# US 2018/0049954 A1 · Photo-curable resin compositions and method of using the same in three-dimensional printing for manufacturing articifial teeth and denture base

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- Number: US 2018/0049954 A1
- Document ID: US20180049954A1
- Status: Published application
- Kind: A1
- Application number: 15/730,673
- Filed: 2017-10-11
- Published: 2018-02-22
- Earliest claimed: 2012-12-18
- Assignees: DENTCA, Inc.
- Applicants: DENTCA, Inc.
- Inventors: Jae Sik LEE
- Web page: https://patentgrep.com/patent/US20180049954A1

## CPC

- A61C 13/0004: {Computer-assisted sizing or machining of dental prostheses}
- A61C 13/0013: {using stereolithographic techniques}
- A61C 13/01: Palates or other bases or supports for the artificial teeth; Making same
- A61C 13/087: Artificial resin teeth {(A61C13/081 takes precedence; preparations A61K6/80)}
- A61C 13/10: Fastening of artificial teeth to denture palates or the like {(A61C8/0048 takes precedence)}
- A61K 6/15: Compositions characterised by their physical properties
- A61K 6/17: Particle size
- A61K 6/62: Photochemical radical initiators
- A61K 6/82: comprising hafnium oxide
- A61K 6/831: comprising non-metallic elements or compounds thereof, e.g. carbon
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K 6/889: Polycarboxylate cements; Glass ionomer cements
- A61K 6/893: Polyurethanes
- B29C 35/0805: {using electromagnetic radiation}
- B29C 64/10: Processes of additive manufacturing
- B29C 64/112: using individual droplets, e.g. from jetting heads
- B29C 64/264: Arrangements for irradiation
- B29C 64/386: Data acquisition or data processing for additive manufacturing
- B29C 71/02: Thermal after-treatment {(B29C71/0063 and B29C71/0072 take precedence)}
- B33Y 10/00: Processes of additive manufacturing
- B33Y 70/10: Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
- B33Y 80/00: Products made by additive manufacturing
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- B29C 2035/0827: {using UV radiation}
- B29C 2071/022: {Annealing}
- B29K 2033/12: {Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate}
- G16H 20/40: relating to mechanical, radiation or invasive therapies, e.g. surgery, laser therapy, dialysis or acupuncture
- A61C: DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE (non-driven toothbrushes A46B; {tongue scrapers A61B17/24;} preparations for dentistry A61K6/00; preparations for cleaning the teeth or mouth A61K8/00, A61Q11/00)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B33Y: ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- G16H: HEALTHCARE INFORMATICS, i.e. INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR THE HANDLING OR PROCESSING OF MEDICAL OR HEALTHCARE DATA

## Abstract

Photo-curable compositions for artificial teeth and denture base and a method for manufacturing denture by a three-dimensional printing system are provided. The compositions include photo-curable organic compounds, surface modified nano-sized inorganic filler, photo-initiator, colorant, and stabilizer. The composition is in a viscous liquid state having 1,000-5,200 cps at room temperature and has a low viscosity of 50-500 cps at 70° C. The composition also has an excellent curing rate for three-dimensional printing. Using the compositions, denture having a distinctive denture base and a set of artificial teeth can be manufactured via an inkjet type or digital light process type three-dimensional printing according to Computer Aided Design (CAD) data.

## Claims

### Claim 1

A composition comprising:
about 40 to about 60 weight % of at least one kind of ethoxylated difunctional bisphenol A dimethacrylate;
about 5 to about 20 weight % of at least one kind of multifunctional methacrylate;
about 20 to about 45 weight % of at least one kind of urethane dimethacrylate;
about 0 to about 15 weight % of at least one kind of silica-based fine particles having methacrylate functionalization layers and having an average particle size of less than about 200 nm;
about 0.2 to about 5.0 weight % of at least one kind of ultraviolet/visible (UV/Vis) light-photo-polymerization initiator;
at least one colorant; and
at least one stabilizer,
wherein viscosity of a liquid state mixture, including the at least one kind of ethoxylated difunctional bisphenol A dimethacrylate, the at least one kind of multifunctional methacrylate, the at least one kind of urethane dimethacrylate, the at least one kind of silica-based fine particles, the at least one kind of UV/Vis light-photo-polymerization initiator, the at least one colorant, and the at least one stabilizer, is from 1000-5200 centipoise (cps) at room temperature or 25° C. and from 50 to 500 cps at 70° C., and
wherein the viscosity is adjusted by controlling a ratio of the at least one kind of ethoxylated difunctional bisphenol A dimethacrylate, the at least one kind of multifunctional methacrylate, the at least one kind of urethane dimethacrylate, the at least one kind of silica-based fine particles, the at least one kind of UV/Vis light-photo-polymerization initiator, the at least one colorant, and the at least one stabilizer in the mixture.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the viscosity is from 1,100-4,000 cps at the room temperature.