Processes Of Preparing A Solid Polymer From At Least One Phosphorous Containing Monomer; Or Compositions Therefore Patents (Class 522/171)
  • Patent number: 6939901
    Abstract: An adhesive composition comprising (a) an acidic group-containing polymerizable monomer; (b) a polymerizable monomer represented by the general formula (I): wherein R1 is hydrogen atom or methyl group; R2 is a halogen atom, hydroxyl group, mercapto group or —O—R3—OH group, wherein R3 is an alkylene group having 6 to 25 carbon atoms; and Y is oxygen atom or sulfur atom; and (c) a hydrophilic polymerizable monomer, wherein the weight ratio of the polymerizable monomer (b)/acidic group-containing polymerizable monomer (a) is 0.001 to 0.5. The adhesive composition of the present invention can be suitably used for bonding a hard tissue with a resin material in the medical field and the dental field.
    Type: Grant
    Filed: May 22, 2002
    Date of Patent: September 6, 2005
    Assignee: Kuraray Medical, Inc.
    Inventors: Kazumitsu Nakatsuka, Koichi Okada
  • Patent number: 6900251
    Abstract: Acrylic ester phosphonic acids of general formula (I), stereoisomers thereof and mixtures of these, wherein n is 1 or 2, on the condition that for n=1 R1 has the meaning and for n=2 R1 has the meaning R2 is a C1 to C12 alkylene radical, C4-C8 cycloalkylene radical or C7 to C15 alkylene phenylene radical; R3 is hydrogen, a C1 to C5 alkyl radical or a C1 to C5 O-alkyl radical; and R4, R5, independently of each other, each stand for a C1 to C5 alkyl radical or a C1 to C5 O-alkyl radical.
    Type: Grant
    Filed: June 25, 2003
    Date of Patent: May 31, 2005
    Assignee: Ivoclar Vivadent AG
    Inventors: Norbert Moszner, Ulrich Salz, Frank Zeuner, Jörg Zimmermann, Volker Rheinberger, Jorg Angermann, Urs Karl Fischer
  • Patent number: 6852773
    Abstract: The invention relates to a photocurable resin composition comprising: (A) a di or more functional urethane (meth)acrylate compound; (B) a monofunctional (meth)acrylate; (C) a photoinitiator; and (D) a polyoxyalkylene alkyl ether phosphate represented by the following formula (2): and to cured products obtained from the resins composition.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: February 8, 2005
    Assignee: DSM IP Assets B.V.
    Inventors: Takayoshi Tanabe, Jiro Ueda, Tetsuya Yamamura, Takashi Ukachi
  • Patent number: 6849669
    Abstract: The invention relates to macromolecular hydrophilic photocrosslinkers having polymeric backbones of substituted ethylene groups carrying photoactive groups. The photocrosslinkers are capable of producing, when being exposed to light of determined wavelengths above 305 nm, radicals which are retained on the macromolecular photocrosslinkers and reacting so as to accomplish a crosslinked network structure. The invention further relates to the preparation of photocrosslinkers, their use in different aqueous systems and their utility in production of medical devices including ophthalmic lenses.
    Type: Grant
    Filed: March 16, 2000
    Date of Patent: February 1, 2005
    Assignee: Pharmacia Groningen BV
    Inventors: Kenneth A. Hodd, Keith Alfred Dillingham, Jacqueline deGroot, Hendrik Haitjema
  • Patent number: 6812266
    Abstract: A dental adhesive composition for bonding dental restoratives to dentin and enamel provides a one-part self-etching, self-priming dental adhesive composition having hydrolysis stable polymerizable acidic adhesive monomers.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: November 2, 2004
    Assignee: Dentsply DeTrey GmbH
    Inventors: Joachim E. Klee, Uwe Walz
  • Patent number: 6790877
    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: September 20, 2001
    Date of Patent: September 14, 2004
    Assignee: Kuraray Co., Ltd.
