Dental composite resin composition with low stickiness

Abstract

Provided is a dental composite resin composition according to one embodiment of the present specification comprising 0.1-3 wt% polyalkylene glycol-based di(meth)acrylate, 0.1-3 wt% alkanediol di(meth)acrylate, 0.1-1 wt% glycerol di(meth)acrylate, and 60-90 wt% filler.

Description

Dental composite resin composition with low stickiness

[0001] This specification relates to a dental composite resin composition with low stickiness.

[0002] Dental photocurable composite resin, also known as Light-Curing Composite Resin or Universal Composite Resin, is used to fill cavities formed in teeth after removing carious parts of the tooth. These dental photocurable composite resins are mainly composed of dimethacrylate-based monomers, photoinitiators, photosensitizers, pigments, other additives, and inorganic fillers, and are cured by a blue light source (blue LED).

[0003] Dental photocurable composite resins are divided into two types: flowable composite resins, which are of a flowing type, and packable composite resins, which are in paste form. The biggest difference between flowable composite resins and packable composite resins lies in their form, and the form of the composite resin is determined by the ratio of polymers and inorganic fillers in the composition. Low-viscosity flowable composite resins have an inorganic filler content of 70 weight% or less and are in a flowing form, whereas packable composite resins have an inorganic filler content of 80 weight% or more and the proportion of polymers and other additives is 20 weight% or less.

[0004] Composite resins with a very high content of inorganic fillers, such as condensed composite resins, have high viscosity and appear in a solid form. Since instruments are used to manipulate these solid, high-viscosity composite resins within a cavity, the stickiness of the composite resin is a factor that determines the ease of tooth restoration. If the composite resin is too sticky, the operator cannot form the desired shape, and the resin may be pulled out in unintended directions, leading to restoration failure.

[0005] Therefore, there is a need to develop a high-viscosity dental composite resin composition that has a high filler content and takes on a high-viscosity solid form, while minimizing stickiness so that it does not stick to dental instruments.

[0006] The details described in this specification are intended to solve the problems of the aforementioned prior art, and one objective of this specification is to provide a high-viscosity dental composite resin composition that has low stickiness and does not adhere to dental instruments.

[0007] According to one aspect, a dental composite resin composition is provided comprising 0.1 to 3 weight% of a polyalkylene glycol-based di(meth)acrylate, 0.1 to 3 weight% of an alkanediol di(meth)acrylate, 0.1 to 1 weight% of a glycerol di(meth)acrylate, and 60 to 90 weight% of a filler.

[0008] In one embodiment, the polyalkylene glycol-based di(meth)acrylate may be one selected from the group consisting of polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol dimethacrylate, polypropylene glycol diacrylate, and combinations of two or more of these.

[0009] In one embodiment, the alkanediol di(meth)acrylate may be one selected from the group consisting of 1,12-dodecanediol dimethacrylate, 1,12-dodecanediol diacrylate, 1,10-decanediol dimethacrylate, 1,10-decanediol diacrylate, 1,9-nonanediol dimethacrylate, 1,9-nonanediol diacrylate, 1,8-octanediol dimethacrylate, 1,8-octanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, and combinations of two or more of these.

[0010] In one embodiment, the glycerol di(meth)acrylate may be one selected from the group consisting of glycerol 1,3-dimethacrylate, glycerol 1,3-diacrylate, glycerol 1,2-dimethacrylate, and combinations of two or more of these.

[0011] In one embodiment, the dental composite resin composition may further comprise 6 to 15 weight% of bisphenol-A-based di(meth)acrylate and 0.1 to 5 weight% of alkylene glycol-based di(meth)acrylate.

[0012] In one embodiment, the bisphenol-A di(meth)acrylate may be one selected from the group consisting of bisphenol-A glycidyl dimethacrylate, bisphenol-A ethoxylate dimethacrylate, bisphenol-A dimethacrylate, bisphenol-A diacrylate, bisphenol-A ethoxylate diacrylate, bisphenol-A diglycidyl ether diacrylate, bisphenol-A epoxy diacrylate, and combinations of two or more of these.

