Sealant Or Adhesive Patents (Class 523/118)
  • Patent number: 6051626
    Abstract: An adhesive composition for dental or surgical treatment comprising (A) 2 to 24 parts by weight of an organic boron compound, (B) 0.002 to 0.5 part by weight of a photopolymerization initiator, (C) 75 to 97 parts by weight of a polymerizable monomer mixture comprising 2 to 20% by weight of a monomer containing an acidic group and 80 to 98% by weight of a monomer containing no acidic group, and (D) optionally, 250 parts or less by weight of a filler.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: April 18, 2000
    Assignee: Sun Medical Co., Ltd.
    Inventors: Weiping Zeng, Akari Shimozono, Tsuyoshi Banba
  • Patent number: 6048913
    Abstract: The present invention relates to a dental coating composition comprising a polymer which has in its molecule one or more phosphorus series acid residues selected from the group consisting of phosphoric acid, phosphonic acid and phosphinic acid and halides and salts thereof and has a weight-average molecular weight of 10,000 to 5,000,000, and water or a lower alcohol. The composition is a dental coating agent which does not easily peel off when drinking or eating, can be removed easily if necessary and does not have a safety problem.
    Type: Grant
    Filed: August 17, 1998
    Date of Patent: April 11, 2000
    Assignee: Kao Corporation
    Inventors: Atsushi Yamagishi, Akira Oshima, Shigeto Kayane, Yukihiro Nakano
  • Patent number: 6037388
    Abstract: A polymerization initiator composition comprising 100 parts by weight of an organic boron compound (A) and 10 to 150 parts by weight of an aprotic solvent (B) having a boiling point of 30 to 150.degree. C.; and a dental or surgical adhesive composition containing the above polymerization initiator composition.
    Type: Grant
    Filed: July 6, 1998
    Date of Patent: March 14, 2000
    Assignee: Sun Medical Co Ltd
    Inventors: Isao Hashimoto, Masami Arata, Weiping Zeng
  • Patent number: 6034152
    Abstract: Dental composites are provided on the basis of customary polymerizable monomers, initiators, fillers and other auxiliaries, which additionally contain the plaque-inhibiting addition of salts of acid-functional polymers having mono- or polyvalent cations.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: March 7, 2000
    Assignees: THERA Patent GmbH & Co. KG, Gesellschaft fur industrielle Schutzrechte
    Inventors: Bernd Burger, Bernd Gangnus, Rainer Guggenberger
  • 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: 6028125
    Abstract: The present invention is an endodontic sealer paste and an endodontic core material for root canal filling, retrofilling, and perforation repair. The endodontic sealer paste contains a dry poly(carboxylic acid), zinc oxide, and an aliphatic acid. The endodontic core material contains a pliant polymer, a dry poly(carboxylic acid), and zinc oxide.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: February 22, 2000
    Assignee: River Valley Endodontics, P.A.
    Inventors: Edward C. Combe, Ernest S. Reeh
  • Patent number: 6015474
    Abstract: The present invention concerns novel methods for enhancing the mechanical performance of tissue adhesives and sealants which comprises employing a primer molecule in association with a tissue adhesive or sealant, wherein the primer molecule serves to enhance the strength of the interface between the tissue and the adhesive matrix. The primer molecules described herein function to interact with collagen present in the tissue, thereby altering its characteristics to make it more amenable to bonding with the adhesive matrix. Primer molecules may be applied to the tissue independently from the tissue adhesive or sealant or may be mixed with the tissue adhesive or sealant prior to application to the tissue.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: January 18, 2000
    Assignee: Protein Polymer Technologies
    Inventor: Erwin R. Stedronsky
  • Patent number: 6001897
    Abstract: The use of polymerizable monomeric conditioning agents for treating the enamel and dentin of a tooth prior to application of a primer and subsequent application of a bonding resin, or a combination of a primer/bonding resin has been found to provide good shear bond strength on both moist and dry dentin. In addition, the contact angles provided by water on dentin conditioned with the polymerizable conditioners as compared to the non-polymerizable phosphoric acid are much lower, reflecting improved spreading over the surface of the tooth.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: December 14, 1999
    Assignee: American Dental Association Health Foundation
    Inventor: Sabine H. Dickens
  • Patent number: 5998499
    Abstract: A liquid crystalline compound, a polymeric product formed by polymerization of the liquid crystalline compound, a dental composition including the liquid crystalline compound and method of using the dental composition. Polymerization of the liquid crystalline compound results in an low volume percent shrinkage and a high conversion to polymer. The composition of the invention is useful for dental adhesive, primer, cement, pit and fissure sealant and restorative.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: December 7, 1999
    Assignee: Dentsply G.m.b.H.
