Dental Utility Patents (Class 522/908)
  • Patent number: 6458865
    Abstract: Photopolymerizable compositions are provided which are the reaction products of a vinyl ether, a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound. These monomeric/oligomeric compositions may also include epoxides, polyols, spiroorthocarbonates. One embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, a spiroorthocarbonate, and a photoinitiator system. Another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, and a photoinitiator system. Still another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, a spiroorthocarbonate, and a photoinitiator system. Still further, another embodiment of the present invention is certain novel spiroorthocarbonate compounds. Each of these novel spiroorthocarbonate compounds include at least one epoxy group as a substituent.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: October 1, 2002
    Assignees: Curators of the University of Missouri, 3M Innovative Properties Company
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Joel D. Oxman
  • Patent number: 6444725
    Abstract: An aesthetic dental sealant comprising a hardenable resin, a hardener, and a colorant, the composition has an initial color prior to exposure to actinic radiation and a final color that is different from the initial color subsequent to the composition being exposed to actinic radiation.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: September 3, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Matthew C. Trom, Joel D. Oxman
  • Patent number: 6426373
    Abstract: Among other things, a photopolymerizing one-component dental material is prepared, containing: 1) 80-10 weight-% of at least one polyfunctional urethane methacrylate and/or at least one polyfunctional urethane acrylate, 2) 10-30 weight-% of at least one polyfunctional acrylate resin, 3) 10-30 weight-% of at least one reactive thinner, 4) 0-20 weight-% of bis-GMA and/or at least one ethoxylated bisphenol-A-dimethacrylate, 5) 0-10 weight-% of at least one filler, 6) 0-1 weight-% of at least one photoinitiator, and. 7) 0-1 weight-% of at least one color pigment.
    Type: Grant
    Filed: August 12, 1999
    Date of Patent: July 30, 2002
    Assignee: Heraeus Kulzer GmbH & Co. KG
    Inventors: Frank Stange, Albert Erdrich, Novica Savic, Teresa Puchalska
  • Patent number: 6407148
    Abstract: A metal free dental filling system is provided which prevents the transmission of destructive forces from the shrinking filling material to the sealed dental hard tissue. The system prevents the transmission of destructive forces by making the bond of the cured adhesive sealant to the dental hard tissue, i.e., the enamel, dentin, and root cement, substantially stronger than the bond of the cured adhesive sealant to the filling material. An intermediate layer material may be arranged between the dental filling material and the cured adhesive sealant. If an intermediate layer is used, the bond between the dental hard tissue and the cured adhesive sealant is much stronger than the bond between the cured adhesive sealant and the intermediate layer in order to ensure that substantially no destructive forces are transmitted from the shrinking filing material to the cured adhesive material on the dental hard tissue. The intermediate layer may be removed prior to application of the filling material.
    Type: Grant
    Filed: May 15, 2000
    Date of Patent: June 18, 2002
    Assignee: 3M Espe AG
    Inventors: Daniela Krejci, Ivo Krejci, Felix Lutz
  • Patent number: 6387981
    Abstract: A dental material comprising a hardenable resin, a non-heavy metal oxide particle and a heavy metal oxide. The dental materials can be radiopaque, strong, translucent, or resistant to toothbrush abrasion, or combinations thereof.
    Type: Grant
    Filed: October 28, 1999
    Date of Patent: May 14, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Xiaodong Zhang, Brant Ulrick Kolb, Douglas Alan Hanggi, Sumita Basu Mitra, Paula D'Nell Ario, Richard Paul Rusin
  • Patent number: 6387979
    Abstract: A tooth treated with a bonding composition with high initial bonding strength and good bonding durability comprising a mixture of polymerizable compound having an acid group, a water-soluble film-forming agent, water, and a curing agent, in which the calcium salt of the acid is insoluble in water, and the film-forming agent is a polymerizable compound miscible with a physiological saline solution, does not require any pre-treatment such as acid-etching or priming treatment.
