisting of Tri-GMA) and combinations thereof.

A self-polymerization initiator is used to polymerize the polymerizable monomer that is the resin cement matrix, and the self-polymerization initiator is t-butyl hydroperoxide or t-amyl hydroperoxide. , p-diisopropylbenzene hydroperoxide, cumene hydroperoxide, pinane hydroperoxide, p-methane hydroperoxide, 1, It may include one or more selected from the group consisting of 1,1,3,3-tetramethylbutyl hydroperoxide and combinations thereof. For example, the hydroperoxide compound may be cumene hydroperoxide.

When the self-polymerization initiator and the reducing agent of the second paste below are mixed, radicals may be formed.

The first inorganic filler and the second inorganic filler may improve the physical properties of the resin cement composition and may be included to provide opacity to X-rays. For example, the first inorganic filler and the second inorganic filler may be quartz, barium glass, quartz/barium mixture glass, silanized glass, silicon dioxide, silica, zirconia/silica mixture, barium glass/silica mixture, alumino silicate. , barium alumino silicate, lithium alumino silicate, and combinations thereof.

The first paste and the second paste may contain a polymerization inhibitor and an antioxidant, respectively.

The polymerization inhibitor serves to slow down the initiation rate by absorbing ultraviolet rays and converting them into heat energy or by decomposing from ultraviolet rays and annihilating free radicals generated. For example, the polymerization inhibitor is benzotriazole, hydro It may include one or more selected from the group consisting of hydroquinone, hydroquinone monomethyl ether, hydroquinone monoethyl ether, and combinations thereof.

The antioxidant is to prevent the polymer, which is the first polymerizable monomer and the second polymerizable monomer, from being oxidized, and the antioxidant is 2,6-ditertbutyl-4-methylphenol (2,6-di -tert-butyl-4-methylphenol), butylated hydroxytoluene, N-octadecyl-3 (3,5-ditetrabutyl-4-hydroxyphenyl) propionate (octadecyl-3- (3,5-di-tetra-butyl-4-hydroxyphenyl) propionate), tri(2,4-di-tetra-buthlyphenyl)phosphite), cyclic neo Cyclic neopentanetetraylbis(octadecyl phosphite), 4,4-butylaidinebis(3-methyl-6-tetra-butylphenyl-ditridecyl)phosphite (4,4'- It may include one or more selected from the group consisting of butylidene-bis (6-tert-butyl-3-methylphenylphenyl-ditridecyl phosphite)) and combinations thereof.

The adhesive monomer may be used to improve the bonding strength between teeth, metal, and resin cement when using the dental self-adhesive resin cement composition of the present invention, and the polymerization conversion rate may vary depending on the content of the adhesive monomer, It may also affect shear bond strength. For example, the adhesive monomers include 11-methacryloxy-1,1-undecane dicarboxylic acid (MAC-10), p-vinylbenzoic acid, 1,4-dimethacryloxyethylpyromellitic acid, 10- 10-methacryloyloxydecyl dihydrogen phosphate, methacrylic acid, maleic acid, 6-methacryloxyethylnaphthalene-1,2,6-tricarboxylic acid, 4-methacryloxymethyltri It may include one or more selected from the group consisting of mellitic acid and its anhydride, 4-methacryloxyethyltrimellitic acid (4-MET), and combinations thereof.

The photopolymerization initiator reacts with light to obtain a hydrogen atom from a tertiary amine compound to generate a radical, for example, acylphosphine oxide derivatives, acetophenone derivatives, triazine derivatives, biimidazole derivatives, and camphorquinone. It may include one or more selected from the group consisting of α-diketone-based carbonyl compounds such as (camphorquinone) and combinations thereof.

The radicals generated from the photopolymerization initiator may react with the tertiary amine-based catalyst containing tertiary amine to cause polymerization.

The tertiary amine-based catalyst is a tertiary amine-based catalyst and may include one or more selected from the group consisting of tributylamine, amino alkyl methacrylate, alkyl amino benzoate, tripropyl amine, and combinations thereof.

The reducing agent that reacts with the self-polymerization initiator of the first paste is N,N-dimethylaniline, N,N-dimethyl-para-toluidine, N, N-dihydroxyethly-p-toluidine (N,N-dihydroxyethly-para-toluidine), N,N-dimethyl-3,4-dimethylaniline (N,N-dimethyl-3,4-dimethylaniline), N, N-bis(2-hydroxyethly)-3(N,N-bis(2-hydroxyethly)-3), N,N-dihydroxymethyl-p-toluidine (N,N-dihydroxymethly-para-toluidine) and it may include one or more selected from the group consisting of combinations thereof.

