IP Library Granted Patent US 11,400,031
Granted Patent B2
US 11,400,031 · App. 17/002,502 · Granted Aug 2, 2022

Dental cement compositions and methods of use

Inventors: Xiangxu Chen (Diamond Bar, CA); Matthew Marc Durban (Fullerton, CA); Lingyan Julia Wang (Irvine, CA)
Assignee: ZEST IP HOLDINGS, LLC
A61K6/889A61K6/19A61K6/40A61K6/79
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Quick Facts
Patent No.
US 11,400,031
App. No.
17/002,502
Granted
Aug 2, 2022
Kind
B2
Abstract

Provided herein are dental compositions and methods for use in dental cementation applications.

Claims (18)

1. A dental composition, wherein said composition comprises, on a surface of a dental substrate,

a bonding agent; and

a paste mixture, wherein the paste mixture was formed by mixing together a previously separated first part and a second part, and wherein the first part comprises at least one polymerizable monomer, a copper (II) compound, and at least one hydroperoxide, wherein said hydroperoxide is a tertiary hydroperoxide; and the second part comprises at least one thiourea compound, wherein said thiourea is selected from the group consisting of 1-(2-Pyridyl)-2-thiourea (PTU), 1-Benzoyl-2-thiourea (BTU), 1-Acetyl-2-thiourea (ATU), 1-(2-Tetrahydrofurfuryl)-2-thiourea (TTU), or a combination thereof; and

wherein the bonding agent comprises 8% to 16% of at least one phosphoric acid containing (meth)acrylic monomer), wherein said phosphoric acid containing (meth)acrylic monomer is selected from the group consisting of GPDM (glycerol phosphate di(meth)acrylate{(meth)acrylate=acrylate or methacrylate}), phenyl-P (phenyl methacryloxyethyl phosphate), PENTA-P (dipentaerithritol pentaacrylate phosphate), 10-MDP (methacryloyloxydecyl phosphate), HEMA-P (hydroxyethylmethacrylate phosphate), HEA-P (hydroxyethylacrylate phosphate), bis(HEMA)-P {bis(hydroxyethylmethacrylate) phosphate), bis(HEA)-P {bis(hydroxyethylacrylate) phosphate), bis((meth)acryloxypropyl)phosphate, and combinations thereof.

2. The dental composition of claim 1 , wherein bond strength of the dental bonding agent on a dental substrate is more than 15 MPa.

3. The dental composition of claim 1 , wherein the hydroperoxide is Cumene hydroperoxide (CHP).

4. The dental composition of claim 1 , wherein the thiourea is 1-(2-Pyridyl)-2-thiourea (PTU).

5. The dental composition of claim 1 , wherein said phosphoric acid containing (meth)acrylic monomer is 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP).

6. The dental composition of claim 1 , wherein the dental substrate is Zirconia.

7. The dental composition of claim 1 , wherein the bonding agent is a single bottle bonding agent.

8. A method of dental restoration, wherein said method comprises:

a first step of applying a dental bonding agent on a dental substrate, wherein the bonding agent comprises at least one phosphoric acid containing (meth)acrylic monomer, wherein said phosphoric acid containing (meth)acrylic monomer is selected from the group consisting of GPDM (glycerol phosphate di(meth)acrylate{(meth)acrylate=acrylate or methacrylate }), phenyl-P (phenyl methacryloxyethyl phosphate), PENTA-P (dipentaerithritol pentaacrylate phosphate), 10-MDP (methacryloyloxydecyl phosphate), HEMA-P (hydroxyethylmethacrylate phosphate), HEA-P (hydroxyethylacrylate phosphate), bis(HEMA)-P {bis(hydroxyethylmethacrylate) phosphate), bis(HEA)-P {bis(hydroxyethylacrylate) phosphate), bis((meth)acryloxypropyl)phosphate, and combinations thereof; and

a second step of applying paste mixture from a device having a first part and a second part separate from each other, wherein said first part and second part form the paste mixture, and wherein the paste mixture from the device comprises at least one polymerizable monomer a copper (II) compound, and at least one hydroperoxide in the first part, wherein said hydroperoxide is a tertiary hydroperoxide; and at least one thiourea compound in the second part, wherein said thiourea is selected from the group consisting of 1-(2-Pyridyl)-2-thiourea (PTU), 1-Benzoyl-2-thiourea (BTU), 1-Acetyl-2-thiourea (ATU), 1-(2-Tetrahydrofurfuryl)-2-thiourea (TTU), or a combination thereof, wherein either the first part or second part of the paste mixture further comprises a copper (II) compound, and wherein bond strength of the dental bonding agent on a dental substrate is more than 15 MPa.

9. The dental composition of claim 1 , wherein either the first part or second part of the paste mixture further comprises a copper (II) compound; wherein bond strength of the dental bonding agent on a dental substrate is more than 15 MP; wherein the hydroperoxide is Cumene hydroperoxide (CHP); wherein the thiourea is 1-(2-Pyridyl)-2-thiourea (PTU); and wherein said phosphoric acid containing (meth)acrylic monomer is 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP).

10. The method of claim 8 , wherein the bonding agent bonds effectively on a dental substrate.

11. The method of claim 8 , wherein the dental substrate is Zirconia.

12. The method of claim 8 , wherein the device is a dual-barrel syringe.

13. The dental composition of claim 1 , wherein the previously separated first part and a second part were separated in a dual-barrel syringe.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2020
From: CHEN, XIANGXU; DURBAN, MATTHEW MARC; WANG, LINGYAN JULIE
To: ZEST IP HOLDINGS, LLC
Reel/Frame 053594/0399 →