Dental prosthetics comprising curable acrylate polymer compositions and methods of their use

Abstract

Disclosed herein are acrylic and methacrylic acid ester-based polymeric materials containing as flexibilizing and brittleness reducing agents 1-60% of C 4 -C 8 polyalkylene or polyalkyldiene compounds, preferably having a molecular weight of 300-2100, and the use of such materials in dentistry and medicine.

1 . A method of performing a dental procedure, comprising
 obtaining a curable composition comprising:
 10-90% by weight of one or more acrylic monomers; and 
 1-60% by weight of an olefinic component comprising oligomers or polymers of one or more straight chain or branched C 4 -C 6  monomers having one or two double bonds per monomer molecule; 
   applying the composition to at least one surface of a tooth or dental appliance; and   allowing the composition to cure.   
   
   
       2 . The method of  claim 1 , wherein the allowing the composition to cure comprises applying heat to the composition. 
   
   
       3 . The method of  claim 1 , wherein the allowing the composition to cure comprises applying UV or visible light to the composition. 
   
   
       4 . The method of  claim 1 , wherein the curable composition is in two parts. 
   
   
       5 . The method of  claim 4 , further comprising mixing the two parts prior to applying. 
   
   
       6 . The method of  claim 1  wherein the one or more acrylic monomers are esters of acrylic or methacrylic acid having one to three acrylate or methacrylate groups per molecule. 
   
   
       7 . The method of  claim 1 , wherein the one or more acrylic monomers are selected from the group consisting of (C 1 -C 4 ) alkylene glycol dimethacrylate, diurethane dimethacrylate, ethoxylated bis-phenol-A dimethacrylate, 2,2-bis[4-(2-hydroxy- -3-methacryloylpropoxy)phenyl]propane, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxybutyl methacrylate, and tetrahydrofurfuryl methacrylate. 
   
   
       8 . The method of  claim 1 , wherein the olefinic component comprises polybutene, polybutadiene, and/or isoprene. 
   
   
       9 . A medical or dental device made from a composition comprising:
 10-90% by weight of one or more acrylic monomers; and   1-60% by weight of an olefinic component comprising oligomers or polymers of one or more straight chain or branched C 4 -C 6  monomers having one or two double bonds per monomer molecule;   wherein said device is a dental restorative material, prosthesis, cement, cavity liner, varnish or sealer.   
   
   
       10 . The composition of  claim 9  wherein the one or more acrylic monomers are esters of acrylic or methacrylic acid having one to three acrylate or methacrylate groups per molecule. 
   
   
       11 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises (C 1 -C 4 ) alkylene glycol dimethacrylate. 
   
   
       12 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises diurethane dimethacrylate. 
   
   
       13 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises ethoxylated bis-phenol-A dimethacrylate. 
   
   
       14 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises 2,2-bis[4-(2-hydroxy- -3-methacryloylpropoxy)phenyl]propane. 
   
   
       15 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises a hydroxy (C 2 -C 4 ) alkyl methacrylate. 
   
   
       16 . The composition of  claim 15 , wherein the hydroxy (C 2 -C 4 ) alkyl methacrylate, comprises hydroxyethyl, hydroxypropyl and/or hydroxybutyl methacrylate. 
   
   
       17 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises tetrahydrofurfuryl methacrylate. 
   
   
       18 . The composition of  claim 9 , wherein the one or more acrylic monomers comprises (C 1 -C 5 ) alkyl monomethacrylates. 
   
   
       19 . The composition of  claim 9 , wherein the olefinic component comprises polybutene. 
   
   
       20 . The composition of  claim 9  wherein the olefinic component comprises polybutadiene. 
   
   
       21 . The composition of  claim 9  wherein the olefinic component comprises isoprene. 
   
   
       22 . The composition of  claim 9 , wherein the olefinic component has an average molecular weight of 300-2500 and viscosity of 25-4500 cp at 23° C. 
   
   
       23 . The composition of  claim 9  further comprising one or more additives selected from the group consisting of polymerization initiators, polymerization activators, stabilizers, UV light absorbers, colorants, fillers, therapeutic agents, flavoring agents and viscosity/rheological modifiers. 
   
   
       24 . The composition of  claim 9  further comprising 1-60% by weight of one or more inorganic fillers. 
   
   
       25 . The composition of  claim 24  wherein the inorganic filler comprises glass, quartz silica, aluminum oxide, zirconium oxide, barium sulfate or mixtures thereof. 
   
   
       26 . The composition of  claim 9  wherein the composition is curable by heat. 
   
   
       27 . The composition of  claim 9 , wherein the composition comprises a first part comprising a peroxide polymerization activator and a second part comprising a tertiary aromatic amine polymerization activator. 
   
   
       28 . The composition of  claim 27  wherein the polymerization activator comprises benzoyl peroxide or its halogen substituted derivatives. 
   
   
       29 . The composition of  claim 27 , wherein the tertiary aromatic amine comprises N,N bis-(2-hydroxyethyl) p-toluidine or N,N diethyl-p-toluidine. 
   
   
       30 . The composition of  claim 27 , further comprising camphoroquinone and tertiary aliphatic amine as light-induced polymerization-activating additives. 
   
   
       31 . The composition of  claim 30 , wherein the amine is selected from the group consisting of trialkylamines, methacroylalkyl-dialkylamines, and combinations thereof. 
   
   
       32 . The composition of  claim 9  wherein the composition is curable by light.