The reducing agent may affect work/curing time depending on its content, and may affect discoloration because it contains tertiary amine. A thiourea derivative may be additionally included to reduce the effect of discoloration caused by the reducing agent.

The thiourea derivatives include 1-(2-pyridyl)-2-thiourea [1-(2-pyridyl)-2-thiourea], 1-acetyl-2-thiourea, 1-(2-tetrahydrofurfuryl)-2-thiourea [1-(2-tetrahydrofurfuryl)-2-thiourea], 1-benzoylthiourea (1-benzoylthiourea), 1-benzoyl-3-phenylthiourea ( It may include one or more selected from the group consisting of 1-benzoyl-3-phenylthiourea), 1,1,3,3-tetramethylthiourea (1,1,3,3-tetramethylthiourea), and combinations thereof. . For example, the thiourea derivative may be benzoyl thiourea.

The second paste may contain red and yellow iron oxide, titanium dioxide, or a mixture thereof as an inorganic pigment for color development.

The dental self-adhesive resin cement composition includes 5 to 10 wt% of methacrylate, 35 to 40 wt% of diurethane dimethacrylate, and 2-hydroxyethyl methacrylate. 5 to 10 wt%, hydroperoxide compound 0.1 to 0.5 wt%, benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertbutyl)-4-methylphenol (2,6-di A first paste consisting of 0.01 to 0.05 wt% of (tertiary butyl)-4-methylphenol), 35 to 40 wt% of silanized glass, and 1 to 5 wt% of silicon dioxide; and 5 to 10 wt% of methacrylate, 35 to 40 wt% of diurethane dimethacrylate, and 5 to 10 wt% of 10-methacryloyloxydecyl dihydrogen phosphate. , benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertiary butyl)-4-methylphenol (2,6-Di(tertiary butyl)-4-methylphenol) 0.01 to 0.05 wt%, ethyl 4 -Dimethylaminobenzoate (ethyl 4-dimethylaminobenzoate) 0.1 to 0.5 wt%, camphorquinone (camphorquinone) 0.1 to 0.5 wt%, thiourea derivative 0.5 to 1.0 wt%, N,N-dimethyl-para-toluidine ( A second paste consisting of 0.5 to 1.0 wt% of N,N-dimethyl-para-toluidine), 35 to 40 wt% of silanized glass, 1 to 5 wt% of silicon dioxide, and 0.005 to 0.01 wt% of iron oxide. It may include.

The second paste may contain a thiourea derivative capable of self-polymerization in combination with the self-polymerization initiator.

By including a hydroperoxide compound in the first paste and a thiourea derivative in the second paste as the self-polymerization initiator, the redox reaction can be accelerated at room temperature and self-polymerization is possible, so the existing initiator operates in an acidic environment. By improving the stability problem of self-polymerization, it can be stable even in an acidic environment and is easy to store.

The dental self-adhesive resin cement composition may be photopolymerized and self-polymerized by mixing the first paste and the second paste. Each of the first paste and the second paste is not cured, but curing can be performed when mixed.

The first paste and the second paste may be mixed in a 1:1 ratio.

The dental self-adhesive resin cement composition may maintain a curing time of 2 to 5 minutes for more than 2 years. The dental self-adhesive resin cement composition has the property of curing within a curing time of 2 to 5 minutes at 35°C, and the properties of the composition according to the present invention can be maintained even after 2 years, enabling long-term storage. .

Hereinafter, the present invention will be described in more detail through examples according to the present invention, but the scope of the present invention is not limited to the examples presented below.

[Example]

Example: Preparation of self-adhesive resin cement composition

To prepare a self-adhesive resin cement composition, the first paste and the second paste were prepared separately and then mixed.

