KR101979874B1 - Manufacturing method of composite resin compositions for dental restoration comprising caprylic acid and composite resin compositions for dental restoration manufactured by the method - Google Patents

Abstract

The present invention includes caprylic acid in a composite resin for dental restoration so as to accelerate the photopolymerization reaction and rapidly cure when repairing a damaged or missing portion of a tooth, thereby minimizing the area in which the resin is uncured and restoring the composite resin The present invention relates to a method of manufacturing a composite resin for dental restoration comprising capric acid which can prevent formation of gaps between teeth and prevent periodontal disease by inhibiting the occurrence of germs and cavities with a gap between the teeth and the composite resin after the procedure, The present invention relates to a composite resin for restoration, and it is an object of the present invention to provide a composite resin for restoration, which is capable of minimizing the occurrence of bubbles in the composite resin by progressing the agitation or aging process in a vacuum atmosphere, There is an advantage that no defoaming agent or defoaming process is necessary. In addition, by including the caprylic acid in the composite resin for dental restoration, the photopolymerization reaction in the composition is promoted upon exposure to light to accelerate the curing, thereby improving the convenience of the procedure, It is possible to minimize the formation of gaps between the teeth and the resin, thereby preventing the generation of germs in the gap between the resin and the teeth and the occurrence of periodontitis through the penetration of germs.

Description

Technical Field [0001] The present invention relates to a method for preparing a dental restorative composite resin containing capric acid and a dental restorative composite resin prepared by the method,

The present invention includes caprylic acid in a composite resin for dental restoration so as to accelerate the photopolymerization reaction and rapidly cure when repairing a damaged or missing portion of a tooth, thereby minimizing the area in which the resin is uncured and restoring the composite resin The present invention relates to a method of manufacturing a composite resin for dental restoration comprising capric acid which can prevent formation of gaps between teeth and prevent periodontal disease by inhibiting the occurrence of germs and cavities with a gap between the teeth and the composite resin after the procedure, And to a composite resin for recovery.

Generally, if a tooth is lost due to damage or deficiency due to caries or fracture, problems occur in pronunciation, chewing, and aesthetics. If the adjacent teeth start to move due to the movement of adjacent teeth in an empty space without teeth, There is a problem that the food is caught between the food and beverage, causing cavities and taste, and bad breath.

In order to solve this problem, the patient's part or all of the teeth have been lost, and all natural teeth and related gingival parts of the dental arch have been replaced with artificial objects to maintain or restore the function of the oral cavity. Restored.

These dental restorative resins have been used in various materials depending on the period of time. The dental restorative resins most commonly used are mercury amalgam, which is advantageous in that it is easy to perform and excellent in abrasion resistance and mechanical strength. However, It is known that the color difference with natural tooth is distinct, the bonding with dental tissues is not good, and mercury gradually leaks out from restored amalgam over time, which is harmful to human body from a long-term point of view.

Therefore, the development of materials that can secure and replace the disadvantages of mercury amalgam has been progressed, and polymer materials are attracting attention as one of them.

As a polymeric material that can be used as a dental restorative resin, acrylic resin is superior to silicate developed after mercury amalgam in terms of mechanical properties such as strength, color stability and waterproofing stability, but it has a low abrasion resistance and a high shrinkage rate There are disadvantages. In order to overcome these drawbacks, a highly complex composite resin using inorganic filler as a reinforcing material has been developed as a dental restorative resin.

Typically, the dental restorative resin composition is composed of an inorganic filler, a prepolymer, a diluent, a light watch (a photoinitiator and a reducing agent), and other additives. The resin composition has mechanical strength to withstand high occlusal pressure generated when food is chewed, It has the same color and gloss as natural tooth for the restoration that can take advantage of the natural feeling as well as the physical characteristics such as thermal expansion rate and low polymerization shrinkage rate to prevent separation from tooth during polymerization hardening. And to be able to do so.

Commonly used as prepolymers of dental restorative resin compositions are dimethacrylate-based 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) Bis-GMA). This is mainly used as a matrix resin because of its advantages such as small volatility and polymerization shrinkage and excellent strength of a polymerized product using the same. However, in order for the inorganic filler to be efficiently mixed with the prepolymer, it is advantageous that the viscosity of the prepolymer is low. However, since the dimethacrylate compound has high viscosity, a diluent such as triethylene glycol dimethacrylate (TEGDMA) , And the physical properties and aesthetics of the cured product can not be maintained for a long time because of the water absorption property due to the hydroxyl group (-OH) in the molecular structure.