    Inventors: Kazumitsu Nakatsuka, Koichi Okada, Satoshi Imazato, Shigeyuki Ebisu, Yasuhiko Tsuchitani
  • Patent number: 6608120
    Abstract: Compounds of the formula: having two double bonds which are activated so that they will take part in a polymerization reaction, the double bonds being sufficiently close together to ensure that cyclopolymerization will preferentially occur. These compounds are used as monomers which preferentially are cyclopolymerized under the influence of ultraviolet or thermal radiation in the production of network polymers, for example coatings or binders.
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: August 19, 2003
    Assignee: Qinetiq Limited
    Inventors: Paul E Milne, Keith M Blackwood, Steven M Kelly, Alan W Hall, John W Goodby
  • Patent number: 6576684
    Abstract: Disclosed are compositions from which radically initiated oligomers/polymers having a controlled molecular weight, low polydispersity and a vinyl or dienyl end group are prepared. Further subjects of the invention are a process for controlled radical polymerization, oligomers/polymers obtainable by said process and the use of specific addition fragmentation agents for the polymerization process. The addition fragmentation agents are new in part and these are also subject of the present invention. The addition fragmentation agents are of the formula (Ia), (Ib) or (Ic) where Y is a group which activates the double bond towards Michael addition.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: June 10, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Vincent Desobry, Peter Murer, Anne Schuwey
  • Patent number: 6531522
    Abstract: The present invention relates to a coating for an optical fiber. The coating includes a monomer. The monomer includes an oxyglycidyl (meth)acrylate component. A coating with the monomeric component has exhibited an excellent polymerization rate. The present invention also relates to methods of making such optical fibers coated in accordance with the invention and the coated glass article.
    Type: Grant
    Filed: November 14, 2000
    Date of Patent: March 11, 2003
    Assignee: Corning Incorporated
    Inventor: Michael J. Winningham
  • Publication number: 20030021943
    Abstract: A photocurable resin composition comprising:
    Type: Application
    Filed: December 3, 2001
    Publication date: January 30, 2003
    Inventors: Hideaki Takase, Jirou Ueda, Takayoshi Tanabe, Takashi Ukachi
  • Patent number: 6512021
    Abstract: A photo-curing sealing agent comprising (a)an (meth)acrylate ester having a solubility parameter of 9 to 14, hydrophobic silica, and a photo reaction initiator. This sealing agent has high adhesion property to a cold-rolled steel, a galvanized steel or an aluminum alloy, to which a press oil, a rust-preventing oil or the like adheres.
    Type: Grant
    Filed: April 6, 2001
    Date of Patent: January 28, 2003
    Assignee: Nichiban Company Limited
    Inventors: Takanori Sugiki, Yuichi Nishida, Yoshio Kishimoto
  • Patent number: 6440519
    Abstract: A photocurable resin composition which comprises (A) a urethane (meth)acrylate oligomer obtained by the reaction of (a) at least one polyol compound preferably selected from the group consisting of polyester polyols and polycarbonate polyols, (b) a polyisocyanate compound, and (c) a hydroxyl group-containing (meth)acrylate compound; (B) a (meth)acrylolylphosphate; (C) a multifunctional (meth)acrylate compound; and (D) a photopolymerization initiator and, optionally, (E) an organosilyl-containing mercapto compound. The composition exhibits a fast cure speed, and the cured products obtained from the composition exhibit superior adhesion under high temperature-high humidity conditions and metal corrosion properties.
    Type: Grant
    Filed: September 25, 1998
    Date of Patent: August 27, 2002
    Assignees: DSM N.V., JSR Corporation, Japan Fine Coatings Co., Ltd.
    Inventors: Hideaki Takase, Ryoji Furuta, Toshihiko Takahashi, Takashi Ukachi, Yuichi Takehana
  • Publication number: 20020115808
    Abstract: Adhesives useful in applying articles, such as tapes, labels, signs, decals, emblems, car moldings, protective or optical films, etc., to surfaces to which articles normally do not adhere well, such as surfaces containing fluorine and polycarbonate, for example. The adhesives include a copolymer of one or more monoethylenically unsaturated alkyl (meth)acrylate monomers, one or more monoethylenically unsaturated secondary or tertiary amide-functional monomers, and optionally one or more acidic monomers.