    Type: Grant
    Filed: May 15, 2000
    Date of Patent: May 14, 2002
    Assignee: Kuraray Co., Ltd.
    Inventor: Kenichi Hino
  • Patent number: 6384099
    Abstract: A method and system are disclosed for curing polymeric materials including dental composites. Preferably, modulated light is used to control the formation of polymer chains in the polymeric material so that a cured polymeric material that has the desired physical characteristics for its intended function is formed. Formation of short chain and long chain polymers from monomers in the polymeric material is initiated and controlled by using a light source with a wavelength suitable for one or more initiators found in the polymeric material.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: May 7, 2002
    Assignee: Laser Med. Inc.
    Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
  • Patent number: 6361925
    Abstract: Compounds of the formula I in which R1 is C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or C1-C4alkoxy and R3, R4, R5, R6 and R7 independently of one another are hydrogen, halogen, C1-C20alkyl, cyclopentyl, cyclohexyl, C2-C12alkenyl, C2-C18alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C1-C4alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C1-C4alkyl and/or C1-C4alkoxy, with the provisos that at least one of the radicals R3, R4, R5, R6 and R7 is other than hydrogen and that, if R1 and R2 are methyl, R3 and R6 are not methyl, and mixtures of such compounds with &agr;-hydroxy ketones, benzophenones and &agr;-amino ketones, are suitable as photoinitiators.
    Type: Grant
    Filed: May 18, 2001
    Date of Patent: March 26, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Manfred Köhler, Andreas Valet
  • Patent number: 6355704
    Abstract: An antibacterial bonding compositions for dental use, which comprises (A) an antibacterial primer that comprises an antibacterial polymerizable monomer having an ethylenic unsaturated group and at least one or more cationic groups selected from the group consisting of ammonium bases, pyridinium bases and phosphonium bases, and a volatile solvent, and(B) an adhesive composition comprising an acid group having polymerizable monomer, a polymerizable monomer, and a polymerization initiator; and an adhesive compositions for dental use, which comprises (P) an adhesive primer comprising an acid group having polymerizable monomer, a hydrophilic polymerizable monomer, and water, and (Q) a bonding agent comprising a polymerizable monomer, and an acylphosphine oxide compound and an &agr;-diketone compound both serving as a polymerization initiator.
    Type: Grant
    Filed: August 19, 1999
    Date of Patent: March 12, 2002
    Assignee: Kuraray Co., Ltd.
    Inventors: Kazumitsu Nakatsuka, Koichi Okada, Satoshi Imazato, Shigeyuki Ebisu, Yasuhiko Tsuchitani
  • Patent number: 6339113
    Abstract: The invention relates to a photopolymerizable composite resin composition for dental restoration i) based on the multifunctional prepolymer mixture of 2,2-bis-(4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl)propane (“Bis-GMA”) and multifunctional prepolymer formed by substituting hydrogen atoms in hydroxyl group with methacrylate groups in this Bis-GMA molecules, and ii) comprising a diluent, an inorganic filler, a photoinitiation system, and other additives. The photopolymerizable composite resin composition for dental restoration based on multifunctional prepolymer mixture has better physical and mechanical properties and biocompatibility than the conventional composition based on only Bis-GMA itself.
    Type: Grant
    Filed: October 30, 2000
    Date of Patent: January 15, 2002
    Assignee: Dentkist Co., Ltd.