In order to solve these problems, research and development on dental restorative composite resin including dentistry composite materials, composite materials, dental fixation materials, and artificial teeth as well as composite dental filling materials for filling and restoring dental cavities of dental teeth .

The first dental composite composite resin has been used in practice since its development in 1942 by Kulzer, Germany, in which PMMA powder and methyl methacrylate (MMA) monomers were blended, and then acrylic resin was used for a long time. However, organic polymers have merits such as aesthetics, simplicity of procedure, and low risk of biohazard. On the other hand, since their physical properties do not have enough hardness, strength and abrasion resistance enough to withstand mastic pressure, A composite resin was developed. Commercial dentistry composite composite resins were developed by Brown in 1962, developed by photopolymerization using ultraviolet light in the 1970s, and then photopolymerized using visible light in the UK in 1980 by ICI. Amount of use is exploding as the use of existing amalgam is eroded.

The dental restorative composite resin can be used for anterior filling, posterior filling, cervical erosion filling, porcelain repair, bracket bonding, abutment construction, (denture treatment), discoloration light dental treatment, and porcelain laminate bonding. In recent years, there has been an increase in the number of patients desiring various aesthetic treatments, as well as restoration of dental caries (cavities) And is applied to various dental treatments for various bonding and cementing applications.

However, due to the above-mentioned various uses, a composite resin including a polymer occupies a firm position as a material for dental restoration. However, in order to improve the strength, hardness, polymerization shrinkage, water absorption rate, solubility, Research and development on composite resins for water-recovery are underway.

Published Patent No. 2016-0077944 (published on July 4, 2014) Registered Patent No. 1,370,658 (Registration Notice)

The present invention further includes a caprylic acid in the composite resin in order to accelerate the curing reaction of the composite resin for dental restoration that can repair the defect part of the tooth through the curing reaction during the procedure, A method of manufacturing a composite resin for dental restoration comprising capric acid which can minimize the area where the resin is uncured and prevent formation of a gap between the teeth and the composite resin restored by accelerating the photopolymerization reaction at the time of restoration, And to provide a composite resin for dental restoration produced through the method.

In order to accomplish the above object, an embodiment of the present invention is a method for manufacturing a toner, comprising: a first stirring step of stirring a plurality of monomers causing a crosslinking reaction to prepare a first mixture; A second agitating step of adding a capric acid to the first mixture and then mixing to prepare a second mixture; A third stirring step of adding a filler to the second mixture and mixing the mixture to prepare a third mixture; A fourth stirring step of further adding a pigment and a polymerization initiator to the third mixture and then mixing them to prepare a fourth mixture; And aging the mixture to agitate the mixture to agitate the mixture. The present invention also relates to a method for preparing a composite resin for dental restoration comprising capric acid, wherein the first agitation step, the second agitation step, And the fourth stirring step may be performed in a vacuum atmosphere.

More preferably, the first stirring step, the second stirring step, the third stirring step and the fourth stirring step may be performed in a vacuum pressure atmosphere of 0.05 to 0.15 MPa.

The cross-linking monomer is preferably selected from the group consisting of 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane (Bis-GMA), ethylene glycol dimethacrylate ), Triethylene glycol dimethacrylate (TEGDMA), ethoxylate bisphenol A dimethacrylate (Bis-EMA), urethane dimethacrylate (UDMA), dipentaerythritol pentaacrylate monophosphate pentaacrylate monophosphate (PENTA), 2-hydrozyethyl methacrylate (HEMA), polyalkenic acid, biphenyl dimethacrylate (BPDM), and glycerol phosphate dimethacrylate It is preferable to use two or more selected from the group consisting of glycerol phosphate dimethacrylate (GPDM).

In addition, the second stirring step may be carried out by adding capric acid to the first mixture, stirring the mixture at 50 to 60 ° C and 15 to 20 RPM for 40 to 50 minutes, heating the capric acid to 50 to 70 ° C, The second mixture may be stirred at room temperature (15 to 25 ° C) at 20 to 30 RPM for 60 to 90 minutes after the filler is added to the second mixture, .