    Inventors: Joachim E. Klee, Holger Frey, Dirk Holter, Rolf Mulhaupt
  • Patent number: 5981621
    Abstract: A biocompatible monomer composition includes: (A) at least one monomer, which forms a medically acceptable polymer; (B) at least one plasticizing agent present in the composition in an amount of from 0.5 wt. % to 15 wt. % of the composition; and (C) at least one acidic stabilizing agent having a pK.sub.a ionization constant of from about 1 to about 7. The composition can be applied to a variety of materials and is particularly suitable as in vivo tissue adhesive. A method of joining together in vivo two surfaces, e.g.
    Type: Grant
    Filed: February 29, 1996
    Date of Patent: November 9, 1999
    Assignee: Closure Medical Corporation
    Inventors: Jeffrey G. Clark, Jeffrey C. Leung
  • Patent number: 5981620
    Abstract: The invention provides polymerizable dental, compounds, compositions, including the compounds and products for mixing the compositions and methods of using the compositions. Aryl acid compounds are provided in accordance with the invention. The compositions include at least one polymerizable aryl acid compound, an effective amount of a polymerization initiator, and at least 10 percent by weight of ceramic, metal and/or metal oxide filler particles having a particle size less than 500 microns. The dental products of the invention include a polymerizable composition in an enclosure having at least two chambers separated by a wall adapted to be ruptured prior to or during mixing of the composition. Compositions of the invention are preferred for use in these enclosures. Core build up material including a polymerizable acid containing compound is used to support dental crowns and adhere them to teeth in accordance with the invention.
    Type: Grant
    Filed: October 17, 1997
    Date of Patent: November 9, 1999
    Assignee: Dentsply Research & Development Corp.
    Inventors: Paul D. Hammesfahr, Kewang Lu, Paul A. Silver
  • Patent number: 5973022
    Abstract: The invention provides dental composition system having curable liquid which is useful alone as a light curable composition and which is useful by mixing with a powder in preselected proportions to form dual cure compositions. The composition system is useful as bonding agent, cement, liner, base, restorative, pit and fissure sealants, and/or core build-up material, having improved adhesion to dentin. After storing the powder and the liquid in separate containers for at least two weeks and then mixing a portion of the powder and a portion of the liquid to form a mixture, the polymerizable compound polymerizes within 20 minutes of the mixing to form a first polymeric material having a flexural strength of at least 50 MPa, and an expansion in water at 37.degree. C. after 90 days of less than 1 percent by volume.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: October 26, 1999
    Assignee: DENTSPLY Research & Development Corp.
    Inventors: Kewang Lu, Paul D. Hammesfahr
  • Patent number: 5955514
    Abstract: The invention provides dental cement compositions and methods of using them for binding hard tooth material, metal and ceramic. The cement compositions include shelf stable complexes of ethylenically unsaturated monomers reacted with cations. The cements have superior adhesion to tooth without separately acid etching dentin or enamel.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: September 21, 1999
    Assignee: Dentsply Research & Development Corp.
