Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1998-05-18
2001-02-20
Sanders, Kriellion (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S116000, C524S117000, C524S118000, C524S356000
Reexamination Certificate
active
06191190
ABSTRACT:
The invention relates to compositions for adhesion to teeth. The invention provides a composition and method of use thereof for adhering to dental tooth surface. The invention provides a dental composition including a polymerizable aryl compound having at least one carboxylic acid group and at least one polymerizable group and a polymerizable compound having at least one polymerizable group and at least one phosphorous containing group. One or more portions of the composition are applied and cured on a cleaned tooth surface to form a treated tooth surface. In a preferred embodiment of the invention, the composition is a priming adhesive or a restorative material which is applied to a dental tooth with a bond strength of at least about 12 MPa.
It is most desirable, when filling a tooth cavity with a filling material, such as a polymerizable dental restorative, to ensure good adhesion between the tooth surrounding the cavity and the set (polymerized) filling material since there is thereby obtained a good seal between the set filling material and the tooth which prevents, or at least markedly inhibits, ingress of mouth fluids and bacteria into the filled cavity and thus prevents further decay or loss of the filling material. In order to achieve good adhesion between the filler material and the tooth enamel, it has been recommended to provide a primer or adhesive bonding layer intermediate the filling material and surfaces of a prepared tooth. The prior art does not disclose a shelf stable single component composition adapted to bond polymerizable acrylate containing restoratives to dentin with a bond strength of at least 12 MPa as is provided by the present invention.
Dental composition in accordance with the invention such as primers and adhesives have unexpectedly superior adhesion to dentin, enamel, cavity liner, bonding materials and filling materials.
It is an object of the invention to provide method of adhering a restorative material to a dental tooth by applying to the tooth a liquid composition including a polymerizable aryl compound, at least 50 percent by weight of a volatile solvent, at least 15 percent by weight of one or more polymerizable acrylate compounds and an effective amount of a photoinitiator, at least a portion of the polymerizable compounds be ing multifunctional polymerizable compounds having at least three acrylate moieties, to form a polymeric material which adheres to dentin with a bond strength of at least 1 2 MPa.
It is an object of the invention to provide a dental composition including a polymerizable aryl compound having at least one carboxylic acid group and at least one polymerizable group and a polymerizable compound having at least one polymerizable group and at least one phosphorous containing group.
It is an object of the invention to provide a restorative material bonded to t he tooth with a bond strength of at least about 12 Mpa.
It is an object of the invention is to provide new dental compositions useful as filling materials, cavity liners and bases, cements, and pit and fissure sealants other restorative materials which are adhesive to tooth structure.
It is an object of the invention to provide a composition which reduces the steps and time required to adhere metal or ceramic to tooth structure.
It is an object of the invention to provide an adhesive composition for adhesion between tooth structure and/or bone and polymeric composites.
Volatile organic solvent(s) as used herein refers to organic solvent(s) which are substantially more volatile than water at 23° C.
“Acrylate” as used herein refers to unsaturated polymerizable compounds within the general formula:
wherein, k is an integer from 1 to 8,
R is hydrogen or methyl,
R
1
is an alkyl having from 1 to 20 carbon atoms,
R
2
is an alkyl having from 1 to 8 carbon atoms, and
R
3
is an alkyl having from 1 to 12 carbon atoms.
“Polymerizable compound” as used herein refers to monomers and/or oligomers. Acrylates are preferred polymerizable compounds.
PENTA as used herein refers to 2,2,6-6 tetra acryloxyloxymethyl-4, 8 dioxa-9-oxo-11-undecyl phosphoric acid, also known as dipentaerythritol pentacrylate phosphoric acid ester.
Phosphates as used herein does not include pyrophosphates.
“Monomer” as used herein means monomer or oligomer.
“Set” as used herein means a polymerizable composition undergoes a change so that it becomes firm, stiff and nonpliable.
As used herein “The MAX Lite” means THE MAX™, a curing unit for light-polymerizable dental materials sold by Dentsply International Inc. through its L.D. Caulk Division.
Throughout this disclosure unless otherwise specified amounts of each component of a composition are in percent by weight.
Bond strength in units of MPa as used to herein unless otherwise indicated refers to bond strength measured as follows: uncontaminated, caries free, extracted human teeth without significant anatomical alterations, defects or restorations were cleaned and disinfected by soaking in 1% sodium hypo chlorite solution for 18 to 24 hours, rinsed with water and are then stored at from 1 to 8 C in 1% sodium chloride in water (saline solution) until used within six months. The wet teeth are then sanded flat by hand using wet 300 grit silicon carbide paper to expose an area of dentine at a plane just below the original interface between the enamel and the dentin, and this area of dentine is polished by hand with wet 600 grit silicon carbide paper. The teeth are kept wet in water until used within from 1 to 12 hours.
The dentine surface is dried lightly with a paper tissue, and the priming/adhesive solution of the invention applied in a thin layer using a dental operatory brush with bristles having a length of 5 mm and a diameter of 0.0025 inch. The solution is allowed to stand on the dentine surface for 10 seconds (unless otherwise noted) and the remaining solvent is evaporated by blowing the tooth gently with a stream of dry oil free air. The layer of primer/adhesive remaining is light cured by irradiating it for ten seconds (unless otherwise noted) with light from a dental light curing unit having a minimum output of 350 milliwatt/square centimeter in the 400 to 500 mm wavelength range (most preferably a Max lite, light curing unit, sold by Dentsply International, Inc., however in Examples 1 through 10 a Prismetics Lite, light curing unit, L.D. Caulk is used). A portion of plastic straw of 5mm internal diameter and about 4 mm long is placed end on to the prepared surface and filled with a light curing dental filling material (Dyract™, Dentrey Dentsply, Konstanz Germany unless otherwise noted). Finally the filling material is cured by irradiating with light from the dental light for forty seconds.
The prepared samples are stored for 24 hours in water at 37° C. before being thermocycled 500 times (unless otherwise noted) between 5° C. and 55° C. with a dwell time in each bath of 20 seconds. The thermocycled samples are left in water at 37° C. overnight before being tested in shear using a Zwick universal testing machine model 145501 with the load cell set for a maximum load of 500 Newtons, and operating at a crosshead speed of 1 mm per minute using a 2 mm diameter cylindrical chisel. The chisel has a tip point formed at the lower end by grinding and polishing a planar surface across the end of the cylinder at a 45 degree angle to the central axis of the cylinder. The tip point is formed at the intersection of a planar surface with the lower end of the chisel. In test position the tip point of the chisel is applied against the composite. Each tooth is vertically mounted in plastic for the test.
SUMMARY OF THE INVENTION
A composition and method of treating a dental tooth. The composition includes a polymerizable aryl compound having at least one carboxylic acid group and at least one polymerizable group, and a polymerizable compound having at least one polymerizable group and at least one phosphorous containing group. A preferred composition includes at least 50 percent by weight of a volatile organic solvent, at least 15 percent by weight of one or more poly
Blackwell Gordon Brian
Fan Mingxin
Hammesfahr Paul D.
Huang Chin-Teh
Lu Kewang
Bieber James B.
Dentsply Research & Development Corp.
Lovercheck Dale R.
Sanders Kriellion
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