    Inventors: Dong-Keun Han, Kwang-Duk Ahn, Jong-Man Kim, Jin-Hee Jeong
  • Patent number: 6335385
    Abstract: The invention provides a curable system and method of making a dental prosthesis. The method of making a dental prosthesis includes providing a one component denture base resin composition which is polymerizable by microwave energy. The one component denture base resin composition is injected into a mold enclosed by a flask having a body wall which is substantially transparent to the microwave energy. The curable system includes microwave energy sensitive initiators and polymerizables (meth)acrylate Monomers having molecular weights preferably between 400 and 20,000. The initiators are adapted to initiate polymerization of the polymerizable Monomers by application of microwave energy to the flask. The initiators are adapted to remain stable and not initiate polymerization of the Monomers for at least one year at 23° C. in the absence of microwave energy.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: January 1, 2002
    Assignee: Dentsply GmbH
    Inventors: Karl Joachin Görlich, Wigbert Hauner, Ralf Janda
  • Patent number: 6313189
    Abstract: Described herein are methods for preparing bioabsorbable polymerization products having interconnecting pore structure by polymerizing compositions containing ethylene glycol- or glycero-oligoester(meth)acrylates monomers and, optionally, other components. The polymerization products are particularly useful for dental lacquers, dental inlays and shaped articles which are bioabsorbable and exhibit an interconnecting pore structure.
    Type: Grant
    Filed: May 4, 1999
    Date of Patent: November 6, 2001
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Robert Wenz, Berthold Nies
  • Patent number: 6300389
    Abstract: A dental restorative material is disclosed, comprising an amorphous inorganic material having a refractive index in a D-line of sodium in the range of 1.470˜1.520 and having an X-ray opacity; a (meth)acrylic ester monomer not having a benzene ring in a molecule thereof; and a polymerization initiator, if desired, the dental restorative material according to the invention further comprises an amorphous inorganic material having a refractive index in a D-line of sodium equal to or less than that of the (meth)acrylic ester monomer not having a benzene ring in a molecule thereof, the dental restorative material of the invention has an X-ray opacity and translucency close to natural teeth, and has superior esthetics not using a monomer having a benzene ring which has a fear of an environmental hormone action.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: October 9, 2001
    Assignee: GC Corporation
    Inventors: Hisashi Sato, Hideki Yarimizu
  • Patent number: 6282013
    Abstract: A method and system are disclosed for curing polymeric materials including dental composites. Preferably, modulated light is used to control the formation of polymer chains in the polymeric material so that a cured polymeric material that has the desired physical characteristics for its intended function. Formation of short chain and long chain polymers from monomers in the polymeric material is initiated and controlled by using a light source with a wavelength suitable for one or more initiators found in the polymeric material.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: August 28, 2001
    Assignee: LaserMed, Inc.
    Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
  • Publication number: 20010012596
    Abstract: Compounds of the formulae I, II, III, IV and V 1
    Type: Application
    Filed: December 12, 2000
    Publication date: August 9, 2001
    Inventors: Kazuhiko Kunimoto, Hidetaka Oka, Masaki Ohwa, Junichi Tanabe, Hisatoshi Kura, Jean-Luc Birbaum
  • Publication number: 20010006674
    Abstract: The invention relates to a mixture for use as wound dressing, which comprises:
    Type: Application
    Filed: October 9, 1998
    Publication date: July 5, 2001
    Inventor: WOLFGANG MUHLBAUER
  • Patent number: 6210759
    Abstract: Single-solution adhesive resin formulations are made of predominantly dimethacrylates or diacrylates containing predominantly) two carboxyl groups and a functionalized methacrylate or acrylate diluent monomer. A novel light-activated initiator can be used for photopolymerization of such adhesives.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: April 3, 2001
    Assignee: American Dental Association Health Foundation
    Inventor: Sabine H. Dickens
  • Patent number: 6206959
    Abstract: Single-solution adhesive resin formulations are made of predominantly dimethacrylates or diacrylates containing (predominantly) two carboxyl groups and a functionalized methacrylate or acrylate diluent monomer. A novel light-activated initiator can be used for photopolymerization of such adhesives.
