Antimicrobial monomers and polymers, and their use in dental devices
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.
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 .