Wherein the aging step comprises: a chilled aging step of aging the fourth mixture at 3 to 5 DEG C for 10 to 14 hours; And a vacuum agitation step of agitating the fourth mixture aged through the refrigeration aging step in a vacuum atmosphere at 15 to 25 RPM for 70 to 110 minutes, and the vacuum agitation step may be performed at a vacuum pressure of 0.05 to 0.15 MPa Atmosphere.

On the other hand, another embodiment of the present invention is a composite resin for dental restoration prepared by the aforementioned manufacturing method.

The present invention is directed to a method for manufacturing a dental composite composite resin, which is capable of minimizing the occurrence of bubbles in the composite resin by performing agitation or aging in a vacuum atmosphere during the manufacturing process of the composite resin for dental restoration, There is no need to use defoamer or defoaming process.

In addition, by including the caprylic acid in the composite resin for dental restoration, the photopolymerization reaction in the composition is promoted upon exposure to light to accelerate the curing, thereby improving the convenience of the procedure, It is possible to minimize the formation of gaps between the teeth and the resin, thereby preventing the generation of germs in the gap between the resin and the teeth and the occurrence of periodontitis through the penetration of germs.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The preferred embodiments of the present invention will now be described in detail with reference to the accompanying drawings. Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. As well as the fact that

Throughout this specification, when an element is referred to as " comprising ", it means that it can include other elements as well, without departing from the other elements unless specifically stated otherwise.

The terms " first ", " second " and the like are intended to distinguish one element from another and should not be limited by these terms. For example, 2 component, and similarly the second component may also be named as the first component.

Hereinafter, a method for preparing a dental restoration composite resin containing caprylic acid according to the present invention and a composite resin for dental restoration prepared thereby will be described in detail.

First, one embodiment of the present invention includes a first stirring step of stirring a plurality of monomers causing a cross-linking reaction to prepare a first mixture; A second agitating step of adding a capric acid to the first mixture and then mixing to prepare a second mixture; A third stirring step of adding a filler to the second mixture and mixing the mixture to prepare a third mixture; A fourth stirring step of further adding a pigment and a polymerization initiator to the third mixture and then mixing them to prepare a fourth mixture; And an aging step of aging the fourth mixture by agitation, thereby preparing a composite resin for dental restoration containing capric acid.

Generally, when the composition is stirred, each component contained in the composition is homogeneously dispersed, so that external air during stirring is contained in the composition, or a reaction product is generated through a reaction caused by mixing each component of the composition Whereby bubbles in the composition can be generated. The generated bubbles have a buffering effect on the shrinkage stress of the composition and the polymerization reaction does not proceed rapidly at the gel point of the composition and the stress is dispersed and hardened so that the physical properties to be obtained through the polymerization reaction are lowered There is a problem.

Particularly, in the case of a composite resin for dental restoration, it is a medical composition that not only has to be cured within a short time during curing through polymerization, but also has a certain strength to prevent the cured resin from being damaged by chewing, In order to reduce bubbles during manufacturing process and to reduce generated bubbles, it is necessary to reduce the amount of bubbles generated during manufacturing process. In addition, since the composite resin for dental restoration has to have a predetermined viscosity in order to facilitate the procedure, it is impossible to use the defoaming machine after the composite resin is manufactured. Therefore, bubble generation in the composition must be minimized during the manufacture of the composite resin for dental restoration.

Accordingly, in order to minimize the occurrence of bubbles in the above-mentioned composition during the production of the composite resin for dental restoration containing capric acid according to the present invention, the first stirring step, the second stirring step, the third stirring step , The fourth stirring step and the aging step, the composite resin for dental restoration containing the caprylic acid of the present invention can be produced under a vacuum pressurized atmosphere.

Specifically, the composite resin for dental restoration containing the caprylic acid of the present invention can be agitated or aged in a vacuum pressure atmosphere of 0.05 to 0.15 MPa. When the vacuum pressure is less than 0.05 MPa, the mixture is agitated or aged through a vacuum pressure It is difficult to expect reduction effects of bubbles and when the vacuum pressure is 0.15 MPa or more, the improvement of the effect according to the overpressure is insignificant, and the economical efficiency may be lowered due to energy waste.

The process for producing a composite resin for dental restoration comprising caprylic acid according to the present invention will be described in detail. The first stirring step is a step for preparing a first mixture by uniformly dispersing a plurality of monomers causing a crosslinking reaction. Any material capable of exhibiting mechanical strength as a solvent and capable of being polymerized is not particularly limited and can be used as a monomer, and a monomer containing an unsaturated double bond can be preferably used.

