IP Library Granted Patent US 12,209,150
Granted Patent B2
US 12,209,150 · App. 17/665,786 · Granted Jan 28, 2025

Photocurable resin composition with low shrinkage and high accuracy for use in additive manufacturing processes

Inventors: Long Ling (Anaheim, CA); Nahal Taremi (Santa Ana, CA)
Assignee: James R. Glidewell Dental Ceramics, Inc.
C08F2/50B29C64/129B33Y10/00B33Y70/00C08F222/102C08K5/132C08K5/45C08K5/5397B29L2031/7536B33Y80/00
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,209,150
App. No.
17/665,786
Granted
Jan 28, 2025
Kind
B2
Abstract

A photo-curable resin composition is suitable for the fabrication of 3D printed objects via digital light processing (DLP) or stereolithography (SLA). The photo-curable resin composition can provide 3D printed objects having lower volumetric shrinkage, high accuracy and favorable mechanical strength for dental application such as building models, implant templates, surgical guides, night guard/occlusal splints, dentures, clear aligners, and temporary restorations.

Claims (18)

1. A photo-polymerizable resin composition used for the fabrication of 3D printed objects for dental application consisting of:

A) a photo-polymerizable structural monomer with ethylenically unsaturated groups consisting of bisphenol A glycidyl methacrylate (BisGMA), ethoxylated bisphenol A dimethacrylate (EBPADMA), or a combination of BisGMA and EBPADMA;

B) a photo-polymerizable diluent monomer consisting of triethyleneglycol dimethacrylate (TEGDMA);

C) a photo-initiator for photo-polymerization;

D) a light stabilizer/blocker; and

E) optionally, an inhibitor;

wherein the photo-curable resin does not include any fillers, and wherein the resin when cured has a volumetric shrinkage of less than 8.5% and a 3D deviation of less than 75 μm.

2. The resin composition of claim 1 , wherein the structural monomer consists of EBPADMA having 2 to 6 units of ethoxylation.

3. The resin composition of claim 1 , wherein the structural monomer consists of EBPADMA having 2 to 4 units of ethoxylation with BisGMA.

4. The resin composition of claim 1 , wherein the photo-initiator is selected from bis (2,4,6-trimethybenzoyl)-phenylphosphine oxide, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate, benzoyldiphenylphosphine oxide, benzil dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-2-methyl propiophenone, or a combination of two or more thereof.

5. The resin composition of claim 1 , wherein the light stabilizer/blocker is selected from 2-hydroxy-4-methoxybenzophenone, 2, 4-dihydroxy benzophenone, 2,5-Bis (5-tert-butyl-2-benzoxazolyl) thiophene, or a combination of two or more thereof.

6. The resin composition of claim 1 , consisting of:

i. about 70-95 wt. % of the structural monomer;

ii. about 5-30 wt. % of the diluent monomer;

iii. about 0.05-3 wt. % of the photo-initiator; and

iv. about 0.005-2 wt. % of UV stabilizer/blocker.

7. The resin composition of claim 1 , wherein the photo-curable resin when cured has flexural strength greater than 70 MPa.

8. The resin composition of claim 1 , wherein the photo-curable resin when cured has tensile strength of 43 MPa or higher.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2022
From: LING, LONG; TAREMI, NAHAL
To: JAMES R. GLIDEWELL DENTAL CERAMICS, INC.
Reel/Frame 059669/0205 →
Continuity (2)
Provisional Application 63147023 · Feb 8, 2021
Related Publication 20220251250A1 · Aug 11, 2022
References Cited (28)
US 4734333A · Leo et al. · 1988 [cited by applicant]
US 5981616A · Yamamura et al. · 1999 [cited by applicant]
US 6025114A · Popat · 2000 [cited by examiner]
US 6200732B1 · Tamura et al. · 2001 [cited by applicant]
US 6451958B1 · Fan et al. · 2002 [cited by applicant]
US 6709271B2 · Yin · 2004 [cited by examiner]
US 7357637B2 · Liechtung · 2008 [cited by applicant]
US 8513326B2 · Trujillo-Lemon · 2013 [cited by examiner]
US 9902860B1 · Li et al. · 2018 [cited by applicant]
US 10788753B2 · Cole · 2020 [cited by applicant]
US 10849724B2 · Sun et al. · 2020 [cited by applicant]
US 11225535B2 · Klun et al. · 2022 [cited by applicant]
US 20100144919A1 · Borbely · 2010 [cited by examiner]
US 20140239527A1 · Lee · 2014 [cited by examiner]
US 20170158803A1 · Amin et al. · 2017 [cited by applicant]
US 20170196657A1 · Nixon et al. · 2017 [cited by applicant]
US 20190282335A1 · Chen et al. · 2019 [cited by applicant]
US 20200247932A1 · Share et al. · 2020 [cited by applicant]
US 20210317297A1 · Jena · 2021 [cited by examiner]
US 20220251250A1 · Ling et al. · 2022 [cited by applicant]
US 20220325049A1 · Lublin · 2022 [cited by applicant]
CN 108504277A · 2018 [cited by applicant]
WO 2015198493A1 · 2015 [cited by applicant]
WO 2020080643A1 · 2020 [cited by applicant]
Zhang et al. Influence of the three-dimensional printing technique and printing layer thickness on model accuracy. J Orofac Orthop 80, 194-204 (2019) (Year: 2019). [cited by examiner]
Marghalani, H.Y. (2015). Resin-Based Dental Composite Materials. In: Antoniac, I. (eds) Handbook of Bioceramics and Biocomposites. Springer, Cham (Year: 2015). [cited by examiner]
Kaisarly et al. Polymerization shrinkage assessment of dental resin composites: a literature review. Odontology 104, 257-270 (2016) (Year: 2016). [cited by examiner]
Lee et al. Accuracy of three-dimensional printing for manufacturing replica teeth. Korean J Orthodontics 2015;45(5):217-225 (Year: 2015). [cited by examiner]