Imidazole and imidazolium resins and methods for preparing curable imidazolium antimicrobial resins

Patent metadata

Field	Value
Publication number	US-RE47512-E
Application number	US-201615172640-A
Country	US
Kind code	E1
Filing date	Jun 3, 2016
Priority date	Jun 22, 2011
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

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.

First claim

What 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, wh

Assignees

• Jin Xiaoming
• Dentsply Sirona Inc

Inventors

• Jin Xiaoming

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• A61K6/69 Primary

  Medicaments · CPC title

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/083

  Human Necessities · mapped topic

• A61K6/0067 Primary

  Human Necessities · mapped topic