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WO2023080303A1 - Procédé destiné à la préparation de résines médicales dentaires et totales destiné à l'impression en 3d à l'aide de xylitol et de propolis - Google Patents

Procédé destiné à la préparation de résines médicales dentaires et totales destiné à l'impression en 3d à l'aide de xylitol et de propolis Download PDF

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WO2023080303A1
WO2023080303A1 PCT/KR2021/016273 KR2021016273W WO2023080303A1 WO 2023080303 A1 WO2023080303 A1 WO 2023080303A1 KR 2021016273 W KR2021016273 W KR 2021016273W WO 2023080303 A1 WO2023080303 A1 WO 2023080303A1
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mixed solution
stirring
dental
mpa
preparing
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정인선
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/15—Compositions characterised by their physical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B33Y70/10—Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y80/00—Products made by additive manufacturing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K11/00—Use of ingredients of unknown constitution, e.g. undefined reaction products

Definitions

  • the present invention relates to a method for manufacturing dental and total medical 3D printing resins using xylitol and propolis, and more specifically, to a method for manufacturing xylitol and By using propolis, it relates to a method for manufacturing dental and total medical 3D printing resins using xylitol and propolis capable of providing stable and excellent mechanical properties as well as increasing antibacterial effects.
  • Dental caries commonly called tooth decay, is a phenomenon in which components such as calcium and phosphorus on the surface of teeth are melted by acid to form holes in the teeth. Such dental caries can cause problems with pronunciation, chewing, and aesthetics. Problems such as damage to the gums may also occur, and when dental caries is intensified due to failure to recognize the invention at an early stage, a problem of removing damaged teeth may occur.
  • dental restorative resin compositions are composed of inorganic fillers, PP polymers, diluents, photoinitiators, and other additives, and have mechanical strength that can withstand high occlusal pressure generated when chewing food, thermal expansion similar to natural teeth, and polymerization. Requirements such as having the same appearance and texture as natural teeth, as well as physical properties of low polymerization shrinkage to prevent separation from teeth during curing, must be met.
  • 3D printing is being introduced to the dental world, and is currently being applied and used to various products such as temporary crowns, splints, surgical guides, and dentures.
  • Saliva exists in the oral cavity, there is a temperature difference depending on the food eaten, masticatory pressure is continuously applied, and abnormal forces such as bruxism and clenching are applied. It should be non-toxic.
  • the present invention has been made to solve the above-described problems, and an object of the present invention is to provide a resin material that can be used not only for dental purposes but also for general medical 3D printing resin materials, and has excellent mechanical properties, aesthetics, and antibacterial properties. is to provide
  • the present invention provides 2,2-bis [4- (2-hydroxy-3-methacryloxypropoxy) phenyl] propane ( Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), ethoxylate bisphenol A dimethacrylate (Bis-EMA), a pretreatment step of performing surface modification by irradiation with urethane dimethacrylate (UDMA); preparing a first mixed solution by adding xylitol to the triethylene glycol dimethacrylate (TEGDMA) and then stirring; 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane (Bis-GMA), ethoxylate bisphenol A dimethacrylate (Bis-EMA) and urethane dimetha
  • a second mixed solution by mixing and stirring acrylate (UDMA)
  • preparing a third mixed solution by mixing and then stirring the first mixed solution and the second mixed solution
  • stirring is performed in a vacuum atmosphere, and stirring is performed for 60 minutes at a light intensity of 600mW/cm 2 to 1,000mW/cm 2 at a temperature of 60° C. to 80° C.
  • a post-treatment step of performing surface modification by irradiating the fourth mixed solution with light corresponding to a wavelength range capable of being absorbed by the photoinitiator further comprising, In the post-treatment step, stirring is performed in a vacuum atmosphere for the same temperature and time as the pre-treatment step, but the agitation is performed at a light intensity higher than that of the pre-treatment step.
  • the light intensity in the post-processing step is 1000mW/cm 2 to 2,000mW/cm 2 .
  • stirring is performed in a vacuum atmosphere for 6 hours or more, but stirring is performed at room temperature in the summer season and at a temperature of 50 ° C to 60 ° C in the winter season.
  • the sixth mixed solution is aged at a temperature of 32° C. to 36° C. for 48 hours or longer.
  • the first mixed solution contains 2% to 10% by weight of xylitol.
  • the fifth mixed solution contains 0.2% to 3.5% by weight of the propolis compared to the fourth mixed solution.
  • the material containing the flavonoids is propolis.
  • the present invention has the following excellent effects.
  • the surface of xylitol is coated with a glycol substrate of triethylene glycol dimethacrylate (TEGDMA) and then mixed with each monomer to prepare a resin, so that xylitol has reduced antibacterial properties due to the phospahte substrate.
