Dental resin cements having improved handling properties

A dental resin cement material comprising

• a) non-acid reactive filler
• b) polymerizable resin, and
• c) an acidic functionality, and
• d) polymerization initiator;
• e) water.

A method of adhering a prefabricated prosthetic device to an oral surface, the method comprising:

• preparing said oral surface;
• applying a dental resin cement material to the prefabricated prosthetic device,
• wherein said dental resin cement material comprises a mixture comprising:
• a) a filler;
• b) a polymerizable component, which may be monomers, oligomers, or polymers, containing a polymerizable group;
• c) a polymeric handling modifier, wherein the polymeric handling modifier has a weight average molecular weight between about 500 and about 100,000, and further wherein the polymeric handling modifier is selected from the group consisting of methacrylate modified polycaprolactonediols, polycaprolactonediols, methacrylate modified polyethylene glycols, polyethylene glycol methyl ethers, methacrylate modified polytetramethylene oxides, polytetramethylene oxides, N-polyvinyl pyrrolidones, polymeric ethoxylated Bisphenol A dimethacrylates, dicarboxy terminated polybutadienes, hydroxyl endcapped polybutadienes, copolymers of Bisphenol A and epichlorohydrin, and combinations thereof;
• and
• d) a polymerization initiator;
• wherein:
• the polymeric handling modifier and the polymerizable component are selected such that upon visual inspection by the unassisted eye of the polymeric handling modifier dispersed in the polymerizable component at 25° C. more than one phase cannot be discerned;
• components a), b), and c) are present in an amount effective to provide a material having a Viscosity vs Shear Rate Curve at a temperature of 25° C.±1° C. that fits a power law model curve fit of F(x)=AxB wherein B is less than about −0.01, and said material correlating to said Curve at a correlation value greater than 0.85 for both increasing and decreasing shear rate over at least ten logarithmically spaced data points for both the increasing direction and the decreasing direction over a shear rate range, having a lowest value of 0.4-0.5 s−1 and a highest value of 20-25 s−1;
• and
• said dental resin cement material does not utilize water as its chemistry for curing;
• seating the device on the prepared oral surface;
• cleaning off the excess resin cement material from the margin between said oral surface and said device;
• and
• causing said dental resin cement material to polymerize and adhere the device to the oral surface.

A method of adhering a direct restorative material to an oral surface, the method comprising:

• preparing said oral surface;
• applying a dental resin cement material to said prepared oral surface, wherein said dental resin cement material comprises a mixture comprising:
• a) a filler;
• b) a polymerizable component, which may be monomers, oligomers, or polymers, containing a polymerizable group;
• c) a polymeric handling modifier, wherein the polymeric handling modifier has a weight average molecular weight between about 500 and about 100,000, and further wherein the polymeric handling modifier is selected from the group consisting of methacrylate modified polycaprolactonediols, polycaprolactonediols, methacrylate modified polyethylene glycols, polyethylene glycol methyl ethers, methacrylate modified polytetramethylene oxides, polytetramethylene oxides, N-polyvinyl pyrrolidones, polymeric ethoxylated Bisphenol A dimethacrylates, dicarboxy terminated polybutadienes, hydroxyl endcapped polybutadienes, copolymers of Bisphenol A and epichlorohydrin, and combinations thereof;
• and
• d) a polymerization initiator;
• wherein:
• the polymeric handling modifier and the polymerizable component are selected such that upon visual inspection by the unassisted eye of the polymeric handling modifier dispersed in the polymerizable component at 25° C. more than one phase cannot be discerned;
• components a), b), and c) are present in an amount effective to provide a material having a Viscosity vs Shear Rate Curve at a temperature of 25° C. ±1° C. that fits a power law model curve fit of F(x)=AxB wherein B is less than about −0.01, and said material correlating to said Curve at a correlation value greater than 0.85 for both increasing and decreasing shear rate over at least ten logarithmically spaced data points for both the increasing direction and the decreasing direction over a shear rate range, having a lowest value of 0.4-0.5 s−1 and a highest value of 20-25 s−1;
• and
• said dental resin cement material does not utilize water as its chemistry for curing;
• placing the direct restorative material on said dental resin cement material applied to said prepared oral surface;
• and
• causing said resin cement to polymerize and adhere the direct restorative material to the oral surface.

