Phosphorus Is Bonded To A Nitrogen Atom Patents (Class 526/276)
  • Publication number: 20130296499
    Abstract: Phosphazenium-based ionomers and methods of making them are disclosed. The ionomers are useful in making membranes for fuel cells and other devices that benefit from extremely base-stable membranes. The polymers (ionomers) contain repeating units of formula: in which all of R1, R2, W, Y and Z are hydrocarbon.
    Type: Application
    Filed: December 5, 2011
    Publication date: November 7, 2013
    Applicant: CORNELL UNIVERSITY
    Inventors: Geoffrey W. Coates, Kevin Noonan
  • Patent number: 7915441
    Abstract: The oligophosphazene compound capable of forming a polymer which can be used as an optical material is a cyclic or linear compound including constituent units represented by the general formula (I) below in a range from 3 to 14. In the general formula (I), k is an integer of 1 to 4 and X1 is one selected from the group consisting of an oxygen atom, a sulfur atom, an NH group and an NCH3 group. A polymer made of this oligophosphazene compound exhibits high transparency and a high refractive index and is also less likely to cause optical dispersion, and thus it can be used as an optical lens, a retardation film, a light transmission body and other optical moldings.
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: March 29, 2011
    Assignee: Fushimi Pharmaceutical Co., Ltd.
    Inventor: Toshiki Fushimi
  • Patent number: 7479530
    Abstract: A polymer comprising one or more macromonomer units selected from the group consisting of polysiloxane, perfluoroalkylpolyether (PFPE), fluorinated poly(meth)acrylate, polyalkyl (meth)acrylate, polyolefin and fluorinated polyolefin, and one or more charged units (such as an anionic, cationic or zwitter-ionic monomer), formed from a polymerization medium containing an aqueous solution of charged units and use of this polymer as an intraocular lens for the implantation into or onto the cornea. Another aspects relates to a process for coating the above polymer with an adhesive comprising covalently coupling co-reactive surface functional groups of a natural or synthetic polymer with functional groups present (or introduced) on the surface of the macromonomer containing polymer, followed by covalently coupling a multifunctionally activated compound having at least one functional group that is co-reactive to the reactive groups of the natural or synthetic polymer.
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: January 20, 2009
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Timothy Charles Hughes, Grace Yim Ngan Chan
  • Patent number: 7208557
    Abstract: The present invention refers to new classes of polymerisable monomers, to molecularly imprinted polymers obtainable by polymerisation of at least one of the monomers and a crosslinking monomer in the presence of a template molecule. The obtained polymers may be used for separation of enantiomers, diastereomers of the template molecule, and also for separation of the template molecule or template molecule analogues from structurally related compounds.
    Type: Grant
    Filed: December 23, 2004
    Date of Patent: April 24, 2007
    Assignee: MIP Technologies AB
    Inventors: Börje Sellergren, Andrew Hall, Karine Chenon, Rohini Karmalkar
  • Patent number: 7166476
    Abstract: The present invention provides an agglutination immunoassay, wherein the agglutination of insoluble carrier particles such as latex are stabilized and uniformized to give good reproducibility, and a reagent therefor. In the agglutination immunoassay which comprises allowing an antigenic substance in a sample to bind to insoluble carrier particles carrying substantially neither antigens nor antibodies thereon, and allowing an antibody or an antibody complex which reacts specifically to the antigenic substance to bind to the antigenic substance to give a selective agglutination of the insoluble carrier particles, a homopolymer prepared by polymerization of a monomer such as 2-methacryloyloxyethyl phosphorylcholine having a phosphorylcholine group and a vinyl group, or a copolymer prepared by polymerization of a monomer having a phosphorylcholine group and a vinyl group, with a monomer having a vinyl group such as n-butyl methacrylate is used.