  • TEGDMA triethylene glycol dimethacrylate
  • the surface of each monomer or mixture is modified by irradiating light of a wavelength capable of being absorbed by the photoinitiator used in the manufacture in the same environment as the temperature generated during the resin polymerization process of 3D printing, It is possible to provide a resin having excellent photopolymerization efficiency and suitable mechanical properties as a resin material for 3D printing that can produce dental and total medical products as well as general dental restoration.
  • FIG. 1 is a flow chart of a resin manufacturing method according to an embodiment of the present invention.
  • the resin manufacturing method according to an embodiment of the present invention has an antibacterial function usable as a dental restorative and medical 3D printing resin material. It relates to a method for manufacturing a resin having a pretreatment step (S1000) for monomers to be used in the manufacture, a first mixture solution preparation step (S2000), a second mixture solution preparation step (S3000), a third mixture solution preparation step (S4000), and a fourth mixture solution preparation step (S4000). It includes a mixture solution preparation step (S5000), a post-processing step (S6000), a fifth mixture solution preparation step (S7000), a sixth mixture solution preparation step (S8000), and a aging step (S9000).
  • pretreatment is performed to modify the surface of monomers (S1000).
  • each monomer performs surface modification by irradiating light in a wavelength range capable of being absorbed by the photoinitiator according to the photoinitiator to be used for preparing the resin.
  • the photoinitiator to be used in resin production is 2,4,6-trimethylbenzoyldiphenylphosphine oxide (TPO)
  • TPO 2,4,6-trimethylbenzoyldiphenylphosphine oxide
  • the surface modification may be performed by irradiation with light having a wavelength of 350 nm to 420 nm, and light having a wavelength of 370 nm to 450 nm in the case of 1-phenyl-1,2-propanedione (PPD) and 420 nm to 420 nm in the case of camphorquinone (CQ).
  • PPD 1-phenyl-1,2-propanedione
  • CQ camphorquinone
  • Surface modification may be performed by irradiating light with a wavelength of 540 nm.
  • a pretreatment process of modifying the surface of the monomer is performed in order to minimize the unpolymerized portion of the resin.
  • the surface of the monomer is irradiated with light of a wavelength capable of being absorbed by the photoinitiator to be used in preparing the resin to perform surface modification, and the surface hydrophilicity of the surface-modified monomer is improved.
  • the pretreatment process (S1000) is preferably performed in a vacuum atmosphere, and for this purpose, a vacuum mixer capable of irradiating a light source and generating a vacuum pressure may be used.
  • stirring may be performed for 60 minutes at a light intensity of 600mW to 1,000mw/cm 2 depending on the wavelength.
  • the pretreatment process (S1000) may be performed at a vacuum pressure of 0.05mpa to 0.2mpa, and at a stirring speed of 5 RPM to 15 RPM.
  • the pretreatment process (S1000) may be performed at a temperature of 60 °C to 80 °C.
  • the pretreatment process (S1000) is performed at a temperature of 60 ° C to 80 ° C because the efficiency of surface modification is excellent when performed under the same conditions as the exothermic temperature generated during polymerization in the resin printing process.
  • the monomers are compounds having an unsaturated double bond, 2,2-bis [4- (2-hydroxy-3-methacryloxypropoxy) phenyl] propane (Bis-GMA), ethylene glycol dimethacrylate (EGDMA) ), ethylene glycol diacrylate (EDGA), triethylene glycol dimethacrylate (TEGDMA), triethylene glycol diacrylate (TEGDA), ethoxylate bisphenol A dimethacrylate (Bis-EMA), urethane dimetha Acrylates (UDMA), polyurethane diacrylate (PUDA), dipentaerythritol pentaacrylate monophosphate (PENTA), 2-hydroxyethyl methacrylate (HEMA), poly and polyalkenoic acid, biphenyl dimethacrylate (BPDM), biphenyl diacrylate BPDA, or glycerol phosphate dimethacrylate (GPDM).
  • Bis-GMA 2,2-bis [4- (2-hydroxy-3-methacryloxypropoxy)
  • TEGDMA triethylene glycol dimethacrylate
  • UDMA Toxylate bisphenol A dimethacrylate
  • TEGDMA triethylene glycol dimethacrylate
  • xylitol is added to the triethylene glycol dimethacrylate (TEGDMA) and stirred to prepare a first mixed solution (S2000).
  • TEGDMA triethylene glycol dimethacrylate
  • the xylitol is a non-cariogenic and anti-cariogenic material, and is a natural material that is more effective in preventing caries than sorbitol or other sugar alcohols.
  • xylitol which is stably used as a food and medicine, was used as an effective material for preventing caries, and a resin having excellent antibacterial properties and mechanical properties compared to conventional fluorine-containing materials was prepared.
  • the process of preparing the first mixed solution (S2000) it is preferable that 2% to 10% by weight of xylitol is added compared to the first mixed solution, which reduces the degree of polymerization by reducing the light transmission efficiency when the xylitol is added in excess. because it drops
  • the process of preparing the first mixed solution (S2000) is prepared by mixing and stirring the triethylene glycol dimethacrylate (TEGDMA) and xylitol in a vacuum atmosphere, vacuum pressure 0.05 mpa to 0.2 mpa, temperature 40 ° C to 50 ° C, It can be carried out for 120 minutes at a stirring speed of 5 RPM to 10 RPM.