    Inventors: Chin-Teh Huang, Kewang Lu, Mingxin Fan, Paul Hammesfahr
  • Patent number: 5932627
    Abstract: The invention provides a fluoride releasing dental primer composition which includes a polymerizable acrylic compound, a light activated catalyst, and an organic amino hydrofluoride. This fluoride releasing dental primer composition is used by applying it to dentin and illuminating it with visible light to polymerize the polymerizable acrylic compound. The invention provides a method of priming dentin by applying a fluoride releasing dental primer composition. The fluoride releasing dental primer composition has a polymerizable acrylic compound, a light activated catalyst, and an organic amino hydrofluoride having from about 2 to about 30 carbon atoms. The polymerizable acrylic compound is adapted to polymerize to form polymeric material. The organic amino hydrofluoride is adapted to leach from the polymeric material, chelate to dentin and release fluoride.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: August 3, 1999
    Assignee: Dentsply GmbH
    Inventor: Gordon Blackwell
  • Patent number: 5929131
    Abstract: A library of diverse molecular configurations containing many combinations and permutations of polymerizable cyclodextrin derivatives (PCDs) is disclosed for use in dental bonding formulations and other applications. Each PCD molecule in the library contains numerous (at least one or more) covalently attached polymerizable groups, and may also contain covalently attached ligand groups, such as free carboxyl groups, tertiary amino groups, or both, which substituents are attached in statistically predetermined proportions by ether or ester linkages. The PCDs may also contain molecularly encapsulated comonomers, polymerization inhibitors (stabilizers), polymerization initiators, and other desirable molecules. The molecular members of the PCD libraries may have quasi-random molecular configurations in the numbers and locations of their various substituents.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: July 27, 1999
    Assignee: American Dental Association Health Foundation
    Inventor: Rafael L. Bowen
  • Patent number: 5925690
    Abstract: A dental composition which comprises (A) a phosphoric acid group-containing monomer, (B) a carboxylic acid groups-containing monomer and (C) water as main components in amounts of 0.5 to 50% by weight, 1 to 50% by weight and 5 to 90% by weight, based on the composition, respectively; and a dental adhesive kit comprising a dental primer composition containing the monomer (A) and water and an adhesive containing a carboxylic acid-containing polyfunctional monomer and a polymerizable initiator.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: July 20, 1999
    Assignee: Tokuyama Corproation
    Inventors: Satoru Fuchigami, Hideki Ohno
  • Patent number: 5922786
    Abstract: A multiple-part dental adhesive primer composition is provided in at least two parts, A and B. Part A comprises an acidic polymerizable compound and a polymerizable diluent. This part is selected such that if water is present the pH of Part A is greater than about 2. Part B comprises an acidic material such that the pH of Part B is below about 2. Methods of bonding substrates are also described.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: July 13, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Sumita B. Mitra, Robert D. Kuehn
  • Patent number: 5919836
    Abstract: The invention relates to the use of a mixture which comprises:a) 1-5 weight % (wt. %) of phosphoric acid;b) 10-90 wt. % of phosphoric acid mono- or di- methacrylates;c) 1-15 wt. % of phosphoric acid trimethacrylates; andd) 3-50 wt. % of diphosphates having between two and four methacrylate ester groups;for the preparation of a composition for preparing a tooth surface for joining with a dental composite material. Using the composition according to the invention, a tooth cavity can be prepared in one step for laying a composite filling. A very high adhesive strength is achieved between the tooth matter and the composite material.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: July 6, 1999
    Assignee: Ernst Muhlbauer KG
    Inventor: Klaus-Jurgen Reinhardt
  • Patent number: 5915969
    Abstract: A tooth having a tooth surface with a plurality of tubules and microchannels defined therein is treated with a polymeric hydrogel formed by a polyphosphazene substance and a metal salt. The polyphosphazene substance is first applied to the tooth surface and then the metal salt is applied thereto. The polyphosphazene substance is reacted with the metal salt to form a polymeric hydrogel inside the tubules.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: June 29, 1999
    Inventor: Lars .ANG.ke Linden
  • Patent number: 5908879
    Abstract: A coated particle is described, which includes a metal fluoride particle and a polysiloxane coating on the surface of the particle. A dental composition is also described, which includes the coated particle, a polymerizable monomer, and a polymerization initiator.
