IP Library Granted Patent US 11,013,583
Granted Patent B2
US 11,013,583 · App. 16/167,591 · Granted May 25, 2021

Three dimensional fabricating material systems and methods for producing layered dental products

Inventors: Benjamin J Sun (York, PA); Dan Ammon (York, PA)
Assignee: DENTSPLY SIRONA Inc.
A61C13/0019A61C13/0004A61C13/0013A61K6/884C08G18/10C08G18/2805C08G18/73C08G18/755C08L75/04A61C2202/01B33Y70/00B33Y80/00
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Quick Facts
Patent No.
US 11,013,583
App. No.
16/167,591
Granted
May 25, 2021
Kind
B2
Abstract

A three-dimensional printed dental device formed from rapid prototyping with printable polymerizable materials, the dental device comprising a polymeric composition, wherein the polymeric composition, after curing, has at least one property of flexural strength, flexural modulus, fracture toughness, and work of fracture that is at least 20% greater in measured value at 37° C. in comparison to measured value at 23° C.

Claims (29)

1. A three-dimensional printed dental device formed from rapid prototyping with printable polymerizable materials, the dental device comprising at least one first layer having a first polymeric composition and at least one second layer having a second polymeric composition that is different from the first polymeric composition,

wherein the first polymeric composition after curing, has a flexural strength ranging from 30 to 100 MPa,

wherein the second polymeric composition after curing, has a flexural strength ranging from 120 to 200 MPa.

2. The dental device of claim 1 , wherein the fracture toughness of the cured first polymeric composition ranges from 2.4 to 2.6 MPa m 1/2 .

3. The dental device of claim 1 , wherein the fracture toughness of the cured second polymeric composition ranges from 1.8 to 2.2 MPa m 1/2 .

4. The dental device of claim 1 , wherein the dental device comprises a denture base, a denture try-in, a dental retainer, an orthodontic appliance, and a dental aligner.

5. The dental device of claim 1 , wherein the first polymeric composition comprises a polymerizable acrylic compound, a crosslinking oligomer compound, a rubber impact modifier, and a photoinitiator.

6. The dental device of claim 5 , wherein the polymerizable acrylic compound comprises a phenyl-based (meth)acrylate compound.

7. The dental device of claim 6 , wherein the phenyl-based (meth)acrylate compound is selected from the group consisting of 2-hydroxy-3-phenoxypropyl acrylate, 2-phenoxyethyl (meth)acrylate, and phenoxy benzyl (meth)acrylate.

8. The dental device of claim 5 , wherein the polymerizable acrylic compound comprises a cycloalkyl-based methacrylate compound.

9. The dental device of claim 8 , wherein the cycloalkyl-based methacrylate compound is selected from the group consisting of cyclohexyl (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, isobornyl cyclohexyl (meth)acrylate, cyclohexyl (meth)acrylate, and tri methylcyclohexyl (meth)acrylate.

10. The dental device of claim 5 wherein the polymerizable acrylic compound comprises a dimethacrylate compound.

11. The dental device of claim 10 , wherein the dimethacrylate compound is selected from the group consisting of ethoxylated bisphenol A-dimethacrylate (EBPADMA), urethane di(meth)acrylate (UDMA), diurethane dimethacrylate (DUDMA), 4,13-dioxo-3,14 dioxa-5,12-diazahexadecane-1,16-diol di(meth)acrylate, and 4,19-dioxo-3,20 dioxa-5,18-diazahexadecane-1,22-dial di(meth)acrylate.

12. The dental device of claim 5 , wherein the crosslinking oligomer compound comprises at least one urethane-functionalized (meth)acrylate-based crosslinking compound.

13. The dental device of claim 12 , wherein the at least one urethane-functionalized (meth)acrylate-based crosslinking compound comprises at least 20% by weight of the polymeric composition.

14. The dental device of claim 5 , wherein the rubber impact modifier comprises at least 2% by weight of the polymeric composition.

15. The dental device of claim 1 , wherein:

the first polymeric composition comprises:

an oligomer formed from the reaction of an isocyanate end-capped intermediate product and a hydroxyl based methacrylate;

at least one polymerizable acrylic compound selected from the group consisting of a phenoxy based methacrylate, a cyclohexyl based methacrylate, a dimethacrylate, and mixtures thereof;

a rubber impact modifier; and

a photoinitiator; and

the second polymeric composition comprises:

a urethane monomer;

a glycol dimethacrylate;

a filler including glass particles having an average particle size from about 0.1 to about 10 micrometers; and

a photoinitiator.

16. The dental device of claim 15 , wherein the fracture toughness of the cured first polymeric composition ranges from 2.4 to 2.6 MPa m 1/2 .

17. The dental device of claim 1 , wherein the fracture toughness of the cured second polymeric composition ranges from 1.8 to 2.2 MPa m 1/2 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2018
From: SUN, BENJAMIN J.; AMMON, DAN
To: DENTSPLY SIRONA INC.
Reel/Frame 047279/0966 →
Continuity (3)
Continuation 15628194 · Jun 20, 2017
Provisional Application 62352320 · Jun 20, 2016
Related Publication 20190053883A1 · Feb 21, 2019