    Type: Grant
    Filed: March 15, 2000
    Date of Patent: March 27, 2001
    Assignee: American Dental Association Health Foundation
    Inventor: Sabine H. Dickens
  • Patent number: 6204302
    Abstract: A photoinitiator composition that includes (a) 1-aryl-2-alkyl-1,2-ethanedione and (b) a rigid 1,2-dione in a weight ratio of (a):(b) in a range of about 1:20 to about 20:1 is disclosed. The photoinitiator composition can be used in a photocurable dental composition in an amount sufficient to achieve a degree of double-bond conversion of at least 50%. Methods for making the photocurable dental composition are also disclosed.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: March 20, 2001
    Assignee: Bisco, Inc.
    Inventors: H. Ralph Rawls, Yeong-Joon Park, Kyu-Ho Chae
  • Patent number: 6194481
    Abstract: Zirconium oxide nanoparticles having at least some surface acid sites functionalized with a silanating agent and at least some surface acid sites finctionalized with zirconate or a zircoaluminate. The nanoparticles are useful in composites comprising photopolymerizable alkene matrix monomers, and are primarily suitable for dental and medical restoration.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: February 27, 2001
    Assignees: Board of Regents of the University of Texas System, Southwest Research Institute
    Inventors: Benjamin R. Furman, Stephen T. Wellinghoff, Henry R. Rawls, Hong Dixon, Barry K. Norling
  • Patent number: 6187833
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin, (b) a hydroxyl containing material and (c) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 100 mV relative to a standard solution of 2.9×10−5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×10−5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: February 13, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • Patent number: 6187836
    Abstract: Photopolymerizable compositions that include free radically active and cationically active functional groups, and methods for polymerizing such compositions, in which the onset of cationic polymerization is controllably delayed to extend the time between formation of a moldable gel and formation of a hardened solid.
    Type: Grant
    Filed: June 5, 1998
    Date of Patent: February 13, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Matthew C. Trom, Dwight W. Jacobs
  • Patent number: 6184339
    Abstract: Disclosed are fluorinated materials for use in dental uses and non-dental uses, e.g., adhesives or coatings. Multifunctional monomers and prepolymers with pendant (meth)acrylate groups were prepared from epoxide ring-opening reactions. Resins based on the fluorinated monomers and prepolymers with diluent comonomers, were photocured as composites with particulate fillers. Fluorine contents of the prepolymers ranged from 15 to 65%. Composites with high transverse strength (up to 120 MPa), low water sorption (as low as 0.11 mass %) and extremely low polymerization shrinkage (as low as 3.4% by volume) were obtained. The fluorinated resins may be employed to produce hydrophobic dental composite materials with high strength and low polymerization shrinkage.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: February 6, 2001
    Assignee: The United States of America as represented by the Secretary of the Commerce
    Inventors: Jeffrey W. Stansbury, Joseph M. Antonucci, Kyung M. Choi
  • Patent number: 6159012
    Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: December 12, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
  • Patent number: 6136881
    Abstract: A photocuring resin composition for orthodontics is disclosed, comprising:(a) 5.about.50% by weight of a urethane bond-free (meth)acrylate having an average molecular weight of 100.about.300 and having at least one unsaturated double bond;(b) 10.about.60% by weight of a urethane bond-containing (meth)acrylate having an average molecular weight of 300.about.5,000 and having at least one unsaturated double bond;(c) 5.about.30% by weight of a crosslinked polyurethane powder;(d) 10.about.50% by weight of an inorganic filler; and(e) 0.03.about.3% by weight of a photocuring initiator.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: October 24, 2000
    Assignee: GC Corporation
    Inventors: Toshihiro Sekiguchi, Shunji Sugano
  • Patent number: 6127445
    Abstract: The present invention relates to anionic photoinitiator compounds, compositions containing them, and methods of using them having the structure: ##STR1## wherein X and Y are independently selected from the group consisting of a direct single bond and --C(.dbd.O)--, wherein at least one of X and Y is --C(.dbd.O)--;R.sup.1 and R.sup.2 are independently selected from the group consisting of H and substituted phenyl, wherein both R.sup.1 and R.sup.2 are not H;and wherein neither --X--R.sup.1 nor --Y--R.sup.2 is --C(.dbd.O)H. The anionic photoinitiators have improved storage stability, without loss of photosensitivity, even when stored with polymerizable or crosslinkable monomer, oligomer, or crosslinkable polymer species.
