USRE47512EActiveUtility
Imidazole and imidazolium resins and methods for preparing curable imidazolium antimicrobial resins
Est. expiryJun 22, 2031(~5 yrs left)· nominal 20-yr term from priority
Inventors:Xiaoming Jin
A61P 31/04A61K 6/69A61K 6/887A61K 6/083A61K 6/0067
47
PatentIndex Score
0
Cited by
14
References
27
Claims
Abstract
Disclosed herein is a composition and method of making a polymerizable antibacterial/antimicrobial resin and using such a bioactive resin in formulated dental compositions.
Claims
exact text as granted — not AI-modifiedWhat I claim is:
1. A dental curable antimicrobial composition comprising:
from about 0.1 weight percent to about 5.0 weight percent of an imidazolium-based polymerizable resin;
from about 5 weight percent to about 60 weight percent of a non-imidazolium-based polymerizable resin;
from about 0.005 weight percent to about 5 weight percent of at least one of a photoinitiator, a thermal/redox initiator or other additive;
from about 40 weight percent to about 90 weight percent of a glass filler having a particle size of from about 10 nm to about 100 microns; and
an optional inert solvent
wherein the imidazolium-based polymerizable resin has a formula of:
(A-X) n —Z—(Y—B—HRQR) m
wherein A is a polymerizable moiety selected from the group consisting of methacrylate, acrylate, epoxy and vinylether,
wherein B is an imidazole or a methyl imidazole imidazolium moiety,
wherein R is a hydrogen atom or an alky group having from 1 to 22 carbon atoms,
wherein H Q is a halogen atom, a chlorine atom, a bromine atom or an iodine atom an imidazolium counter ion,
wherein X and Y are the same or different and are an ether, ester, amide, imide, direct link, alkyl, or aromatic,
wherein Z is an alkyl or an aromatic, and
wherein n and m are integers of at least 1.
2. The dental curable antimicrobial composition according to claim 1 , wherein the imidazolium-based polymerizable resin demonstrates antibacterial activity capable of killing at least 99 percent of S. mutans.
3. The dental curable antimicrobial composition according to claim 1 , wherein the dental composition in its entirety is capable of an imidazolium-based polymerizable resin demonstrates antibacterial activity capable to of killing more than 99 percent of S. mutans and S. aureus.
4. A curable antimicrobial composition according to claim 1, wherein the imidazolium-based polymerizable resin is an alkylimidazoliumbromide-dimethacrylate resin having a formula selected from:
5. A curable antimicrobial composition comprising: at least one ionic imidazolium moiety, and a polymerizable moiety, the imidazolium-based polymerizable resin selected from a HEMA-based monoimidazoliumbromide-dimethacrylate resin, a 3-dodecanylimidazoliumbromide-dimethacrylate resin, a bis(3-dodecanylimidazoliumbromide)-bisacrylate resin, a bis(3-butylimidazoliumbromide)-bisacrylate resin, a EGAMA-based monoimidazoliumbromide-monomethacrylate resin, a 3-dodecanylimidazoliumbromide-monomethacrylate resin, a AMAHP-based monoimidazolium-methacrylate resin, a isosorbide-based bisimidazoliumbromide-dimethacrylate resin, a isosorbide-based bis(3-butylimidazoliumbromide)-dimethacrylate resin, and a 1,6-hexane-bisimidazoliumbromide-dimethacrylate resin.
6. A curable antimicrobial composition according to claim 5, wherein the imidazolium-based polymerizable resin having a formula selected from:
(a) a bisimidazolium-dimethacrylate resin that has a formula selected from one of a:
an isosorbide-based bisimidazoliumbromide-dimethacrylate resin
a bis(3-dodecanylimidazoliumbromide)-bisacrylate resin
a bis(3-butylimidazoliumbromide)-bisacrylate resin
A 1,6-hexane-bisimidazoliumbromide-dimethacrylate resin
(b) a monoimidazolium-dimethacrylate resin that has a formula of a HEMA-based monoimidazoliumbromide-dimethacrylate resin
(c) a monoimidazolium-dimethacrylate resin that has a formula of a EGAMA-based monoimidazoliumbromide-monomethacrylate resin
7. A curable antimicrobial composition according to claim 5, wherein the imidazolium-based polymerizable resin is present from about 0.1 weight percent to about 20.0 weight percent, based on the total weight of the composition.
8. A curable antimicrobial composition according to claim 7, comprising: one or more acidic resins or polymers, or reactive acidic glass powders complexed with the imidazolium-based polymerizable resin to form one of a soluble liquid resin, soft gel, hard gel and highly-crosslinked solid.
9. A curable antimicrobial composition according to claim 8, comprising:
about 5 weight percent to about 99 weight percent of a non-imidazolium based polymerizable resin; from about 0.001 weight percent to about 5 weight percent initiators and other additives; from about 40 weight percent to about 90 weight percent of filler particles having a size of from about 10 nm to about 100 micron, an optional inert solvent, wherein all weight percents are based on the total weight of the curable antimicrobial composition.
10. A curable antimicrobial composition according to claim 8, comprising:
from about 5 weight percent to about 60 weight percent of a non-imidazolium-based polymerizable resin; from about 0.005 weight percent to about 5 weight percent of at least one of a photoinitiator, a thermal/redox initiator or other additive;
wherein the imidazolium-based polymerizable resin is present from about 0.1 weight percent to about 5.0 weight percent, and
wherein all weight percents are based on the total weight of the curable antimicrobial composition.