[0013] In one embodiment, the alkylene glycol-based di(meth)acrylate may be one selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, and combinations of two or more of these.

[0014] In one embodiment, the bisphenol-A-based di(meth)acrylate may comprise 1 to 5 weight% of bisphenol-A glycidyl dimethacrylate and 5 to 10 weight% of bisphenol-A ethoxylate dimethacrylate.

[0015] In one embodiment, the filler may be one selected from the group consisting of fumed silica, barium silicate, barium aluminum silicate, aluminum silicate, lithium aluminum silicate, strontium aluminum silicate, zirconium silicate, glass, barium silicate glass, strontium silicate glass, and combinations of two or more of these.

[0016] In one embodiment, the filler may comprise 50 to 80 weight percent of microfillers having an average particle size greater than 0.1 μm and less than or equal to 100 μm, and 1 to 10 weight percent of nanofillers having an average particle size greater than 1 nm and less than or equal to 100 nm.

[0017] In one embodiment, the dental composite resin composition may further include one or more selected from the group consisting of a photosensitizer, a photoinitiator, a curing inhibitor, a UV absorber, and a pigment.

[0018] A dental composite resin composition according to one aspect of the present specification has a high viscosity due to a high filler content, and at the same time has low stickiness when manipulated with a dental instrument so that it does not stick to the instrument, thereby making tooth restoration easier.

[0019] The effects of one aspect of this specification are not limited to the effects described above, and should be understood to include all effects that can be inferred from the configurations described in the detailed description or claims of this specification.

[0020] Hereinafter, one aspect of this specification will be described based on specific examples. However, the details described in this specification may be implemented in various different forms and are therefore not limited to the embodiments described herein.

[0021] Throughout the specification, when a part is described as "including" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but rather allows for the inclusion of additional components.

[0022] When a range of numerical values ​​is described in this specification, unless a specific range is otherwise described, the value has the precision of significant figures provided according to the standard rules in chemistry for significant figures. For example, 10 includes a range of 5.0 to 14.9, and the number 10.0 includes a range of 9.50 to 10.49.

[0023] Dental composite resin composition

[0024] A dental composite resin composition according to one aspect of the present specification comprises 0.1 to 3 weight% of polyalkylene glycol-based di(meth)acrylate, 0.1 to 3 weight% of alkanediol di(meth)acrylate, 0.1 to 1 weight% of glycerol di(meth)acrylate, and 60 to 90 weight% of filler.

[0025] The above dental composite resin composition has a high viscosity due to the high filler content, and at the same time, by controlling the type and content of di(meth)acrylate-based monomers, it has low stickiness when manipulated with dental instruments so that it does not stick to the instruments, thereby facilitating tooth restoration.

[0026] The content of the above polyalkylene glycol-based di(meth)acrylate may be 0.1 to 3 weight percent based on the total weight of the dental composite resin composition. For example, it may be 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.1 wt%, 1.2 wt%, 1.3 wt%, 1.4 wt%, 1.5 wt%, 1.6 wt%, 1.7 wt%, 1.8 wt%, 1.9 wt%, 2 wt%, 2.1 wt%, 2.2 wt%, 2.3 wt%, 2.4 wt%, 2.5 wt%, 2.6 wt%, 2.7 wt%, 2.8 wt%, 2.9 wt%, 3 wt%, or a range between two of these values. If the content of polyalkylene glycol-based di(meth)acrylate is below the above range, the flexibility of the polymer matrix is ​​reduced, which may result in reduced softness when handling the resin composition, and if it exceeds the above range, the stickiness of the resin composition increases, which may cause it to stick to dental instruments.

[0027] The above polyalkylene glycol-based di(meth)acrylate may be one selected from the group consisting of polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol dimethacrylate, polypropylene glycol diacrylate, and combinations of two or more of these, but is not limited thereto.