    Type: Application
    Filed: June 11, 1999
    Publication date: August 22, 2002
    Inventors: RICHARD L. PELOQUIN, ALBERT I. EVERAERTS, ELLEN O. AELING
  • Patent number: 6428862
    Abstract: An ink for ink-jet recording contains a coloring agent, a polymerizable oligomer, water, and a photopolymerization initiator having a solubility in water of 3 percent by weight or more. Another ink for ink-jet recording contains a coloring agent, a polymerizable oligomer having at least two acryloyl groups and a solubility in water of 10 percent by weight or more, a photopolymerization initiator, and water. The specified polymerizable oligomer or photopolymerization initiator reduces bleeding of the ink on recording media.
    Type: Grant
    Filed: April 20, 1999
    Date of Patent: August 6, 2002
    Assignee: Canon Kabushiki Kaisha
    Inventor: Hiromichi Noguchi
  • Patent number: 6399672
    Abstract: Radiation curable compositions for coatings, adhesives, inks, and molded articles are disclosed.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: June 4, 2002
    Assignee: Sartomer Technologies Co., Inc.
    Inventors: Gary W. Ceska, James P. Horgan, Thomas W. Hazell, William R. Schaeffer
  • 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: 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: 6306924
    Abstract: This invention provides an improved coating composition for glass substrates that comprises a tetrasubstituted compound. The introduction of a tetrasubstituted compound in a coating composition for a glass substrate, and in particular an optical fiber, acts to delay the rate of deterioration of the glass or optical fiber due to moisture, and improves adhesion between the glass substrate and the coating composition. The introduction of a tetrasubtituted compound into a polymeric coating composition also improves the interlayer adhesion when more than one coating is applied to a glass substrate. This invention further relates to an outer primary coating composition or matrix material that comprises an acid functional ethylenically unsaturated monomer.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: October 23, 2001
    Assignee: DSM Desotech, Inc.
    Inventor: David M. Szum
  • Publication number: 20010002410
    Abstract: This invention provides an improved coating composition for glass substrates that comprises a tetrasubstituted compound. The introduction of a tetrasubstituted compound in a coating composition for a glass substrate, and in particular an optical fiber, acts to delay the rate of deterioration of the glass or optical fiber due to moisture, and improves adhesion between the glass substrate and the coating composition. The introduction of a tetrasubstituted compound into a polymeric coating composition also improves the interlayer adhesion when more than one coating is applied to a glass substrate. This invention further relates to an outer primary coating composition or matrix material that comprises an acid functional ethylenically unsaturated monomer.
    Type: Application
    Filed: August 21, 1998
    Publication date: May 31, 2001
    Inventor: DAVID M. SZUM
  • Patent number: 6194482
    Abstract: UV-hardenable and thermally hardenable epoxy resins for the underfilling process in electrical and electronic components are provided. A new casting resin component has an increased storage stability at room temperature of at least 6 months and improved characteristics for the underfilling process including faster hardening and lower viscosity. Filler material with a maximum grain size of 20 &mgr;m and a siloxane component are provided in addition to the casting resin formulation.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: February 27, 2001
    Assignee: Siemens Aktiengesellschaft
    Inventors: Barbara Lehner, Recai Sezi
  • Patent number: 6171675
    Abstract: An adhesive composition including (a) a polymerizable (meth)acrylate compound having a phosphate group, (b) a thiol compound, (c) a polymerizable compound having a double bond and having no phosphate group, and (d) a photopolymerization initiator. The adhesive composition is suitably used for fabrication of optical discs.
    Type: Grant
    Filed: May 20, 1999
    Date of Patent: January 9, 2001
    Assignee: Nagase-Ciba Ltd.