    Type: Grant
    Filed: July 25, 1997
    Date of Patent: June 1, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Mitsunobu Kawashima, Kenichi Hino
  • Patent number: 5866631
    Abstract: There is provided a dental primer composition capable of obtaining high adhesive strength to both dentin and enamel, as a pretreatment material for a chemically polymerizable adhesive. This composition is a dental primer composition comprising a polymerizable monomer containing an acidic group, water, aryl borate and transition metal compound.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: February 2, 1999
    Assignee: Tokuyama Corporation
    Inventors: Hiroyuki Nakagawa, Hideki Ohno
  • Patent number: 5866629
    Abstract: Tissue infiltrating primer formulations and methods of using such formulations, e.g., in the dental or medical fields, are described. The formulations of the invention include an effective amount of a tissue infiltrating agent and a primer. The tissue infiltrating primer formulations provide enhanced penetration of a biomaterial into a target substrate, e.g. hard tissues, when compared to their non-tissue infiltrating primer formulation counterparts.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: February 2, 1999
    Assignee: The University of Toronto Innovations Foundation
    Inventors: Paul Joseph Santerre, Keith Titley, Robert Chernecky, Phillip Watson
  • Patent number: 5866630
    Abstract: Coatings for hard tissue and surfaces of the oral environment are provided that reduce adhesion of bacteria and proteinaceous substances to these surfaces. Methods of reducing adhesion of these materials to such surfaces, and polymers for incorporation into such coatings are also provided.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 2, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Sumita B. Mitra, Charles E. Shelburne, Sharon M. Rozzi, Brant L. Kedrowski
  • Patent number: 5866632
    Abstract: A polymerization initiator composition comprising 100 parts by weight of an organic boron compound (A) and 10 to 150 parts by weight of an aprotic solvent (B) having a boiling point of 30.degree. to 150.degree. C.; and a dental or surgical adhesive composition containing the above polymerization initiator composition.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: February 2, 1999
    Assignee: Sun Medical Co., Ltd.
    Inventors: Isao Hashimoto, Masami Arata, Weiping Zeng
  • Patent number: 5849270
    Abstract: The adhesion of resin material to the solid substance of the tooth and to metals and metal alloys, for example, dental alloys, can be improved with a photo-polymerizable formulation containing hydroxyalkyl(meth)acrylates, urethanedi(meth)acrylates and, if applicable, esters of aromatic polycarboxylic acids possessing methacryloyloxy groups.
    Type: Grant
    Filed: January 22, 1997
    Date of Patent: December 15, 1998
    Assignee: Heraeus Kulzer GmbH
    Inventors: Wolfgang Podszun, Werner Finger
  • Patent number: 5847020
    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: June 6, 1997
    Date of Patent: December 8, 1998
    Assignee: Den-Mat Corporation
    Inventors: Robert L. Ibsen, William R. Glace
  • Patent number: 5847046
    Abstract: A surgical bonding material includes a continuous phase and a discontinuous phase. The continuous phase is formed from a polymerizable liquid. The discontinuous phase includes particles of bioabsorbable polymer. The bonding material may be partially or completely bioabsorbable.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: December 8, 1998
    Assignee: United States Surgical Corporation
    Inventors: Ying Jiang, Mark Roby
  • Patent number: 5846075
    Abstract: A one package, shelf-stable, light-curing orthodontic band cement is disclosed. That cement comprises about 35 to about 80 weight percent finely divided inorganic filler, about 15 to about 45 weight percent of one or more dimethacrylate esters, zero to about 30 weight percent of one or more diluent mono- or trimethacrylate esters, about 5 to about 25 weight percent of one or more dimethacrylate esters containing two carboxylic acid groups and a photo-curing system present in an amount sufficient to effect cure within about two minutes or less upon direct irradiation of the cement with light. The cement's weight ratio of the dimethacrylate ester portion plus diluent mono- or trimethacrylate ester portion to the two carboxylic acid-containing dimethacrylate ester portion is about 3:1 to about 1.5:1. All of the methacrylates present constitute about 20 to about 65 weight percent of the cement. A process for using the cement to affix an orthodontic band to a tooth is also disclosed.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: December 8, 1998
    Assignee: Bisco, Inc.
    Inventors: Byoung I. Suh, Paul A. Gange
  • Patent number: 5844019
    Abstract: A tooth-surface treatment agent for use with dental glass ionomer cement comprises (a) a polymer of an .alpha.-.beta. unsaturated carboxylic acid having a specific molecular weight, (b) a compound containing one or more of the elements selected from the group of aluminum, iron, tin, and calcium, and (c) water. This agent ensures the dissolution and removal of the smear layer, and improves and stabilizes the bonding strength of the glass ionomer cement to tooth structure. Also, the agent has a milder effect than the effects had by phosphoric acid, and has an action on reducing irritation to the dental pulp and is harmless thereto because it enables the smear plugs to remain in dentinal tubules.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: December 1, 1998
    Assignee: GC Corporation
    Inventor: Shinichi Kato
  • Patent number: 5834532
    Abstract: A curable composition comprising a polymerizable monomer having an acidic group in its molecule and an initiator. The composition has a viscosity in the range of from 100 to 30,000 cP at 37.5.degree. C. and may have additionally contain other polymerizable monomer and/or a filler. The composition is applied to a tooth surface directly or after applying a primer composition. There is also provided the primer composition which comprises a polymerizable monomer having an acidic group and a solvent.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: November 10, 1998
    Assignee: Sun Medical Co., Ltd.
