IP Library Granted Patent US 11,998,622
Granted Patent B2
US 11,998,622 · App. 17/878,768 · Granted Jun 4, 2024

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 11,998,622
App. No.
17/878,768
Granted
Jun 4, 2024
Kind
B2
Abstract

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

Claims (37)

1. A dental composition kit comprising:

a first composition; and

a second composition to be mixed with the first composition to form a paste mixture,

wherein the first composition comprises at least one polymerizable monomer, a copper (II) compound, and a tertiary hydroperoxide,

wherein the second composition comprises a thiourea compound, and

wherein the thiourea compound 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), and combinations thereof.

2. The dental composition kit of claim 1 , further comprising a bonding agent.

3. The dental composition kit of claim 2 , wherein the bonding agent comprises 8% to 16% of a phosphoric acid containing (meth)acrylic monomer.

4. The dental composition kit of claim 3 , wherein the phosphoric acid containing (meth)acrylic monomer is selected from the group consisting of GPDM (glycerol phosphate di(meth)acrylate{(meth)acrylate=acryl ate 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.

5. The dental composition kit of claim 2 , wherein bond strength of a bond formed by a paste mixture and the bonding agent is more than 15 MPa.

6. The dental composition kit of claim 1 , wherein the tertiary hydroperoxide includes cumene hydroperoxide (CHP).

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

8. The dental composition kit of claim 3 , wherein the phosphoric acid containing (meth)acrylic monomer includes 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP).

9. A device to apply a dental paste mixture comprising:

a first chamber containing a first composition; and

a second chamber containing a second composition to be mixed with the first composition to form a paste mixture,

wherein the first composition comprises at least one polymerizable monomer, a copper (II) compound, and a tertiary hydroperoxide, and

wherein the second composition comprises a thiourea compound, wherein the thiourea compound 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), and combinations thereof.

10. The device of claim 9 , further comprising at least one extruder to extrude the first composition from the first chamber and the second composition from the second chamber.

11. The device of claim 9 , wherein the tertiary hydroperoxide includes cumene hydroperoxide (CHP).

12. The device of claim 9 , wherein the thiourea compound is 1-(2-Pyridyl)-2-thiourea (PTU).

13. A dental restoration kit comprising:

the device of claim 9 ; and

a bonding agent to form a bond with the paste mixture,

wherein bond strength of a bond formed by the paste mixture and the bonding agent is more than 15 MPa.

14. The dental restoration kit of claim 13 , wherein the bonding agent comprises 8% to 16% of a phosphoric acid containing (meth)acrylic monomer.

15. The dental restoration kit of claim 14 , wherein the phosphoric acid containing (meth)acrylic monomer is selected from the group consisting of GPDM (glycerol phosphate di(meth)acrylate{(meth)acrylate=acrylate or methacryate }), 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.

16. The dental restoration kit of claim 14 , wherein the phosphoric acid containing (meth)acrylic monomer includes 10-Methacryloyloxydecyl dihydrogen phosphate (10-MDP).

17. A method of dental restoration, wherein the method comprises:

applying a bonding agent on a dental substrate

mixing a first composition comprising at least one polymerizable monomer, a copper (II) compound, and a tertiary hydroperoxide and a second composition comprising a thiourea compound, wherein the thiourea compound 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), and combinations thereof; and

applying the mixed first and second compositions the dental substrate applied with the bonding agent.

18. The method of claim 17 , wherein the bonding agent comprises 8% to 16% of a phosphoric acid containing (meth)acrylic monomer.

19. The method of claim 18 , wherein the 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.

20. The method of claim 19 , wherein bond strength of a bond formed by the mixed first and second compositions and the bonding agent is more than 15 MPa.

21. The method of claim 17 , wherein the dental substrate includes Zirconia.

22. The method of claim 17 , wherein the tertiary hydroperoxide includes cumene hydroperoxide (CHP).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2022
From: CHEN, XIANGXU; DURBAN, MATTHEW MARC; WANG, LINGYAN JULIA
To: ZEST IP HOLDINGS, LLC
Reel/Frame 061610/0613 →