[0028] In one embodiment, the polyalkylene glycol-based di(meth)acrylate may be polyethylene glycol dimethacrylate (PEGDMA). Polyethylene glycol dimethacrylate contains a bulky methyl group within the molecule and has a relatively long ethylene oxide chain compared to triethylene glycol dimethacrylate, resulting in excellent chain flexibility. Accordingly, the polymer matrix has excellent flexibility, allowing for soft characteristics when manipulating the resin composition.

[0029] The content of the above alkanediol di(meth)acrylate may be 0.1 to 3 weight percent based on the total weight of the dental composite resin composition. For example, it may be 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, 1.1 wt%, 1.2 wt%, 1.3 wt%, 1.4 wt%, 1.5 wt%, 1.6 wt%, 1.7 wt%, 1.8 wt%, 1.9 wt%, 2 wt%, 2.1 wt%, 2.2 wt%, 2.3 wt%, 2.4 wt%, 2.5 wt%, 2.6 wt%, 2.7 wt%, 2.8 wt%, 2.9 wt%, 3 wt%, or a range between two of these values. If the content of alkanediol di(meth)acrylate is below the above range, the flexibility of the polymer matrix is ​​reduced, which may decrease the softness during manipulation of the resin composition and reduce the curing speed of the resin composition. If the content of alkanediol di(meth)acrylate exceeds the above range, the stickiness of the resin composition increases rapidly, causing it to adhere to dental instruments; consequently, the operator cannot form the desired shape with the composite resin, and the composite resin may be pulled out in unintended directions, potentially leading to restoration failure.

[0030] The above alkanediol di(meth)acrylate may be one selected from the group consisting of 1,12-dodecanediol dimethacrylate, 1,12-dodecanediol diacrylate, 1,10-decanediol dimethacrylate, 1,10-decanediol diacrylate, 1,9-nonanediol dimethacrylate, 1,9-nonanediol diacrylate, 1,8-octanediol dimethacrylate, 1,8-octanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, and combinations of two or more of these, but is not limited thereto.

[0031] In one embodiment, the alkanediol di(meth)acrylate may be 1,12-dodecanediol dimethacrylate (1,12-DDDMA). 1,12-dodecanediol dimethacrylate has a hydrophobic backbone structure, which can increase the fluidity of the molecular structure and, accordingly, impart rapid curing characteristics and flexibility to the polymer matrix.

[0032] The content of the glycerol di(meth)acrylate may be 0.1 to 1 wt% based on the total weight of the dental composite resin composition. For example, it may be 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, 0.5 wt%, 0.6 wt%, 0.7 wt%, 0.8 wt%, 0.9 wt%, 1 wt%, or a range between two of these values. If the content of the glycerol di(meth)acrylate is below the above range, the bonding strength between the polymer matrix and the filler is reduced, which may cause the resin to crack or tear. If the content of the glycerol di(meth)acrylate exceeds the above range, the stickiness of the resin composition increases rapidly and may adhere to dental instruments; consequently, the operator may not be able to form the desired shape with the composite resin, and the composite resin may be pulled out in an unintended direction, which may lead to restoration failure.

[0033] The above glycerol di(meth)acrylate may be one selected from the group consisting of glycerol 1,3-dimethacrylate, glycerol 1,3-diacrylate, glycerol 1,2-dimethacrylate, and combinations of two or more of these, but is not limited thereto.

[0034] In one embodiment, the glycerol di(meth)acrylate may be glycerol 1,3-dimethacrylate (GDMA). Glycerol 1,3-dimethacrylate contains a hydrophilic hydroxyl group (-OH) and can bond well with a hydrophilic filler, thereby imparting properties to the composite resin that prevent it from cracking or tearing. In addition, it may have excellent stability due to lower water absorption compared to 2-hydroxyethyl methacrylate (HEMA) of a similar class.

[0035] The above dental composite resin composition may further include additional di(meth)acrylate-based monomers in addition to the polyalkylene glycol-based di(meth)acrylate, the alkanediol di(meth)acrylate, and the glycerol di(meth)acrylate.

[0036] In one embodiment, the dental composite resin composition may further include a bisphenol-A-based di(meth)acrylate, an alkylene glycol-based di(meth)acrylate, or a combination thereof.

