Dental resin composition, method of manufacture, and method of use thereof
View Patent ↗A curable restorative composition is disclosed, comprising a polymerizable mono(meth)acrylate resin having a vapor pressure of 1 mm Hg or less at 20° C., a plasticizer; and a curing system for the mono(meth)acrylate resin. The composition is particularly useful for making temporary restorations. Methods of used and kits comprising the composition are also disclosed.
1. A curable temporary removable restorative cement composition comprising:
a polymerizable mono(meth)acrylate resin having a vapor pressure of 1 mm Hg or less at 20° C., wherein the polymerizable mono(meth)acrylate resin comprises the reaction product of lactide, glycolide, caprolactone, or a mixture comprising one or more thereof, and a hydroxyl-functional mono(meth)acrylate resin;
a plasticizer; and
a curing system for the mono(meth)acrylate resin, wherein the composition comprises, based on the total weight of the composition, about 20 to about 90 wt.% of a polymerizable mono(meth)acrylate; about 5 to about 80 wt.% of a non reactive plasticizer; and about 0.01 to about 5 wt.% of a curing system, wherein solid resins are excluded from the composition,
wherein the composition, upon being cured, has a compression strength of less than 50 MPa, measured per ANSI/ADA Specification No. 66.
2. The curable temporary removable restorative cement composition of claim 1 , wherein the hydroxyl-functional mono(meth)acrylate resin comprises a hydroxyalkyl (meth)acrylate wherein the alkyl group has from 1 to 12 carbons.
3. The curable temporary removable restorative cement composition of claim 2 , wherein the hydroxyl-functional mono(meth)acrylate resin is 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate, tetraethyleneglycol monomethacrylate, tetraethyleneglycol monoacrylate, pentaethyleneglycol methacrylate, hydroxypolyethyl methacrylate, pentaethyleneglycol monoacrylate, dipropyleneglycol monomethacrylate, dipropyleneglycol monoacrylate, phenoxyhydroxyphenyl methacrylate, or a mixture comprising at least one of the foregoing.
4. The curable temporary removable restorative cement composition of claim 1 , wherein the mono(meth)acrylate comprises 2-(caprolactone)ethyl methacrylate.
5. The curable temporary removable restorative cement composition of claim 1 , wherein the curable mono(meth)acrylate is a liquid.
6. The curable temporary removable restorative cement composition of claim 1 , further comprising a curable (meth)acrylate different from the curable mono(methacrylate) resin.
7. The curable temporary removable restorative cement composition of claim 6 , wherein the different curable (meth)acrylate is a liquid.
8. The curable temporary removable restorative cement composition of claim 6 , wherein the curable (meth)acrylate comprises a carboxylic, phosphonic, phosphoric, or sulfonic moiety.
9. The curable temporary removable restorative cement composition of claim 6 , wherein the curable (meth)acrylate comprises a reaction product of a hydroxy-containing (meth)acrylate monomer and an aromatic compound comprising anhydride or dicarboxylic acid functionality.
10. The curable temporary removable restorative cement composition of claim 1 , excluding any curable resin component having a vapor pressure of greater than or equal to 1 mm Hg at 20° C.
11. The curable temporary removable restorative cement composition of claim 1 , excluding any component having a vapor pressure of greater than or equal to 10 mm Hg at 20° C.
12. The curable temporary removable restorative cement composition of claim 1 , excluding any curable resin component that is a solid.
13. The curable temporary removable restorative cement composition of claim 1 , wherein the plasticizer is a hydrocarbon oil, silicone oil, glycerin, glyceride, polyethylene oxide, polyvinyl alcohol, xathan gum, cellulose, a phthalate resin, a polyalkylene glycol, a halogenated hydrocarbon wax, a hydrogenated wax or wax ester from the reaction of a fatty alcohol and an acid, or a combination comprising at least one of the foregoing plasticizers.
14. The curable temporary removable restorative cement composition of claim 1 , wherein the plasticizer comprises a polyethylene glycol.
15. The curable temporary removable restorative cement composition of claim 1 , wherein the mono(meth)acrylate comprises 2-(caprolactone)ethyl methacrylate and the plasticizer comprises polyethylene glycol.
16. The curable temporary removable restorative cement composition of claim 1 , wherein the curing system is a light-activated system, a self-curing two-part system, or a combination comprising at least one of the foregoing systems.
17. The curable temporary removable restorative cement composition of claim 16 , further comprising a heat-activated curing system, wherein the heat-cure initiators are activated by the heat of reaction generated by the light-activated polymerization process.
