Antimicrobial compounds and methods
Antimicrobial compounds are provided that are polymerizable. The compounds include monomers with antimicrobial properties. The compounds have cross-linking properties. 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 the structure:
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, R4, R5, and R6:
wherein m is an integer from 1 to 30;
wherein n is an integer from 0 to 20;
wherein A is A1:
wherein X is selected from the group consisting of F, Cl, Br, I, CF 3 SO 3 (triflate), 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; wherein, for clarity, it is noted that R 1 and R1 are different; and
wherein L is selected from the group consisting of L3, L4, L5, L6, L7, L8, L9, L10, and L11:
2. The compound of claim 1 , wherein R is R1, R′ is R1, each Y is methyl, and L is L7; whereby said compound has the structure:
3. The compound of claim 2 , wherein X is F or Br, m is 14, and R 1 is benzyl.
4. The compound of claim 1 , where at least one of R and R′ is acrylamide.
5. The compound of claim 1 , wherein X is selected from the group consisting of F, Cl, Br, I, CF 3 SO 3 (triflate), acetate, and gluconate.
6. The compound of claim 1 , wherein each Y is a methyl group.
7. The compound of claim 1 , wherein each Y is an ethyl group.
8. The compound of claim 1 , wherein Z is methyl or ethyl.
9. The compound of claim 1 , wherein each Y is a methyl group, and Z is hydrogen.
10. The compound of claim 1 , wherein each Y is hydrogen, and Z is a methyl or ethyl group.
11. The compound of claim 1 , wherein R 1 is benzyl, and wherein m is 2, 3, 4, 6, 8, 10, 11, 12, 14, 16, or 18.
12. The compound of claim 1 , wherein R 1 is a methyl or ethyl group, and wherein m is 6, 8, 10, 11, 12, 14, 16, or 18.
13. The compound of claim 1 , wherein R 1 is an unsubstituted aliphatic group containing 3, 4, 6, 8, 10, 11, 12, 14, 16, or 18 carbons; and wherein m is 2, 3, 4, 6, 8, 10, 11, 12, 14, 16, or 18.
14. The compound of claim 1 , wherein R and R′ are the same.
15. A dental composite containing 0.5% to 10% of the compound of claim 1 .
16. A denture base material containing 0.5% to 10% of the compound of claim 1 .
17. A dental bonding agent containing 0.5% to 5% of the compound of claim 1 .
18. A dental sealant containing 0.5% to 10% of the compound of claim 1 .
19. A dental resin cement containing 0.5% to 10% of the compound of claim 1 .
20. A medical device containing 0.5% to 10% of the compound of claim 1 .