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WO2025116270A1 - Composition de restauration photodurcissable comprenant une composition céramique et une prothèse dentaire utilisant une imprimante 3d - Google Patents

Composition de restauration photodurcissable comprenant une composition céramique et une prothèse dentaire utilisant une imprimante 3d Download PDF

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Publication number
WO2025116270A1
WO2025116270A1 PCT/KR2024/015520 KR2024015520W WO2025116270A1 WO 2025116270 A1 WO2025116270 A1 WO 2025116270A1 KR 2024015520 W KR2024015520 W KR 2024015520W WO 2025116270 A1 WO2025116270 A1 WO 2025116270A1
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Prior art keywords
composition
weight
parts
photocurable
ceramic composition
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PCT/KR2024/015520
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English (en)
Korean (ko)
Inventor
이상혁
고지현
이찬희
강로라
유호균
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Ez Ceramics Forum Co Ltd
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Ez Ceramics Forum Co Ltd
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Publication of WO2025116270A1 publication Critical patent/WO2025116270A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C13/00—Dental prostheses; Making same
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C13/00—Dental prostheses; Making same
    • A61C13/08—Artificial teeth; Making same
    • A61C13/083—Porcelain or ceramic teeth
    • 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
    • A61K6/62—Photochemical radical initiators
    • 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
    • A61K6/64—Thermal radical initiators
    • 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
    • A61K6/802—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics
    • 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
    • A61K6/802—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics
    • A61K6/818—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics comprising zirconium oxide

