Nanostructured antibacterial and remineralizing dental bonding agents and dental bonding systems

Patent metadata

Field	Value
Publication number	US-9554971-B2
Application number	US-201314377313-A
Country	US
Kind code	B2
Filing date	Feb 8, 2013
Priority date	Feb 10, 2012
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The present invention provides dental bonding agents and dental bonding systems comprising the dental bonding agents. The dental bonding agents of the invention are characterized by having antibacterial properties, and in some aspects of the invention, remineralizing properties.

First claim

What is claimed is:

1. A dental bonding system comprising (i) a dental primer and (ii) a dental adhesive, wherein the dental primer comprises a primer and one or more antibacterial agents and wherein the dental adhesive comprises an adhesive and one or more antibacterial agents, wherein one or more of the antibacterial agents of the dental primer and/or the dental adhesive is an antibacterial monomer selected from the group consisting of dimethylamino hexyl methacrylate (DMAHM), dimethylamino heptyl methacrylate (DMAHPM), dimethylamino octyl methacrylate (DMAOM), dimethylamino nonyl methacrylate (DMANM), dimethylamino decyl methacrylate (DMADM), dimethylamino undecyl methacrylate (DMAUDM), dimethylamino dodecyl methacrylate (DMADDM), dimethylamino tridecyl methacrylate (DMATDM), dimethylamino tetradecyl methacrylate (DMATTDM), dimethylamino pentadecyl methacrylate (DMAPDM), dimethylamino hexadecyl methacrylate (DMAHDM), dimethylamino heptadecyl methacrylate (DMAHPDM), dimethylamino octadecyl methacrylate (DMAODM), dimethylamino nonadecyl methacrylate (DMANDM), dimethylamino icosyl methacrylate (DMAIOM), dimethylamino henicosyl methacrylate (DMAHOM), and dimethylamino docosyl methacrylate (DMADOM).

2. The dental bonding system of claim 1 , wherein the primer comprises one or more primers selected from the group consisting of bisphenol A diglycidyl methacrylate (Bis-GMA), glycerol dimethacrylate (GDMA), 2-hydroxyethyl methacrylate (HEMA), mono-2-methacryloyloxyethyl phthalate (MMEP), methacrylic acid (MA), methyl methacrylate (MMA), 4-acryloyloxyethyl trimellitate anhydride (4-AETA), N-phenylglycine glycidyl methacrylate (NPG-GMA), N-tolylglycine glycidyl methacrylate or N-(2-hydroxy-3-((2-methyl-1-oxo-2-propenyl)oxy)propyl)-N-tolyl glycine (NTG-GMA), pyromellitic diethylmethacrylate or 2,5-dimethacryloyloxyethyloxycarbonyl-1,4-benzenedicarboxylic acid (PMDM), pyromellitic glycerol dimethacrylate or 2,5-bis(1,3-dimethacryloyloxyprop-2-yloxycarbonyl)benzene-1,4-dicarboxylic acid (PMGDM), and triethylene glycol dimethacrylate (TEGDMA).

3. The dental bonding system of claim 1 , wherein the primer comprises (a) 35-45% 2-hydroxyethylmethacrylate (HEMA), 10-20% copolymer of acrylic and itaconic acids, 40-50% water, or the primer comprises (b) PMGDM/HEMA at 3.3/1 ratio+1% BAPO+50% acetone.

4. The dental bonding system of claim 1 , wherein the adhesive comprises one or more adhesives selected from the group consisting of ethoxylated bisphenol A glycol dimethacrylate (Bis-EMA), bisphenol A diglycidyl methacrylate (Bis-GMA), 2-hydroxyethyl methacrylate (HEMA), triethylene glycol dimethacrylate (TEGDMA), urethane dimethacrylate (UDMA), 4-methacryloyloxyethyl trimellitate anhydride (4-META), methacrylic acid (MA), methyl methacrylate (MMA), 4-acryloyloxyethyl trimellitate anhydride (4-AETA), ethyleneglycol dimethacrylate (EGDMA), glycerol dimethacrylate (GDMA), glycerol phosphate dimethacrylate (GPDM), pyromellitic glycerol dimethacrylate or 2,5-bis(1,3-dimethacryloyloxyprop-2-yloxycarbonyl)benzene-1,4-dicarboxylic acid (PMGDM).

5. The dental bonding system of claim 1 , wherein the adhesive comprises (a) 60-70% BisGMA and 30-40% HEMA, or the adhesive comprises (b) BisGMA/TEGMA at 7/3 ratio+1% BAPO.

6. The dental bonding system of claim 1 , wherein a further antibacterial agent present in the dental primer is selected from the group consisting of, silver-containing nanoparticles (NAg), quaternary ammonium salts (QAS), chlorhexidine particles, TiO2 particles and ZnO particles, and wherein a further antibacterial agent present in the dental adhesive is selected from the group consisting of, silver-containing nanoparticles (NAg), quaternary ammonium salts (QAS), chlorhexidine particles, TiO2 particles and ZnO particles.

7. The dental bonding system of claim 1 , wherein when the antibacterial monomers are selected from the group consisting of DMADDM, DMATDM, DMATTDM, DMAPDM and DMAHDM.

8. The dental bonding system of claim 1 , wherein the combined amount of antibacterial monomers present in the dental primer or the dental adhesive ranges from about 2.5% to about 12.5% of the mass of the dental primer or the dental adhesive.

9. The dental bonding system of claim 6 , wherein when the one or more antibacterial agents include NAg, NAg is present in the dental primer or the dental adhesive in an amount ranging from about 0.05% to about 1% of the mass of the dental primer or the dental adhesive.

10. The dental bonding system of claim 6 , wherein when the one or more antibacterial agents include QAS, QAS is present in the dental primer or the dental adhesive in an amount ranging from about 3% to about 15% of the mass of the dental primer or the dental adhesive.

11. The dental bonding system of claim 1 , wherein the dental primer or the dental adhesive, or both, further comprises a remineralizing agent.

12. The dental bonding system of claim 11 , wherein the remineralizing agent is nanoparticles of amorphous calcium phosphate (NACP) present in the dental primer or the dental adhesive in an amount ranging from about 5% to about 45% of the dental primer or the dental adhesive.

13. The dental bonding system of claim 1 , wherein the dental bonding system is a two-component dental bonding system, a three-step dental bonding system, a two-step dental bonding system or a one-step self-adhesive bonding system.

14. The dental bonding system of claim 7 , wherein the combined amount of antibacterial monomers present in the dental primer or the dental adhesive ranges from about 2.5% to about 12.5% of the mass of the dental primer or the dental adhesive.

Assignees

• Univ Maryland

Inventors

• Xu Huakun
• Weir Michael

Classifications

• A61K6/69 Primary

  Medicaments · CPC title

• A61K6/30

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• A61K6/816

  comprising titanium oxide · CPC title

• A61K6/864

  Phosphate cements (apatite A61K6/838) · CPC title

• A61K6/887

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