Dental Utility Patents (Class 522/908)
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Patent number: 6458865Abstract: 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: GrantFiled: January 15, 1999Date of Patent: October 1, 2002Assignees: Curators of the University of Missouri, 3M Innovative Properties CompanyInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Joel D. Oxman
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Patent number: 6444725Abstract: 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: GrantFiled: January 21, 2000Date of Patent: September 3, 2002Assignee: 3M Innovative Properties CompanyInventors: Matthew C. Trom, Joel D. Oxman
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Patent number: 6426373Abstract: 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: GrantFiled: August 12, 1999Date of Patent: July 30, 2002Assignee: Heraeus Kulzer GmbH & Co. KGInventors: Frank Stange, Albert Erdrich, Novica Savic, Teresa Puchalska
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Patent number: 6407148Abstract: 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: GrantFiled: May 15, 2000Date of Patent: June 18, 2002Assignee: 3M Espe AGInventors: Daniela Krejci, Ivo Krejci, Felix Lutz
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Patent number: 6387981Abstract: 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: GrantFiled: October 28, 1999Date of Patent: May 14, 2002Assignee: 3M Innovative Properties CompanyInventors: Xiaodong Zhang, Brant Ulrick Kolb, Douglas Alan Hanggi, Sumita Basu Mitra, Paula D'Nell Ario, Richard Paul Rusin
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Patent number: 6387979Abstract: 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: GrantFiled: May 15, 2000Date of Patent: May 14, 2002Assignee: Kuraray Co., Ltd.Inventor: Kenichi Hino
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Patent number: 6384099Abstract: 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: GrantFiled: December 8, 1999Date of Patent: May 7, 2002Assignee: Laser Med. Inc.Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
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Patent number: 6361925Abstract: 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: GrantFiled: May 18, 2001Date of Patent: March 26, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Köhler, Andreas Valet
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Patent number: 6355704Abstract: 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: GrantFiled: August 19, 1999Date of Patent: March 12, 2002Assignee: Kuraray Co., Ltd.Inventors: Kazumitsu Nakatsuka, Koichi Okada, Satoshi Imazato, Shigeyuki Ebisu, Yasuhiko Tsuchitani
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Patent number: 6339113Abstract: 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: GrantFiled: October 30, 2000Date of Patent: January 15, 2002Assignee: Dentkist Co., Ltd.Inventors: Dong-Keun Han, Kwang-Duk Ahn, Jong-Man Kim, Jin-Hee Jeong
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Patent number: 6335385Abstract: 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: GrantFiled: March 2, 2001Date of Patent: January 1, 2002Assignee: Dentsply GmbHInventors: Karl Joachin Görlich, Wigbert Hauner, Ralf Janda
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Patent number: 6313189Abstract: 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: GrantFiled: May 4, 1999Date of Patent: November 6, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Robert Wenz, Berthold Nies
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Patent number: 6300389Abstract: 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: GrantFiled: December 30, 1998Date of Patent: October 9, 2001Assignee: GC CorporationInventors: Hisashi Sato, Hideki Yarimizu
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Patent number: 6282013Abstract: 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: GrantFiled: April 27, 1998Date of Patent: August 28, 2001Assignee: LaserMed, Inc.Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
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Publication number: 20010012596Abstract: Compounds of the formulae I, II, III, IV and V 1Type: ApplicationFiled: December 12, 2000Publication date: August 9, 2001Inventors: Kazuhiko Kunimoto, Hidetaka Oka, Masaki Ohwa, Junichi Tanabe, Hisatoshi Kura, Jean-Luc Birbaum
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Publication number: 20010006674Abstract: The invention relates to a mixture for use as wound dressing, which comprises:Type: ApplicationFiled: October 9, 1998Publication date: July 5, 2001Inventor: WOLFGANG MUHLBAUER
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Patent number: 6210759Abstract: 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: GrantFiled: March 15, 2000Date of Patent: April 3, 2001Assignee: American Dental Association Health FoundationInventor: Sabine H. Dickens
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Patent number: 6206959Abstract: 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: GrantFiled: March 15, 2000Date of Patent: March 27, 2001Assignee: American Dental Association Health FoundationInventor: Sabine H. Dickens
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Patent number: 6204302Abstract: 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: GrantFiled: November 19, 1999Date of Patent: March 20, 2001Assignee: Bisco, Inc.Inventors: H. Ralph Rawls, Yeong-Joon Park, Kyu-Ho Chae
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Patent number: 6194481Abstract: 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: GrantFiled: May 19, 1999Date of Patent: February 27, 2001Assignees: Board of Regents of the University of Texas System, Southwest Research InstituteInventors: Benjamin R. Furman, Stephen T. Wellinghoff, Henry R. Rawls, Hong Dixon, Barry K. Norling
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Patent number: 6187833Abstract: 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: GrantFiled: July 28, 1999Date of Patent: February 13, 2001Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 6187836Abstract: 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: GrantFiled: June 5, 1998Date of Patent: February 13, 2001Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Matthew C. Trom, Dwight W. Jacobs
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Patent number: 6184339Abstract: 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: GrantFiled: November 12, 1997Date of Patent: February 6, 2001Assignee: The United States of America as represented by the Secretary of the CommerceInventors: Jeffrey W. Stansbury, Joseph M. Antonucci, Kyung M. Choi
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Patent number: 6159012Abstract: 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: GrantFiled: September 1, 1999Date of Patent: December 12, 2000Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
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Patent number: 6136881Abstract: 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: GrantFiled: September 3, 1998Date of Patent: October 24, 2000Assignee: GC CorporationInventors: Toshihiro Sekiguchi, Shunji Sugano