    Type: Grant
    Filed: August 28, 2001
    Date of Patent: January 23, 2007
    Assignees: Kyowa Medex Co., Ltd., NOF Corporation
    Inventors: Kayoko Shigenobu, Kenshiro Shuto, Shujiro Sakaki
  • Patent number: 7022789
    Abstract: The present invention relates to telechelic polymers having crosslinkable end groups of the formula and methods for preparing the same wherein n is an integer; is an alkadienyl group; Y is an alkyl group; and Z is crosslinkable end group. In general, the inventive synthesis involves reacting a functionalized chain transfer agent having crosslinkable ends with a cycloalkene in the presence of a ruthenium or osmium catalyst of the formula wherein: M is ruthenium or osmium; X and X1 are independently any anionic ligand; L and L1 are any neutral electron donor ligand; R and R1 are each hydrogen or a substituted or unsubstituted substituent wherein the substituent is selected from the group consisting of C1–C20 alkyl, C2–C20 alkenyl, C2–C20 alkynyl, aryl, C1–C20 carboxylate, C1–C20 alkoxy, C1–C20 alkenyloxy, C2–C20 alkynyloxy, aryloxy, C2–C20 alkoxycarbonyl, C1–C20 alkylthio, C1–C20 alkylsulfonyl and C1–C20 alkylsulfinyl.
    Type: Grant
    Filed: February 22, 2005
    Date of Patent: April 4, 2006
    Assignee: California Institute of Technology
    Inventors: Bob R. Maughon, Takeharu Morita, Robert H. Grubbs
  • Patent number: 6867274
    Abstract: The present invention relates to telechelic polymers having crosslinkable end groups of the formula and methods for preparing the same wherein n is an integer; is an alkadienyl group; Y is an alkyl group; and Z is crosslinkable end group. In general, the inventive synthesis involves reacting a functionalized chain transfer agent having crosslinkable ends with a cycloalkene in the presence of a ruthenium or osmium catalyst of the formula wherein: M is ruthenium or osmium; X and X1 are independently any anionic ligand; L and L1 are any neutral electron donor ligand; R and R1 are each hydrogen or a substituted or unsubstituted substituent wherein the substituent is selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C1-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.
    Type: Grant
    Filed: May 21, 2002
    Date of Patent: March 15, 2005
    Assignee: California Institute of Technology
    Inventors: Bob R. Maughon, Takeharu Morita, Robert H. Grubbs
  • Publication number: 20030166812
    Abstract: The present invention has an object to provide a flame retardant excellent in heat resistance and hard to cause juicing or mold deposits in molding. A flame retardant relating to the present invention has a feature to be made of a polymer constituted of at least one kind, as a building block, among phosphazene compounds each having, in a molecule thereof, at least one of one kind of polymerizable functional group selected from the group consisting of a vinyl group, an allyl group, an acryloyloxy group, a methacryloyloxy group, an acryloyl group, and a methacryloyl group.
    Type: Application
    Filed: April 14, 2003
    Publication date: September 4, 2003
    Inventors: Masatoshi Taniguchi, Yuji Tada, Yoichi Nishioka, Shinji Nakano
  • Patent number: 6465590
    Abstract: The present invention relates to telechelic polymers having crosslinkable end groups of the formula and methods for preparing the same wherein n is an integer; is an alkadienyl group; Y is an alkyl group; and Z is crosslinkable end group. In general, the inventive synthesis involves reacting a functionalized chain transfer agent having crosslinkable ends with a cycloalkene in the presence of a ruthenium or osmium catalyst of the formula wherein: M is ruthenium or osmium; X and X1 are independently any anionic ligand; L and L1 are any neutral electron donor ligand; R and R1 are each hydrogen or a substituted or unsubstituted substituent wherein the substituent is selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: October 15, 2002
    Assignee: California Institute of Technology
    Inventors: Bob R. Maughon, Takeharu Morita, Robert H. Grubbs
  • Patent number: 6306991
    Abstract: A method of crosslinking an oxidative polymer having oxidatively crosslinkable functional groups and a two-pack composition used therein. The oxidatively crosslinkable functional groups on the oxidative polymer are crosslinked by contacting the oxidative polymer with a catalytic amount of an oxidizing enzyme, such as horseradish peroxidase. The present invention is further directed to a two-pack coating composition which includes a polymeric component and a catalytic component, which are mixed together prior to use.