[0037] The content of the bisphenol-A-based di(meth)acrylate may be 6 to 15 wt% based on the total weight of the dental composite resin composition. For example, it may be 6 wt%, 6.5 wt%, 7 wt%, 7.5 wt%, 8 wt%, 8.5 wt%, 9 wt%, 9.5 wt%, 10 wt%, 10.5 wt%, 11 wt%, 11.5 wt%, 12 wt%, 12.5 wt%, 13 wt%, 13.5 wt%, 14 wt%, 14.5 wt%, 15 wt%, or a range between two of these values.

[0038] The content of the above alkylene glycol-based di(meth)acrylate may be 0.1 to 5 wt% based on the total weight of the dental composite resin composition. For example, it may be 0.1 wt%, 0.5 wt%, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, 5 wt%, or a range between two of these values.

[0039] The above dental composite resin composition may further include 6 to 15 weight% of bisphenol-A-based di(meth)acrylate and 0.1 to 5 weight% of alkylene glycol-based di(meth)acrylate.

[0040] The above bisphenol-A di(meth)acrylate may be one selected from the group consisting of bisphenol-A glycidyl dimethacrylate, bisphenol-A ethoxylate dimethacrylate, bisphenol-A dimethacrylate, bisphenol-A diacrylate, bisphenol-A ethoxylate diacrylate, bisphenol-A diglycidyl ether diacrylate, bisphenol-A epoxy diacrylate, and combinations of two or more of these, but is not limited thereto.

[0041] The above alkylene glycol-based di(meth)acrylate may be one selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, and combinations of two or more of these, but is not limited thereto. However, the above alkylene glycol-based di(meth)acrylate does not include polyalkylene glycol-based di(meth)acrylate.

[0042] The above bisphenol-A-based di(meth)acrylate may comprise 1 to 5 weight% of bisphenol-A glycidyl dimethacrylate and 5 to 10 weight% of bisphenol-A ethoxylate dimethacrylate.

[0043] The content of the bisphenol-A glycidyl dimethacrylate may be 1 to 5 weight% based on the total weight of the dental composite resin composition. For example, it may be 1 weight%, 1.5 weight%, 2 weight%, 2.5 weight%, 3 weight%, 3.5 weight%, 4 weight%, 4.5 weight%, 5 weight%, or a range between two of these values.

[0044] The content of the bisphenol-A ethoxylate dimethacrylate may be 5 to 10 weight% based on the total weight of the dental composite resin composition. For example, it may be 5 weight%, 5.5 weight%, 6 weight%, 6.5 weight%, 7 weight%, 7.5 weight%, 8 weight%, 8.5 weight%, 9 weight%, 9.5 weight%, 10 weight%, or a range between two of these values.

[0045] The content of the filler may be 60 to 90 weight% based on the total weight of the dental composite resin composition. For example, it may be 60 weight%, 61 weight%, 62 weight%, 63 weight%, 64 weight%, 65 weight%, 66 weight%, 67 weight%, 68 weight%, 69 weight%, 70 weight%, 71 weight%, 72 weight%, 73 weight%, 74 weight%, 75 weight%, 76 weight%, 77 weight%, 78 weight%, 79 weight%, 80 weight%, 81 weight%, 82 weight%, 83 weight%, 84 weight%, 85 weight%, 86 weight%, 87 weight%, 88 weight%, 89 weight%, 90 weight%, or a range between two of these values. If the filler content is below the above range, the viscosity of the resin composition may decrease and take on a liquid form, and the flowability may increase, making it difficult to restore the cavity. If the filler content exceeds the above range, it may be difficult to form a polymer through the curing of the composite resin.

[0046] The above filler may be an inorganic filler, an organic filler, or a combination thereof.

[0047] The above filler may be one selected from the group consisting of fumed silica, barium silicate, barium aluminum silicate, aluminum silicate, lithium aluminum silicate, strontium aluminum silicate, zirconium silicate, glass, barium silicate glass, strontium silicate glass, and combinations of two or more of these, but is not limited thereto, and known inorganic fillers generally used in dental composite resin compositions may be used.