    Inventors: Takashi Yamamoto, Weiping Zeng, Masami Arata, Tsuyoshi Banba, Harumi Tanaka
  • Patent number: 5814682
    Abstract: The present invention provides a method of luting a provisional prosthetic device to tooth structure using glass ionomer cement systems having reduced bulk shear adhesion. The invention also provides a kit for luting a prosthetic device to tooth structure. The kit contains at least three containers of glass ionomer luting cement compositions. The kit advantageously can be utilized for providing both a provisional and a permanent luting cement depending upon which components are admixed.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: September 29, 1998
    Inventors: Richard P. Rusin, Paula D. Ario, Dwight W. Jacobs, Joel D. Oxman, Sumita B. Mitra, Ronald M. Randklev
  • Patent number: 5801214
    Abstract: A composition for retaining dentures in the mouth of a denture wearer including 5-8% w/w of an hydrophilic gelling agent, 2-7% w/w of a thickening agent, 5-20% w/w of ail agent that imparts water resistance to the composition, 0.2-5% w/w of humectant(s) and the balance being water, the composition being formable into a viscous hydrophobic film in use. A method of retaining dentures in the mouth of a denture wearer by applying to the denture or the mouth tissue the composition and placing the denture into position in the mouth in a manner such that the composition substantially forms a seal between the mouth tissue and the denture to thereby assist in the retention of the denture.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: September 1, 1998
    Assignee: Confi-Dent Pty Limited
    Inventors: John Alexander Staton, Luke Thomas
  • Patent number: 5773490
    Abstract: Pressure sensitive adhesives for transdermal absorption formulations comprising a segmented polyurethane, which can control dissolution and a releasing property of drugs of various kinds which are solid at normal temperature; said segment being an alkylene oxide chain which is in a liquid state at a temperature of around normal temperature to around body temperature, and said segment containing a hydrophilic alkylene oxide chain and a hydrophobic alkylene oxide chain, or comprising one or both of them and an alkylene oxide chain in which a hydrophilic moiety and a hydrophobic moiety are present in the mixed manner.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: June 30, 1998
    Assignee: Takiron Co., Ltd.
    Inventors: Yasuo Shikinami, Kunihiro Hata
  • Patent number: 5763554
    Abstract: This invention relates to an improved denture adhesive composition having extended holding power accompanied by adhesion building properties during use and having increased gel adhesion, which composition consists essentially of (a) from about 10 to about 35 wt. % lower alkyl vinyl ether-maleic acid copolymer wherein from 0 to about 90 wt. % of the copolymer carboxyl units are converted to a mixture of salts selected from the group of calcium, sodium, strontium, aluminum, zinc, magnesium and potassium; (b) 10-35 wt. % of a crosslinked terpolymer of alkyl vinyl ether, maleic anhydride and a C.sub.16 -C.sub.20 alkyl acrylate or methacrylate, or vinyl ether; crosslinked with a C.sub.6 -C.sub.14 diene, e.g. 9-decadiene, and their salts; (c) 10-35 wt. % of a cohesive agent; in a weight ratio of between about 2:1 and about 1:2 with respect to the copolymer; and (d) from about 30 to about 70 wt. % of an oil base as a carrier.
    Type: Grant
    Filed: October 11, 1996
    Date of Patent: June 9, 1998
    Assignee: ISP Investments Inc.
