Method of manufacturing dental restorations

• US 20040249015A1
• Filed: 06/04/2004
• Published: 12/09/2004
• Est. Priority Date: 08/11/2000
• Status: Active Grant

• Current Assignee: Pentron Clinical Technologies, LLC (Danaher Corporation)
• Original Assignee: Pentron Clinical Technologies, LLC (Danaher Corporation)
• Inventors: Jin, Shuhua, Jia, Weitao
• Granted Patent: US 7,275,933 B2
• Time in Patent Office: Days
• US Class Current: 523/115
• CPC Class Codes: A61K 6/50 Preparations specially adapted for dental root treatment
• CPC Class Codes: A61K 6/54 Filling; Sealing
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61K 6/891 Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 24/04 containing macromolecular materials
• CPC Class Codes: A61L 2430/12 for dental implants or prostheses
• CPC Class Codes: A61L 27/446 with other specific inorganic fillers other than those covered by A61L27/443 or A61L27/46
• CPC Class Codes: A61L 27/46 with phosphorus-containing inorganic fillers
• CPC Class Codes: C08L 29/04 Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C08L 67/07 having terminal carbon-to-carbon unsaturated bonds

Abstract

Method of manufacturing dental restorations using curable compositions including degradable macromonomers having one or more terminal acrylate or methacrylate functionality, a curing composition, a filler composition including bioactive particles of bioactive glass, bioactive glass-ceramics, calcium phosphates, calcium apatites, or mixtures thereof and optionally one or more polymerizable acrylate or methacrylate comonomers. Degradable macromonomers are manufactured from cyclic monomers with compounds having acrylate or methacrylate functionality. Depending on their use, the degradable macromonomer compositions further include one or more organic or inorganic fillers, including a calcium-based compound and/or a radiopacity-imparting agent. The compositions are particularly suitable for root canal sealants, implants, bone cements, and pulp capping materials.

Claims

1-29. -29. (cancelled)

30. A method of forming a dental or medical restoration comprising:

preparing a site to be restored in a tooth or bone; and

applying a composition comprising

(a) at least one degradable macromonomer having terminal acrylate or methacrylate groups;

(b) a curing composition;

(c) a filler composition comprising bioactive particles of bioactive glass, bioactive glass-ceramics, bioactive calcium phosphates, bioactive calcium apatites, or mixtures thereof; and

(d) optionally one or more co-polymerizable acrylate or methacrylate monomers; and

curing the compostions.

31. The method of claim 30, wherein the degradable macromonomer having terminal acrylate or methacrylate groups is the reaction product of lactide, glycolide, caprolactone, or a mixture thereof in the presence of a compound having at least one active hydrogen and at least one acrylate or methacrylate functionality.

32. The method of claim 31, wherein the active hydrogen is a hydroxyl hydrogen.

33. The method of claim 31, wherein the compound is selected from the group consisting of hydroxyalkyl acrylates and methacrylates wherein the alkyl group has from 1 to 12 carbons, and mixtures comprising at least one of the foregoing.

34. The method of claim 33, wherein the compound is selected from the group consisting of 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, and mixtures comprising at least one of the foregoing.

35. The method of claim 30, wherein the degradable macromonomer having terminal acrylate or methacrylate groups is 2-(caprolactone)ethyl methacrylate.

36. The method of claim 30, wherein the co-polymerizable acrylate or methacrylate monomer is a diluent monomer present in an amount effective to provide delivery to the restoration site using an applicator.

37. The method of claim 36, wherein the diluent monomer is selected from the group consisting of liquid dimethacrylate, trimethacrylate, glycerol dimethacrylate, ethylene glycol dimethacrylate, tri(ethylene glycol) dimethacrylate, tetra(methylene glycol) dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, 1,6-hexanediol dimethacrylate, 2-hydroxyethyl acrylate, and 1,3-butanediol dimethacrylate.

38. The method of claim 30, wherein the curing composition is selected from the group consisting of light-activated polymerization initiators, heat-cure initiators, a self-curing two-part system, and combinations thereof.

39. The method of claim 30, wherein the curing composition is a self-curing two-part system mixed prior to use comprising an initiator in one part and an accelerator in a second part whereby the two parts contain equal or various amounts of the degradable macromonomer and co-polymerizable acrylate or methacrylate monomer.

40. The method of claim 30, wherein the filler composition further comprises non-bioactive particles comprising inorganic calcium compounds, calcium phosphates, calcium hydroxide, calcium oxide, tricalcium phosphate, poly(lactide), poly(glycolide), poly(lactide-co-glycolide), poly(methacrylate), silica, fumed silica, silicate glass, glass fibers, quartz, barium silicate, strontium silicate, barium borosilicate, strontium borosilicate, borosilicate, lithium silicate, amorphous silica, ammoniated or deammoniated calcium phosphate and alumina, zirconia, tin oxide, and titania and combinations thereof.