[0048] The above filler may comprise 50 to 80 weight percent of microfillers having an average particle size greater than 0.1 μm and less than or equal to 100 μm, and 1 to 10 weight percent of nanofillers having an average particle size greater than 1 nm and less than or equal to 100 nm.

[0049] In one embodiment, the microfiller may be a barium silicate filler surface-treated with a coupling agent, and the nanofiller may be a fumed silica filler surface-treated with a coupling agent.

[0050] The above dental composite resin composition may further include one or more additives selected from the group consisting of photosensitizers, photoinitiators, curing inhibitors, UV absorbers, and pigments.

[0051] The above photosensitizer is a substance that reacts by absorbing light of a wavelength of 400 to 500 nm, and may use quinone-based or phosphine oxide-based substances, but is not limited thereto. The content of the above photosensitizer may be 0.01 to 2 weight% based on the total weight of the dental composite resin composition.

[0052] The above photoinitiator may be a tertiary amine-based photoinitiator, but is not limited thereto. The content of the above photoinitiator may be 0.01 to 4 weight% based on the total weight of the dental composite resin composition.

[0053] The above-mentioned curing inhibitor serves to stabilize the composition so that the di(meth)acrylate-based monomer does not cure at room temperature, and may use an aromatic monomer containing a hydroxyl group, but is not limited thereto. The content of the above-mentioned curing inhibitor may be 0.01 to 1 weight% based on the total weight of the dental composite resin composition. If the content of the curing inhibitor exceeds the above range, curing may not occur even when sufficient blue LED is applied.

[0054] The above UV absorber is a substance that absorbs light with a wavelength of 400 nm or less to prevent the resin from being easily cured by an external light source such as a fluorescent lamp, and may use light absorbers of the benzotriazole, benzophenone, oxalanilide, or triazine series, but is not limited thereto. The content of the above UV absorber may be 0.01 to 1 weight% based on the total weight of the dental composite resin composition.

[0055] Iron oxide-based pigments may be used as the above pigments, but are not limited thereto. The content of the above pigment may be 0.01 to 0.1 weight% based on the total weight of the dental composite resin composition.

[0056] The above dental composite resin composition may be in the form of a paste.

[0057] The above dental composite resin composition may have an area of ​​0.5 to 1 mJ calculated through a distance-force graph when a cylindrical probe with a diameter of 5 mm is lowered using a rheometer until it touches the surface of the resin composition, the resin is pressed with a force of 2 N for 5 seconds, and then the probe is raised vertically at a speed of 10 mm / s. For example, it may be 0.5 mJ, 0.6 mJ, 0.7 mJ, 0.8 mJ, 0.9 mJ, 1 mJ, or a range between two of these values. The area of ​​the graph indicates the degree of stickiness of the resin composition, and if the area of ​​the graph exceeds the above range, the resin may stick to the instrument during manipulation using a dental instrument, making it difficult to form the desired shape.

[0058] The embodiments of this specification will be described in more detail below. However, the following experimental results represent only representative results among the above embodiments, and the scope and content of this specification should not be interpreted as being narrowed or limited by the embodiments. The respective effects of various embodiments of this specification not explicitly presented below will be described in detail in the relevant sections.

[0059] Examples and Comparative Examples

[0060] Polyethylene glycol dimethacrylate (PEGDMA), 1,12-dodecanediol dimethacrylate (1,12-DDDMA), glycerol 1,3-dimethacrylate (GDMA), a mixture of bisphenol-A glycidyl dimethacrylate (BisGMA) and triethylene glycol dimethacrylate (TEGDMA) (weight ratio of BisGMA to TEGDMA is 8:2), bisphenol-A ethoxylate dimethacrylate (BisEMA), and additives were placed in a mixing vessel according to the composition of Table 1 below, and in an environment of 50 ℃ Mixing was performed at 50 rpm for 10 minutes. As additives, a mixture of the photosensitizer camphorquinone, the photoinitiator ethyl-4-dimethylaminobenzoate (EDAB), the curing inhibitor butyl-hydroxytoluene, the UV absorber 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, and an iron oxide-based dye was used.

