Antimicrobial monomers and polymers, and their use in dental devices

Patent metadata

Field	Value
Publication number	US-9920062-B2
Application number	US-201414782936-A
Country	US
Kind code	B2
Filing date	Apr 8, 2014
Priority date	Apr 9, 2013
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

Antimicrobial compounds are provided that are polymerizable. The compounds include monomers with antimicrobial properties. The compounds have cross-linking properties and are hydrolytically stable. The compounds may be utilized in dental and/or medical applications, including dental composites, dentures, bonding agents, sealants, resins and medical devices.

First claim

What is claimed is:

1. A compound having either of the following structures:

wherein R and R′ may be the same or different; and R and R′ are independently selected from the group consisting of R1, R2, R3, R5, and R6:

wherein m is an integer from 1 to 30;
wherein n is an integer from 0 to 20;
wherein A is selected from the group consisting of A2, A3, A4, and A5:

wherein X is selected from the group consisting of F, Cl, Br, I, CF 3 SO 3 , acetate, and gluconate;
wherein Y is hydrogen or an unsubstituted aliphatic group containing 1 to 6 carbons, and
wherein the various Y groups may be the same or different;
wherein Z is selected from the group consisting of one hydrogen atom, two hydrogen atoms, and an unsubstituted aliphatic group containing 1 to 6 carbons;
wherein R 1 is selected from the group consisting of hydrogen, an unsubstituted aliphatic group containing 1 to 18 carbons, benzyl, and a cyclic aliphatic or aromatic group containing 5 to 18 carbons; and
wherein L is selected from the group consisting of L1, L2, L3, L4, L5, L6, L7, L8, L9, L10, and L11:

2. The compound of claim 1 , where at least one of R and R′ is acrylamide.

3. The compound of claim 1 , wherein each Y is a methyl group.

4. The compound of claim 1 , wherein Z is methyl or ethyl.

5. The compound of claim 1 , wherein X is selected from the group consisting of F, Cl, Br, and I.

6. The compound of claim 1 , wherein each Y is a methyl group, and Z is hydrogen.

7. The compound of claim 1 , wherein each Y is hydrogen, and Z is a methyl or ethyl group.

8. The compound of claim 1 , wherein X is selected from the group consisting of F, Cl, Br, and I.

9. The compound of claim 1 , wherein R 1 is hydrogen, and wherein m is selected from the group consisting of 6, 8, 10, 11, 12, 14, 16, and 18.

10. The compound of claim 1 , wherein R 1 is a methyl or ethyl group, and wherein m is selected from the group consisting of 6, 8, 10, 11, 12, 14 and 16.

11. The compound of claim 1 , wherein R and R′ are the same.

12. A dental composite containing approximately 0.5% to approximately 10% of a compound of claim 1 .

13. A denture base material containing approximately 0.5% to approximately 10% of a compound of claim 1 .

14. A dental bonding agent containing approximately 0.5% to approximately 5% of a compound of claim 1 .

15. A dental sealant containing approximately 0.5% to approximately 10% of a compound of claim 1 .

16. A dental resin cement containing approximately 0.5% to approximately 10% of a compound of claim 1 .

17. A medical device containing approximately 0.5% to approximately 10% of a compound of claim 1 .

Assignees

• Xu Xiaoming
• Costin Stephen
• Univ Louisiana State

Inventors

• Xu Xiaoming
• Costin Stephen

Classifications

• A61K6/60

  comprising organic or organo-metallic additives · CPC title

• C07D487/08 Primary

  Bridged systems · CPC title

• C07C229/14

  to carbon atoms of carbon skeletons containing rings · CPC title

• A61K6/083

  Human Necessities · mapped topic

• A61K6/0047

  Human Necessities · mapped topic