Definitions

  • the present invention relates to a photocurable restorative composition comprising a ceramic composition and a dental prosthesis using a 3D printer, and more specifically, to a photocurable restorative composition manufactured including a silane-treated ceramic composition, and a dental prosthesis manufactured using the photocurable restorative composition using a 3D printer.
  • dental prosthesis An artificial replacement for a tooth or dental tissue is called a dental prosthesis.
  • Dental prosthetics include removable dentures and non-removable crowns and bridges.
  • Polymers, metals, alloys, ceramics, and composite materials are used as materials for dental prosthetics, and generally, precious metal materials such as gold, non-precious metal alloy materials such as nickel-chromium alloys or cobalt-chromium alloys, and ceramic materials are widely used.
  • zirconia As a ceramic material, the use of dental prosthetics using zirconia is increasing due to its mechanical performance such as strength and durability; however, zirconia has limitations in terms of aesthetics due to its cloudy surface color.
  • dental prostheses manufactured by coating a porcelain layer on a zirconia core are becoming more preferred over dental prostheses manufactured using only zirconia as a material.
  • Patent Document 1 KR 2023-0073986
  • the present invention was derived from the aforementioned necessity, and its purpose is to obtain a dental prosthesis having improved gloss, superior heat resistance and hardness, and improved uniformity and reliability.
  • the photocurable restorative composition according to the embodiment may include a mixture of a silane-treated ceramic composition and a photoinitiator in a weight ratio of 1:1 to 20:1.
  • the above silane-treated ceramic composition can be manufactured by mixing a silane solution into a ceramic composition including a silica mixture, ZrO 2, and BaO.
  • the above ZrO 2 may be included in an amount of 1 to 20 parts by weight per 100 parts by weight of the silica mixture.
  • the above BaO may be included in an amount of 1 to 20 parts by weight per 100 parts by weight of the silica mixture.
  • the above ceramic composition and the silane solution can be mixed and dried at a weight ratio of 1:1 to 5:1 to produce the silane-treated ceramic composition.
  • the above photoinitiator mixture may include an acrylate monomer, a photoinitiator, and a thermal initiator.
  • the above-mentioned photoinitiator may be included in an amount of 0.1 to 4 parts by weight per 100 parts by weight of the above-mentioned acrylate monomer.
  • the above photoinitiator includes TPO, and the TPO can be included in an amount of 0.1 to 3 parts by weight based on 100 parts by weight of the acrylate monomer.
  • the above photoinitiator comprises BAPO, and the BAPO may be included in an amount of 0.1 to 1 part by weight per 100 parts by weight of the acrylate monomer.
  • the above thermal initiator may be included in an amount of 0.1 to 5 parts by weight per 100 parts by weight of the acrylate monomer.
  • a method for manufacturing a photocurable restorative composition comprises the steps of mixing and drying a silane solution into a ceramic composition including a silica mixture, ZrO 2, and BaO to manufacture a silane-treated ceramic composition;
  • the method may include a step of preparing a photocurable restorative composition by adding a photoinitiator mixture to the silane-treated ceramic composition at a weight ratio of 1:1 to 20:1.
  • a method for manufacturing a dental prosthesis comprises the steps of forming a core by laminating and curing a photocurable restorative composition manufactured by the above method using a 3D printer;
  • a step of performing heat treatment on the above core may be included.
  • a dental prosthesis according to an embodiment may be manufactured according to the above method.
  • a dental prosthesis having improved gloss, superior heat resistance and hardness, and improved uniformity and reliability can be obtained.
  • Figure 1 is a graph showing the relationship between temperature and hardness during the manufacture of dental prosthetics according to an embodiment.
  • Figures 2 to 4 are examples of dental prostheses manufactured according to embodiments of the present invention.
  • the above photocurable restorative composition means a restorative composition including a material that is cured by light irradiation, and may include a silane-treated ceramic composition and a photoinitiator mixture in a weight ratio of 1:1 to 20:1, preferably 1:1 to 10:1, and more preferably 1:1 to 4:1.
  • the content of the silane-treated ceramic composition according to the present invention is within the above range, the crosslinking density after photo-curing is increased, the gloss of the dental composition is improved, excellent heat resistance reliability is secured, uniformity is further improved, and the dielectric constant can be significantly reduced.
  • the uniformity may be poor, long-term reliability may be low, or the developability of the photocurable restorative composition may be deteriorated due to the high refractive index of silica.
  • the dielectric constant may increase significantly, and workability may be reduced because sufficient hardness and stiffness are not secured.
  • the method for producing the photocurable restorative composition comprises the steps of mixing and drying a silane solution into a ceramic composition including a silica mixture, ZrO 2, and BaO to produce a silane-treated ceramic composition;
  • the silica mixture may include first silica (SiO 2 ) particles and second silica (SiO 2 ) particles having different average particle diameters.