    Inventors: William E. Prosise, Yoon Tae Kwak
  • Patent number: 5760101
    Abstract: A condensation product of a hydroxy(meth)acrylate compound corresponding to the formula ##STR1## in which R.sub.1 is hydrogen or methyl, A is a trivalent aliphatic residue with 3 to 15 C-atoms which is unsubstituted or substituted with OH groups and optionally contains up to 5 ether bridges, and an aromatic carboxylic acid anhydrides compound of the formula (II) or an aromatic carboxylic acid anhydride chloride compound of the formula (II) ##STR2## in which Ar is a benzene ring or a naphthalene ring, n is 1 or 2, and m is 0, 1 or 2. The condensation product has a molar mass of 300 and to 10,000 daltons. The condensation product is useful as an adhesive to bond dental filling materials to teeth.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: June 2, 1998
    Assignee: Heraeus Kulzer GmbH
    Inventors: Ludger Heiliger, Wolfgang Podszun, Werner Finger
  • Patent number: 5756560
    Abstract: An etchant/primer composition is provided which includes (a) a compound having the formulaRN(CH.sub.2 YCO.sub.2 M).sub.2 (I)wherein R=R.sup.1 or R.sup.2 ;R.sup.1 =an aromatic group;R.sup.2 =a conjugated aliphatic group;Y=a single bond, CH.sub.2, CHCH.sub.3 or C.dbd.CH.sub.2 ; andeach M is independently H, an alkali metal, an alkaline earth metal, aluminum, a transition or redox metal or an alkyl group having 1 to 18 carbon atoms, with the proviso that when both M groups are alkyl groups, the compound corresponding to formula I be capable of being easily hydrolyzed, displaced or exchanged with other reagents present in the etchant/primer composition and (b) a polar solvent system. An etchant/primer/adhesive monomer composition is also provided which includes the etchant/primer composition and an adhesive monomer system. One and two step simplified methods for adhering and for preparing a substrate surface, such as a dental substrate surface, to a polymeric material are also provided.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: May 26, 1998
    Assignee: The United States of America as represented by the Secretary of the Commerce
    Inventors: Joseph M. Antonucci, Patricia A. Bennett
  • Patent number: 5750591
    Abstract: A denture adhesive with significantly improved hold performance is comprised of the mixed partial salts of polymethyl vinyl ether maleic acid. At least one of said salts comprises zirconium while a second salt is selected from the group consisting of calcium, zinc, magnesium, iron, strontium and mixtures thereof. Optionally, a tripartite salt formulation may be prepared utilizing sodium, lithium or potassium. The adhesives are formulated in a standard pharmaceutically acceptable vehicle comprised of waxes, oils, colorants, viscosity modifiers and the like as is known in the art. The denture adhesive may be formulated as a paste, powder or liquid which has rapid absorption characteristics for faster swelling softening and superior coalescence.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: May 12, 1998
    Assignee: The Block Drug Company
    Inventors: Hal C. Clarke, Hyung-Kook Ahn, Eddie Wong, Robert C. Gasman, Alfred J. Smetana, Joseph Synodis, Tiang Shing Chang
  • Patent number: 5739177
    Abstract: A dental composition containing an acid such as maleic acid, phosphoric acid or citric acid; an organosulfonate and/or an organosulfinate such as an acid group-containing (meth)acrylate monomer having in the molecules thereof a carboxyl group or a phosphoric acid group, a sodium benzenesulfonate or a sodium p-toluenesulfinate; a water-soluble organic solvent such as ethanol or propanol; and the water: but without substantially containing any polymerizable monomer except the above acid group-containing (meth)acrylate monomer, or further containing a hydroxy- or a dihydroxyalkyl (meth)acrylate monomer. For adhesion of a dental filling material to teeth, the composition of the invention is used as a pre-treatment agent on teeth prior to applying an adhesive. This makes it possible to treat enamel and dentin simultaneously and to accomplish strong adhesive strength to both of them.