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Patent number: 6127445Abstract: 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: GrantFiled: November 3, 1998Date of Patent: October 3, 2000Assignee: The University of Georgia Research Foundation, Inc.Inventors: Charles R. Kutal, Yoshikazu Yamaguchi
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Patent number: 6114408Abstract: 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: GrantFiled: February 6, 1998Date of Patent: September 5, 2000Assignee: American Dental Association Health FoundationInventor: Sabine Dickens
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Patent number: 6103453Abstract: 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: GrantFiled: March 17, 1999Date of Patent: August 15, 2000Assignee: BASF AktiengesellschaftInventors: Bernhard Prantl, Erich Beck, Matthias Lokai, Christof Kandzia
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Patent number: 6090865Abstract: 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: GrantFiled: October 26, 1998Date of Patent: July 18, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Christopher Curtis Dudman, Allan Francis Cunningham, Martin Kunz
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Patent number: 6043295Abstract: 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: GrantFiled: July 28, 1999Date of Patent: March 28, 2000Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 6034151Abstract: 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: GrantFiled: March 25, 1998Date of Patent: March 7, 2000Assignee: Ivoclar AGInventors: Norbert Moszner, Thomas Voelkel, Frank Zeuner, Sabine Stein, Volker Rheinberger
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Patent number: 6031016Abstract: 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: GrantFiled: September 18, 1998Date of Patent: February 29, 2000Assignee: Den-Mat CorporationInventors: Robert L. Ibsen, William R. Glace
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Patent number: 6031015Abstract: 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: GrantFiled: July 17, 1996Date of Patent: February 29, 2000Assignee: Ivoclar AGInventors: Helmut Ritter, Georg Draheim, Norbert Moszner, Ulrich Salz, Volker Rheinberger
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Patent number: 6025406Abstract: 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: GrantFiled: April 11, 1997Date of Patent: February 15, 2000Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 6008264Abstract: 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: GrantFiled: April 27, 1998Date of Patent: December 28, 1999Assignee: Laser Med, Inc.Inventors: Calvin D. Ostler, Kevin D. Ostler, David W. Kaufman
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Patent number: 5998495Abstract: 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: GrantFiled: April 11, 1997Date of Patent: December 7, 1999Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Dwight W. Jacobs
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Patent number: 5980253Abstract: 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: GrantFiled: January 12, 1998Date of Patent: November 9, 1999Assignee: 3M Innovative Properties CompanyInventors: Joel D. Oxman, Hoa T. Bui, Dwight W. Jacobs
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Patent number: 5977199Abstract: 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: GrantFiled: February 17, 1998Date of Patent: November 2, 1999Assignee: The Kerr CorporationInventor: Xiaoyi Xie
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Patent number: 5871360Abstract: 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: GrantFiled: December 31, 1996Date of Patent: February 16, 1999Assignee: GC CorporationInventor: Shinichi Kato
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Patent number: 5869178Abstract: 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: GrantFiled: August 25, 1994Date of Patent: February 9, 1999Assignee: The University of North Carolina at Chapel HillInventors: Robert P. Kusy, Kenneth C. Kennedy, II
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Patent number: 5856373Abstract: 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: GrantFiled: October 3, 1997Date of Patent: January 5, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: David A. Kaisaki, Sumita B. Mitra, William J. Schultz, Robert J. DeVoe
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Patent number: 5767170Abstract: 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: GrantFiled: April 30, 1996Date of Patent: June 16, 1998Assignee: Den-Mat CorporationInventors: Robert L. Ibsen, Alan B. Matthews, William R. Glace
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Patent number: 5749733Abstract: 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: GrantFiled: April 25, 1997Date of Patent: May 12, 1998Assignee: Bisco, Inc.Inventors: Xuejun Qian, Byoung I. Suh, Martin Hamer, Russell H. Tobias
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Patent number: 5744511Abstract: 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: GrantFiled: April 18, 1996Date of Patent: April 28, 1998Assignee: Tokuyama CorporationInventors: Hideki Kazama, Takeshi Satoh, Makoto Oguri
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Patent number: 5709548Abstract: 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: GrantFiled: February 18, 1997Date of Patent: January 20, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Joel D. Oxman, Scott E. Anderson
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Patent number: 5663214Abstract: 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: GrantFiled: April 8, 1996Date of Patent: September 2, 1997Assignee: GC CorporationInventor: Junichi Okada
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Patent number: 5658963Abstract: 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: GrantFiled: February 2, 1995Date of Patent: August 19, 1997Assignee: Bisco, Inc.Inventors: Xuejun Qian, Byoung I. Suh, Martin Hamer, Russell H. Tobias
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Patent number: 5635545Abstract: 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: GrantFiled: February 13, 1995Date of Patent: June 3, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Joel D. Oxman, Lani S. Kangas, F. Andrew Ubel, III
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Patent number: 5591786Abstract: 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: GrantFiled: May 19, 1995Date of Patent: January 7, 1997Assignee: Minnesota Mining And Manufacturing CompanyInventors: Joel D. Oxman, F. Andrew Ubel, III, Lani S. Kangas
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Patent number: 5554665Abstract: 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: GrantFiled: April 28, 1995Date of Patent: September 10, 1996Assignee: Dentsply Research & Development Corp.Inventors: Louis H. Tateosian, Scott E. Shaffer, Mark A. Latta