[0061] After adding the microfiller according to the composition of Table 1 below, the mixture was mixed at 20 rpm for 2 hours in a 50 ℃ environment. As the microfiller, barium silicate filler surface-treated with a coupling agent having an average particle size greater than 0.1 μm (average particle size range 0.7–2.0 μm, 6.0% silane treatment, Schott 8235 series) was used.

[0062] After adding the nano filler according to the composition of Table 1 below, the mixture was mixed at 5 rpm for at least 4 hours in a 50 ℃ environment. As the nano filler, fumed silica filler surface-treated with a coupling agent having an average particle size of 100 nm or less (2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propylester or diemthyldichlorosilane surface treatment, Evonik R972, R7200) was used.

[0063] When the mixture formulation became a paste, it was removed from the container, kneaded by hand, and returned to the container. The mixture was then mixed at 5 rpm while lowering the container temperature to 25 ℃. After the container temperature was lowered to 25 ℃, a vacuum was applied, and the mixture was degassed at 1 rpm for 30 minutes to 1 hour to obtain a dental composite resin composition in paste form.

[0064] Classification (Weight%) Preliminary Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 PEGDMA 2.3 2.3 2.3 2.3 2.3 2.3 4.2 1,12-DDDMA 2.8 2.8 3.5 4.2 2.8 0 2.3 GDMA 0.7 0 0 1.4 4.2 0 BisGMA, TEGDMA Mixture 2.5 2.5 2.5 2.5 2.5 2.5 2.5 BisEMA 9.3 9.3 9.3 9.3 9.3 9.3 3 Additive 2.4 2.6 2.4 2.2 2.2 2.2 1.7 Micro Filler 76.2 76.7 76.2 75.7 75.7 75.7 76.2 Nano Filler 3.8 3.8 3.8 3.8 3.8 3.8 3.8

[0065] Experimental Example

[0066] The stickiness of the dental composite resin compositions prepared by the methods of the above Examples and Comparative Examples 1 to 6 was measured using a rheometer.

[0067] A cylindrical probe with a diameter of 5 mm was lowered until it touched the surface of the resin, and after pressing the resin with a force of 2 N for 5 seconds, the probe was raised vertically upward at a speed of 10 mm / s. The work done by the resin on the probe was calculated by measuring the area under the distance-force graph. In addition, the length of the resin stretched when it separated from the probe was measured. The calculated graph area and stretch length represent the degree of stickiness; a larger graph area and a longer stretch length indicate greater stickiness. The results are shown in Table 2 below.

[0068] Classification Preliminary Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Graph Area (mJ) 0.677 0.473 1.27 2.25 1.8 1.12 1.64 Elongation Distance (mm) 0.975 0.899 1.475 2.70 12.275 1.35 2.05

[0069] Referring to Table 2 above, when comparing Comparative Examples 1 to 3, it was confirmed that as the content of 1,12-DDDMA in the composition increased, the graph area and elongation distance increased, indicating increased stickiness. When comparing the Example, Comparative Example 1, and Comparative Example 4, it was confirmed that as the content of GDMA in the composition increased, the graph area and elongation distance increased, indicating increased stickiness; however, the Example with a GDMA content of 0.7 wt% showed a smaller increase in stickiness compared to Comparative Example 1, which did not add GDMA, whereas Comparative Example 4, in which the GDMA content was increased to 1.4 wt%, showed a significant increase in stickiness.

[0070] Comparing Comparative Example 3 and Comparative Example 5, 1,12-DDDMA exhibited a much stickier characteristic compared to GDMA when the same amount was added. Additionally, comparing Comparative Example 3 and Comparative Example 6, 1,12-DDDMA exhibited a stickier characteristic compared to PEGDMA when the amounts were reversed.

