Compositions: coating or plastic – Coating or plastic compositions – Dental
Reexamination Certificate
2000-03-15
2001-03-27
Seidleck, James J. (Department: 1711)
Compositions: coating or plastic
Coating or plastic compositions
Dental
C522S908000, C522S008000, C522S038000, C522S048000, C522S182000, C522S122000, C522S121000, C522S064000, C433S217100, C433S222100, C433S226000, C433S228100, C523S118000, C523S111000, C523S116000, C523S300000
Reexamination Certificate
active
06206959
ABSTRACT:
BACKGROUND OF THE INVENTION
Most bonding systems that contain carboxylated monomers for priming and hydrophilic monomers for bonding require a number of consecutive procedural steps after conditioning with an acid which are aimed at optimizing the adhesion to dentin. These include (1) priming of a primer monomer with a co-monomer/co-initiator, usually a secondary or tertiary aromatic amine, e.g. mono- or bivalent salts of bis-(N-tolyl glycine glycidyl methacrylate) and (2) priming of the prepared dentin surface with this mixture (Bowen, 1985; Bowen, 1986; Bowen, 1987; Venz and Dickens, 1991; Venz and Dickens, 1993; Bowen, 1993; Bowen, 1994; Ibsen et al., 1994; Suh et al., 1994). The third step comprises application of an unfilled bonding resin, which will then be light-cured. The bonding resin consists mainly of 2,2-bis[p(2′-hydroxy-3′-methacryloxypropoxy)phenylene]-propane (bis-GMA) and 2-hydroxyethyl methacrylate (2-HEMA).
A different approach was taken by Waknine (1992) who disclosed a three-step adhesive system that contains a nonacidic carbonate monomer instead of the carboxylated resin and a different type of amine accelerator. The bond strengths reported by Waknine are on the order of about 10 MPa.
Recently, abstracts describing bonding to dentin with one-component (better described as one-solution) adhesive resin systems have been reported (Jia et al., 1996; Kelsey et al., 1996; Latta et al., 1996; Qian et al., 1996; Dickens et al., 1997). More recently, a patent (Qian et al., August 1997, U.S. Pat. No. 5,658,963) has been issued describing one-step formulations. These adhesive resin formulations comprise in a single solution the components that were applied in the multistep system in several sequential steps as described above. The components are: the bonding resin consisting of a viscous monomer, bis-GMA, and the diluent monomer 2-HEMA, as well as light-sensitive polymerization catalysts, an amine accelerator, and acetone and/or ethanol as the solvent(s).
Various U.S. patents disclose use of other one-solution systems. Bunker and Fields, (1985); Aasen, (1988); Bunker, (1994) describe polymerizable phosphate esters. However, these bonding systems yielded a relatively low bond strength to dentin of about 9 MPa. Also, these bonding systems contain a multitude of polymerizable components in their systems, among which are phosphate esters. These esters can hydrolyze, thus releasing free acid, which can, in turn, lead to hydrolysis of methacrylate esters resulting in the release of methacrylic acid and loss of the polymerizable functionality on the resin. Thus, phosphate esters are less stable than the carboxylic acid esters described in this invention. Bunker et al. (1985), reported mixing the adhesive with a solution of sodium benzene sulfinate as a coinitiator, which adds another step to these so-called one-step formulations.
James (1987) describes adhesive compositions for tooth enamel, but does not teach adhesion to dentin.
Blackwell and Huang (1987, 1989) and Huang and Blackwell (1990) describe phosphate esters of mono- or dipentaerythritol. However, use of the experimental formulations reported by Blackwell and Huang (1987, 1989) resulted in relatively low bond strengths to dentin (about 8.4 MPa). Higher bond strengths were reported by Huang and Blackwell (1990) but only if an unfilled bonding resin was applied as a second step after priming. Also, the storage stability of these phosphate-containing resins was less than desirable, possibly due to the above described hydrolysis of the ester group.