At this time, the plurality of monomers causing the cross-linking reaction may be selected from the group consisting of 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane (Bis- (TGDMA), triethylene glycol dimethacrylate (TEGDMA), ethoxylate bisphenol A dimethacrylate (Bis-EMA), urethane dimethacrylate (UDMA), dipentaerythritol pentaacrylate But are not limited to, dipentaerythritol pentaacrylate monophosphate (PENTA), 2-hydrozyethyl methacrylate (HEMA), polyalkenic acid, biphenyl dimethacrylate (BPDM) Glycerol phosphate dimethacrylate (GPDM), and more preferably at least two kinds selected from the group consisting of 2,2-bis- (4- (2-hydroxy-3-methacryloyloxy Propoxy) phenyl) propane (Bis-GMA), It is preferable to use ethoxylate bisphenol A dimethacrylate (Bis-EMA) and urethane dimethacrylate (UDMA).

This means that the 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane contains two hydroxyl groups (-OH) in the molecule, It has the property of enhancing the affinity between the resin and the inorganic filler and has a property of absorbing moisture due to strong hydrophilicity. When 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane having such a characteristic absorbs organic resin and moisture after photo-curing, The binding force with the filler is weakened, so that the filler particles are detached from the composition and the physical properties such as strength and abrasion resistance may be deteriorated, which may lead to cytotoxicity, and food may be absorbed into the restoration, resulting in discoloration . Accordingly, at least one of the two hydroxyl groups present in the molecule of the 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane is converted into a methacrylate group It is possible to substitute to reduce the hydrophilicity of the 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane to prevent the aforementioned problems (causes of physical, Polymerization shrinkage and moisture absorption) can be prevented.

Specifically, the first stirring step may be carried out by reacting 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane (Bis-GMA) with ethoxylate bisphenol A dimethacryl A first stirring step in which Bis-EMA is stirred at 40 to 50 DEG C for 15 to 20 RPM for 20 to 40 minutes; After the urethane dimethacrylate (UDMA) is added to the 1-1 mixture prepared through the 1-1 stirring step, it is stirred at room temperature (15-25 ° C) at 15-20 RPM for 20-40 minutes And may further comprise a 1-2 stirring step.

The composition and the content of the plurality of monomers included in the first stirring step play an important role in the degree of dispersion of the composition during the polymerization reaction at the subsequent stage and affect the operability at the time of dental treatment using the composition, Resistance or durability. Therefore, the composition and the content of the plurality of monomers can be appropriately adjusted according to the composition and content of the composite resin for dental restoration according to the method of use, the part to be used, and the purpose of use. However, if the content of the plurality of monomers is too low in the total composition of the dental restoration composite for dental restoration, it is difficult to form the polymer or the polymer content is insufficient, so that it is not easy to mix with the filler contained in the rear end, It is difficult to expect the desired hardness of the hardened cured body. If the excessive amount of hardened cured body is contained, the flowability of the composite resin for dental restoration is increased.

For example, the content of 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane (Bis-GMA) The content of 10 to 20 wt% of the composition and ethoxylate bisphenol A dimethacrylate (Bis-EMA) may be contained in an amount of 15 to 25 wt% of the total composition, The first mixture can be prepared through a first 1-2 stirring step in which the produced first-1 mixture further contains 6 to 15 wt% urethane dimethacrylate (UDMA) of the entire composition and stirred.

At this time, the composition of the plurality of monomers included in the 1-1 stirring step and the 1-2 stirring step can improve the dispersibility of the dental restorative composite resin containing capric acid of the present invention, And a composite resin for dental restoration containing homogeneous capric acid is prepared. Thus, it is possible to provide a dental restorative composite resin having desirable strength not only in restoration to teeth but also in a most preferable manner to improve the convenience of the procedure through appropriate viscosity and preferable curing time Composition ratio.

The second agitating step of adding the capric acid to the first mixture prepared through the first agitating step to produce the second mixture is characterized in that capric acid, which is one of the saturated fatty acids obtained from natural products, So that the curing reaction during dental procedures can be promoted and convenience of the procedure can be improved. In addition, by minimizing the uncured portion of the resin, it is possible to reduce the occurrence of gaps between the cured resin and the teeth, thereby allowing bacteria and foreign matter to penetrate between the resin and the teeth, thereby preventing the occurrence of tooth decay or periodontal disease.

