Dual-curing dental compositions with high stability

Patent metadata

Field	Value
Publication number	US-11020324-B2
Application number	US-201916285708-A
Country	US
Kind code	B2
Filing date	Feb 26, 2019
Priority date	Feb 26, 2019
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

Two-part dual-curing dental compositions containing a hydroperoxide, a thiourea derivative and an acetylacetonate salt as redox radical initiator system, are provided. The dental compositions may contain an acidic monomer for use as a self-adhesive cement. The dental compositions possess enhanced shelf-life stability for working/setting time, bonding strength, color stability, slump, flexural strength/modulus, and when kept at 50° C. for more than 16 weeks.

First claim

We claim:

1. A two-part curable dental composition comprising
a) a first part comprising
a polymerizable monomer having an acidic functional group,
a first polymerizable monomer having no acidic functional group, and
a hydroperoxide compound; and

b) a second part comprising
a second polymerizable monomer having no acidic functional group,
a composition comprising [4-(trifluoromethyl) phenyl]thiourea, and
an acetylacetonate compound,

wherein the first part, the second part, or both, optionally comprise a filler.

2. The two-part dental composition of claim 1 , where the first part is a paste and the second part is a paste.

3. The two-part dental composition of claim 1 , wherein the polymerizable monomer having an acidic functional group comprises methacryloyloxydecyl phosphate, glyceryldimethacrylate phosphate, hydroxyethylmethacrylate phosphate, phenyl methacryloxyethyl phosphate (phenyl-P), dipentaerythritol pentaacrylate phosphate, or bis(hydroxyethylmethacrylate) phosphate, or a combination thereof.

4. The two-part dental composition of claim 1 , wherein the polymerizable monomer having an acidic functional group comprises 4-methacryloxyethyl trimellitic acid, or 10-methacryloxydecyl malonic acid, or a combination thereof.

5. The two-part dental composition of claim 1 , wherein the polymerizable monomer having an acidic functional group has a concentration of 1% by weight to 20% by weight of the first part.

6. The two-part dental composition of claim 1 , wherein the hydroperoxide compound comprises cumene hydroperoxide, t-butyl hydroperoxide, p-diisopropylbenzene hydroperoxide, t-amyl hydroperoxide, pinane hydroperoxide, p-menthane hydroperoxide, or 1,1,3,3-tetramethylbutyl hydroperoxide, or a combination thereof.

7. The two-part dental composition of claim 1 , wherein the hydroperoxide compound has a concentration of 0.1% by weight to 5% by weight of the first part.

8. The two-part dental composition of claim 1 , wherein the second part comprises vanadyl acetylacetonate, vanadium(III) acetylacetonate or copper(II) acetylacetonate, or a combination thereof.

9. The two-part dental composition of claim 1 , wherein the first part comprises a filler, and the second part comprises a second filler that is different from the first filler.

10. The two-part dental composition of claim 1 , wherein the composition is a dual-curing composition and the second part further comprises a photoinitiator.

11. The two-part dental composition of claim 1 , wherein the composition further comprises a stabilizer.

12. A dental device having a two-part dental composition comprising
a dispensing syringe comprising at least two compartments,
a dental composition comprising
i) a first paste in a first compartment comprising
a polymerizable acidic monomer,
a polymerizable non-acidic monomer, and
a hydroperoxide compound; and

ii) a second paste in a second compartment that is separated from the first compartment,
comprising
a non-acidic monomer,
a photoinitiator system,
a composition comprising [4-(trifluoromethyl) phenyl]thiourea
an acetylacetonate salt,

wherein the dental composition comprises at least one filler, and
wherein the dental composition, stored for at least 16 weeks at 50° C., is curable upon mixing the first paste and the second paste.

13. The dental device of claim 12 , wherein the two-part dental composition, stored for at least 16 weeks at 50° C., has a working time and a setting time of at least 90 seconds and less than 10 minutes.

14. The dental device of claim 12 , wherein the two-part dental composition stored for at least 16 weeks at 50° C. has a delta E of less than 3.

15. The dental device of claim 12 , wherein the hydroperoxide compound comprises cumene hydroperoxide, t-butyl hydroperoxide, p-diisopropylbenzene hydroperoxide, t-amyl hydroperoxide, pinane hydroperoxide, p-menthane hydroperoxide, or 1,1,3,3-tetramethylbutyl hydroperoxide, or a combination thereof.

16. A curable dental composition comprising
a) a first paste comprising:
at least one polymerizable monomer having an acidic functional group,
at least one polymerizable monomer having no acidic functional group, and
a hydroperoxide compound; and

b) a second paste comprising
at least one polymerizable monomer having no acidic functional group,
a composition comprising [4-(trifluoromethyl)phenyl]thiourea
a photoinitiator, and
an acetylacetonate compound,

wherein the dental composition further comprises a filler.

17. The curable dental composition of claim 16 , wherein the at least one polymerizable monomer having an acidic functional group comprises a phosphate group, a carboxylic acid group, or sulfonic acid group.

Assignees

• Glidewell James R Dental Ceramics Inc

Inventors

• Ling Long
• Chen Yulin
• Ma Yumeng

Classifications

• A61K6/30

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• A61K6/77

  Glass · CPC title

• A61K6/61

  Cationic, anionic or redox initiators · CPC title

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/76

  comprising silicon-containing compounds · CPC title