Method and composition for adhering to metal dental structure

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...

Reexamination Certificate

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C523S118000, C524S116000, C524S117000, C524S118000, C524S356000, C524S770000, C526S318100, C526S326000

Reexamination Certificate

active

06391940

ABSTRACT:

This invention relates to bonding compositions. In a preferred embodiment the invention provides an improved dental metal bonding composition. Beneficially the invention provides a single component adhesive system which bonds to dentin, to composite and to metal including metal and metal alloys used in dentistry. Preferred alloys used in dentistry contain at least 15 percent by weight of gold (Au), platinum (Pt), palladium (Pd) and/or silver (Ag), and are bonded to composite without leaving a gap at the bonding margin between the composite and the metal. Thus, the invention provides a one component self-priming light-curable adhesive for bonding composite materials to dental metals and dental alloys without the need for retention beads. Accordingly, the composition of the invention is useful for adhering crowns and bridges, inlays and onlays.
The invention relates to compositions for adhesion to teeth including dental primer, adhesive and composite filling material. The invention provides a composition and method of use thereof for adhering to dental tooth surface. The invention provides a dental composition including a polymerizable aryl compound having at least one carboxylic acid group and at least one polymerizable group and a polymerizable compound having at least one polymerizable group and at least one phosphorous containing group. One or more portions of the composition are applied and cured on a cleaned tooth surface to form a treated tooth surface. In a preferred embodiment of the invention, the composition is a priming adhesive or a restorative material which is applied to a dental tooth with a bond strength of at least about 12 MPa.
It is most desirable, when filling a tooth cavity with a filling material such as a polymerizable dental restorative, to ensure good adhesion between the tooth surrounding the cavity and the set (polymerized) filling material since there is thereby obtained a good seal between the set filling material and the tooth which prevents, or at least markedly inhibits, ingress of mouth fluids and bacteria into the filled cavity and thus prevents further decay or loss of the filling material. In order to achieve good adhesion between the filler material and the tooth enamel, it has been recommended to provide a primer or adhesive bonding layer intermediate the filling material and surfaces of a prepared tooth. The prior art does not disclose a shelf stable single component composition adapted to bond polymerizable acrylate containing restoratives to dentin with a bond strength of at least 12 MPa as is provided by the present invention.
Dental compositions in accordance with the invention are useful as dental primers and adhesives having unexpectedly superior adhesion to metal, dentin, enamel, cavity liner, bonding materials and filling materials.
It is an object of the invention to provide method of adhering a composite material to a dental metal by applying to the treated metal surface with or without retention beads a liquid composition including a polymerizable aryl compound, at least 50 percent by weight of volatile solvent, at least 15 percent by weight of one or more polymerizable acrylate compounds and effective amount of a photoinitiator, at least a portion of the polymerizable compounds being multifunctional polymerizable compounds having at least three acrylate moieties, to form a polymeric material which adheres to metal other than semiprecious and precious metals such as Au, Pt, Pd and Ag with a bond strength of at least 20 MPa.
It is an object of the invention to provide method of adhering a restorative material to a dental tooth by applying to the tooth a liquid composition including a polymerizable aryl compound, at least 50 percent by weight of a volatile solvent, at least 15 percent by weight of one or more polymerizable acrylate compounds and an effective amount of a photoinitiator, at least a portion of the polymerizable compounds being multifunctional polymerizable compounds having at least three acrylate moieties, to form a polymeric material which adheres to dentin with a bond strength of at least 12 MPa.
It is an object of the invention to provide a dental composition including a polymerizable aryl compound having at least one carboxylic acid group and at least one polymerizable group and a polymerizable compound having at least one polymerizable group and at least one phosphorous containing group.
It is the object of the invention to provide a restorative material bonded to nonprecious dental metal and alloy comprising for example Ti, Zn, Cu, Sn, Fe and/or Al (which are other than semiprecious and precious metals and alloys comprising at least 15% by weight of Au, Pt, Pd and/or Ag) with bond strength of at least 20 MPa.
It is the object of the invention to provide a restorative material bonded to Au, Pt, Pd and and/or Ag and alloys thereof with bond strength of at least 10 MPa.
It is an object of the invention to provide a restorative material bonded to the tooth with a bond strength of at least about 12 MPa.
It is an object of the invention is to provide new dental compositions useful as filling materials, cavity liners and bases, cements, and pit and fissure sealants other restorative materials which are adhesive to tooth structure.
It is the object of the invention to provide a composition that reduces the steps and time required to adhere composite materials to dental metals.
It is an object of the invention to provide a composition which reduces the steps and time required to adhere metal or ceramic to tooth structure.
It is an object of the invention to provide an adhesive composition for adhesion between composite restoratives and dental metal substrates.
It is an object of the invention to provide an adhesive composition for adhesion between tooth structure and/or bone and polymeric composites.
Volatile organic solvent(s) as used herein refers to organic solvent(s) which are substantially more volatile than water at 23° C. “Acrylate” as used herein refers to unsaturated polymerizable compounds within the general formula:
wherein, k is an integer from 1 to 8,
R is hydrogen or methyl,
R
1
is an alkyl having from 1 to 20 carbon atoms,
R
2
is an alkyl having from 1 to 8 carbon atoms, and
R
3
is an alkyl having from 1 to 12 carbon atoms.
“Polymerizable compound” as used herein refers to monomers and/or oligomers. Acrylates are preferred polymerizable compounds.
PENTA as used herein refers to 2,2,6-6 tetra acryloxyloxymethyl4, 8 dioxa-9-oxo-11-undecyl phosphoric acid, also known as dipentaerythritol pentacrylate phosphoric acid ester.
Phosphates as used herein does not include pyrophosphates.
“Monomer” as used herein means monomer or oligomer.
“Set” as used herein means a polymerizable composition undergoes a change so that it becomes firm, stiff and nonpliable.
As used herein “The MAX Lite” means THE MAX™, a curing unit for light-polymerizable dental materials sold by DENTSPLY International Inc. through its L.D. Caulk Division. Other curing units for light-polymerizable dental materials are Spectrum™ (sold by L.D. Caulk, a division of DENTSPLY International Inc.); Liculite (sold by DeTrey, a division of DENTSPLY International Inc.); Triad 2000 (sold by Trubyte, Division of DENTSPLY International Inc.); and Prismetics Lite (Sold by DENTSPLY International Inc.).
Throughout this disclosure unless otherwise specified amounts of each component of a composition are in percent by weight.
Relevant patents include U.S. Pat. Nos. 5,348,988; 4,755,620 and 5,564,030.
In the following Examples, Shear Bond Strength (SBS) is tested according to ISO 10477 using metal as substrate and composite restoratives as post. These methods were used to measure the bonding strengths of composites to precious metal alloys, non-precious metal alloys and other metal substrate by using compositions of present invention. Substrate Preparation: Prior to application of the adhesive composition, the surfaces of metal substrate were treated as follows. 1) Metal surfaces were polished with #320 and #600 grit SiC papers sequentially. 2) The pol

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