  • TEGDMA triethylene glycol dimethacrylate
  • the second mixed solution preparation process (S3000) is prepared by mixing and stirring in a vacuum atmosphere, vacuum pressure 0.05mpa to 0.2mpa, temperature 40 °C to 50 °C, stirring speed 5 RPM to 10 RPM for 60 minutes.
  • a third mixed solution is prepared by mixing and stirring the first mixed solution and the second mixed solution (S4000).
  • the third mixture preparation process (S4000) is prepared by mixing and stirring in a vacuum atmosphere, vacuum pressure 0.05mpa to 0.2mpa, temperature 40 °C to 50 °C, stirring speed 5 RPM to 10 RPM for 120 minutes.
  • the 2,2-bis [4- (2-hydroxy-3-methacryloxypropoxy) phenyl] propane (Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), ethoxylate bisphenol A Mixing dimethacrylate (Bis-EMA) and urethane dimethacrylate (UDMA) and the xylitol at the same time does not perform stirring, which is a phosphate substrate of the remaining monomers except for triethylene glycol dimethacrylate (TEGDMA).
  • the xylitol is mixed with the triethylene glycol dimethacrylate (TEGDMA) to form a glycol substrate of the triethylene glycol dimethacrylate (TEGDA).
  • TEGDMA triethylene glycol dimethacrylate
  • TAGDA triethylene glycol dimethacrylate
  • a fourth mixed solution is prepared by mixing the nano-filler with the prepared third mixed solution and then stirring (S5000).
  • the nano-filler means a filler of nano-sized particles, and various known organic/inorganic fillers for improving wear resistance and mechanical strength of a resin may be manufactured and used in nano-size.
  • the fourth mixed solution manufacturing process (S5000) is prepared by mixing and stirring 2 to 10% by weight of the nano-filler with 90 to 98% by weight of the third mixed solution compared to the fourth mixed solution.
  • the fourth mixture preparation process (S5000) is prepared by mixing and stirring in a vacuum atmosphere, vacuum pressure of 0.05 mpa to 0.2 mpa, temperature of 40 °C to 50 °C, stirring speed 10 RPM to 25 RPM for 240 minutes or more can
  • a material having a flavonoid component is added to the fourth mixed solution to prepare a fifth mixed solution (S6000).
  • the flavonoid is a component having antibacterial, antiviral, and antiallergic effects
  • propolis vitamin P, hesperadin, anthocyanidin, naringenin, isoflavone, etc.
  • propolis vitamin P, hesperadin, anthocyanidin, naringenin, isoflavone, etc.
  • propolis vitamin P, hesperadin, anthocyanidin, naringenin, isoflavone, etc.
  • the fifth mixture preparation process (S6000) is prepared by mixing and stirring in a vacuum atmosphere, the vacuum pressure is 0.05 mpa to 0.2 mpa, the temperature is room temperature to 60 ° C, and the stirring speed is 5 RPM to 15 RPM for 360 minutes or more can be performed
  • the manufacturing process of the fifth mixed solution (S6000) may be prepared by varying the temperature according to the summer season and the winter season.
  • the process of preparing the fifth mixed solution may be performed at room temperature in summer and at a temperature of 50° C. to 60° C. in winter. This is because dew condensation and moisture in the chamber can occur due to the difference in temperature between the outside and the inside of the chamber of the vacuum mixer that performs stirring, which can cause product quality deterioration and contamination, as well as an obstacle to maintaining polymer softening during the mixing process. am.
  • the fifth mixture is irradiated with light in a wavelength range that can be absorbed by the photoinitiator to perform post-treatment for surface modification (S7000).
  • the post-treatment process (S7000) performs surface modification by irradiating light in a wavelength range capable of being absorbed by the photoinitiator to be used for manufacturing, but with higher light intensity than in the pre-treatment process (S1000). is performed with
  • the post-processing process (S7000) is performed in a vacuum atmosphere at a light intensity of 1,000 mW/cm 2 to 2,000 mW/cm 2 depending on the wavelength for 60 minutes, a vacuum pressure of 0.05 mpa to 0.2 mpa, a temperature of 60 °C to 80 °C, and Agitation may be performed at a speed of 5 RPM to 15 RPM.
  • the reason for performing the surface modification with a higher light intensity than in the pre-treatment process (S1000) in the post-treatment process (S7000) is to increase the light transmission efficiency because the fifth mixture is mixed with nano-fillers, and furthermore, the resin This is to maximize the surface modification of the monomers before polymerization of
  • a photoinitiator and other additives are mixed with the fifth mixed solution and stirred to prepare a sixth mixed solution (S8000).
  • a pigment for adjusting the color tone of the fissure sealant may be used.
  • a reaction accelerator may be used.
  • a diluent may be used.
  • the photoinitiator is 2,4,6-trimethyl benzoyl diphenyl phosphine (2,4,6-trimethyl benzoyl diphenyl phosphine, TPO), 1-phenyl-1,2-propane dione (1-phenyl-1 ,2-propanedione, PPD), and camphorquinone (Camphorquinoe, CQ) can be selected and used.
  • the sixth mixed solution is prepared by mixing and stirring in a vacuum atmosphere, and may be performed at a vacuum pressure of 0.05 mpa to 0.2 mpa, a temperature of 40 ° C to 50 ° C, and a stirring speed of 5 RPM to 15 RPM for 240 minutes or more.
  • the prepared sixth mixed solution is aged in a room temperature or lukewarm environment (S9000).
  • the sixth mixed solution is aged in a room temperature or lukewarm environment, and in detail, naturally aged at a temperature of 32 ° C to 36 ° C for 48 hours or more.