First, the first paste contains 5 to 10 wt% of methacrylate, 35 to 40 wt% of diurethane dimethacrylate, 5 to 10 wt% of 2-hydroxyethyl methacrylate, 0.1 to 0.5 wt% of hydroperoxide compound, and benzotriazole. It was prepared by mixing 0.01 to 0.05 wt% of 2,6-di(tertbutyl)-4-methylphenol, 35 to 40 wt% of silanized glass, and 1 to 5 wt% of silicon dioxide, and the second paste was Methacrylate 5 to 10 wt%, diurethane dimethacrylate 35 to 40 wt%, 10-methacryloyloxydecyl dihydrogen phosphate 5 to 10 wt%, benzotriazole 0.01 to 0.05 wt%, 2,6-dimethacrylate (tertbutyl)-4-methylphenol 0.01 to 0.05 wt%, ethyl 4-dimethylaminobenzoate 0.1 to 0.5 wt%, camphorquinone 0.1 to 0.5 wt%, thiourea derivative 0.5 to 1.0 wt%, N,N-dimethyl -It was prepared by mixing 0.5 to 1.0 wt% of para-toluidine, 35 to 40 wt% of silanized glass, 1 to 5 wt% of silicon dioxide, and 0.005 to 0.01 wt% of iron oxide.

A composition was prepared by mixing the first paste and the second paste prepared above in a ratio of 1:1.

Experimental Example 1: Accelerated aging test

In order to test whether the composition of the prepared example maintains the curing time even after a certain period of time has elapsed at a curing temperature of 35°C, an accelerated aging test was performed.

The accelerated aging factor (AAF) was determined according to the following calculation formula, and the accelerated aging time (AAT) was set.

In the above equation, Q10 refers to the aging coefficient value when the temperature increases or decreases by 10°C. When calculating the aging coefficient using a general and traditional method, the Q10 value is set to 2, and the range of the Q10 value is usually 2.2 to 2.5. use.

In addition, the accelerated aging temperature (TAA) was set at 35°C, and the room temperature environment temperature (TRT), which refers to the actual storage and use temperature of the product at the storage location or ambient temperature, was set at 25°C.

In the above equation, the required shelf life (RT) was set to 2 years (730 days), which is the shelf life of the example composition (product), and the accelerated aging factor (AAF) was set to 2 according to the AAF equation.

The results of measuring the curing time in 3-month increments based on the accelerated aging time (365 days) according to the accelerated aging calculation formula are shown in Figure 1.

As shown in Figure 1, as a result of checking the curing time of the example composition stored at room temperature and in an oven (35 ° C.), the curing time of the example composition stored at room temperature was maintained at 3 minutes, and the curing time of the example composition stored at room temperature (35 ° C.) was maintained at 3 minutes. In the example, the curing time was maintained at 3 minutes and 30 seconds, which was 30 seconds longer than room temperature.

Through the accelerated aging test, it was confirmed that the curing time of 2 to 5 minutes was maintained for more than 2 years.

Experimental Example 2: Compressive strength

A compressive strength test (ISO 9917-1:2007) of the prepared example composition was performed.

Specifically, a specimen was manufactured by irradiating light on both sides of a mold with a thickness of 6 mm and a diameter of 4 mm under standard conditions, and the maximum load until destruction was applied at a speed of 0.75 ± 0.30 mm/min (Cross-Head Speed) using an analysis device. Compressive strength (C) was calculated using the following formula.

In the above equation, ρ is the maximum load (N), and d is the diameter of the specimen (mm).

The compressive strength calculated according to the above formula is shown in Table 1 below in comparison with the compositions of 3M, GC, and Kerr. The results of measuring examples 1 to 5 times are shown in Table 2 below.

Referring to Table 1, it was confirmed that the compressive strength was 1 to 3% higher than that of other companies' products.

Experimental Example 3: Flexural strength

A flexural strength test (ISO 4049:2009) of the prepared example composition was performed.

Specifically, a specimen was manufactured by irradiating light under standard conditions on both sides of a mold with a thickness of 2 mm, a width of 25 mm, and a height of 2 mm, and the maximum load until failure was measured at a speed of 0.75 mm/min (Cross-Head Speed) on an analysis device. Then, the bending strength (σ, MPa) was calculated using the formula below.

In the above equation, F is the maximum load (N), l is the distance between supports (mm), b is the area of the specimen (mm), and h is the height of the specimen (mm).

The flexural strength measured 1 to 5 times in the above examples was calculated according to the above formula and is shown in Table 2 below.

Referring to Table 2 below, the flexural strength was measured to be 108.36 to 117.55 MPa, and was found to be more than 120% higher than the ISO 4049:2009 standard (50 MPa).

Experimental Example 4: Film degree

A film coating test (ISO 4049:2009) was performed on the prepared example composition.