[0071] When manipulated using dental instruments, it was confirmed that the dental composite resin composition of the example satisfying a graph area of ​​0.5 to 1 mJ did not stick to the instrument, making tooth restoration easy. On the other hand, the resin compositions of Comparative Examples 2 to 6, which had a graph area exceeding 1 mJ, exhibited sticky characteristics, and there was a problem where the resin stuck to the instrument, making it difficult to form the desired shape. The resin composition of Comparative Example 1, which did not contain GDMA, was not sticky, but there was a problem where the resin cracked or tore due to low bonding strength with the filler.

[0072] The foregoing description of this specification is for illustrative purposes only, and those skilled in the art to which one aspect of this specification pertains will understand that other specific forms can be easily modified without altering the technical concept or essential features described in this specification. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. For example, each component described as a single unit may be implemented in a distributed manner, and components described as distributed may likewise be implemented in a combined form.

[0073] The scope of this specification is defined by the claims set forth below, and all modifications or variations derived from the meaning and scope of the claims and equivalent concepts thereof should be interpreted as being included within the scope of this specification.

Claims

1. Polyalkylene glycol-based di(meth)acrylate 0.1~3 wt%, Alkanediol di(meth)acrylate 0.1~3 wt%, 0.1 to 1 wt% of glycerol di(meth)acrylate and A dental composite resin composition comprising 60 to 90 weight percent of filler.

2. In Paragraph 1, A dental composite resin composition in which the above polyalkylene glycol-based di(meth)acrylate is one selected from the group consisting of polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol dimethacrylate, polypropylene glycol diacrylate, and combinations of two or more of these.

3. In Paragraph 1, A dental composite resin composition wherein the above alkanediol di(meth)acrylate is one selected from the group consisting of 1,12-dodecanediol dimethacrylate, 1,12-dodecanediol diacrylate, 1,10-decanediol dimethacrylate, 1,10-decanediol diacrylate, 1,9-nonanediol dimethacrylate, 1,9-nonanediol diacrylate, 1,8-octanediol dimethacrylate, 1,8-octanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, and combinations of two or more of these.

4. In Paragraph 1, A dental composite resin composition in which the above glycerol di(meth)acrylate is one selected from the group consisting of glycerol 1,3-dimethacrylate, glycerol 1,3-diacrylate, glycerol 1,2-dimethacrylate, and combinations of two or more of these.

5. In Paragraph 1, A dental composite resin composition further comprising 6 to 15 weight% of bisphenol-A-based di(meth)acrylate and 0.1 to 5 weight% of alkylene glycol-based di(meth)acrylate.

6. In Paragraph 5, A dental composite resin composition wherein the above bisphenol-A di(meth)acrylate is one selected from the group consisting of bisphenol-A glycidyl dimethacrylate, bisphenol-A ethoxylate dimethacrylate, bisphenol-A dimethacrylate, bisphenol-A diacrylate, bisphenol-A ethoxylate diacrylate, bisphenol-A diglycidyl ether diacrylate, bisphenol-A epoxy diacrylate, and combinations of two or more of these.

7. In Paragraph 5, A dental composite resin composition in which the above-mentioned alkylene glycol-based di(meth)acrylate is one selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, and combinations of two or more of these.

8. In Paragraph 5, The above bisphenol-A-based di(meth)acrylate comprises 1 to 5 weight% of bisphenol-A glycidyl dimethacrylate and 5 to 10 weight% of bisphenol-A ethoxylate dimethacrylate, forming a dental composite resin composition.

9. In Paragraph 1, A dental composite resin composition in which the above filler is one selected from the group consisting of fumed silica, barium silicate, barium aluminum silicate, aluminum silicate, lithium aluminum silicate, strontium aluminum silicate, zirconium silicate, glass, barium silicate glass, strontium silicate glass, and combinations of two or more of these.

10. In Paragraph 1, A dental composite resin composition comprising 50 to 80 weight% of microfillers having an average particle size greater than 0.1 μm and less than or equal to 100 μm, and 1 to 10 weight% of nanofillers having an average particle size greater than 1 nm and less than or equal to 100 nm.

11. In Paragraph 1, A dental composite resin composition comprising one or more selected from the group consisting of photosensitizers, photoinitiators, curing inhibitors, UV absorbers, and pigments.