Photo-curable resin compositions and method of using the same in three-dimensional printing for manufacturing artificial teeth and denture base

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 2000-5200 centipoise (cps) at room temperature 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.

A method for manufacturing a denture using a three-dimensional printer and light-curable materials based on denture information, the method comprising:

• manufacturing a denture base from a first composition;
• and
• manufacturing at least one artificial tooth from a second composition that is different from the first composition,
• wherein:
• the first composition comprises:
• 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 a 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 first 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 2000-5200 centipoise (cps) at room temperature and from 50 to 500 cps at 70° C., and
• wherein the viscosity of the first liquid state mixture 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;
• and
• the second composition comprises:
• about 50 to about 75 weight % of at least one kind of ethoxylated difunctional bisphenol A dimethacrylate;
• about 5 to about 15 weight % of at least one kind of multifunctional methacrylate having two or more methacryloxy groups;
• about 15 to about 35 weight % of at least one kind of urethane dimethacrylate;
• about 5 to about 35 weight % of at least one kind of a silica-based fine particles having or 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 second 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 2000-5200 centipoise (cps) at room temperature and from 50 to 500 cps at 70° C., and
• wherein the viscosity of the second liquid state mixture 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.