    Type: Grant
    Filed: August 11, 2000
    Date of Patent: October 23, 2001
    Assignee: Rohm and Haas Company
    Inventors: Gordon Charles Fischer, Gary Robert Larson
  • Patent number: 6291618
    Abstract: The present invention relates to cyclic phosphazene azides and their use in a process for producing a rheology modified polymer which comprises contacting a polymer with a cyclic phosphazene azide at a temperature which is at least the decomposition temperature of the cyclic phosphazene azide. When the cyclic phosphazene azide reacts with the polymer, at least two separate polymer chains are advantageously joined and the molecular weight of the polymer chain is increased.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: September 18, 2001
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Michael B. McIntosh
  • Patent number: 6107424
    Abstract: A method for preparing a polymer, comprising the step of polymerizing a monomer of the formula ##STR1## in the presence of a specific initiator containing at least one amino subotituent and one aromatic substituent on a phosphorus atom.
    Type: Grant
    Filed: August 18, 1998
    Date of Patent: August 22, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Stephan Jungling, Thieo E. Hogen-Esch, Dimo Dimov, Axel H. E. Muller, Herbert Konigsmann
  • Patent number: 6060583
    Abstract: This invention relates to a polymerizable phosphazene derivative with a general structural formula[.brket open-st.NP(A).sub.a (B).sub.b).brket close-st.]xwherein the groups A and B are bonded to phosphorus atoms through --O--, --S--, --NH--, or --NR-- (with R=C.sub.1 -C.sub.6) alkyl), and wherein A stands more precisely for a vinyl ether group or a styrene ether group, and B stands more precisely for a hydrocarbon group. The invention also relates to procedures for synthesizing such phosphazene derivatives. The phosphazenes derivatives of the invention can be cured by a process that is initiated cationically, which leads to a large number of advantages. The phosphazene derivatives of the invention can, in particular, be used as curable binders for paints, coatings, fillers, mastics, adhesives, moldings, or films. Paints or coatings comprising the phosphazene derivatives of the invention show especially high mechanical resistance and scratch resistance.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: May 9, 2000
    Assignee: DaimlerChrysler A.G.
    Inventors: Thomas Raith, Wolfgang Nuding
  • Patent number: 6020081
    Abstract: This invention relates to a polymerizable phosphazene derivative with a general structural formula.brket open-st.NP(A).sub.a (B).sub.b).brket close-st..sub.xwherein the groups A and B are bonded to phosphorus atoms through --O--, --S--, --NH--, or --NR-- (with R=C.sub.1 -C.sub.6) alkyl), and wherein A stands more precisely for a vinyl ether group or a styrene ether group, and B stands more precisely for a hydrocarbon group. The invention also relates to procedures for synthesizing such phosphazene derivatives. The phosphazenes derivatives of the invention can be cured by a process that is initiated cationically, which leads to a large number of advantages. The phosphazene derivatives of the invention can, in particular, be used as curable binders for paints, coatings, fillers, mastics, adhesives, moldings, or films. Paints or coatings comprising the phosphazene derivatives of the invention show especially high mechanical resistance and scratch resistance.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: February 1, 2000
    Assignee: Daimler-Benz Aktiengesellschaft
    Inventors: Thomas Raith, Wolfgang Nuding
  • Patent number: 5977257
    Abstract: A high molecular material and a medical material which is a mixed material containing a copolymer A produced by copolymerization of a monomer composition containing a monomer having a side chain represented by the formula (1) ##STR1## (R.sup.1, R.sup.2, R.sup.3 ; H or a C1-4 alkyl group) and a hydrophobic monomer, and one or more sorts of hydrophobic polymer B other than the copolymer A; wherein structure of said mixed material shows phase separation in which domains of several hundred micrometers or less in size consisting of the copolymer A are uniformly distributed in a phase consisting of said hydrophobic polymer B. A liquid high molecular composition in which the copolymer A and the hydrophobic polymer B are dissolved in a mixed solvent consisting of a halogenated hydrocarbon solvent and a lower alcohol solvent, which has turbidity of 60% or less.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: November 2, 1999