Since the capric acid exists in a solid state having white needle-shaped crystals at room temperature (15 to 25 ° C), when capric acid is contained in the first mixture in the second stirring step, capric acid is heated to 50 to 70 ° C, It is preferable to add capric acid in the liquid state.

The second stirring step may be performed by adding capric acid to the first mixture and then stirring the mixture at 50 to 60 ° C and 15 to 20 RPM for 40 to 50 minutes to prepare a second mixture. At this time, if the stirring temperature deviates from the above-mentioned range, the capric acid may not be solidified and dispersed evenly in the second mixture, or the fluidity of the second mixture may be increased, so that bubbles may be generated or bubbles may be incorporated.

In addition, the capric acid contained in the second stirring step may be contained in an amount of 0.8-1.2 wt% of the total composition. When the content of capric acid contained in the whole composition is out of the range mentioned above, Promoting, etc.) may not be expressed, or the strength and durability of the tooth-receiving resin may be lowered.

The third stirring step in which the filling material is injected into the second mixture and mixed is a method for improving the abrasion resistance and strength of the composite resin for dental restoration comprising the caprylic acid of the present invention. The filling material is an inorganic filler, an organic filler, Or a mixed filler containing two or more of these. Preferably, the third stirring step may be performed at room temperature (15 to 25 ° C) at 20 to 30 RPM for 60 to 90 minutes, since heat is generated due to the reaction during the stirring of the filler and the second mixture. . In addition, since the stirring time varies depending on the season, the mixing time can be shortened in the summer when the room temperature is high, and the stirring time can be increased in the winter when the room temperature is low.

The inorganic filler is not particularly limited as long as it is a known inorganic filler generally used in dental resins. Examples of the filler include silica, amorphous synthetic silica, crystalline natural silica, barium aluminum silicate, barium glass, kaolin, talc, A radioactive impermeable glass powder (such as strontium aluminum silicate), a zirconia compound, and other acid-reactive fillers. One or two or more of these may be used in a mixed form, and silica and Barum glass may be preferably used.

In general, since the inorganic filler is chemically hydrophilic, compatibility with a plurality of hydrophobic monomers is poor. Therefore, the inorganic filler can be surface-treated with a binder or a silane coupling agent capable of improving the bonding property in the third stirring step And the binding property to a plurality of monomers can be improved. Specific examples of the method of surface-treating the inorganic filler with the silane coupling agent and the silane coupling agent used in the surface treatment are well known in the art, and therefore, a detailed description thereof will be omitted.

The organic filler may be prepared by synthesizing a monomer for forming a matrix upon curing of a composite resin for dental restoration or a monomer having compatibility with the matrix by bulk polymerization, emulsion polymerization, suspension polymerization or the like, Can be used.

The stabilizer is a material capable of chemically and physically stabilizing a mixture or a composite resin for dental restoration, preferably a phenolic and / or phosphate stabilizer.

Preferably, the filler contained in the second mixture may have a particle size of 0.2 to 5 占 퐉. When the particle diameter of the filler is smaller than the above-mentioned range, the particles are uniformly dispersed in the second mixture Dispersion may be difficult, and bubbles may be generated in the interior due to the viscosity correspondence or miscibility may be lowered. On the other hand, when the particle size of the filler is larger than the above-mentioned range, as the ratio of the height to the radius increases, the prepared composite resin for dental restoration is deteriorated in abrupt bond strength and physical properties (internal cracking) The abrasion may cause the particles to separate from the resin, which may reduce the lubricity of the resin and deteriorate the aesthetic feeling.

In the third stirring step, the second mixture may further contain, in addition to the filler, other known compounds used as a dental resin within a range that does not deteriorate the effects of the present invention. For example, polymerization inhibitors, A colorant, a fluorine additive, a diluent, a coupling agent, a photocatalyst, or a light stabilizer, may be further included in the second mixture.

The fourth stirring step of further adding the pigment and the polymerization initiator to the third mixture and then mixing them to prepare the fourth mixture preferably further comprises the step of adding a pigment, a polymerization initiator, a reaction promoter and a diluent to the third mixture The fourth mixture can be prepared, and more preferably, the fourth mixture can be prepared by stirring at room temperature (15 to 25 DEG C) at 20 to 30 RPM for 60 to 90 minutes.