    Type: Grant
    Filed: June 6, 1996
    Date of Patent: April 14, 1998
    Assignee: Tokuyama Corporation
    Inventors: Hideki Ohno, Mikio Kimura, Satoru Fuchigami, Makoto Oguri
  • Patent number: 5733968
    Abstract: The invention relates to a multi-component dental cement which contains as a first component an ethylenically unsaturated polymerisable compound, as a second component calcium hydroxide, calcium oxide or a precursor thereof and also a polymerisation initiator, the constituents of which can be contained in one or more cement components, which is characterized in that the ethylenically unsaturated polymerisable compound has both at least one .beta.-dicarbonyl group and also at least one acrylic, alkacrylic or vinyl aromatic group. Also included are a process for the production of a multi-component dental cement and the use of the described polymerisable .beta.-dicarbonyl compounds in calcium hydroxide dental cements.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: March 31, 1998
    Assignee: Ivoclar AG
    Inventors: Norbert Moszner, Ulrich Salz, Volker Rheinberger
  • Patent number: 5730601
    Abstract: A composition for use in dental treatments of damaged or diseased teeth is provided. The composition comprises a combined filler material, photoinitiator and comonomer resin mixture polymerizable upon incidence of light. The comonomer resin mixture comprises a comonomer resin blend comprising at least two monomers from the same monomer series with at least a first monomer having a first molecular weight and a second monomer having a second molecular weight with the second molecular weight being greater than the first molecular weight of the first monomer. The comonomer resin mixture further comprises a third monomer combined with the comonomer resin blend.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: March 24, 1998
    Assignee: The Regents of the University of Colorado
    Inventors: Christopher N. Bowman, Kristi S. Anseth, Anandkumar R. Kannurpatti, Michael D. Goodner
  • Patent number: 5718924
    Abstract: A fluoride releasing dental composition comprising a polymer, a monomer and a metal fluoride. The polymer may be an acrylate polymer, a methacrylate polymer or a copolymer thereof. The monomer may be a monomeric heterocyclic acrylic ester, a monomeric heterocyclic methacrylic ester, a C.sub.3 -C.sub.16 alkyl acrylic ester or a C.sub.3 -C.sub.16 methacrylic ester. The metal fluoride is a nontoxic, biologically acceptable metal fluoride. In certain embodiments, the metal fluoride is sodium fluoride. The metal fluoride may comprise from approximately 0.1% to approximately 2% of the composition by weight.
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: February 17, 1998
    Assignee: Eastman Dental Institute
    Inventors: Michael Braden, Mangala Prakesh Patel, Gavin John Pearson
  • Patent number: 5717005
    Abstract: Chlorhexidine gluconate-containing adhesives have dispersed therein solid chlorhexidiene particles which will pass through a 125 .mu.m sieve and at least about 30% of the total volume of particles has a size of not less than 5 .mu.m. The adhesive may be a vinyl ether adhesive and may be coated upon a backing layer such as a hydrophilic polyurethane to produce products suitable for use as wound dressings, IV dressing or incise drapes. The chlorhexidine gluconate may be obtained as a freeze-dried solid and added directly, in suspension, to the adhesive mass without further milling.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: February 10, 1998
    Assignee: Smith & Nephew PLC
    Inventor: Mark Christopher Richardson
  • Patent number: 5707611
    Abstract: A tooth surface treating agent is provided which comprises a polymerization catalyst and an acidic compound, both water-soluble, the treating agent being capable of enhancing tooth adhesion. The tooth surface treating agent imparts strong adhesion to the enamel and dentin of teeth through simultaneous treatment thereof. The invention is mainly intended for use in the field of dentistry, but is also applicable as a treating agent for vital hard tissues in such fields as surgery, and orthopaedic or plastic surgery.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: January 13, 1998
    Assignee: Kabushiki Kaisha Shofu
    Inventors: Kunio Ikemura, Yoshiaki Kouro, Hisaaki Tachidokoro, Katsuya Kimoto
  • Patent number: 5708052
    Abstract: Compositions and methods for priming or sealing dental or biological substrates for subsequent bonding. The primer is particularly useful for priming dentin of a tooth to prepare the dentin for bonding with a resinous material. The primer comprises a mixture of a polymerization initiator such as camphoroquinone and a polymerizable promoter such as methacrylic acid. Polymerizable promoters within the scope of the present invention have at least one ethylenically unsaturated group and at least one carboxylic acid group. The primer may further comprise a solvent such as ethanol, a natural resin such as Canadian balsam and a polymerizable resin such as 2-hydroxyethyl methacrylate (HEMA). The primer can also be formed from a mixture of a polymerization initiator, a natural resin and a polymerizable resin.
    Type: Grant
    Filed: July 8, 1996
    Date of Patent: January 13, 1998
    Assignee: Ultradent Products, Inc.