    Assignees: NOF Corporation, Japan Science and Technology Corporation
    Inventors: Kazunori Waki, Daijiro Shiino, Kazuo Matsuyama, Nobuo Nakabayashi, Kazuhiko Ishihara
  • Patent number: 5965660
    Abstract: A desensitizing solution for lithography is disclosed which contains at least one member selected from acyclic amine and ammonium compounds each containing specific structures. The desensitizing solution does not cause environmental pollution, is stable to long-term storage, continuous use, and fluctuations in environmental conditions, is effective in reducing the time required for etching treatment, and has excellent desensitization performance.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: October 12, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Seishi Kasai, Ryosuke Itakura, Eiichi Kato
  • Patent number: 5912321
    Abstract: This invention relates to a polymerizable phosphazene derivative with a general structural formula.brket open-st.NP(A).sub.a (B).sub.b).brket close-st..sub.xwherein the groups A and B are bonded to phosphorus atoms through --O--, --S--, --NH--, or --NR-- (with R=C.sub.1 -C.sub.6) alkyl), and wherein A stands more precisely for a vinyl ether group or a styrene ether group, and B stands more precisely for a hydrocarbon group. The invention also relates to procedures for synthesizing such phosphazene derivatives. The phosphazenes derivatives of the invention can be cured by a process that is initiated cationically, which leads to a large number of advantages. The phosphazene derivatives of the invention can, in particular, be used as curable binders for paints, coatings, fillers, mastics, adhesives, moldings, or films. Paints or coatings comprising the phosphazene derivatives of the invention show especially high mechanical resistance and scratch resistance.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: June 15, 1999
    Assignee: Mercedes-Benz
    Inventors: Thomas Raith, Wolfgang Nuding
  • Patent number: 5444123
    Abstract: Halogen-free flameproofed thermoplastic molding materials based on polyphenylene ethers and polystyrene containing, as essential components,A) from 5 to 92% by weight of one or more polyphenylene ethers,B) from 5 to 92% by weight of a vinylaromatic polymer andC) from 3 to 25% by weight of a flameproofing agent based onC1) from 20 to 100% by weight (based on the total amount of C) of a polymeric phosphorus compound which is obtained by polymerizing or copolymerizing one or more compounds of the following structure: ##STR1## where ##STR2## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.10 and R.sup.11 are each hydrogen, alkyl, cycloalkyl, aralkyl or aryl,R.sup.7, R.sup.8 and R.sup.9 are each alkylidene, cycloalkylidene, aralkylidene or arylidene,m, p, q, r, s, t, u and v are each 0 or 1,n is 0, 1 or 2,U is COO, O, S or NR.sup.9,V, W, X and Y are each O, S or NR.sup.9 andZ is O, S or NR.sup.10 R.sup.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: August 22, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Doris Zeltner, Norbert Niessner, Friedrich Seitz, Ranier Neumann, Stefan Seelert
  • Patent number: 5304585
    Abstract: Organic esters of chlorine-containing or bromine-containing phosphorus acids and BIS-GMA, and organic esters of phosphorus acids having chlorine or bromine bonded directly to phosphorus (are described), the organic radical of said esters containing at least one polymerizable functional group. Also described are dental line, restorative, composite, and adhesive compositions containing such organic esters, as well as methods for using such compositions to repair or veneer dental tissue.
    Type: Grant
    Filed: September 3, 1992
    Date of Patent: April 19, 1994
    Assignee: Minnesota Mining and Manufacturing
    Inventor: James E. Bunker
  • Patent number: 5280090
    Abstract: A curable phosphazene composition contains a curable phosphazene compound and a silicone-modified curable compound. The curable phosphazene composition is coated on a substrate and cured to form a coated article. The cured coating is excellent in surface hardness, slip properties and water repellency.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: January 18, 1994
    Assignee: Idemitsu Petrochemical Company, Limited
    Inventors: Akihiko Kurahashi, Masahiro Kitayama
  • Patent number: 5276256