  • the above first silica particles may have an average particle diameter of 0.1 ⁇ m to 1 ⁇ m, preferably 0.1 ⁇ m to 0.7 ⁇ m, and more preferably 0.1 ⁇ m to 0.5 ⁇ m.
  • the above second silica particles may have an average particle diameter of 0.1 ⁇ m to 50 ⁇ m, preferably 0.1 ⁇ m to 40 ⁇ m, and more preferably 0.1 ⁇ m to 20 ⁇ m.
  • the first silica particles and the second silica particles may be included in the silica mixture in a weight ratio of 9:1, preferably 8:2, more preferably 7:3.
  • the packing density per unit area is maximized, and the physical structure of the final product can be configured more densely.
  • the ZrO 2 may be included in an amount of 1 to 20 parts by weight, preferably 1 to 10 parts by weight, and more preferably 2 to 7 parts by weight, relative to 100 parts by weight of the silica mixture.
  • the strength of the final product can be further improved.
  • the above ZrO 2 may have an average particle size of 0.1 ⁇ m to 1 ⁇ m, preferably 0.1 ⁇ m to 0.5 ⁇ m, and more preferably 0.1 ⁇ m to 0.3 ⁇ m.
  • the BaO may be included in an amount of 1 to 20 parts by weight, preferably 1 to 10 parts by weight, and more preferably 2 to 7 parts by weight, per 100 parts by weight of the silica mixture.
  • Heat resistance can be improved by including the above BaO in a numerical value within the above range.
  • the above silane-treated (coated) ceramic composition may be manufactured by mixing and drying the ceramic composition and the silane solution in a weight ratio of 1:1 to 5:1, preferably in a weight ratio of 1:1 to 3:1, and more preferably in a weight ratio of 1:1 to 1.5:1 (through the mixing and drying process).
  • the above silane solution can be prepared by mixing a silane coupling agent and a solvent.
  • Silane coupling agents include vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, At least one selected from the group consisting
  • the above silane solution may contain 1 to 20 silane coupling agents, preferably 1 to 10 silane coupling agents, and more preferably 1 to 8 silane coupling agents per 100 parts by weight of the silane solution.
  • the shape of the final product can be well fixed without collapsing.
  • the silane-treated ceramic composition may include all/part of the silane-treated ceramic composition initially obtained by mixing and drying in step (a).
  • the photoinitiator mixture is defined as a mixture including a photoinitiator, and may include an acrylate monomer, a photoinitiator, and a thermal initiator.
  • the above acrylate monomers are bisphenol A-glycidyl methacrylate (Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), ethylene glycol dimethacrylate (TGDMA), ethoxylated bisphenol A dimethacrylate (Bis-EMA), urethane dimethacrylate (UDMA), dipentaerythritol pentacrylate monophosphate (PENTA), 2-hydroxyethyl methacrylate (HEMA), polyalkenic acid, biphenyl dimethacrylate (BPDM), glycerol phosphate dimethacrylate (GPDM), and 1,6-hexanediol diacrylate. It can be characterized by at least one selected from the group consisting of diacrylate.
  • the above acrylate monomer may include UDMA, TEGDMA, and HEMA in a weight ratio of 1:1:1 to 10:10:1, preferably 1:1:1 to 9:8:1.
  • the above photoinitiator is a component that induces photopolymerization by being excited by ultraviolet (UV) light or visible light, and any photoinitiator commonly known in the art can be used in the present invention without limitation.
  • UV ultraviolet
  • visible light any photoinitiator commonly known in the art can be used in the present invention without limitation.
  • the photoinitiator may be characterized by including at least one selected from the group consisting of camphorquinone, 2-(dimethylamino methacrylates), phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO), and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO).
  • camphorquinone 2-(dimethylamino methacrylates)
  • BAPO phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide
  • TPO diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide
  • the photoinitiator may be included in an amount of 0.1 to 4 parts by weight, 0.1 to 2 parts by weight, and more preferably 0.1 to 1 part by weight, relative to 100 parts by weight of the acrylate monomer.
  • the above photoinitiator may include BAPO and TPO.
  • the above BAPO may be included in an amount of 0.1 to 1 part by weight, preferably 0.1 to 0.5 part by weight, and more preferably 0.1 to 0.3 part by weight, relative to 100 parts by weight of the above acrylate monomer.
  • the above TPO may be included in an amount of 0.1 to 3 parts by weight, preferably 0.1 to 1 part by weight, and more preferably 0.1 to 0.5 parts by weight, relative to 100 parts by weight of the above acrylate monomer.
  • the above thermal initiator is an initiator used in thermal polymerization, and at least one selected from the group consisting of benzoyl peroxide (BPO) and 2,2-azobisisobutyronitrile (AIBN) can be used.
  • BPO benzoyl peroxide
  • AIBN 2,2-azobisisobutyronitrile
  • the above thermal initiator may be included in an amount of 0.1 to 5 parts by weight, preferably 0.1 to 3 parts by weight, and more preferably 0.1 to 1 part by weight, relative to 100 parts by weight of the acrylate monomer.
  • the silane-treated ceramic composition and the photoinitiator mixture can be included in a weight ratio of 1:1 to 20:1, preferably 1:1 to 10:1, more preferably 1:1 to 4:1, to produce a photocurable restorative composition.
  • the content of the silane-treated ceramic composition according to the present invention is within the above range, the crosslinking density after photo-curing is increased, the gloss of the dental composition is improved, excellent heat resistance reliability is secured, uniformity is further improved, and the dielectric constant can be significantly reduced.
