Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1996-04-25
2001-11-06
Szekely, Peter (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C523S115000, C524S361000, C524S547000, C433S217100
Reexamination Certificate
active
06313191
ABSTRACT:
This is a continuation-in-part of U.S. patent application Ser. No. 08/294,931 filed Aug. 26, 1994; and a continuation-in-part of U.S. patent application Ser. No. 08/292,104 filed Aug. 22, 1994.
The invention relates to adhesion of restoratives to teeth. The invention provides a method and composition for adhering to dental tooth surface. One or more portions of the composition are applied and cured to form polymeric material on a cleaned tooth surface to form a treated tooth surface. A restorative material is applied to the tooth with a bond strength of at least about 12 MPa. The polymeric material has a yield strength of at least 50 MPa, an elastic modulus of at least 1,000 MPa, a resilience of at least 0.4 MPa when measured after storage in water at 37° C. for 24 hours, and/or an initial marginal integrity between the restorative material and etched dentin or etched enamel of least 90 percent. It is most desirable, when filling tooth cavity with a filling material, such as a polymerizable dental restorative, to ensure good adhesion (at the margin) 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.
Bowen in U.S. Pat. No. 3,785,832 discloses Dental Primer varnish. Pluddemann in U.S. Pat. No. 3,884,886 discloses Cationic Unsaturated Amine-Functional Silane Coupling Agents. Lee, Jr. et al in U.S. Pat. No. 4,107,845 discloses Dental Adhesive Composites. Yamauchi et al in U.S. Pat. No. 4,182,035 discloses Adhesive Compositions for the Hard Tissues of the Human Body. Omura et al. in U.S. Pat. No. 4,499,251 discloses Adhesive Compositions. Billington in U.S. Pat. No. 4,514,342 discloses Polyethylenically Unsaturated Monophosphates. Omura et al in U.S. Pat. No. 4,515,930 discloses Highly Water-Resistant Adhesive. Martin in U.S. Pat. No. 4,525,256 discloses Photopolymerizable Composition Including Catalyst Comprising Diketone Plus. Omura et al. in U.S. Pat. No. 4,537,940 discloses Adhesive Compositions. Bunker in U.S. Pat. No. 4,540,722 discloses Dentin and Enamel Adhesive. Bunker in U.S. Pat. No. 4,544,467 discloses Light-Curable Dentin ad Enamel Adhesive. Aasen in U.S. Pat. No. 4,553,941 discloses Acetal and Hemiacetal Dentin and Enamel Adhesive Primers. U.S. Pat. No. 4,589,756 relates to similar aromatic based compositions employed in dentistry. Asmussen et al. in U.S. Pat. No. 4,593,054 disclose Adhesion Promoting Agent, Process for its preparation and use thereof on Collageneous Material. Janda in U.S. Janda in U.S. Pat. No. 4,636,533 discloses Photopolymerizable Adhesion Promoting Dental Composition. Janda in U.S. Pat. No. 4,640,936 discloses Photopolymerizable Phosphate-Containing Adhesive Promoting Dental Composition. James in U.S. Pat. No. 4,645,456 discloses Adhesive Composition for Tooth Enamel. Bunker in U.S. Pat. No. 4,669,983 discloses Dentin and Enamel Adhesive. Bunker in U.S. Pat. No. 4,670,576 discloses Polymerizable Phosphorus Esters. Aasen in U.S. Pat. No. 4,719,149 discloses Method for Priming Hard Tissue. Blackwell et al in U.S. Pat. No. 4,816,495 discloses Biologically Compatible Adhesive Visible Light Curable Compositions. Bunker in U.S. Pat. No. 4,855,475 discloses (Meth)Acrylic Esters of Phosphoric Acid Ester Dihalides. Montgomery in U.S. Pat. No. 4,863,993 discloses Surface Priming Composition for Proteinaceous Substrates; Method of Making and Using Same. Engelbrecht in U.S. Pat. No. 4,872,936 teaches dental cement mixtures