    Abstract: A molding composition containing, based on the total weight of the composition:A) at least 40% by weight of at least one halogen-free polycarbonate;B) 5-40% by weight of at least one halogen-free graft copolymer composed of;1) 40-80% by weight of an elastomer with a glass transition temperature below 0.degree. C., which elastomer is composed of, at least 50% by weight of a diene or of an at least C.sub.4 -alkyl acrylate, 1-40% by weight of a halogen-free phosphorus compound of the formula ##STR1## 2) 20-60% by weight of a shell composed of, 40-98% by weight of styrene, .alpha.-alkylstyrene, nuclear-substituted styrene and/or C.sub.1 -C.sub.8 -alkyl (meth)acrylate, and 2-60% by weight of (meth)acrylonitrile and/or maleic anhydride;C) 5-40% by weight of a halogen-free thermoplastic copolymer composed of, 50-95% by weight of styrene, .alpha.-alkylstyrene, nuclear-substituted styrene and/or C.sub.1 -C.sub.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Niessner, Rainer Neumann, Karl Ruppmich, Friedrich Seitz, Doris Zeltner
  • Patent number: 5239029
    Abstract: A curable resin composition is a blend of a curable phosphazene compound with a pentaerythritol acrylate compound and/or a bis(4-acryloxydialkoxyphenyl)alkane compound in a ratio of the former to the latter ranging from 90 to 10 to 5 to 95. The curable resin composition is provided with excellent properties such as a surface hardness, transparency and so on, and it can be cured at an improved curing rate.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: August 24, 1993
    Assignee: Idemitsu Petrochemical Company Limited
    Inventor: Atsunori Yaguchi
  • Patent number: 5219907
    Abstract: A flame retardant molding composition contains a halogen-free polycarbonate at least one halogen-free graft copolymer assembled from copolymerized units of an elastomer and certain ethylenically unsaturated monomers which include 1-50% by weight of an organic phosphorus compound of the formula (I) ##STR1## a halogen-free thermoplastic copolymer comprising styrene, .alpha.-alkylstyrene, nuclear-substituted styrene and/or C.sub.1 -C.sub.8 -alkyl (meth)acrylate, and (meth)acrylonitrile and/or maleic anhydride, as well as 1-46% by weight of a halogen-free phosphorus compound of the formula (I): Optionally a monophosphate additive and up to 5% by weight of a polytetrafluoroethylene with a median particle size of from 0.05 to 20 .mu.m may be added.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: June 15, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Niessner, Rainer Neumann, Karl Ruppmich, Friedrich Seitz, Doris Zeltner
  • Patent number: 5001203
    Abstract: A composition comprising a polyorganophosphazene having at least some N-(acryloxyhydrocarbyl)carbamyloxyhydrocarbyloxy groups and an amount sufficient to impart cure of an aliphatic or aromatic poly acrylate ester can be cured by irradiation of the composition with ultraviolet light.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: March 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Michel De Poortere, Suae-Chen Chang
  • Patent number: 4980433
    Abstract: This invention relates to novel polymer compositions which are useful for water treatment. These novel compostions are comprised of polymers of -60 ,.beta. ethylenically unsaturated monomer(s), preferably containing carboxylic acid or carboxylic amide functionalities, and amine-containing allyl ether monomers.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: December 25, 1990
    Assignee: Betz Laboratories, Inc.
    Inventors: Fu Chen, William S. Carey
  • Patent number: 4874828
    Abstract: Novel thermoset polymers are prepared by reacting an allyl or vinyl aryl or aryloxy substituted cyclophosphazene with a bis-maleimide.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: October 17, 1989
    Assignee: Hercules Incorporated
    Inventor: Alexander Lukacs, III
  • Patent number: 4806606
    Abstract: Disclosed are nadimido-substituted cyclophosphazene derivatives and thermosets thereof. The thermosets are useful as high temperature, flame resistant matrices for composites and as metal adhesives.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: February 21, 1989
    Assignee: Hercules Incorporated
    Inventor: Alexander Lukacs, III
  • Patent number: 4806607
    Abstract: Disclosed are nadimido-substituted cyclophosphazene derivatives and thermosets thereof. The thermosets are useful as high temperature, flame resistant matrices for composites and as metal adhesives.