11. A curable antimicrobial composition according to claim 10, comprising
about 80 weight percent of a glass filler having a particle size of from about 10 nm to about 100 microns; and
wherein the imidazolium-based polymerizable resin is present from about 0.9 weight percent to about 1.8 weight percent, and
wherein all weight percents are based on the total weight of the curable antimicrobial composition.
12. A curable antimicrobial composition comprising:
an imidazolium-based polymerizable resin comprising:
at least one polymerizable group, and
at least one imidazolium moiety comprising a linear long alkyl chain of from eight to fourteen carbon atoms.
13. A curable antimicrobial composition according to claim 12, the at least one polymerizable group selected from methacrylate, acrylate, epoxy and vinylether.
14. A curable antimicrobial composition according to claim 12, the at least one polymerizable group selected from acrylate, methacrylate and polyacrylate.
15. A curable antimicrobial composition according to claim 14, the at least one polymerizable group comprising two methacrylate groups, and the at least one imidazolium moiety comprising a linear alkyl chain of twelve carbon atoms.
16. A curable antimicrobial composition according to claim 12 having a formula selected from:
a HEMA-based monoimidazoliumbromide-dimethacrylate resin
a EGAMA-based monoimidazoliumbromide-monomethacrylate resin
17. A curable antimicrobial composition according to claim 12, wherein the imidazolium-based polymerizable resin is present from about 0.1 weight percent to about 20.0 weight percent based on the total weight of the composition.
18. A curable antimicrobial composition according to claim 17, comprising: one or more acidic resins or polymers, or reactive acidic glass powders complexed with the imidazolium-based polymerizable resin to form one of a soluble liquid resin, a gel, and a crosslinked solid.
19. A curable antimicrobial composition according to claim 18, comprising:
about 5 weight percent to about 99 weight percent of a non-imidazolium based polymerizable resin; from about 0.001 weight percent to about 5 weight percent initiators and other additives; from about 40 weight percent to about 90 weight percent of filler particles having a size of from about 10 nm to about 100 micron, an optional inert solvent, wherein all weight percents are based on the total weight of the curable antimicrobial composition.
20. A curable antimicrobial composition according to claim 18, comprising:
from about 5 weight percent to about 60 weight percent of a non-imidazolium-based polymerizable resin; from about 0.005 weight percent to about 5 weight percent of at least one of a photoinitiator, a thermal/redox initiator or other additive;
wherein the imidazolium-based polymerizable resin is present from about 0.1 weight percent to about 5.0 weight percent, and
wherein all weight percents are based on the total weight of the curable antimicrobial composition.
21. A curable antimicrobial composition according to claim 20, comprising
about 80 weight percent of a glass filler having a particle size of from about 10 nm to about 100 microns; and
wherein the imidazolium-based polymerizable resin is present from about 0.9 weight percent to about 1.8 weight percent, and
wherein all weight percents are based on the total weight of the curable antimicrobial composition.
22. A curable antimicrobial composition according to claim 12,
wherein the imidazolium-based polymerizable resin has a formula of:
(A-X) n —Z—(Y—B—QR) m
wherein A is a polymerizable moiety selected from the group consisting of methacrylate, acrylate, epoxy and vinylether, wherein B is an imidazole or a methyl imidazole, wherein R is a hydrogen atom or an alky group having from 1 to 22 carbon atoms, wherein Q is an imidazolium counter ion, wherein X and Y are the same or different and are an ether, ester, amide, imide, direct link, alkyl, or aromatic, wherein Z is an alkyl or an aromatic, and wherein n and m are integers of at least 1.
23. A curable antimicrobial composition according to claim 22, wherein Q is a halogen.
24. A curable antimicrobial composition according to claim 22, wherein Q is selected from chlorine, bromine, and iodine.
25. An imidazole-based precursor for forming an imidazolium-based polymerizable resin, comprising:
a polymerizable imidazole-based resin selected from a monoimidazole resin and a polyimidazole(meth)acrylate resin, the moniomidiazole resin having a formula selected from:
the polyimidazole(meth)acrylate resin having a formula selected from:
26. An imidazole-based polymerizable resin comprising: an imidazole moiety, the imidazole-based polymerizable resin selected from a isosorbide-based bisimidazole-dimethacrylate resin, a TCDC-based bisimidazole-dimethacrylate resin, a butanediol-based bisimidazole-dimethacrylate resin, a TCDC-based bisimidazole-dimethacrylate resin, a paraxylenediol-based bisimidazole-dimethacrylate resin, a HEMA-based monoimidazole-dimethacrylate Resin, a AMAHP-based monoimidazole-monomethacrylate resin, and a EGAMA-based monoimidazole-monomethacrylate.
27. A curable antimicrobial composition according to claim 26, wherein the imidazole based polymerizable resin has a formula selected from:
(a) a bisimidazole-dimethacrylate resin that has a formula selected from:
a isosorbide-based bisimidazole-dimethacrylate resin
a TCDC-based bisimidazole-dimethacrylate resin
CDI-based reaction pathways to bisimidazole-dimethacrylate resins
a butanediol-based bisimidazole-dimethacrylate resin
a paraxylenediol-based bisimidazole-dimethacrylate resin
(b) a Monoimidazole-dimethacrylate resin that has a formula:
a HEMA-based monoimidazole-dimethacrylate resin
(c) a monoimidazole-methacrylate resin that has a formula selected from:
a AMAHP-based monoimidazole-methacrylate resin
a EGAMA-based monoimidazole-methacrylate resinCited by (0)
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