    Inventor: Takafumi Iida
  • Patent number: 5905099
    Abstract: A heat-activatable adhesive comprising an acrylic copolymer, which copolymer comprises a monomer consisting of an acrylate or methacrylate ester of a non-tertiary alkyl alcohol having a Tg of about 0.degree. C. or lower; a monomer consisting of an acrylate or methacrylate ester of an alcohol having a Tg of at least about 5.degree. C.; and a functional monomer. Selected embodiments include a retroreflective article comprising a film having a substantially flat surface and a structured surface, the structured surface comprising a plurality of precisely shaped projections, a colored layer disposed on the structured surface and adhered thereto in a plurality of discrete locations, and a heat-activatable adhesive layer disposed on the colored layer.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: May 18, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Albert I. Everaerts, Yoshinori Araki, Michiru Hata
  • Patent number: 5805358
    Abstract: UV-curable Fresnel lens resin compositions ?1a! comprising a (meth)acrylate containing hydroxyl group and aromatic ring (A1), a urethane group-containing (meth)acrylate (A2) comprising an aromatic diol, an aromatic ring-containing monofunctional (meth)acrylate (A3), and a photopolymerization initiator (B) and ?1b! comprising (A1), a mono- or di(meth)acrylate monomer (A4), and (B), further supplemented with a polyester (C1) comprising an aromatic diol and a phosphate (C2) for the formation of a Fresnel lens on a sheet or plate made of a methyl methacrylate (co)polymer; a Fresnel lens formed by UV cure of composition ?1a! or ?1b!; and a rear projection screen including a sheet or plate carrying said Fresnel lens. The Fresnel lens has high refractive index, antistatic properties and is satisfactory in adhesion to a sheet or plate.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: September 8, 1998
    Assignees: Sanyo Chemical Industries, Ltd., Dainippon Printing Co., Ltd.
    Inventors: Tsutomu Yamashita, Michiharu Okubo, Makoto Honda, Futoshi Osawa
  • Patent number: 5800952
    Abstract: A photopolymerizable composition for a color filter, which comprises a photopolymerization initiator system, a compound having at least one ethylenically unsaturated double bond, a colorant, and a phosphoric (meth)acrylate compound and/or an organic carboxylic anhydride having a molecular weight of at most 800, wherein the content of the colorant is from 20 to 90 wt % based on the total solid content.
    Type: Grant
    Filed: October 23, 1996
    Date of Patent: September 1, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiyuki Urano, Ryuichiro Takasaki, Jiro Kamimura, Shingo Ikeda, Noriko Endo, Yuzuru Chika, Tameichi Ochiai
  • Patent number: 5576357
    Abstract: A one-component reactive resin system which is stable in storage but nevertheless can readily be cured completely comprises a mixture of commercially available epoxy resins and phosphorus-containing glycidyl esters, in particular phosphonic acid diglycidyl esters, as well as cationic photoinitiators. The low-viscosity reactive resin systems cannot be cured purely by means of heat and can be processed at high temperatures and in particular can have a high filler content. The reactive resin systems, which are stable to storage even after UV activation, can be cured to flame-resistant molded materials under moderate conditions.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: November 19, 1996
    Assignee: Siemens Aktiengesellschaft
    Inventors: Heiner Bayer, Winfried Plundrich, Ernst Wipfelder
  • Patent number: 5472824
    Abstract: Photosensitive composition comprising, inter alia, thermoplastic-elastomer block copolymer binders and addition-polymerizable monomer having terminal ethylenically unsaturated end groups wherein at least one monomer has one acrylate or methacrylate group, said monomer forms a homopolymer having a solubility parameter in the range between 7.6 and 9.6 and a glass transition temperature below 0.degree. C. and, further wherein, at least one monomer has more than one acrylate or methacrylate groups, said monomer forms a homopolymer having a solubility parameter in the range between 9.6 and 12.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: December 5, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Manfred Schober, Hans L. Schroder
  • Patent number: 5456984
    Abstract: A halogen-free radiation curable flame retardant composition that comprises an end-capped oligomer of a phosphonate polyol and a polyisocyanate and an organic monomer.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: October 10, 1995
    Assignee: DSM Desotech, Inc.