    Inventors: Dan E. Fischer, Steven D. Jensen
  • Patent number: 5705581
    Abstract: Described are novel fluoride ion-releasing acrylic or methacrylic acid-based monomers, fluoride ion-releasing dental resin materials prepared from the monomers, and processes for preparing the monomers and dental resin materials. The monomers of the invention are prepared in good yield from readily available starting materials. Dental resin materials of the invention exhibit excellent sustained fluoride ion release.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: January 6, 1998
    Assignee: Indiana University Foundation
    Inventors: Wilmer K. Fife, Martel Zeldin, Slawomir Rubinsztajn
  • Patent number: 5698020
    Abstract: The invention relates to dental materials which contain a photochromic material such as for example a photochromic dye, a photochromic glass, a photochromic ceramic and/or a photochromic glass ceramic and which can be visually distinguished from natural tooth material after irradiating with light, but which assume their original colour again after a certain period has expired.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: December 16, 1997
    Assignee: Ivoclar AG
    Inventors: Ulrich Salz, Peter Burtscher, Volker Rheinberger, Heinz Durr
  • Patent number: 5696181
    Abstract: An improved denture adhesive composition is comprised of a highly cross-linked lower alkyl ether/maleic acid or maleic anhydride copolymer in which up to about 85% of the initial free carboxyl groups are reacted with one or more cross-linking agents. The cross-linking agents are mixtures of inorganic divalent cations such as calcium, magnesium and zinc together with organic bifunctional compounds comprised of polyhydroxyl compounds such as propylene glycol, glycerin and the like. The copolymer has a specific viscosity of no less than 1.5. A hydrophilic polymer such as sodium alginate or carboxymethyl cellulose may also be added to the lower alkyl vinyl ether/maleic acid or maleic anhydride copolymer which is then formulated with other excipients in a paste, powder, liquid, gel or cream composition.
    Type: Grant
    Filed: September 22, 1995
    Date of Patent: December 9, 1997
    Assignee: The Block Drug Company, Inc.
    Inventors: Tiang-Shing Chang, Donna DiFerdinando
  • Patent number: 5670559
    Abstract: A primer composition for the treatment of a tooth surface, which comprises a) at least one metal compound selected from the group consisting of an iron compound, a copper compound and a cobalt compound, b) a polymerizable monomer having an acidic group, and c) water or water and an organic solvent miscible with water; and a method of forming an adhesive layer on a tooth surface, which comprises applying this primer composition to the tooth surface and then applying a curable composition containing trialkylborane or partial oxide thereof and a polymerizable monomer. According to the present invention, both the enamel and the dentin of a tooth can be simultaneously surface-treated without acid treatment or washing with water, and adhesion dental treatment can be reliably carried out by a simple operation without causing pains on a patient.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: September 23, 1997
    Assignee: Sun Medical Co., Ltd.
    Inventors: Weiping Zeng, Masami Arata, Tsuyoshi Banba
  • Patent number: 5662886
    Abstract: A modified amalgam composition forming an adhesive bond with tooth structure treated with a dental adhesive. The modified amalgam can be prepared by admixing particulate additives into conventional amalgam alloy powder to form a modified alloy powder and then triturating the modified alloy powder with mercury. The modified amalgam when applied to a prepared tooth cavity that has been precoated with an acrylate- or methacrylate-functional dental adhesive results in an adhesive bond between the modified amalgam and coated tooth structure. Preferred particulate additives for the amalgam alloy powder are acrylate- or methacrylate-functional polymers, metal salts of acrylates or methacrylates, nonmetallic fillers, oxidizing agents and reducing agents.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: September 2, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Joel David Oxman, Jon Wallace Fundingsland
  • Patent number: 5645429
    Abstract: A method is provided for clinical retention of restorative material by a natural tooth. A first portion of photopolymerizable liquid primer/adhesive dental composition is applied to a tooth surface. After leaving the first portion of the liquid composition on the tooth surface undisturbed for at least 15 seconds on the tooth surface air is conveyed against the first portion of the liquid. The light is impinged on the first portion of the liquid composition whereby at least a portion of the first portion of the liquid composition polymerizes to form a first coating on the tooth. A second portion of the liquid composition is applied to the first coating, and air is substantially immediately conveyed to the second portion of the liquid composition.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: July 8, 1997
    Assignee: Dentsply Research & Development Corp.
    Inventors: Gordon Blackwell, Chin-Teh Huang, Steven Jefferies