Dental composites

Patent metadata

Field	Value
Publication number	US-10071027-B2
Application number	US-201515126751-A
Country	US
Kind code	B2
Filing date	Mar 17, 2015
Priority date	Mar 17, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

Disclosed herein are methacrylate compounds that can be used as components of dental composites. Also disclosed are dental composites comprising the compositions and thiourethane oligomers.

First claim

The invention claimed is:

1. A compound of the formula:

wherein X is aryl or 1-4 carbon alkyl;
Y is N or C;
R 1 is H or alkyl and R 2 is no atom when Y is N;
R 1 is H or alkyl and R 2 is H or alkyl when Y is C; and
R 3 and R 4 are H or alkyl; and
provided that R 1 and R 2 are not H when X is butyl.

2. The compound of claim 1 wherein X is benzyl.

3. The compound of claim 2 wherein R 3 and R 4 are each methyl.

4. The compound of claim 3 wherein Y is N and R1 is selected from the group of H, methyl, and ethyl.

5. The compound of claim 3 wherein Y is C and R 1 and R 2 are each methyl.

6. The compound of claim 1 wherein X is butyl.

7. The compound of claim 6 wherein Y is N and R 1 is selected from methyl and ethyl.

8. The compound of claim 6 wherein Y is C and R 1 and R 2 are both methyl.

9. A dental composite composition comprising:
a resin composition comprising the compound of claim 1 ;
a thiourethane oligomer; and
a filler composition.

10. The dental composite of claim 9 wherein the thiourethane oligomer is thiol terminated.

11. The dental composite of claim 9 wherein the thiourethane oligomer is isocyanate terminated.

12. A method of preparing a dental composite, the method comprising:
contacting an isocyanate compound selected from 1,6 hexanediol-diisocyanate, 1,3-bis(1-isocyanato-1methylethylbenzen e), or bis(4-isocyanotocyclohexyl) methane with a thiol compound selected from methyl-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopriopionate, and trimethylol-tris-3-mercaptopriopionate in the presence of trimethylamine to make a thiourethane oligomer, wherein the isocyanate compound is added in sufficient excess that the thiourethane oligomer comprises pendant thiols; and
combining the thiourethane oligomer with a tertiary amine, d-camphorquinone, an inhibitor, a filler composition, and a compound of the formula:

wherein X is aryl or 1-4 carbon alkyl;
Y is N or C;
R 1 is H or alkyl and R 2 is no atom when Y is N;
R 1 is H or alkyl and R 2 is H or alkyl when Y is C; and
R 3 and R 4 are H or alkyl;

provided that R 1 and R 2 are not H when X is butyl; to form the dental composite;
wherein the thiourethane oligomer comprises at least 10% of the composite.

13. The method of claim 12 wherein the isocyanate compound is added to the thiol compound in a 2:1 ratio.

14. The method of claim 12 wherein the composite comprises at least 0.6% by weight dimethylaminobenzoate.

15. The method of claim 12 wherein the composite comprises at least 0.5% by weight 2,6-di-tert-butyl-4-methylphenol.

16. The method of claim 12 wherein the composite comprises at least 0.2% by weight d-camphorquinone.

17. The method of claim 12 wherein the composite comprises one or more of barium glass, zirconia, or silica.

18. The method of claim 12 wherein the composite comprises at least 25% filler.

19. The method of claim 12 further comprising adding benzoyl peroxide to the composite.

Assignees

• Univ Oregon Health & Science

Inventors

• Pfeifer Carmem S
• Ferracane Jack L

Classifications

• A61K6/68 Primary

  Thermochromic dyes · CPC title

• A61K6/887 Primary

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

• A61K6/818

  comprising zirconium oxide · CPC title

• A61K6/30

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

• A61K6/77

  Glass · CPC title