    Inventors: Timothy E. Bishop, Erwin S. Poklacki
  • Patent number: 5414025
    Abstract: A method for the crosslinking of polymeric electrolytes is presented. The method achieves crosslinking by means of ultraviolet radiation. The resulting crosslinked polymers are stable and useful as solid state battery electrolytes.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: May 9, 1995
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Constance J. Nelson, William D. Coggio
  • Patent number: 5321053
    Abstract: A dental composition comprising a vinyl monomer containing at least one acidic group in the molecule thereof and an initiator capable of photopolymerizing said monomer by visible light, characterized in that said initiator consisting essentially of:(a) a photosensitizer selected from an .alpha.-diketone, a quinone and a derivative thereof, and,(b) an accelerator selected from a compound containing at least one mercapto group in the molecule thereof is provided by the present invention.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 14, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Kenichi Hino, Junichi Yamauchi, Koji Nishida
  • Patent number: 5254432
    Abstract: The present invention relates to a photosensitive composition comprising an o-quinonediazide compound and a polyurethane resin having a phosphonic acid group, a phosphoric acid group or its ester group. The photosensitive composition of the present invention provides an excellent adhesion to the support, an excellent developability with an aqueous alkali developer, and a high printing durability.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: October 19, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 5215860
    Abstract: Energy polymerizable compositions comprising at least one cyanate monomer and as curing agent an organometallic compound are disclosed. The compositions are useful in applications requiring high performance, such as high temperature performance; in composites, particularly structural composities; structural adhesives; tooling for structural composities; electronic applications such as printed wiring boards and semiconductor encapsulants; graphic arts; injection molding and prepregs; and high performance binders.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: June 1, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
  • Patent number: 5069929
    Abstract: An actinic radiation-curable, rust-preventive coating composition suitable for use in temporary protection of steel products from rusting and having improved rust preventing property even in the presence of oil on the steel surface is disclosed. The coating composition comprises: (A) from 10 to 50 parts by weight of a vinyl polymer having a glass transition temperature of not lower than 5.degree. C. and a solubility parameter in the range of 9 to 11.5; (B) from 50 to 90 parts by weight of one or more polymerizable compounds having at least one unsaturated group capable of initiating reaction by actinic radiation; and (C) from 0.1 to 20 parts by weight of an organic phosphate of the formula: ##STR1## wherein R.sub.1 is hydrogen or methyl; Y is a straight or branched chain alkylene having 2 to 20 carbon atoms which may be interrupted by one or more ester or oxy linkages and/or aromatic rings; and n is an integer of 1 to 3.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: December 3, 1991
    Assignees: Sumitomo Metal Industries, Ltd., Nippon Paint Co., Ltd.