    Type: Grant
    Filed: November 3, 1998
    Date of Patent: October 3, 2000
    Assignee: The University of Georgia Research Foundation, Inc.
    Inventors: Charles R. Kutal, Yoshikazu Yamaguchi
  • Patent number: 6114408
    Abstract: Single-solution adhesive resin formulations are made of predominantly dimethacrylates or diacrylates containing (predominantly) two carboxy groups and a functionalized methacrylate or acrylate diluent monomer. A novel light-activated initiator can be used for photopolymerization of such adhesives.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: September 5, 2000
    Assignee: American Dental Association Health Foundation
    Inventor: Sabine Dickens
  • Patent number: 6103453
    Abstract: A photoinitiator blend, containinga) at least one monoacylphosphine oxide of formula I ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.18 alkyl; C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl, phenyl, naphthyl, biphenyl, all substituted by halogen or C.sub.1 -C.sub.6 alkoxy; phenyl, naphthyl or biphenylyl, all mono- or poly-substituted by halogen, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxy; or a monovalent N--, O--, or S--containing 5-membered or 6-membered heterocyclic radical,R.sup.2 denotes phenyl, naphthyl, biphenylyl; phenyl, naphthyl or biphenylyl, all mono- or poly-substituted by halogen, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxy; a monovalent N--, O--, or S--containing 5-membered or 6-membered heterocyclic radical, C.sub.1 -C.sub.18 alkoxy, phenoxy; phenoxy substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; benzyloxy, cyclohexyloxy or R.sup.2 and R.sup.1 form a ring together with the phosphorus atom,R.sup.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: August 15, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Prantl, Erich Beck, Matthias Lokai, Christof Kandzia
  • Patent number: 6090865
    Abstract: Compounds of formula (I), ##STR1## wherein X is CH, C--CH.sub.3, C--Cl, C--O--C.sub.1 -C.sub.8 alkyl or N; R is C.sub.1 -C.sub.6 alkyl, benzyl, CH.sub.2 COOR.sub.3 or a group (a); R.sub.1 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.2 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen or CF.sub.3 ; R.sub.3 is hydrogen, C.sub.1 -C.sub.12 alkyl or benzyl; Y is unsubstituted or C.sub.1 -C.sub.6 alkoxy-substituted C.sub.1 -C.sub.6 alkyl, or Y is C.sub.1 -C.sub.6 alkoxy, halogen, CF.sub.3, NO.sub.2, benzyloxy or phenyloxy, wherein the phenyl ring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.