A method of adhering a direct restorative material or a prefabricated prosthetic device to a hard oral surface, the method comprising:

• etching said oral surface;
• applying an adhesive composition comprising polymerizable monomer and polymerization initiator to said etched oral surface;
• causing said adhesive composition to polymerize on said surface;
• applying a dental resin cement material to said adhesive treated surface, wherein said dental resin cement material comprises a mixture comprising:
• a) a filler;
• b) a polymerizable component, which may be monomers, oligomers, or polymers, containing a polymerizable group;
• c) a polymeric handling modifier, wherein the polymeric handling modifier has a weight average molecular weight between about 500 and about 100,000, and further wherein the polymeric handling modifier is selected from the group consisting of methacrylate modified polycaprolactonediols, polycaprolactonediols, methacrylate modified polyethylene glycols, polyethylene glycol methyl ethers, methacrylate modified polytetramethylene oxides, polytetramethylene oxides, N-polyvinyl pyrrolidones, polymeric ethoxylated Bisphenol A dimethacrylates, dicarboxy terminated polybutadienes, hydroxyl endcapped polybutadienes, copolymers of Bisphenol A and epichlorohydrin, and combinations thereof;
• and
• d) a polymerization initiator;
• wherein:
• the polymeric handling modifier and the polymerizable component are selected such that upon visual inspection by the unassisted eye of the polymeric handling modifier dispersed in the polymerizable component at 25° C. more than one phase cannot be discerned;
• components a), b), and c) are present in an amount effective to provide a material having a Viscosity vs Shear Rate Curve at a temperature of 25° C.±1° C. that fits a power law model curve fit of F(x)=AxB wherein B is less than about −0.01, and said material correlating to said Curve at a correlation value greater than 0.85 for both increasing and decreasing shear rate over at least ten logarithmically spaced data points for both the increasing direction and the decreasing direction over a shear rate range, having a lowest value of 0.4-0.5 s−1 and a highest value of 20-25 s−1;
• and
• said dental resin cement material does not utilize water as its chemistry for curing;
• applying the direct restorative material or the prefabricated prosthetic device to said dental resin cement material applied to said adhesive treated surface;
• and
• causing said dental resin cement material to polymerize and adhere the direct restorative material or prefabricated prosthetic device to the hard oral surface.

A method of adhering a prefabricated prosthetic device to a hard oral surface, the method comprising;

• etching said oral surface;
• applying an adhesive composition comprising polymerizable monomer and polymerization initiator to said etched oral surface;
• causing said adhesive composition to polymerize on said surface;
• applying a dental resin cement material to said prefabricated prosthetic device, wherein said dental resin cement material comprises a mixture comprising:
• a) a filler;
• b) a polymerizable component, which may be monomers, oligomers, or polymers, containing a polymerizable group;
• c) a polymeric handling modifier, wherein the polymeric handling modifier has a weight average molecular weight between about 500 and about 100,000, and further wherein the polymeric handling modifier is selected from the group consisting of methacrylate modified polycaprolactonediols, polycaprolactonediols, methacrylate modified polyethylene glycols, polyethylene glycol methyl ethers, methacrylate modified polytetramethylene oxides, polytetramethylene oxides, N-polyvinyl pyrrolidones, polymeric ethoxylated Bisphenol A dimethacrylates, dicarboxy terminated polybutadienes, hydroxyl endcapped polybutadienes, copolymers of Bisphenol A and epichlorohydrin, and combinations thereof;
• and
• d) a polymerization initiator;
• wherein:
• the polymeric handling modifier and the polymerizable component are selected such that upon visual inspection by the unassisted eye of the polymeric handling modifier dispersed in the polymerizable component at 25° C. more than one phase cannot be discerned;
• components a), b), and c) are present in an amount effective to provide a material having a Viscosity vs Shear Rate Curve at a temperature of 25° C.±1° C. that fits a power law model curve fit of F(x)=AxB wherein B is less than about −0.01, and said material correlating to said Curve at a correlation value greater than 0.85 for both increasing and decreasing shear rate over at least ten logarithmically spaced data points for both the increasing direction and the decreasing direction over a shear rate range, having a lowest value of 0.4-0.5 s−1 and a highest value of 20-25 s−1;
• and
• said dental resin cement material does not utilize water as its chemistry for curing;
• seating the device on the adhesive treated surface;
• cleaning off the excess dental resin cement material from the margin between said adhesive treated surface and said device;
• and
• causing said dental resin cement material to polymerize and adhere the device to the hard oral surface.