18. A kit for the restoration of a tooth, comprising the curable temporary restorative cement composition of claim 1 .
19. The kit of claim 18 , wherein the kit further comprises a glaze, a crown and bridge material, a clear impression material, or a combination comprising at least one of the foregoing materials.
20. A method of restoring a tooth, comprising
preparing a site on a tooth for restoration;
applying to at least a portion of the site the curable temporary restorative cement composition of claim 1 ; and
curing the curable composition.
21. The method of claim 20 , further comprising contacting a temporary dental restoration to the curable temporary restorative cement composition prior to curing.
22. The method of claim 20 , wherein the site to be restored is a tooth root.
23. A kit for the preparation of a temporary laboratory dental restoration, comprising the curable temporary restorative composition of claim 1 .
24. The kit of claim 23 , wherein the kit further comprises a glaze, a cement, a crown and bridge material, a clear impression material, or a combination comprising at least one of the foregoing materials.
25. A kit for the preparation of a temporary chairside dental restoration, comprising the curable temporary restorative composition of claim 1 .
26. The kit of claim 25 , wherein the kit further comprises a glaze, a cement, a crown and bridge material, a clear impression material, or a combination comprising at least one of the foregoing materials.
27. A curable temporary removable restorative composition comprising:
about 30 to about 80 wt. % of a polymerizable mono(meth)acrylate resin having a vapor pressure of 1 mm Hg or less at 20° C., wherein the mono(meth)acrylate resin 2-(caprolactone)ethyl methacrylate;
about 10 to about 60 wt. % of a non-reactive plasticizer; and
a curing system for the mono(meth)acrylate resin;
wherein the plasticizer is a hydrocarbon oil, silicone oil, glycerin, glyceride, polyethylene oxide, polyvinyl alcohol, xathan gum, cellulose, a phthalate resin, a polyalkylene glycol, a halogenated hydrocarbon wax, a hydrogenated wax or wax ester from the reaction of a fatty alcohol and an acid, or a combination comprising at least one of the foregoing plasticizers, and
wherein the composition, upon being cured, has a compression strength of less than 50 MPa, measured per ANSI/ADA Specification No. 66.
28. The curable temporary removable restorative composition of claim 27 , wherein the plasticizer comprises a polyethylene glycol.
29. The curable temporary removable restorative composition of claim 27 , further comprising a curable (meth)acrylate comprising a reaction product of a hydroxy-containing (meth)acrylate monomer and an aromatic compound comprising anhydride or dicarboxylic acid functionality.
30. The curable temporary removable restorative composition of claim 27 , wherein the composition has a compression strength of less than or equal to about 30 MPa.
31. The curable temporary removable restorative composition of claim 30 , wherein the composition has a compression strength of less than or equal to about 10 MPa.
32. A curable temporary removable restorative composition comprising:
about 20 to about 80 wt. % of a polymerizable mono(meth)acrylate resin having a vapor pressure of 1 mm Hg or less at at 20° C., wherein the mono(meth)acrylate resin 2-(caprolactone)ethyl methacrylate;
about 10 to about 60 wt. % of a non-reactive plasticizer; and
a curing system for the mono(meth)acrylate resin;
a curable (meth)acrylate that is a reaction product of a hydroxy-containing (meth)acrylate monomer and an aromatic compound comprising anhydride or dicarboxylic acid functionality,
wherein the plasticizer is a hydrocarbon oil, silicone oil, glycerin, glyceride, polyethylene oxide, polyvinyl alcohol, xathan gum, cellulose, a phthalate resin, a polyalkylene glycol, a halogenated hydrocarbon wax, a hydrogenated wax or wax ester from the reaction of a fatty alcohol and an acid, or a combination comprising at least one of the foregoing plasticizers, and
wherein the composition, upon being cured, has a compression strength of less than about 30 MPa, measured per ANSI/ADA Specification No. 66.
33. The curable temporary removable restorative composition of claim 32 , wherein the plasticizer is a hydrocarbon oil, silicone oil, glycerin, glyceride, polyethylene oxide, polyvinyl alcohol, xathan gum, cellulose, a phthalate resin, a polyalkylene glycol, a halogenated hydrocarbon wax, a hydrogenated wax or wax ester from the reaction of a fatty alcohol and an acid, or a combination comprising at least one of the foregoing plasticizers.
34. The curable temporary removable restorative composition of claim 32 , wherein the plasticizer comprises a polyethylene glycol.
35. The curable temporary removable restorative composition of claim 32 , wherein the composition has a compression strength of less than or equal to about 10 MPa.