The pigment is not particularly limited as long as it is ordinarily used in a dental resin, and it may contain a suitable amount of a pigment appropriately selected to improve the aesthetics of the user. As an example, the pigment may be an iron oxide-based inorganic pigment of yellow, navy blue (black) and red or titanium dioxide inorganic pigment.

The polymerization initiator is an initiator for the polymerization reaction of two or more monomers. Depending on the type of the catalyst used in the polymerization reaction, the polymerization initiator can proceed to a cation forming mechanism, an anion forming mechanism, a radical forming mechanism, etc. Among these, And the polymerization reaction may proceed through a photopolymerization reaction or a thermal polymerization reaction through cations, anions, and radicals generated through the polymerization initiator.

Preferably, the composite resin for dental restoration comprising the caprylic acid of the present invention can be cured by photopolymerization in the procedure. The photopolymerization reaction is activated by visible light to cause a polymerization reaction of the monomer. At this time, a photopolymerization initiator can be used as a polymerization initiator that initiates the photopolymerization reaction.

Specifically, when the composite resin for dental restoration containing capric acid is exposed to a light source in a visible light range which is harmless to the human body, the photopolymerization initiator and the catalyst generate radicals, and the produced radicals are used in the first stirring step The polymerization reaction of the plurality of monomers is initiated and cured, whereby the composite resin for dental restoration containing the caprylic acid in the teeth can be restored.

Therefore, the polymerization initiator used in the fourth stirring step of the present invention is preferably a photopolymerization initiator, which may be a carbonyl compound of an? -Diketone system or an acylphosphine oxide system. Preferably, the polymerization initiator used in the fourth stirring step 4 The mixture may further contain a tertiary amine compound, which is a hydrogen donor, as a reaction promoter.

More preferably, camphorquinone (CQ), which is one of the carbonyl compounds of the? -Diketone system, can be used as the photopolymerization initiator, and as the tertiary amine compound, N, N-dimethylaminoethyl methacrylate N, N-dimethylaminoethyl methacrylate) or ethyl p-dimethyl aminobenzoate may be used.

The diluent is added to improve the chemical stability and the storage stability by decreasing the viscosity of the fourth mixture. Preferably, the diluent is methyl methacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol Dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, 1-methyl-1,3-propanediol dimethacrylate, 1,6-bis 2-ethoxycarbonylamino) -2,2,4-trimethylhexane and the like can be used.

The composite resin for dental restoration comprising the caprylic acid of the present invention can be produced through the aging step of aging the fourth mixture. In the aging step, the components of the composition are sufficiently adhered to the surface of the filler in the fourth mixture, and not only part of the physical properties of the respective components are recovered through the stirring process, but also the pigment contained in the fourth stirring step By imparting the tension, the color stability can be improved when the composite resin for dental restoration containing the caprylic acid is restored to the teeth.

Specifically, the aging step comprises: a chilled aging step of aging the fourth mixture at 3 to 5 DEG C for 10 to 14 hours; And a vacuum agitation step in which the fourth mixture aged through the refrigeration aging step is stirred in a vacuum atmosphere at 15 to 25 RPM for 70 to 110 minutes.

In the refrigerating and aging step, the filling material contained in the fourth mixture and the respective components are brought into close contact with each other. Preferably, the fourth mixture can be aged at 3 to 5 ° C for 10 to 14 hours, If the temperature of the refrigeration aging or refrigeration aging time is out of the range, the filling material and the respective components are not sufficiently adhered to each other, so that the strength of the hardened resin may be lowered or the filling material may be detached from the resin after the restoration.

In addition, in the vacuum agitation step, the fourth aged mixture is agitated in a vacuum atmosphere at 15 to 25 rpm for 70 to 110 minutes to partially recover the physical properties of the respective components of the fourth mixture, Can be given.

Meanwhile, another embodiment of the present invention is a composite resin for dental restoration produced by the above-mentioned manufacturing method, wherein the content of capric acid is in a preferable range (0.8 to 1.2 wt% in the total composition) The reaction is promoted and the hardening proceeds rapidly, so that not only the convenience of the treatment can be improved but also the cracks between the teeth and the resin are prevented from being formed by minimizing the sites of uncured sites, It is possible to prevent the occurrence of periodontitis through inhibition of generation and infiltration of bacteria.

In addition, by conducting the stirring or aging process in the vacuum atmosphere during the production of the composite resin for dental restoration, the generation of bubbles in the composite resin can be minimized, so that not only excellent physical properties can be obtained in restoration of teeth, There is no need to use defoamer or defoaming process.

