IP Library › Granted Patent US 9,168,206
Granted Patent B2
US 9,168,206 · App. 14/479,391 · Granted Oct 27, 2015

Curable dental compositions and articles comprising polymerizable ionic liquids

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Quick Facts
Patent No.
US 9,168,206
App. No.
14/479,391
Granted
Oct 27, 2015
Kind
B2
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 (26)

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.

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.

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066435/0654 →