IP Library Granted Patent US 11,259,995
Granted Patent B2
US 11,259,995 · App. 15/331,176 · Granted Mar 1, 2022

Dental compositions and methods of use

Inventors: Xiangxu Chen (Diamond Bar, CA); Matthew Marc Durban (Fullerton, CA)
Assignee: ZEST IP HOLDINGS, LLC
A61K6/887A61C5/00A61K6/17A61K6/60A61K6/76A61K6/77A61K6/822A61K6/836A61K6/84
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Quick Facts
Patent No.
US 11,259,995
App. No.
15/331,176
Granted
Mar 1, 2022
Kind
B2
Abstract

Provided herein are high performance dental restoration compositions, particularly two-part compositions having good self-cure times. Also provided herein are methods for restoring or filling a cavity in a tooth in an individual with the two-part dental restoration compositions. In particular, compositions provided herein are useful in restoring large cavities, including Class I and Class II cavities.

Claims (22)

1. A method for restoring a tooth in an individual, the process comprising:

a. combining a first composition with a second composition to form a mixed composition,

the first composition comprising a hydroperoxide and a copper (II) compound, the second composition comprising a thiourea and a copper (II) catalyst, and one or both of the first and/or second compositions comprising a polymerizable monomer and a filler, the polymerizable monomer comprising an ethylenic group;

b. filling in bulk a cavity of the individual with the mixed composition; and

c. curing the mixed composition under ambient conditions,

wherein the mixed composition further comprises Ytterbium Fluoride (YbF3), and the mixed composition is hardened to have a radiopacity of greater than 300% aluminum, wherein upon curing the total volume of the mixed composition within the cavity shrinks by less than 5%, wherein flexural strength is greater than 100 MPa, compression strength is greater than 150 Mpa, wherein diametral strength is greater than 30 Mpa, wherein the mixed composition further comprises an acid, wherein the amount of acid is less than 1 wt. % acid, relative to the weight of the mixed composition excluding weight of the filler, wherein the curing occurs in about 2 minutes or less, and wherein the cavity has a depth of at least 5 mm.

2. The method of claim 1 , wherein the cavity is a Class I cavity.

3. The method of claim 1 , wherein the cavity is a Class II cavity.

4. The method of claim 1 , wherein upon curing of the mixed composition within the cavity, a microleakage-free filling is formed therein.

5. The method of claim 1 , wherein the mixed composition comprises less than 0.5 wt. % acid, relative to the weight of the mixed composition excluding weight of the filler.

6. The method of claim 1 , wherein the hydroperoxide is a tertiary aryl hydroperoxide.

7. The method of claim 1 , wherein the hydroperoxide is cumene hydroperoxide.

8. The method of claim 1 , wherein the thiourea is pyridyl thiourea.

9. The method of claim 1 , wherein upon combination of the first composition and the second composition, the combined weight of the thiourea and the hydroperoxide constitute less than 10% (w/w) of the mixed composition, relative to the monomer.

10. A method for restoring a tooth in an individual, the process comprising:

a. combining a first composition with a second composition to form a mixed composition,

the first composition comprising a tertiary hydroperoxide and a copper (II) compound,

the second composition comprising pyridyl thiourea and a copper (II) catalyst, and one or both of the first and/or second compositions comprising a polymerizable monomer and a filler, the polymerizable monomer comprising an ethylenic group, upon combination of the first composition and the second composition, the combined weight of the thiourea and the hydroperoxide constituting less than 10% (w/w) in the mixed composition, relative to the monomer,

the mixed composition further comprises an acid, wherein the amount of acid is less than 1 wt. % acid, relative to the weight of the mixed composition excluding weight of the filler;

b. filling in bulk a cavity of the individual with the mixed composition; and

c. curing the mixed composition to form a microleakage free filling within the cavity, the volume of the mixed composition shrinking by less than 5% during curing wherein the mixed composition further comprises Ytterbium Fluoride (YbF3), and the mixed composition is hardened to have a radiopacity of greater than 300% aluminum, wherein flexural strength is greater than 100 MPa, compression strength is greater than 150 Mpa, wherein diametral strength is greater than 30 Mpa, wherein the curing occurs in about 2 minutes or less, and wherein the cavity has a depth of at least 5 mm.

11. The method of claim 10 , wherein the cavity is a Class II cavity.

Assignments (5)
RELEASE (REEL 045240 / FRAME 0211) Recorded Feb 8, 2023
From: ROYAL BANK OF CANADA
To: ZEST IP HOLDINGS, LLC
Reel/Frame 062685/0446 →
LIEN Recorded Mar 15, 2018
From: ZEST IP HOLDINGS, LLC
To: CITIBANK, N.A.
Reel/Frame 045223/0508 →
LIEN Recorded Mar 15, 2018
From: ZEST IP HOLDINGS, LLC
To: ROYAL BANK OF CANADA (NY BRANCH)
Reel/Frame 045240/0211 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2016
From: DANVILLE MATERIALS, LLC
To: ZEST IP HOLDINGS, LLC
Reel/Frame 040259/0060 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2016
From: CHEN, XIANGXU; DURBAN, MATTHEW MARC
To: DANVILLE MATERIALS, LLC
Reel/Frame 040091/0823 →
Continuity (4)
Continuation PCTUS2016016901 · Feb 5, 2016
Provisional Application 62260193 · Nov 25, 2015
Provisional Application 62113899 · Feb 9, 2015
Related Publication 20170035662A1 · Feb 9, 2017