Hereinafter, an embodiment of the present invention will be described. However, the scope of the present invention is not limited to the following preferred embodiments. Those skilled in the art can implement various modified embodiments of the present invention within the scope of the present invention.

[Manufacturing Example]

Manufacturing method of composite resin for dental restoration

BIS-GMA (80) and BIS-EMA were dissolved in methylene chloride (100 ml). At this time, the amounts of dissolved BIS-GMA (80) and BIS-EMA were contained to be 14 wt% and 19 wt% in the composite resin for whole dental restoration (hereinafter, the whole composition). The composition in which BIS-GMA (80) and BIS-EMA were dissolved was placed in a vacuum blending machine (USS-5020) After stirring, UDMA (an amount of 11 wt% in the total composition) was added thereto and stirred at room temperature (15 캜) at 15 RPM for 30 minutes. Subsequently, capric acid (Sigma-Aldrich) in liquid form, which was melted by heating at 60 DEG C, was added to the composition in an amount of 0.6 wt%, 0.8 wt%, 1.2 wt%, 1.0 wt%, 1.4 wt %, And the mixture was stirred at 20 RPM at an average temperature of 55 캜 for 45 minutes so that capric acid could be uniformly dispersed. Subsequently, silica and barium glass were added as fillers, and the mixture was stirred at room temperature (15 ° C) for 70 minutes. Then, a pigment, camphorquinone (Sigma-Aldrich), a reaction accelerator (Sigma-Aldrich) (Sigma-Aldrich), and the mixture was stirred at room temperature (15 DEG C) at 20 RPM for 70 minutes to prepare a mixture. At this time, stirring was continuously carried out in a vacuum pressure atmosphere as shown in Table 1 below.

The mixture was allowed to stand in a refrigerator having an average temperature of 4 ° C for 12 hours and aged. The mixture was stirred at room temperature (15 ° C) at 20 RPM for 90 minutes under a vacuum pressure atmosphere as shown in Table 1, Comparative Examples 1 to 5 were prepared.

Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Example 1 Example 2 Example 3 Example 4 Example 5 all
Composition
My Cap
Lysan
content
(wt%) 1.0 1.0 1.0 0.6 1.4 1.0 1.0 1.0 0.8 1.2 vacuum
pressure
(MPa.) O 0.01 0.2 0.1 0.1 0.05 0.1 0.15 0.1 0.1

[Experimental Example 1]

Of dental restorative composite resin Degree of polymerization  Measure

In order to confirm the degree of polymerization according to the light exposure of Examples 1 to 5 and Comparative Examples 1 to 5, which are composite resins for dental restoration prepared in the above Preparation Example, a transparent film having a diameter of 4 mm × height 5 mm, a metal mold of Examples 1 to 5 and Comparative Examples 1 to 5 was filled, a transparent film was placed on the upper portion of the metal mold, and then pressure was applied to each of the metal molds of Example 1 To 5 and Comparative Examples 1 to 5 were removed. After irradiation for 15 minutes, the depth of polymerization with exposure time was measured with a precision of 0.01 mm using a micrometer. The results are shown in Table 2.

Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Example 1 Example 2 Example 3 Example 4 Example 5 polymerization
depth
(mm) 9.0 9.1 8.9 8.7 9.7 9.8 9.9 9.8 9.5 9.8

[Experimental Example 2]

Strength measurement of composite resin for dental restoration

In order to confirm the strength of Examples 1 to 5 and Comparative Examples 1 to 5, which are the composite resins for dental restoration prepared in the above Preparation Example, the indirect tensile strength and flexural strength were measured.

The indirect type tensile strength is determined by setting the disk type specimen in the radial direction and applying a compressive load to induce a tensile stress in the specimen. The disk type specimen is obtained by using Examples 1 to 5 and Comparative Examples 1 to 5 After pouring the specimen into a mold with a diameter of 6 mm and a thickness of 3.6 mm, a disk-shaped specimen was prepared and visible light was irradiated until the specimen fractured at a cross-head speed of 0.5 ± 0.2 mm / sec using a tensile tester The indirect tensile strength was calculated by the following equation (1).

...식(1)

... (1)

The bending strength was measured by irradiating light on both sides of a mold of 25 mm x 2 mm x 2 mm, and then stored for 24 hours in distilled water at 37 ° C. The flexural strength was calculated using the following equation (2) by applying a force to the specimen at a cross-head speed of 0.75 ± 0.25 mm / sec using a tensile tester.

