Curable dental compositions and articles comprising polymerizable ionic liquids

• US 9,168,206 B2
• Filed: 09/08/2014
• Issued: 10/27/2015
• 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:
  US14/479,391
• Publication Number:
  US 20140377717A1
• Time in Patent Office: 414 Days
• Field of Search: 526/263, 526/287, 526/312, 526/319, 522/167, 522/173, 433/217.1, 523/118
• US Class Current: 1/1
• 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 an ethylenically unsaturated compound with acid functionality and a polymerizable ionic liquid, wherein the polymerizable ionic liquid comprises an anion, a cation, and at least one free-radically polymerizable group 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 curable dental composition comprises 5 wt-% to 60 wt-% of the ethylenically unsaturated compound with acid functionality, based on the total weight of the unfilled curable dental composition.

3. The curable dental composition of claim 1 wherein the polymerizable ionic liquid comprises at least 25 wt-% of the total curable dental composition excluding inorganic filler.

4. The curable dental composition of claim 1 wherein the curable dental composition comprises water, alcohol or a combination thereof.

5. The curable dental composition of claim 1 wherein the curable dental composition comprises up to 10 wt-% of 2-hydroxylethyl methacrylate.

6. The curable dental composition of claim 1 wherein the curable dental composition is free of 2-hydroxylethyl methacrylate.

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

C.

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

9. The curable dental composition of claim 1 wherein the curable dental composition is a primer.

10. A method of use of a curable dental composition comprising:

providing the curable dental composition of claim 1; and

applying the composition to a tooth surface.

11. The method of claim 10 wherein the curable dental composition comprises water, alcohol or a combination thereof.

12. The method of claim 10 wherein the curable dental composition comprises up to 10 wt-% of 2-hydroxylethyl methacrylate.

13. The method of claim 10 wherein the curable dental composition is free of 2-hydroxylethyl methacrylate.

14. The method of claim 10 wherein the curable dental composition is a primer.

20. The method of claim 14 wherein the composition is cured in air.

15. A method of use of a curable dental primer composition comprising:

applying a curable dental primer composition to a tooth surface forming a primed tooth surface, wherein the curable dental primer composition comprises a polymerizable ionic liquid, comprising an anion, a cation, and at least one free-radically polymerizable group 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;

applying a curable dental adhesive composition to the primed tooth surface or a dental restoration, or a combination thereof;

contacting the dental restoration with the primed tooth surface, and

curing the primer and dental adhesive composition.

16. The method of claim 15 wherein the dental restoration is a crown, bridge, or a restoration for a dental implant.

17. The method of claim 15 wherein the curable dental adhesive composition comprises a polymerizable ionic liquid and a photoinitiator.

18. The method of claim 15 wherein the curable dental adhesive composition is free of 2-hydroxylethyl methacrylate.

19. The method of claim 15 wherein the curable dental adhesive composition is free of monomers derived from bisphenol A.