containing polymerizable unsaturated monomers and/or oligomers and/or prepolymers containing acid groups and/or their reactive acid-derivative groups. Aasen et al in U.S. Pat. No. 4,880,660 discloses Method for Priming Hard Tissue. Montgomery in U.S. Pat. No. 4,913,939 discloses Method of Making and Using Surface Priming Composition for Proteinaceous Substrates. Bunker in U.S. Pat. No. 4,929,746 discloses Dentin and Enamel Adhesive. Muggee et al in U.S. Pat. No. 4,945,006 discloses Low Odor Adhesive Compositions and Bonding Method Employing Same. Horn et al in U.S. Pat. No. 4,948,366 discloses Adhesive Bond Strength Control for Orthodontic Brackets. Haas in U.S. Pat. No. 4,948,367 discloses orthodontic Accessories and Method of Applying the Same. Huang et al in U.S. Pat. No. 4,966,934 discloses Biological Compatible Adhesive Containing a Phosphorous Adhesion Promoter and Accelerator. Omura et al in U.S. Pat. No. 5,064,495 discloses Method of Adhesion with a Mercapto Group Containing Adhesive. Omura et al in U.S. Pat. No. 5,085,726 discloses Method of Adhesion with a Sulfide Group Containing Adhesive. Eppinger et al in U.S. Pat. No. 5,089,051 discloses Adhesion-Promoting Dental Composition. Omura in U.S. Pat. No. 5,091,441 discloses Dental Composition. Orlowski in U.S. Pat. No. 5,141,436 discloses Method of Bonding Article to Teeth Employing a Light Curable Primer. Bunker in U.S. Pat. No. 5,177,121 discloses Dentin and Enamel Adhesive. Kawashima et al. in U.S. Pat. No. 5,186,783 discloses Method of Bonding with Adhesive Composition Containing a Thiocarboxylic Acid Compound. Blackwell in U.S. Pat. No. 5,218,070 discloses Dental/Medical Composition and Use. Imai et al. in U.S. Pat. No. 5,252,629 discloses Adhesives for Dentin. Kawashima et al. in U.S. Pat. No. 5,254,198 discloses Method of Bonding a Metal or Alloy Utilizing a Polymerizable Thiocarboxylic Acid or a Derivative Thereof. Oxmnan et al. in U.S. Pat. No. 5,256,447 discloses Adhesive Composition and Method. Ikemura et al. in U.S. Pat. No. 5,264,513 discloses Primer Composition. Wong in U.S. Pat. No. 5,295,824 discloses Plastic Bracket with Adhesive Primer Layer and Methods of Making. Betush in U.S. Pat. No. 5,295,825 discloses Control System for Dental Handpieces. Bunker in U.S. Pat. No. 5,304,585 discloses Dentin and Enamel Adhesive.
Dental primers and adhesives in accordance with the invention have unexpectedly superior adhesion to dentin, enamel, cavity liner, bonding materials and filling materials.
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 comprising including 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. The polymeric material has a yield strength of at least 50 MPa, an elastic modulus of at least 1,000 MPa, a resilience of at least 0.4 MPa and/or a marginal integrity of at least 90 percent with a restorative material.
It is an object of the invention to provide a method of adhering material to a tooth surface by sequentially including applying portions of a liquid priming/adhesive composition to a cleaned tooth surface and curing them to form the polymeric material has a yield strength of at least 50 MPa, an elastic modulus of at least 1,000 MPa, a resilience of at least 0.4 MPa and/or a marginal integrity of at least 90 percent with a restorative material.
Unless otherwise stated herein elastic modulus, yield strength and resilience modulus are measured according to the method discussed herein under the heading “Measurement of physical properties”.
Volatile organic solvent(s) as us
Bieber James B.
Dentsply GmbH
Lovercheck Dale R.
Szekely Peter
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