Dental primer adhesive system and optional hydrophobic resin

Abstract

The present application relates to a polymerizable dental primer/adhesive system comprising a primer component having a relatively hydrophilic monomer component in an amount that renders the system relatively hydrophilic before polymerization of the system and capable of penetrating a prepared dental surface such as etched tooth dentin or enamel, and a multi-functional cross-linking agent in an amount that renders the system relatively hydrophobic after polymerization. A polymerizable hydrophobic monomer component is also included in the primer. The inclusion of said hydrophobic polymerizable monomer and said multi-functional cross-linking agent improves the long term stability or durability of the polymerized primer system to the dental restoration and to the tooth, dentin, enamel and other dental surfaces. An additional hydrophobic resin can also be employed with the primer adhesive system. The dental primer adhesive system exhibits greater stability and durability over time when compared to other dental adhesive systems.

What is claimed is: 
     
         1 . A polymerizable dental adhesive system for adhering dental restorations to dentin, enamel, and other dental surfaces comprising a first primer component comprising NTG-GMA, NPG, or other amino acids and their metal salts and a second primer component comprising BPDM, PMDM, or other polymerizable acidic monomers that do not interfere with polymerization of the primer system, the system comprising:
 a. including in the second primer component:
 (i) a relatively hydrophilic monomer in an amount that renders the system relatively hydrophilic before polymerization of the system and capable of penetrating a prepared dental surface such as etched tooth dentin or enamel, and a multi-functional cross-linking agent in amounts that renders the system relatively hydrophobic after polymerization; and 
 (ii) a relatively hydrophobic polymerizable monomer that is relatively hydrophobic after polymerization of the system; 
   b. wherein the inclusion of said hydrophobic polymerizable monomer and said multi-functional cross-linking agent improves the long term stability or durability of the polymerized primer system to the dental restoration and to the tooth, dentin, enamel and other dental surfaces.   
     
     
         2 . A dental adhesive system comprising:
 a. a first portion and a second portion operable to be mixed prior to application to a dental surface, wherein
 (i) the first portion comprises ethanol and N(p-tolyl) glycine glycidyl methacrylate magnesium salt; 
 (ii) the second portion comprises biphenyl dimethacrylate (BPDM), 2-hydroxyethyl-methacrylate (HEMA), Bis-phenol glycidlymethacrylate (BisGMA), dipentaerythritol pentaacrylate (DEPA) and a light cure initiator system; and 
 (iii) wherein the resultant adhesive system comprises a hybrid layer when applied to dentin that has been treated with an acidic solution. 
   
     
     
         3 . The dental adhesive system of  claim 2 , wherein the resultant adhesive system does not show a significant reduction in bond strength when exposed to an aqueous solution. 
     
     
         4 . The dental adhesive system of  claim 2 , wherein the resultant adhesive system does not show a significant reduction in bond strength when exposed to an aqueous solution for more than one month. 
     
     
         5 . The dental adhesive system of  claim 2 , wherein the resultant adhesive system does not show a significant reduction in bond strength when exposed to an aqueous solution for more than twenty-four months. 
     
     
         6 . The dental adhesive system of  claim 2 , wherein the resultant adhesive system does not show a significant reduction in bond strength when exposed to an aqueous solution for forty-five months or less. 
     
     
         7 . The dental adhesive system of  claim 2 , further comprising a resin operable to be placed over a cured or partially cured mixture of the first portion and the second portion, and wherein the resin is without a hydrophilic monomer. 
     
     
         8 . The dental adhesive system of  claim 7 , wherein the hydrophilic monomer is 2-hydroxyethyl methacrylate (HEMA). 
     
     
         9 . The dental adhesive system of  claim 2 , further comprising a multifunctional cross-linking agent. 
     
     
         10 . The dental adhesive system of  claim 9 , wherein the multifunctional cross-linking agent is a polymerizable monomer having four or more (meth)acrylate groups. 
     
     
         11 . The dental adhesive system of  claim 9 , wherein the multifunctional polymerizable monomer is selected from the group comprising pentaacrylate and hexacrylate. 
     
     
         12 . A dental adhesive system showing improved stability and durability hydrolytic degradation of bonds, the adhesive system comprising:
 a. a primer adhesive portion formed by the mixture of a part A comprising ethanol and N(p-tolyl) glycine glycidyl methacrylate magnesium salt with a part B comprising a hydrophilic resin comprising biphenyl dimethacrylate (BPDM), 2-hydroxyethyl-methacrylate (HEMA), Bis-phenol glycidlymethacrylate (BisGMA), dipentaerythritol pentaacrylate (DPEPA), and a light cure initiator system; and
 b. a hydrophobic resin. 
   
     
     
         13 . The dental adhesive system of  claim 12 , wherein the hydrophobic resin further comprises a filler. 
     
     
         14 . The dental adhesive system of  claim 13 , wherein the filler comprises approximately 10%-50% by weight of the adhesive system. 
     
     
         15 . The dental adhesive system of  claim 14 , wherein the hydrophilic Part B comprises approximately 10% BPDM, about 38.75% HEMA, about 10% DPEPA, about 41% BisGMA, about 0.25% CQ, and about 10% dipentaerythritol pentaacrylate. 
     
     
         16 . The dental adhesive system of  claim 14 , further comprising use of a hydrophobic resin comprising approximately 25% BisGMA, approximately 25% urethane dimethacrylate (UDMA), approximately 47.77% triethyleneglycol dimethacrylate (Tri-EDMA), approximately 1.75% ethyl 4-dimethylaminobenzoate (EDMAB), approximately 0.45% camphorquinone CQ, and approximately 0.001% 4-methoxyphenol (MEHQ). 
     
     
         17 . A polymerizable dental adhesive system for adhering dental restorations to dentin, enamel, and other dental surfaces comprising a first primer component comprising a magnesium salt of NTG-GMA, or other amino acids and their metal salts and a second primer component comprising BPDM, PMDM, or other polymerizable acidic monomers that do not interfere with polymerization of the primer system, the system comprising:
 a. a first portion formed by the mixture of a relatively hydrophilic part comprising approximately 10% biphenyl dimethacrylate (BPDM), about 38.75% 2-hydroxyethyl-methacrylate (HEMA), about 10% dipentaerythritol pentaacrylate (DPEPA), about 41% Bis-phenol glycidlymethacrylate (BisGMA), about 0.25% of a light cure initiator system, and about 10% dipentaerythritol pentaacrylate;   b. a relatively hydrophobic resin comprising 25% Bis-phenol glycidlymethacrylate (BisGMA), approximately 25% urethane dimethacrylate (UDMA), approximately 47.77% triethyleneglycol dimethacrylate (Tri-EDMA), approximately 1.75% ethyl 4-dimethylaminobenzoate (EDMAB), approximately 0.45% of a light cure initiator system and optionally approximately 0.001% 4-methoxyphenol (MEHQ).