Specifically, after placing two molds of glass plates (contact area 200 ± 5 mm2 or more, thickness 5 mm) on the film measuring device, the total thickness was measured and the thickness was designated as A. The glass plates were removed and 0.1 ± 0.05 ml of mixture was mixed. The cement was placed in the center of the lower glass plate, and the glass plate was returned to its original position. After applying a force of 150N using a film measuring device, the overall thickness was measured, the thickness was designated as B, and the difference between A and B was calculated.

The coating degree measured 1 to 5 times for the above examples is shown in Table 2 below.

Referring to Table 2 below, the film thickness was measured to be 14㎛, and it was found that the film thickness was 70% lower than the ISO 4049:2009 standard (50㎛). This means that the lower the coating value, the easier it is for excess cement to come out and be removed, and the fewer internal defects affect the maintenance of the prosthesis, which means that the effect of the composition of this example is further improved.

Claims (12)

Methacrylate 5 to 10 wt%, diurethane dimethacrylate 35 to 40 wt%, 2-hydroxyethyl methacrylate 5 to 10 wt%, hydroperoxide ) Compound 0.1 to 0.5 wt%, benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertiary butyl)-4-methylphenol (2,6-di(tertiary butyl)-4-methylphenol) 0.01 to 0.05 wt%, a first paste consisting of 35 to 40 wt% silanized glass and 1 to 5 wt% silicon dioxide; and
Methacrylate 5 to 10 wt%, diurethane dimethacrylate 35 to 40 wt%, 10-methacryloyloxydecyl dihydrogen phosphate 5 to 10 wt%, Benzotriazole 0.01 to 0.05 wt%, 2,6-di(tertiary butyl)-4-methylphenol (2,6-Di(tertiary butyl)-4-methylphenol) 0.01 to 0.05 wt%, ethyl 4- Dimethylaminobenzoate (ethyl 4-dimethylaminobenzoate) 0.1 to 0.5 wt%, camphorquinone 0.1 to 0.5 wt%, thiourea derivative 0.5 to 1.0 wt%, N,N-dimethyl-para-toluidine (N , N-dimethyl-para-toluidine) 0.5 to 1.0 wt%, silanized glass (silanized glass) 35 to 40 wt%, silicon dioxide (silicon dioxide) 1 to 5 wt%, and iron oxide 0.005 to 0.01 wt%. A dental self-adhesive resin cement composition comprising:
delete According to paragraph 1,
The hydroperoxide compound includes t-butyl hydroperoxide, t-amyl hydroperoxide, p-diisopropylbenzene hydroperoxide, and cumene hydroperoxide. cumene hydroperoxide, pinane hydroperoxide, p-methane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide (1,1,3, A dental self-adhesive resin cement composition comprising at least one selected from the group consisting of 3-tetramethylbutyl hydroperoxide) and combinations thereof.
In paragraph 1.
The second paste is a dental self-adhesive resin cement composition, characterized in that it contains a thiourea derivative capable of self-polymerization in combination with the hydroperoxide compound.
delete delete According to paragraph 1,
A dental self-adhesive resin cement composition, characterized in that the first paste and the second paste contain a polymerization inhibitor and an antioxidant, respectively.
delete According to clause 4,
The thiourea derivatives include 1-(2-pyridyl)-2-thiourea [1-(2-pyridyl)-2-thiourea], 1-acetyl-2-thiourea, 1-(2-tetrahydrofurfuryl)-2-thiourea [1-(2-tetrahydrofurfuryl)-2-thiourea], 1-benzoylthiourea (1-benzoylthiourea), 1-benzoyl-3-phenylthiourea ( A dental product containing one or more selected from the group consisting of 1-benzoyl-3-phenylthiourea), 1,1,3,3-tetramethylthiourea (1,1,3,3-tetramethylthiourea), and combinations thereof. For self-adhesive resin cement compositions.
According to paragraph 1,
The dental self-adhesive resin cement composition,
A dental self-adhesive resin cement composition, characterized in that light-curing and self-curing by mixing the first paste and the second paste.
According to paragraph 1,
A dental self-adhesive resin cement composition, characterized in that the first paste and the second paste are mixed in a 1:1 ratio.
According to paragraph 1,
The dental self-adhesive resin cement composition is characterized in that the dental self-adhesive resin cement composition maintains a curing time of 2 to 5 minutes for more than 2 years.