    Inventors: Tetsuzo Arai, Yasushi Yamamoto, Mitsuyuki Raijo, Isao Fujita
  • Patent number: 4990291
    Abstract: Diacetylinic phosophocholines have distinctly different endothermic and exothermic transition temperatures. Lipid tubules are formed by hydrating a diacetylinic phosphocholine at a temperature above its endothermic transition temperature. The hydrated lipid is then cooled slowly to a formation temperature 1.degree. to 10.degree. C. below the exothermic transition temperature to form tubule structures. The tubules structures can be polymerized to form permanent tubules. The tubules can be used in the same manner as a liposome vesicle or they can be metal coated for a variety of applications.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: February 5, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Paul E. Schoen, Paul Yager, Joel M. Schnur
  • Patent number: 4983644
    Abstract: A dental adhesive composition containing as major components:(a) at least one isocyanate-group-containing urethane prepolymer,(b) at least one isocyanate-group-containing silane compound,(c) at least one radical-polymerizable unsaturated monomer, and(d) at least one initiator selected from the group consisting of redox polymerization initiators and photopolymerization initiatorsis disclosed.This composition is excellent in bonding properties when it is used to bond a living dental tissue with a restoring material such as a metal, organic polymer, and ceramic. Also, this adhesive composition does not require a troublesome pretreatment of the restoring material with an etching agent such as phosphoric acid when the restorating material is required to bond to the living tissue.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: January 8, 1991
    Assignee: Mitsubishi Rayon Company, Limited
    Inventors: Nobuhiro Mukai, Hitoshi Ige, Takayuki Makino, Junko Atarashi
  • Patent number: 4977066
    Abstract: Esters of trihydric or tetrahydric alcohols with alkenylphosphonic or -phosphinic acids, which can be polymerized by means of actinic light, are disclosed. They are combined with polymeric binders, in particular water-soluble polymers, and free-radical-forming photoinitiators to form photopolymerizable mixtures which are suitable for the preparation of photoresists and the production of printing plates. The mixtures show reduced temperature sensitivity and have long shelf lives.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: December 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Joachim Gersdorf, Hans-Jerg Kleiner
  • Patent number: 4968725
    Abstract: Disclosed are dental adhesive compositions consisting essentially of(a) at least one urethane prepolymer containing one or more isocyanate groups, or a blend of the urethane prepolymer and an inert diluent;(b) at least one radical-polymerizable unsaturated monomer;(c) a photopolymerization initiator;and, if desired,(d) a polymerizable phosphoric ester compound having a specific structure.These dental adhesive compositions can be used to bond a restorative material to dentin without requiring any troublesome pretreatment with an etching agent such as phosphoric acid, and can exhibit bonding power sufficient for practical purposes.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: November 6, 1990
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Nobuhiro Mukai, Hitoshi Ige, Takayuki Makino, Junko Atarashi
  • Patent number: 4966934
    Abstract: A biologically compatible adhesive dental primer that is shelf stable as a single component adhesive and includes a mixture of an adhesive promoting and polymerizable monomer system having a free radical polymerizable monomer or prepolymer having ethylenic unsaturation and a phosphorus containing adhesion promoter which is free from halogen atoms bonded directly to a phosphorus atom, and optionally a free radical polymerization catalyst, and an accelerator for the catalyst.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: October 30, 1990
    Assignee: Dentsply Research & Development Corp.
    Inventors: Chin-Teh Huang, Gordon B. Blackwell
  • Patent number: 4925772
    Abstract: A cover layer for micro-electronic components and VLSI circuits is provided for protecting the components and circuits against alpha radiation. The cover layer is produced by ultraviolet cross linking of a negative resist, wherein, as a constituent for absorbing the alpha rays, the negative resist contains a substituted triphosphazene of the formula (I) whose organic radicals are bonded to phosphorus via oxygen and wherein, on a statistical average, 1 through 3 radicals have cross-linkable, light-sensitive groups. The cover layer provided good protection from alpha rays, has low shrinkage during curing and, given high thermal resistance, can be combined when mixing with other negative resists.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: May 15, 1990
    Assignee: Siemens Aktiengesellschaft
    Inventors: Ferdinand Quella, Oskar Nuyken, Klaus Budde, Thomas Suefke
  • Patent number: 4816495
    Abstract: A biologically compatible adhesive that is shelf stable as a single component adhesive and includes a mixture of an adhesive promoting and polymerizable monomer system having a free radical polymerizable monomer or prepolymer having ethylenic unsaturation and a phosphorus containing adhesion promoter which is free from halogen atoms bonded directly to a phosphorus atom, a free radical polymerization catalyst, and an accelerator for the catalyst, the accelerator selected from the group consisting of sulfinic acid or salt thereof, amine or amine salt and mixtures thereof.
    Type: Grant
    Filed: December 9, 1986
    Date of Patent: March 28, 1989
    Assignee: Dentsply Research & Development Corp.