    Type: Grant
    Filed: October 26, 1998
    Date of Patent: July 18, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Christopher Curtis Dudman, Allan Francis Cunningham, Martin Kunz
  • Patent number: 6043295
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin and (b) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 0 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: March 28, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • Patent number: 6034151
    Abstract: Polymerizable and hydrolyzable vinylcyclopropane silanes and in particular silicic acid condensates which can be prepared therefrom are described, which exhibit only a low volume shrinkage on polymerization and produce polymers with high mechanical strength and therefore can be used above all as dental material or a constituent thereof.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: March 7, 2000
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Thomas Voelkel, Frank Zeuner, Sabine Stein, Volker Rheinberger
  • Patent number: 6031016
    Abstract: A single package adhesive for tooth bonding application comprising a solvent-based homogeneous mixture ofa) an ethylenically unsaturated functional and hygroscopically functional monomer;b) an ethylenically unsaturated functional and hygroscopically functional coupling agent that is capable of (a) chemically reacting with and through the ethylenic bond of the ethylenically unsaturated functional monomer of 1) above and (b) chemically bonding to the surface to which the adhesive is applied;c) a poly-ethylenically unsaturated functional crosslinking agent that is capable of reacting with the monomer of 1) above and the coupling agent of 2) above; andd) a photoinitiator that induces addition polymerization of an ethylenically unsaturated compound.A method for forming a composite and composite structure are included that emply the single package adhesive.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: February 29, 2000
    Assignee: Den-Mat Corporation
    Inventors: Robert L. Ibsen, William R. Glace
  • Patent number: 6031015
    Abstract: A dental material based on polymerizable monomers is described which contains at least one polymerizable monomer which has liquid crystalline properties. Compared with traditional materials, the dental material displays a lower decrease in volume upon polymerization and, because of its low viscosity, higher filler contents can be achieved.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: February 29, 2000
    Assignee: Ivoclar AG
    Inventors: Helmut Ritter, Georg Draheim, Norbert Moszner, Ulrich Salz, Volker Rheinberger
  • Patent number: 6025406
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin and (b) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 0 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: February 15, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • Patent number: 6008264
    Abstract: A method and system are disclosed for curing polymeric materials including dental composites. Preferably, modulated light is used to control the formation of polymer chains in the polymeric material so that a cured polymeric material that has the desired physical characteristics for its intended function. Formation of short chain and long chain polymers from monomers in the polymeric material is initiated and controlled by using a light source with a wavelength suitable for one or more initiators found in the polymeric material.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: December 28, 1999
    Assignee: Laser Med, Inc.
    Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
  • Patent number: 5998495
    Abstract: Photocurable, addition polymerizable compositions contain an epoxy resin and a photoinitiator system containing (a) an epoxy resin, (b) a hydroxyl containing material and (c) a photoinitiator system comprising: (i) an iodonium salt; (ii) a visible light sensitizer; and (iii) an electron donor compound, wherein the photoinitiator system has a photoinduced potential of at least about 100 mV relative to a standard solution of 2.9.times.10.sup.-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5.times.10.sup.-5 moles/g camphorquinone in 2-butanone. The compositions cure on exposure to light in the visible spectrum and are useful in a variety of applications, including dental adhesives and composites.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: December 7, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Dwight W. Jacobs
  • Patent number: 5980253
    Abstract: In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.
    Type: Grant
    Filed: January 12, 1998
    Date of Patent: November 9, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
  • Patent number: 5977199
    Abstract: The invention describes a dental composition, delivery system and method for making temporary crowns and bridges in which the composition comprises two free-radical polymerizable pastes, one a catalyst paste and the other a base paste, wherein the catalyst paste comprises at least one polymerizable monomer, at least one polymerization initiator which is a peroxide oxidizing agent, at least one first polymerization inhibitor and a filler, and wherein the base paste comprises at least one polymerizable monomer, at least one polymerization accelerator, at least one second polymerization inhibitor, at least one non-polymerizable plasticizer and a filler. These catalyst and base pastes are stored in a dual cartridge from which they can be dispensed with a dispenser, preferably in a 1:1 volume ratio, and can be mixed in a static mixer to form a moldable polymerizing material, which is then applied to a prepared area of one or more teeth in a patient's mouth to form a crown or a bridge.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 2, 1999