  • the uniformity may be poor, long-term reliability may be low, or the developability of the photocurable restorative composition may be deteriorated due to the high refractive index of silica.
  • the dielectric constant may increase significantly, and workability may be reduced because sufficient hardness and stiffness are not secured.
  • a method for manufacturing a dental prosthesis comprises the steps of forming a core by laminating and curing a photocurable restorative composition manufactured by the above method using a 3D printer;
  • a step of performing heat treatment on the above core may be included.
  • the shape of the above core can be designed based on a scan of a tooth model.
  • the above core is the part that fills the space by coming into contact with the tooth to be restored, supports the remaining tooth structure, strengthens the retention of the prosthesis, and provides insulation to the tooth nerve area.
  • the core can be designed by scanning a tooth model manufactured by taking a direct impression of a natural tooth with an extraoral scanner, and then designing and correcting the model using a CAD (Computer Aided Design) program.
  • CAD Computer Aided Design
  • the design can be made by scanning a tooth model manufactured using an intraoral scanner with an extraoral scanner, and then designing and correcting it using a CAD (Computer Aided Design) program.
  • CAD Computer Aided Design
  • the above curing can be accomplished by irradiating ultraviolet (UV) light, visible light, laser, etc., and preferably by irradiating ultraviolet (UV) light.
  • UV ultraviolet
  • the step of forming the core may be characterized by being performed by layering and curing the photocurable restorative composition using a 3D printer.
  • the photocurable restorative composition be in the form of a slurry. Accordingly, the photocurable restorative composition can be manufactured into a slurry of an appropriate viscosity by supplying moisture using distilled water when necessary, and then injected into the slurry tube of the 3D printer and sprayed.
  • the above 3D printer can use a DLP (Digital Light Processing), SLA (Stereolithography Apparatus), or SLS (Selective Laser Sintering) method, and preferably a Poly-Jet method that combines FDM (Fused Deposition Modeling) and DLP.
  • DLP Digital Light Processing
  • SLA Stepolithography Apparatus
  • SLS Selective Laser Sintering
  • the DLP method is a method of creating a molded object by irradiating ultraviolet light with a beam projector onto a photocurable polymer in a liquid tank. Since the polymer is hardened by irradiating light, the strength of the printed molded object is low, but the work speed is fast and the surface of the molded object is smooth and precise.
  • the SLA method is similar to the DLP method, but the difference is that DLP uses ultraviolet light using a beam projector, whereas the SLA method uses laser light.
  • the SLS method is a method of obtaining a molded body by irradiating a laser on a powdered material to melt all or part of the powder particles and induce bonding between the particles.
  • Poly-Jet method is a printing method that sprays materials through a nozzle like FDM method and then solidifies them by irradiating them with ultraviolet light like DLP method.
  • the printing materials used are mainly liquid or solid polymer printing materials, and have the advantage of being economical while ensuring high levels of precision and productivity.
  • the above heat treatment may be characterized by being performed by heating the core to 135°C to 145°C, preferably 137°C to 142°C, and then drying and cooling.
  • a dental prosthesis having a hardness of 80 Hv to 90 Hv, preferably 83 Hv to 86 Hv, can be obtained.
  • the above heat treatment conditions correspond to conditions that can secure the core's own strength.
  • a ceramic composition was prepared including a silica mixture including 70 g of first silica particles having an average particle size of 0.3 ⁇ m and 30 g of second silica particles having an average particle size of 10 ⁇ m, 5 g of ZrO 2 (zirconium oxide) having an average particle size of 0.13 ⁇ m, and 5 g of BaO (barium oxide).
  • Urethane dimethacrylate 50g Triethylene glycol dimethacrylate (TEGDMA) 40g 2-hydroxyethyl methacrylate (HEMA) 10g Diphenyl(2,4,6-Trimethylbenzoyl)Phosphine Oxide (TPO) 0.3g Phenylbis(2,4,6-trimethylbenzoyl)phosphineoxide ((BAPO) Phenylbis(2,4,6-trimethylbenzoyl) phosphineoxide) 0.1g Benzoyl Peroxide (BPO) 0.5g
  • CAD Computer Aided Design
  • the photocurable restorative composition of Manufacturing Example 1 was placed in a slurry tube of a 3D printer, and the photocurable restorative composition was laminated using a 3D printer (Illumina), and cured by UV irradiation (at 405 nm for 30 seconds) to form a core.
  • a 3D printer Illumina
  • UV irradiation at 405 nm for 30 seconds
  • the printed core was placed in a ceramic sintering furnace, heated to 140°C, dried, and cooled to obtain a sintered core.
  • Comparative Example 1 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 120°C.
  • Comparative Example 2 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 130°C.
  • Comparative Example 3 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 150°C.
  • Comparative Example 3 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 160°C.
  • Comparative Example 3 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 170°C.
  • Comparative Example 3 produced a dental prosthesis using the same method as Manufacturing Example 2, except that the temperature of the heat applied to the core in Manufacturing Example 2 was set to 180°C.
  • the strength of the manufactured dental prosthesis was measured through a Vickers Hardness Test, and the results are shown in Table 2 and Figure 1 below.