...식(2)

... (2)

The results of indirect tensile strength and flexural strength of Examples 1 to 5 and Comparative Examples 1 to 5, which are the composite resins for dental restoration prepared in the above Preparation Examples, are shown in Table 3 below.

Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Example 1 Example 2 Example 3 Example 4 Example 5 Indirect
Seal
burglar
(MPa) 36 38 37 39 35 42 45 44 43 42 curve
burglar
(MPa) 125 124 129 130 119 136 137 135 135 131

From the results of Experimental Example 1 and Experimental Example 2, it was confirmed that bubbles were formed in the composition of Comparative Example 1 manufactured through agitation and aging in a state of not being vacuum, And the indirect tensile strength and flexural strength were also significantly lower than those of Comparative Examples 2 to 5 and Examples 1 to 5 prepared in a vacuum atmosphere.

Further, when comparing Comparative Examples 2 and 3 and Examples 1 to 3 prepared by varying the vacuum pressure, there was no significant difference in the polymerization depth and strength measurement results of Comparative Example 1 in the case of Comparative Example 2 in which the vacuum pressure was weak In the case of Comparative Example 3, the polymerization was not smoothly performed due to the fact that the polymerization was not performed uniformly by stirring at a high pressure, so that the polymerization depth was low and the result was low in the strength measurement.

On the other hand, in Comparative Examples 4 and 5 and Examples 2, 4 and 5 prepared by varying the content of capric acid, in the case of Comparative Example 4 in which the content of capric acid was small, the effect of promoting polymerization was small, And in Comparative Example 5 in which the content of capric acid was excessively contained, it was confirmed that the content of capric acid, which is a fatty acid, was excessive and the strength of the cured product significantly decreased.

Claims (7)

A first stirring step of stirring the plurality of monomers causing the crosslinking reaction to prepare a first mixture;
A second agitating step of adding a capric acid to the first mixture and then mixing to prepare a second mixture;
A third stirring step of adding a filler to the second mixture and mixing the mixture to prepare a third mixture;
A fourth stirring step of further adding a pigment and a polymerization initiator to the third mixture and then mixing them to prepare a fourth mixture; And
And aging the mixture to agitate the mixture,
The first stirring step, the second stirring step, the third stirring step and the fourth stirring step are performed in a vacuum atmosphere,
Wherein the aging step comprises aging the fourth mixture at 3 to 5 DEG C for 10 to 14 hours and the fourth mixture aged through the refrigeration aging step at a temperature of 15 to 25 RPM for 70 to 110 minutes Wherein the step of mixing the caprylic acid and the caprylic acid is carried out in a vacuum agitation step. The method according to claim 1,
In the first stirring step, the second stirring step, the third stirring step and the fourth stirring step, stirring is performed in a vacuum pressure atmosphere of 0.05 to 0.15 MPa, and the vacuum stirring step is performed in a vacuum pressure atmosphere of 0.05 to 0.15 MPa A method for producing a composite resin for dental restoration comprising capric acid The method according to claim 1,
The monomer causing the cross-
Methacryloyloxypropoxy) phenyl) propane (Bis-GMA), ethylene glycol dimethacrylate (TGDMA), triethylene glycol dimethacrylate (TEGDMA), ethoxylate bisphenol A dimethacrylate (Bis-EMA), urethane dimethacrylate (UDMA), dipentaerythritol pentaacrylate monophosphate (PENTA), 2- (2-hydrozyethyl methacrylate (HEMA), polyalkenic acid, biphenyl dimethacrylate (BPDM), and glycerol phosphate dimethacrylate (GPDM) ). ≪ / RTI > 11. A method for manufacturing a composite resin for dental restoration comprising capric acid. The method according to claim 1,
Wherein the second stirring step comprises:
After adding capric acid to the first mixture, the mixture is stirred at 50 to 60 ° C at 15 to 20 RPM for 40 to 50 minutes,
Wherein the capric acid is caproic acid in a molten liquid state heated to 50 to 70 占 폚. The method according to claim 1,
Wherein the third stirring step comprises:
Wherein the second mixture is stirred at 20 to 30 RPM for 60 to 90 minutes at room temperature (15 to 25 DEG C) after the filling of the filler, . delete A composite resin for dental restoration prepared by the method of any one of claims 1 to 5.