  • the surface of the activated nano-filler can be deposited to make resin discharge smooth, and the mechanical properties of monomers damaged by stirring can be restored in the process of making mixed solutions, and furthermore, the cross-linking of xylitol and propolis can be strengthened. It has the advantage of increasing functionality as well as mechanical properties.
  • Bis-GMA 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane
  • TEGDMA triethylene glycol dimethacrylate
  • UDMA urethane dimethacrylate
  • CQ camphorquinone
  • xylitol 1.1 g, 2.2 g, 4.4 g, and 11 g of xylitol were added to each 200 g of the pretreated triethylene glycol dimethacrylate (TEGDMA) in a vacuum mixer, and then the temperature was 50 ° C, the stirring speed was 15 RPM, and the vacuum pressure was 0.2 mpa. The mixture was stirred for 4 minutes to prepare a first mixed solution.
  • TEGDMA triethylene glycol dimethacrylate
  • the mixture was prepared by stirring in a vacuum mixer at a temperature of 50 ° C., a stirring speed of 25 RPM, and a vacuum pressure of 0.2 mpa for 24 hours.
  • Each of the prepared fourth mixed solutions was heated in a vacuum mixer at a temperature of 60° C., a stirring speed of 15 RPM, a vacuum pressure of 0.2 mpa, and a light intensity of 400 nm corresponding to the absorption wavelength of camphorquinone (CQ), a photoinitiator to be used for the preparation, at an optical intensity of 2,000 mw/ It was stirred for 60 minutes in a state irradiated with cm 2 .
  • CQ camphorquinone
  • a resin was prepared in the same manner as in Example, but in the process of preparing the first mixed solution, fluorine was added instead of xylitol to prepare the resin.
  • Comparative Examples 1 to 4 it can be classified into Comparative Examples 1 to 4 according to the content (concentration) of the composition contained in the prepared resin, and the content of each composition is shown in Table 2 below.
  • a flexural strength test was performed by making five specimens each of Examples and Comparative Examples.
  • the wavelength of light was 500 nm and the light intensity was 1,500 mw/cm 2 , and photopolymerization was performed by irradiating twice for 25 seconds.
  • the adhesive strength test of the resin according to the xylitol content of the examples and the fluorine content of the comparative example was performed, and each prepared resin was tested by making specimens using a 20x100x4mm mold.
  • a pair of specimens were made in each of Examples and Comparative Examples, and the pair of specimens were overlapped by 5 mm in the longitudinal direction, and dentin adhesive was applied uniformly to the overlapping area, and then bonded.
  • Example 4 Based on the content of each composition in Example 4, a prototype resin was prepared and the depth of polymerization was measured. In the case of not performing both the pre- and post-treatment processes during the manufacturing process, only the pre-treatment process, and the post-treatment process The depth of polymerization was measured when only the polymerization was performed and when the pretreatment and posttreatment processes were performed together.
  • the test method for measuring the depth of polymerization was carried out in accordance with the ISO 4049 depth of polymerization test method. In each case, 5 prototype resins were manufactured. When manufacturing the prototype resin, the wavelength of light was 500 nm and the light intensity was 1,500 mw/cm2 for 25 seconds. Photopolymerization was performed by irradiation twice.
  • the polymerization depth was significantly greater when the pre-treatment or post-treatment process was performed, or when both the pre-treatment process and the post-treatment process were performed than when the pre-treatment process and the post-treatment process were not performed.
  • the polymerization depth is more than twice as high as when the pre-treatment process and the post-treatment process are not performed, compared to the case where only the pre-treatment process or the post-treatment process is performed. there is.
  • Example 4 Five circular specimens of Example 4 and Comparative Example 5 were each produced with a size of 20x20x2mm, and Streptococcus mutans (S.mutans, ATCC 25175) was used to 'JIS Z 2801: 2006 Antimicrobial products Test for antimicrobial activity and efficacy' Antimicrobial activity was evaluated accordingly.
  • Streptococcus mutans S.mutans, ATCC 25175
  • the wavelength of light was 500 nm and the light intensity was 1,500 mw/cm 2 , and photopolymerization was performed by irradiating twice for 25 seconds.
  • Example 1 95% 94.3% 95.2% 93.7% 95.6% 94.6% Comparative Example 5 68.4% 67.2% 70.1% 65.9% 66.5% 67.6%
  • Example 4 As a result of the antibacterial test, referring to Table 6, 2,2-bis[4-(2-hydroxy-3-methacrylic acid) was added to the first mixture obtained by mixing xylitol and triethylene glycol dimethacrylate (TEGDMA) first.
  • the resin prepared by the resin manufacturing method of the present invention shows excellent antibacterial properties of 94% or more because xylitol and propolis are used together, and further It has the advantage of being usable as a resin material for 3D printing that can produce not only dental products but also various medical products, as it exhibits excellent mechanical properties such as flexural strength of 112 MPa or more, adhesive strength of 11.3 MPa or more, and polymerization depth of 2.1 mm or more.
  • the present invention can also be used industrially as a medical 3D printing resin material.