    Type: Grant
    Filed: February 11, 1988
    Date of Patent: February 21, 1989
    Assignee: Hercules Incorporated
    Inventor: Alexander Lukacs, III
  • Patent number: 4619965
    Abstract: A dispersion stabilizer for dispersing solid particles into a liquid medium, which comprises resin particles bearing a zwitter-ionic group in the molecule, said resin particles each having substantially an average particle size of not more than 1500 .ANG. when measured by electron microscopic observation.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: October 28, 1986
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Keizou Ishii, Takeo Kurauchi, Jun Nozue, Shinichi Ishikura
  • Patent number: 4601843
    Abstract: A functional fluid composition is provided which comprises a plurality of different phosphazene compounds of the general formula (P=N).sub.n (R).sub.a (R').sub.b (R").sub.c (R'").sub.d wherein R is at least one alkoxy moiety described by the general formula --OCH.sub.2 (CF.sub.2).sub.y X, with X being hydrogen or fluorine and y being equal to 1 to about 10; R', R" and R'" are different aryloxy moieties, each of R', R" and R'" being selected from the group consisting of phenoxy, alkoxy phenoxys, alkyl phenoxys, chlorinated phenoxys, fluorinated phenoxys, aryl phenoxys, phenoxy phenoxys, fluoroalkyl phenoxys, fluoroalkoxy phenoxys, chlorinated phenoxy phenoxys, fluorinated phenoxy phenoxys and mixtures thereof; n is equal to 3 to about 4 for each of said phosphazene compounds, each of a, b, c and d is equal to or greater than zero such that the sum a+b+c+d is equal to 2n; and for the composition as a whole, the average value of each of a, b, c and d is greater than 0.
    Type: Grant
    Filed: April 2, 1985
    Date of Patent: July 22, 1986
    Assignee: Borg-Warner Chemicals, Inc.
    Inventors: Lawrence J. Carr, George M. Nichols, Selwyn H. Rose
  • Patent number: 4579880
    Abstract: A dental filling composite material is disclosed, which contains 10-99% by weight of phosphazene of the formula: ##STR1## in which at least one of R.sub.1 and R.sub.2 represent radicals having not less than 3 carbon atoms and being polymerizable.The filling composite material is low in polymerization shrinkage, thermal expansion coefficient and water absorption and may be quickly polymerized and cured to form a polymer of high compressive strength, flexural strength and hardness.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: April 1, 1986
    Assignee: Nihon University
    Inventors: Masayoshi Ohashi, Misaki Anzai
  • Patent number: 4540760
    Abstract: In a process for producing a polymer of monoallylamine comprising polymerizing monoallylamine, the polymerization is carried out using as a monomer inorganic acid salts (e.g., hydrochloride, sulfate, etc.) of monoallylamine in the presence of an azo type radical initiator.By the process, polymers of monoallylamine having a high degree of polymerization can be obtained in high yield.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: September 10, 1985
    Assignee: Nitto Boseki Co. Ltd.
    Inventors: Susumu Harada, Kiyoshi Shimizu, Hajime Serizawa
  • Patent number: 4539382
    Abstract: An adhesive composition comprises 100 parts by weight of a polymerizable monomer comprising (a) 1.5 to 100 parts by weight of a compound represented by general formula I or II: ##STR1## where R.sub.1 and R.sub.1 ' each stand for hydrogen or a methyl group, R.sub.2 stands for a divalent organic residue having 4 to 40 carbon atoms, X.sub.1 and X.sub.2 each stand for --O--, --S-- or --NH--, a is 0 or 1, and R.sub.3 stands for a group of the formula ##STR2## having 6 to 40 carbon atoms, where R.sub.4 and R.sub.4 ' each stand for a hydrocarbon group having 1 to 29 carbon atoms, and optionally replaced by a halogen atom, or a hydroxyl, amino or carboxyl group, b is an integer of 0 to 3, and Z stands for --O--, --COO-- or --NH--, a plurality of R.sub.4 ' (when b is 2 or 3) being the same or different, at least one of R.sub.4 and R.sub.4 ' having at least three carbon atoms, and (b) 0 to 98.5 parts by weight of a vinyl monomer copolymerizable with the above compound; and 0.01 to 20 parts by weight of a curing agent.
    Type: Grant
    Filed: August 22, 1983
    Date of Patent: September 3, 1985
    Assignee: Kuraray Co., Ltd.
    Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
  • Patent number: 4537940
    Abstract: This invention provides an adhesive composition which comprises 1 part by weight of (a) a compound of the general formula: ##STR1## wherein R.sub.1 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, COOR', wherein R' represents a hydrocarbon group of 1-20 carbon atoms optionally containing halogen or halogen;R.sub.2 is as defined for R.sub.1 ;R.sub.3 represents H, a hydrocarbon group of 1-6 carbon atoms optionally containing halogen, halogen or CN;R.sub.4 represents (COX.sub.2).sub.m1 (CO).sub.m2 (ZCO).sub.m3 (Z).sub.m4 Ra wherein Ra represents an organic residue of 6-60 carbon atoms and a valency of m+n ; m1, m2, m3 and m4 each represents an integer of 0-4 and satisfies m1+m2+m3+m4.ltoreq.m; X.sub.2 represents O, S or NRb, (wherein Rb represents H or alkyl of 1-4 carbon atoms and Z represents O or S;X.sub.1 is as defined for X.sub.
    Type: Grant
    Filed: October 10, 1984
    Date of Patent: August 27, 1985
    Assignee: Kuraray Co., Ltd.
    Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
  • Patent number: 4525493
    Abstract: An adhesive which comprises (a) 1 part by weight of a compound represented by the formula ##STR1## (where R.sub.1 and R.sub.1 ' denote H or a methyl group,X.sub.1, X.sub.1 ', X.sub.2, and X.sub.2 ' denote O, S, or NR.sub..alpha. [where R.sub..alpha. is H or a C.sub.1-6 alkyl group],m is an integer of 1 to 4,n is an integer of 0 to 4,k and k' are 0 or 1,R.sub.a is a C.sub.8-40 organic residue having a valence of (m+1), andR.sub.a ' is a C.sub.1-40 organic residue having a valence of (n+1)), and(b) 0 to 199 parts by weight of a monomer which is copolymerizable with said compound (a).This adhesive firmly adheres to hard tissues of the living body such as teeth and bones, metallic materials, organic polymeric materials, and ceramics. It keeps the high adhesive strength for a long period of time under wet conditions. This adhesive is particularly useful in dentistry.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: June 25, 1985
    Assignee: Kuraray Co., Ltd.
    Inventors: Ikuo Omura, Junichi Yamauchi
  • Patent number: 4515930
    Abstract: An adhesive which comprises (a) 1 part by weight of a polymerizable monomer represented by the formula ##STR1## (where R.sub.1 denotes H or CH.sub.3 ; R.sub.a denotes a C.sub.6-40 organic residue having a valence of m+1; X.sub.1 and X.sub.2 denote O, S, or NR' [where R' denotes H or a C.sub.1-6 hydrocarbon group], two of X.sub.1 may be different from each other when m is 2; Z denotes a halogen; and m is 1 or 2 and k is 0 or 1), and (b) 0 to 199 parts by weight of monomer which is copolymerizable with said monomer (a).This adhesive firmly adheres to hard tissues of the living body such as teeth and bones, metallic materials, organic polymeric materials, and ceramics. It keeps the high adhesive strength for a long period of time under a wet condition. This adhesive is useful particularly in dentistry.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: May 7, 1985
    Assignee: Kuraray Co., Ltd.
    Inventors: Ikuo Omura, Junichi Yamauchi
  • Patent number: 4504640
    Abstract: By polymerizing an inorganic acid salt of monoallylamine in a polar solvent in the presence of a radical initiator having, in its molecule, an azo group and a group having cationic nitrogen atom, a polymer of monoallylamine having a high degree of polymerization can be obtained in high yield.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: March 12, 1985
    Assignee: Nitto Boseki Co., Ltd.
    Inventors: Susumu Harada, Sakuro Hasegawa
  • Patent number: 4463147
    Abstract: A mixture consisting of a polymaleimide and a copolymerizable monomer or a prepolymer formed from these two compounds contains, as the polymerization catalyst, an ethane which is substituted by aromatic groups and hydroxyl groups or halogen (cf. formula II), such as benzpinacol. The mixture is stable on storage and heat-curable. It can be cured, while at the same time being shaped to give mouldings, sheet-like structures, laminates, adhesive bonds or foams, for example by casting or compression moulding.
    Type: Grant
    Filed: December 13, 1982
    Date of Patent: July 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Diethelm, Abdul-Cader Zahir
  • Patent number: 4348427
    Abstract: A method for coating various surfaces is disclosed, which comprises the step of preparing a mixture composed by at least one compound such as an epoxy-acrylic resin, a polyester alpha-omega-acrylate resin, an unsaturated polyester resin, or a urethane-acrylate resin and by at least one unsaturated compound of the amide, lactam, piperidone and urea classes and using said mixture for compounding a varnish to be applied to the selected substrate and then irradiated with an appropriate radiation (range 200 to 400 nm wavelength).