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Ceramic Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Biophysics (AREA)
  • Dental Preparations (AREA)
  • Manufacturing & Machinery (AREA)

Abstract

La présente invention concerne : une composition de restauration photodurcissable comprenant une composition céramique ; et une prothèse dentaire utilisant une imprimante 3D. Plus précisément, la présente invention concerne : une composition de restauration photodurcissable comprenant une composition céramique traitée au silane ; et une prothèse dentaire fabriquée à l'aide de la composition de restauration photodurcissable au moyen d'une imprimante 3D. Selon la présente invention, il est possible d'obtenir une prothèse dentaire présentant un brillant amélioré, une excellente résistance thermique et une excellente dureté, ainsi qu'une uniformité et une fiabilité améliorées.
PCT/KR2024/015520 2023-11-28 2024-10-14 Composition de restauration photodurcissable comprenant une composition céramique et une prothèse dentaire utilisant une imprimante 3d Pending WO2025116270A1 (fr)

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KR10-2023-0168008 2023-11-28
KR1020230168008A KR102708301B1 (ko) 2023-11-28 2023-11-28 세라믹 조성물을 포함하는 광경화성 수복 조성물 및 3d 프린터를 이용한 치과 보철물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102708301B1 (ko) * 2023-11-28 2024-09-23 주식회사 이지세라믹연구회 세라믹 조성물을 포함하는 광경화성 수복 조성물 및 3d 프린터를 이용한 치과 보철물

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Publication number Priority date Publication date Assignee Title
KR20160055727A (ko) * 2013-04-18 2016-05-18 덴카, 인크. 광경화성 수지 조성물 및 인공 치아 및 의치상 제조를 위한 3차원 인쇄에 이를 이용하는 방법
WO2022087464A1 (fr) * 2020-10-23 2022-04-28 Hybrid Ceramic Composition polymérisable pour impression 3d de dent et de matériau dentaire
KR20220094487A (ko) * 2020-12-29 2022-07-06 주식회사 올덴솔루션 리튬디실리케이트 결정화 유리 조성물을 포함하는 치과 보철물의 제조방법
KR20220096250A (ko) * 2020-12-30 2022-07-07 주식회사 쿠보텍 고강도 및 고심미성의 치아 수복용 강화 복합소재 및 그 제조방법
KR20230122736A (ko) * 2022-02-15 2023-08-22 주식회사 하스 적층가공형 하이브리드 세라믹 치과 보철물
KR102708301B1 (ko) * 2023-11-28 2024-09-23 주식회사 이지세라믹연구회 세라믹 조성물을 포함하는 광경화성 수복 조성물 및 3d 프린터를 이용한 치과 보철물

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160055727A (ko) * 2013-04-18 2016-05-18 덴카, 인크. 광경화성 수지 조성물 및 인공 치아 및 의치상 제조를 위한 3차원 인쇄에 이를 이용하는 방법
WO2022087464A1 (fr) * 2020-10-23 2022-04-28 Hybrid Ceramic Composition polymérisable pour impression 3d de dent et de matériau dentaire
KR20220094487A (ko) * 2020-12-29 2022-07-06 주식회사 올덴솔루션 리튬디실리케이트 결정화 유리 조성물을 포함하는 치과 보철물의 제조방법
KR20220096250A (ko) * 2020-12-30 2022-07-07 주식회사 쿠보텍 고강도 및 고심미성의 치아 수복용 강화 복합소재 및 그 제조방법
KR20230122736A (ko) * 2022-02-15 2023-08-22 주식회사 하스 적층가공형 하이브리드 세라믹 치과 보철물
KR102708301B1 (ko) * 2023-11-28 2024-09-23 주식회사 이지세라믹연구회 세라믹 조성물을 포함하는 광경화성 수복 조성물 및 3d 프린터를 이용한 치과 보철물

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