Dental adhesive compositions and methods

Abstract

Two-part and one-part self-etching dental adhesives containing polymerizable acidic monomers. Methods include one-coat application without need for tooth etching.

Description

RELATED APPLICATION[0001]This application is a continuation of U.S. patent application Ser. No. 11 / 899,124 having a filing date of Sep. 4, 2007 which is a continuation of U.S. patent application Ser. No. 10 / 844,628 having a filing date of May 13, 2004 which claims the benefit of Provisional Application No. 60 / 469,938 filed on May 13, 2003.TECHNICAL FIELD[0002]The present invention generally relates to dental adhesives. More particularly the invention relates to self-etching adhesives. Specifically the invention relates to adhesives containing polymerizable acidic monomers.BACKGROUND OF THE INVENTION[0003]Table of Abbreviations Used HereinAbbreviationFull term4-META4-methacryloxyethyltrimellitic AnhydrideAHPMA3-(Acryloyloxy)2-hydroxypropyl methacrylateBHTButylated HydroxytolueneBMAPBis(2-methacryloxyethyl) phosphateCAFCetylamine HydrofluorideCQCamphorquinoneDHEPTDihydroxylethyl-p-toluidineDMABADimethylaminobenzoic acidDMABNDimethylaminobenzonitrileEDAB4-ethyldimethylaminbenzoateEGMPE...

AI Technical Summary

Benefits of technology

[0036]2P-SEA is a LC / SC Dual Cure Self-Etching Adhesive system that is applied onto tooth cavity surfaces with premixed Solutions A and B prior to bonding the direct light cure composite restorations or indirect cemented restorations. The preferred 2P-SEA composition contains optimized mixture of polymerizable acidic monomers with phosphoric acid and / or carboxylic acid groups, various hydrophilic and hydrophobic meth(acrylates) monomers, structure resin monomer, crosslinker, curing agent (L-TPO plus CQ / EDAB (or CQ / DMABN) and cure-promoting additives (NaTs), stabilizer, water and other solvents (such as Acetone, or other alcohols (methanol, ethanol, t-butanol)). Unlike previous self-etching adhesives, the 2P-SEA solution according to the invention can be used to bond both Visible Light Cured (VLC) composite type restorations and cemented indirect restorations (prefabricated metal / porcelain / composite Inlays / Onlays / Veneers / Crowns / Bridges) to human teeth substrate (enamel and dentine) without the need of separate acid-etching or priming pre-treatment teeth bonding step. The 2P-SEA application procedure remains the same, i.e. [Part A / B Mix ratio=2 / 1 by w / w / or v / v, 1 Coat / 20 seconds wet, air dry, LC 10″ or 20″], whether it is for direct or indirect bonding restorations. The 2P-SEA also showed improved bonding performance over prior art products, with enamel bond strength of at least greater than 20 MPa and dentin bond strength of at least greater than 15-20 MPa. The bonding performance sustained even after excessive thermal stressing (1800× or 5000×, 55 / 5-° C. thermal cycling) or up to 12 week / 50° C. thermal aging, indicating good bonding durability and materials shelf-life stability. In comparison with current commercial Self-Etching Adhesive products, 2P-SEA also shows better or equivalent bonding performance, with more versatility in applications.

[0037]1P-SEA according to the inventions is a Single Step Light Cured Self-Etching Adhesive that is contained in one single package (bottle or single unit-dose) prior to applying onto tooth cavity surfaces to bond the direct light cure composite type restorations. The preferred 1P-SEA composition contains optimized mixture of polymerizable acidic monomers with phosphoric acid and / or carboxylic acid groups, various hydrophilic and hydrophobic meth(acrylates) monomers, structure resin monomer, crosslinker, curing agent (L-TPO and / or CQ / DMABN (or CQ / EDAB), stabilizer, water and other solvents (acetone, or alcohol). Unlike previous self-etching adhesives, one-component SEA materials shows high initial bonding strength and good bonding durability and long-term bonding performance as well, with enamel bond strength of at least greater than 20 MPa and dentin bond strength of at least greater than 15-20 MPa. The new 1P-SEA materials achieve good adhesion performance with a simple “one-coat” application technique, without separate acid-etching or tooth-priming step. The bonding performance of 1P-SEA sustains even after excessive thermal stressing (1800× or 5000×, 55 / 5-° C. thermal cycling) or 4 week / 50° C. thermal aging, indicating good bonding durability and materials shelf-life stability. In comparison with current commercial Self-Etching Adhesive products, 1P-SEA shows better or equivalent bonding performance, with better storage stability and longer shelf life. The 1P-SEA shows improved bonding performance over prior art products, with high initial and sustained long-term bonding performance [enamel bond strength of at least greater than 20 MPa and dentin bond strength of at least greater than 15-20 MPa] and good bonding durability. Unlike prior art self-etching adhesive products in which the active ingredients of the composition have to be divided into two or more parts in different packages to avoid composition degradation or polymerization, the 1P-SEA overcome the one-package storage stability issue by choosing the optimum ingredients of appropriate acidic strength acidic monomers, effective and stable VLC photoinitiator in acidic aqueous solution, A bifunctional hydrophilic monomer with higher crosslinking and less tendency to hydrolysis, and minimum amount of water incorporated into a water-miscible polar aprotic organic solvent. Optionally, micro- or nanosized fillers and fluoride-releasing agent can also be added to enhance the product performance and provide fluoride release feature. When used with a separate Self-Cure Activator component, the 1P-SEA application can be expanded to bond cemented indirect restorations (prefabricated metal / porcelain / composite Inlays / Onlays / Veneers / Crowns / Bridges) with human teeth substrate (enamel and dentine) without separate acid-etching or priming pre-treatment step.

[0038]Both 2P-SEA, and 1P-SEA materials can achieve good adhesion performance with a simple one-coat application, without the need of using phosphoric acid tooth gel in its specific indications as follows.

Problems solved by technology

It is apparent that it takes time in many bonding steps to accomplish such handling and that no adhesion with confidence is attained.