Curable dental compositions and articles comprising polymerizable ionic liquids

• US 8,853,338 B2
• Filed: 12/06/2010
• Issued: 10/07/2014
• Est. Priority Date: 12/22/2009
• Status: Active Grant

• Current Assignee: Solventum Intellectual Properties Company (Solventum Corp.)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Wang, Yizhong, Oxman, Joel D., Krepski, Larry R., Zhu, Peiwang, Lewandowski, Kevin M., Holmes, Brian N.
• Primary Examiner(s): BERNSHTEYN, MICHAEL
• Application Number:
  US13/510,991
• Publication Number:
  US 20120276503A1
• Time in Patent Office: 1,401 Days
• Field of Search: 526/263, 526/287, 526/312, 526/319, 522/167, 522/173, 433/217.1, 523/118
• US Class Current: 526/263
• CPC Class Codes: A61C 13/26 Dentures without palates; Partial dentures, e.g. bridges
• CPC Class Codes: A61C 5/70 Tooth crowns; Making thereof
• CPC Class Codes: A61K 6/20 Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: A61K 6/40 Primers for dental adhesives A61K6/30
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 220/606 and containing other heteroatoms
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers

Abstract

Presently described are curable dental compositions comprising a polymerizable ionic liquid. The polymerizable ionic liquid comprises one or more ethylenically unsaturated (e.g. free-radically polymerizable) groups. Various embodiments of curable dental compositions are described. In some embodiments, the polymerizable ionic liquid is a monofunctional polymerizable ionic liquid comprising an ethylenically unsaturated group. In other embodiments, the polymerizable ionic liquid is a multifunctional polymerizable ionic liquid comprising at least two ethylenically unsaturated groups. The curable dental compositions describe herein can be utilized as dental primers, dental adhesives, dental sealants, and dental composites. In many embodiments, the curable dental compositions further comprise an initiator such as a photoinitiator.

Claims

1. A curable dental composition comprising a polymerizable ionic liquid, wherein the dental composition is an adhesive, sealant or composite and the polymerizable ionic liquid is a multifunctional polymerizable liquid comprising an anion, a cation, and at least two free-radically polymerizable groups, wherein the free-radically polymerizable group is selected from (meth)acryl, vinyl, or vinyl ethers, and wherein the polymerizable ionic liquid has an air to nitrogen curing exotherm ratio of at least 0.90.

2. The curable dental composition of claim 1 wherein the polymerizable ionic liquid further comprises a monofunctional ionic liquid.

3. The curable dental composition of claim 1 further comprising at least one other ethylenically unsaturated monomer, oligomer, or polymer having an air to nitrogen curing exotherm ratio of no greater than 0.50.

4. The curable dental composition of claim 2 wherein the monofunctional polymerizable ionic liquid comprises a polymerizable cation.

5. The curable dental composition of claim 2 wherein the monofunctional polymerizable ionic liquid comprises a substituted imidazolium cationic group.

6. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises an anion, a cationic group, and at least two ethylenically unsaturated groups bonded to the cation.

7. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises a substituted ammonium cationic group.

8. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises a sulfonate anion.

9. The curable dental composition of claim 1 wherein the dental composition comprises at least one photoinitiator.

10. The curable dental composition of claim 1 wherein the dental composition further comprises a filler.

11. The curable dental composition of claim 3 wherein the other ethylenically unsaturated monomer, oligomer, or polymer is present in an amount of 25 wt-% to about 65 wt-% of the total unfilled dental composition.

12. The curable dental composition of claim 1 wherein the polymerizable ionic liquid has a melting point below 25°

C.

13. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises as organic anion.

14. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises a polymerizable anion.

15. A dental article comprising the cured composition of claim 1 wherein the dental article is a filling, crown, bridge, or restoration for an implant.

16. A method of making a dental restoration comprising:

providing the curable dental composition of claim 1;

forming a dental restoration from the composition; and

curing the composition.

17. A method of use of a dental composition comprising:

providing the curable dental composition of claim 1;

applying the composition to a tooth surface; and

curing the composition.

18. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises a polymerizable aromatic cation comprising at least one free-radically polymerizable group and a polymerizable anion comprising at least one free-radically polymerizable group.

19. The polymerizable ionic liquid of claim 18 wherein the polymerizable ionic liquid has the general formula:

20. The polymerizable ionic liquid of claim 18 wherein the polymerizable ionic liquid has the general formula:

21. The method of claim 17 wherein the dental composition is a dental primer, dental adhesive, or dental sealant.

22. The method of claim 16 wherein the curable dental composition is cured in air.

23. The method of claim 17 wherein the curable dental composition is cured in air.