    Assignee: The Kerr Corporation
    Inventor: Xiaoyi Xie
  • Patent number: 5871360
    Abstract: A method for restoration of a cavity of a tooth including firmly bonding a tooth and a dental composite resin by using a resin reinforced type glass ionomer cement. The method includes a step where the cavity of the tooth is treated with a tooth surface treating agent containing an aqueous solution of acid as a main component or a pre-treating agent containing an unsaturated organic compound as a main component; a step where the resin reinforced type glass ionomer cement is filled in or spread to the cavity; a step where a dental composite resin is then filled in the cavity before or after the resin reinforced type glass ionomer cement is hardened; and a step where the dental composite resin is hardened.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: February 16, 1999
    Assignee: GC Corporation
    Inventor: Shinichi Kato
  • Patent number: 5869178
    Abstract: Disclosed are profiles of fiber-reinforced polymeric plastic and a pultrusion apparatus and method for the manufacture thereof. The apparatus is preferably vertically disposed. As one or more fibers is fed into the apparatus, each fiber is spread and wetted with monomer resin in a bundle spreader, formed in a die, and then subjected in a curing chamber to a source of radiation which initiates polymerization of the monomer, resulting in a fiber-reinforced polymeric plastic exiting from the pultrusion apparatus. Suitably, the radiation is ultraviolet, the monomer resin is methacrylate resin, and the fiber is quartz. The resultant profile is long and thin like a structural steel wire, but typically will have only 1/4 the weight thereof while having a strength comparable thereto. Thus, the profile is useful as an orthodontic wire as a replacement instead of structural steel wires used as orthodontic wires.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: February 9, 1999
    Assignee: The University of North Carolina at Chapel Hill
    Inventors: Robert P. Kusy, Kenneth C. Kennedy, II
  • Patent number: 5856373
    Abstract: A visible-light photopolymerizable composition comprising a) a cationically polymerizable epoxy resin, b) a hydroxyl-containing material c) an aryliodonium salt and d) a visible light sensitizer that is an alpha-dicarbonyl compound having an extinction coefficient less than about 1000. Particularly preferred compositions of the present invention are dental materials.
    Type: Grant
    Filed: October 3, 1997
    Date of Patent: January 5, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: David A. Kaisaki, Sumita B. Mitra, William J. Schultz, Robert J. DeVoe
  • Patent number: 5767170
    Abstract: A single package adhesive for tooth bonding applications which comprises a bulk-water-free solvent-based homogeneous liquid containing:1) An ethylenically unsaturated monomer that possesses a hygroscopic functional group that (a) is capable of chemically reacting with and through the ethylenic bond of the ethylenically unsaturated-functional monomer of 2) below, and (b) provides the capacity for chemical bonding to the surface to which the adhesive is applied.
    Type: Grant
    Filed: April 30, 1996
    Date of Patent: June 16, 1998
    Assignee: Den-Mat Corporation
    Inventors: Robert L. Ibsen, Alan B. Matthews, William R. Glace
  • Patent number: 5749733
    Abstract: Primer/bonding-resin compositions include certain hydrophilic monomers, reactive diluent monomers, high viscosity adhesive resins and photo-initiator systems, all provided in a one-component solution containing ethanol or acetone or other suitable solvents. Methods of use of such compositions include a single step application for priming and imparting enhanced adhesion between dental substrates and dental restoratives or components.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: May 12, 1998
    Assignee: Bisco, Inc.
    Inventors: Xuejun Qian, Byoung I. Suh, Martin Hamer, Russell H. Tobias
  • Patent number: 5744511
    Abstract: A visible-ray polymerizable composition comprising:(1) a monomer comprising a (meth)acrylate monomer; and(2) a visible-ray polymerization initiator comprising:(A) a coumarin dye;(B) at least one photo acid generator selected from the group consisting of a halo-alkyl substituted s-triazine derivative and a diphenyliodonium salt compound; and(C) an aryl borate compound.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 28, 1998
    Assignee: Tokuyama Corporation
    Inventors: Hideki Kazama, Takeshi Satoh, Makoto Oguri
  • Patent number: 5709548
    Abstract: Thermoplastic compositions are used for the fabrication of provisional (i.e., temporary) prosthetic devices, especially for the fabrication of crowns and bridges, and as liners for crowns. Preferably, the thermoplastic compositions comprise free-radically polymerizable functionality so that the material can be polymerized after being shaped to a desired configuration.