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  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
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  • Oral & Maxillofacial Surgery (AREA)
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  • Dental Preparations (AREA)

Abstract

La présente invention concerne un procédé destiné à la préparation de résines médicales dentaires et totales pour l'impression en 3D à l'aide de xylitol et de propolis et, plus particulièrement, un procédé destiné à la préparation, à l'aide de xylitol et de propolis, des résines médicales dentaires et totales pour l'impression en 3D qui peuvent améliorer les effets antibactériens à l'aide de matériaux naturels, le xylitol et la propolis, remplaçant des ions fluorure habituellement utilisés pour des effets antibactériens, et qui peuvent en outre fournir des propriétés mécaniques stables et excellentes.
PCT/KR2021/016273 2021-11-08 2021-11-09 Procédé destiné à la préparation de résines médicales dentaires et totales destiné à l'impression en 3d à l'aide de xylitol et de propolis Ceased WO2023080303A1 (fr)

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KR1020210152402A KR102691351B1 (ko) 2021-11-08 2021-11-08 자일리톨 및 프로폴리스를 활용한 치과용 및 토탈 의료용 3d 프린팅 레진 제조 방법
KR10-2021-0152402 2021-11-08

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KR102712379B1 (ko) 2023-11-30 2024-10-04 정인선 항균성 및 중합깊이가 향상된, 리소자임을 포함하는 심미수복용 복합레진 및 이의 제조방법
KR102842142B1 (ko) 2024-09-25 2025-08-04 정인선 강도 및 성형성이 향상된 3d 프린팅용 레진 조성물 및 이의 제조방법
KR102808527B1 (ko) * 2024-12-31 2025-05-16 정인선 3d 프린팅용 레진 조성물, 이의 제조방법 및 이를 포함하는 투명교정장치

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