There is a need in the art for new methods and compositions for adhesives for use in restoring teeth in which the bond strength is good, the steps and reagents are kept to a minimum, and the time required for the restoration is short.
SUMMARY OF THE INVENTION
It is an object of the invention to provide an adhesive resin formulation.
It is another object of the invention to provide a method of bonding a composite resin to a prepared surface.
It is still another object of the invention to provide a method of producing a formulation for bonding a composite resin to a prepared surface.
It is yet another object of the invention to provide kits for bonding a composite resin to a prepared surface.
These and other objects of the invention are provided by one or more embodiments described below. In one embodiment a single-solution adhesive resin formulation for bonding a composite resin to enamel, dentin or nonprecious metal is provided. The formulation can also be used for bonding a ceramic or a nonprecious metal to dentin. The formulation comprises: not more than two polymerizable monomers and a photoinitiator, wherein a first of the two monomers is an acidic monomer and the second of the two monomers is a diluent monomer.
In another embodiment of the invention a single-solution adhesive resin formulation for bonding a composite resin to enamel, dentin or nonprecious metal is provided. The formulation can also be used for bonding a ceramic or a nonprecious metal to dentin. The formulation comprises: not more than two polymerizable monomers, a solvent, and a photoinitiator, wherein a first of the two monomers is pyromellitic glycerol dimethyacrylate (PMGDM) monomer, the second of the two monomers is 2-HEMA monomer, and the photoinitiator is 2, 4, 6-trimethylbenzoyldiphenylphosphine oxide.
In another embodiment of the invention a method of bonding a composite resin to enamel, dentin or nonprecious metal is provided. The method can also be used for bonding a ceramic or a nonprecious metal to dentin. The method comprises: applying an adhesive resin formulation onto a prepared surface selected from the group consisting of enamel, dentin or nonprecious metal; air drying the adhesive resin formulation; repeating the steps of applying and air drying between 0 and 2 times; photopolymerizing the adhesive resin formulation; contacting the formulation with a composite resin; and photopolymerizing the composite resin to form a bond having a shear bond strength of at least 20 MPa.
According to another aspect of the invention a method of producing a formulation for bonding a composite resin to enamel, dentin, or nonprecious metal, or a ceramic or a non-precious metal to dentin, is provided. The formulation can also be used for bonding a ceramic or a nonprecious metal to dentin. The method comprises the step of: combining not more than two monomers and a photoinitiator, wherein a first of the two monomers is an acidic monomer and the second of the two monomers is a diluent monomer.
In yet another embodiment of the invention a kit for bonding a composite resin to enamel, dentin or metal is provided. The kit can also be used for bonding a ceramic or a nonprecious metal to dentin. The method comprises:
a formulation which comprises not more than two monomers and a photoinitiator, wherein a first of the two monomers is a carboxylic acid monomer and the second of the two monomers is a diluent monomer; and a composite resin.
The present invention thus provides the art with a single-solution adhesive resin formulation for bonding to enamel, dentin, or nonprecious metal, or for bonding a ceramic or a nonprecious metal to dentin. This formulation simplifies and economizes the bonding procedure by allowing application of the bonding system to conditioned tooth surfaces or to nonprecious metal surfaces in a single step, in contrast to the multistep procedure employed in conventional systems.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It is a discovery of the present inventor that a successful adhesive resin formulation can be made by simply combining a single acidic primer monomer with a single functionalized diluent monomer in a solvent. The mixture preferably also contains a photoinitiator (camphorquinone) and a tertiary amine accelerator (such as 4-N,N-(dimethylamino)benzoate (4-EDMAB), or, as an alternative, a photoinitiator that does not require an amine accelerator as does camphorquinone. The solution can be painted onto the dentin once, air dried and then optionally appl
American Dental Association - Health Foundation
Banner & Witcoff , Ltd.
McClendon Sanza L.
Seidleck James J.
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