    Type: Grant
    Filed: February 18, 1997
    Date of Patent: January 20, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Joel D. Oxman, Scott E. Anderson
  • Patent number: 5663214
    Abstract: A photocuring denture base lining material is disclosed, comprising:a powder component comprising a methacrylic acid ester polymer powder and/or a methacrylic acid ester polymer powder having from 0.01 to 5% by weight of a photocuring catalyst compounded therewith; anda liquid component comprising (a) from 10 to 40% by weight of benzyl methacrylate, (b) from 20 to 40% by weight of at least one of compounds represented by the following structural formula (1): ##STR1## wherein R represents an alkyl group, (c) from 20 to 70% by weight of at least one of methacrylic acid esters having two or three methacryloyl groups in one molecule, and (d) from 0.01 to 5% by weight of a photocuring catalyst. The photocuring denture base lining material of the invention is extremely low in the unpleasant odors and irritation, is superior in the fitness and the operability, and has a high surface hardness after curing.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: September 2, 1997
    Assignee: GC Corporation
    Inventor: Junichi Okada
  • Patent number: 5658963
    Abstract: Primer/bonding-resin compositions include certain hydrophilic monomers, reactive diluent monomers, high viscosity adhesive resins and photo-initiator systems, all provided in a one-component solution containing ethanol or acetone or other suitable solvents. Methods of use of such compositions include a single step application for priming and imparting enhanced adhesion between dental substrates and dental restoratives or components.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: August 19, 1997
    Assignee: Bisco, Inc.
    Inventors: Xuejun Qian, Byoung I. Suh, Martin Hamer, Russell H. Tobias
  • Patent number: 5635545
    Abstract: Thermoplastic molding compositions are made from a mixture of thermoplastic material (for example, polycaprolactone), a free-radically polymerizable resin (for example, a urethane diacrylate oligomer), and free-radical initiator (for example, a visible-light cure photoinitiator). The mixture is solid at 38.degree. C., has a melting or softening point that comfortably can be withstood by oral tissues, and can be imprinted with a heat-stable custom shape memory and semi-thermoplastic properties by shaping the composition to a desired shape and then causing or permitting the resin to undergo polymerization.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 3, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Joel D. Oxman, Lani S. Kangas, F. Andrew Ubel, III
  • Patent number: 5591786
    Abstract: Thermoplastic molding compositions are made from a mixture of thermoplastic material (for example, polycaprolactone), a free-radically polymerizable resin (for example, a urethane diacrylate oligomer), and free-radical initiator (for example, a visible-light cure photoinitiator). The mixture is solid at 38.degree. C., has a melting or softening point that comfortably can be withstood by oral tissues, and can be imprinted with a heat-stable custom shape memory and semi-thermoplastic properties by shaping the composition to a desired shape and then causing or permitting the resin to undergo polymerization.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: January 7, 1997
    Assignee: Minnesota Mining And Manufacturing Company
    Inventors: Joel D. Oxman, F. Andrew Ubel, III, Lani S. Kangas
  • Patent number: 5554665
    Abstract: A method of forming dental products, such as dentures, denture relines, dental crowns, dental bridges and dental restorative materials, temporary crown, temporary bridge, provisional crown or provisional bridge, from two polymerizable paste compositions each having a complimentary component of a free radical catalyst system and a polymerizable acrylic compound. One of these paste compositions includes an oxidizing agent and a stabilizer and the other includes a reducing agent as components of a redox catalyst system for free radical polymerization. These paste compositions are mixed in a static mixer to form a polymerizing paste composition, which is then shaped into a dental prosthesis. A handheld mixing dispenser useful in carrying out this method, includes a static mixing conduit, and two containers enclosing the polymerizable paste compositions. The static mixing conduit encloses a static mixing member. The containers are adapted to be connected in fluid flow communication with the static mixing conduit.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: September 10, 1996
    Assignee: Dentsply Research & Development Corp.
    Inventors: Louis H. Tateosian, Scott E. Shaffer, Mark A. Latta