    Inventors: Gordon B. Blackwell, Chin-Teh Huang
  • Patent number: 4762862
    Abstract: A process for preparing particulate water-soluble cationic acrylic polymers having a high molecular weight, an excellent water solubility and a uniform particle size with a good productivity by adding a combined photoinitiator system of an azoguanyl compound and other usual photoinitiator to an aqueous monomer solution containing a cationic vinyl monomer, irradiating the aqueous monomer solution in the form of a thin layer on a moving support with ultraviolet rays in at least two stages, and finely dividing the produced aqueous polymer gel in a wet state by a roller cutter and then by a vertical cutter.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: August 9, 1988
    Assignee: Dai-ichi Kogyo Seiyaku Co. Ltd.
    Inventors: Akira Yada, Shusaku Matsumoto, Yoshihiro Kawamori, Yoshitugu Adachi, Yoshio Hatakawa
  • Patent number: 4743631
    Abstract: Adhesion promoters for metal substrates for paints cross-linkable with U.V. or E.B. radiations or with peroxides of general formula: ##STR1## (wherein R, m and n have the meaning which we will specify in the disclosure), obtained by means of the reaction of glycidyl acrylate and/or glycidyl methacrylate with dihydrophosphonoacetic acid.
    Type: Grant
    Filed: September 6, 1985
    Date of Patent: May 10, 1988
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Alberto Greco, Renato Butturini, Sergio Arrighetti
  • Patent number: 4738870
    Abstract: A highly adherent photopolymerizable composition comprises a (hydroxy)phosphinylalkyl monomer of the formula ##STR1## wherein R is hydrogen, methyl or ethyl and R' and R" are selected independently from hydrogen and alkyl of 1-10 carbon atoms; at least one copolymerizable ethylenically unsaturated monomer and a photoinitiator.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventors: John G. Green, Gerald K. McEwen, David G. Hunt
  • Patent number: 4657941
    Abstract: A biologically compatible adhesive that is shelf stable as a single component adhesive and includes a mixture of an adhesive promoting and polymerizable monomer system having a free radical polymerizable monomer or prepolymer having ethylenic unsaturation and a phosphorus containing adhesion promoter, a free radical polymerization catalyst, and an accelerator for the catalyst, the accelerator selected from the group consisting of sulfinic acid or salt thereof, amine or amine salt and mixtures thereof.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: April 14, 1987
    Assignee: Dentsply Research & Development Corp.
    Inventors: Gordon B. Blackwell, Chin-Teh Huang
  • Patent number: 4657983
    Abstract: Radiation curable copolymers useful in coating compositions are prepared by reacting part of the glycidyl groups of a glycidyl acrylate copolymer with acrylic or methacrylic acid followed by esterifying the remaining glycidyl groups with phosphoric acid.
    Type: Grant
    Filed: December 5, 1984
    Date of Patent: April 14, 1987
    Assignee: Interez, Inc.
    Inventor: Ronald J. Skiscim
  • Patent number: 4640936
    Abstract: A dental composition which when used together with a photopolymerizable dental sealing composition promotes adhesion of resin-based dental restorative materials to the tooth consisting ofa solution of (i) at least one phosphate selected from the group consisting of methacryloyloxyethyl dihydrogen phosphate and bis-(methacryloyloxyethyl) hydrogen phosphate and (ii) a photopolymerization catalyst comprising camphor quinone and an amine, in acetone.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: February 3, 1987
    Assignee: Kulzer & Co. GmbH
    Inventors: Ralf Janda, Bernhard Eppinger
  • Patent number: 4636533
    Abstract: A dental composition which when used together with a photopolymerizable dental sealing composition promotes adhesion of resin-based dental restorative materials to the tooth consisting of a solution of tetramethacryloyloxyethyl pyrophosphate and a photopolymerization catalyst comprising camphor quinone and an amine in acetone.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: January 13, 1987
    Assignee: Kulzer & Co. GmbH
    Inventors: Ralf Janda, Bernhard Eppinger