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: September 7, 1982
    Assignee: ANIC, S.p.A.
    Inventors: Aldo Priola, Giampaolo Giuliani
  • Patent number: 4329441
    Abstract: A process for the polymerization of allyl ammonium salts is disclosed wherein allyl ammonium salt is polymerized in the presence of a phosphorus compound.
    Type: Grant
    Filed: November 12, 1980
    Date of Patent: May 11, 1982
    Assignee: AGFA-Gevaert AG Aktiengesellschaft
    Inventor: Peter Bergthaller
  • Patent number: 4321217
    Abstract: Di-alkylated phosphazene oligomers of the general formula: (NP(X.sub.2))..n NPRR' wherein X represents chloride, bromide, or iodide, R and R' represent a linear or branched, saturated or unsaturated hydrocarbon and n represents an integer from 2 to 8, are prepared by reacting, in a nonoxidizing atmosphere, a perhalopolyphosphazene, a Grignard reagent and a cuprous complex in solution, followed by the addition of alkyl iodide or an activated alkyl halide. Polymers, useful as high-temperature elastomers, are prepared from the above oligomers by heating them at a temperature from about 200.degree. C. to about 300.degree. C., followed by a reaction with an amine, metal alkoxide, or a metal aryloxide at a temperature from 20.degree. C. to 200.degree. C.
    Type: Grant
    Filed: June 5, 1980
    Date of Patent: March 23, 1982
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Harry R. Allcock, Paul J. Harris
  • Patent number: 4297468
    Abstract: The invention relates to new cross-linked copolymers containing carboxyl groups and especially useful as thickening agents for aqueous and organic solvents, which copolymers contain(A) 20 to 100% by weight of olefinically unsaturated carboxylic acids,(B) 0 to 80% by weight of at least one mono-olefinically unsaturated monomer copolymerizable with the components A and C, and(C) 0.1 to 4% by weight, calculated on the total quantity of monomers, of allyl monomer of the general formula ##STR1## in which n=0, 1 or 2,m=1, 2 or 3, wherein n+m=3,R.sub.1 =hydrogen, or an alkyl, alkoxyalkyl, haloalkyl, cycloalkyl, aryl, alkaryl, aralkyl or alkenyl radical, andR.sub.2 and R.sub.3, which may be the same or different, each represents hydrogen or an allyl, alkyl, cycloalkyl, aryl, aralkyl or alkaryl radical,wherein at least two of the radicals R.sub.1, R.sub.2 and R.sub.3 must be an allyl radical or a substituted allyl radical.
    Type: Grant
    Filed: May 16, 1979
    Date of Patent: October 27, 1981
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Miroslay Chmelir, Kurt Dahmen
  • Patent number: 4200721
    Abstract: Homopolymers, copolymers and terpolymers of a styrene based monomer are prepared by:(1) polymerizing at least one oxidized styrylphosphine monomer selected from the group of:(C.sub.6 H.sub.5).sub.2 P(O)N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2,(C.sub.6 H.sub.5 O).sub.2 P(O)N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2,(C.sub.6 H.sub.5).sub.2 C.sub.3 N.sub.3 N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2 and(C.sub.6 H.sub.5)C.sub.3 N.sub.3 [N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2 ].sub.2 ; or(2) polymerizing p-diphenylphosphinestyrene and then oxidizing said polymerized p-diphenylphosphinestyrene monomer with an organoazide selected from the group of (C.sub.6 H.sub.5).sub.2 P(O)N.sub.3,(C.sub.6 H.sub.5 O).sub.2 P(O)N.sub.3,(C.sub.6 H.sub.5).sub.2 C.sub.3 N.sub.3 (N.sub.3) and C.sub.6 H.sub.5 C.sub.3 N.sub.3 (N.sub.3).sub.2.
    Type: Grant
    Filed: May 19, 1978
    Date of Patent: April 29, 1980
    Inventors: James C. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Fletcher, Kazimiera J. L. Paciorek
  • Patent number: 4092466
    Abstract: Homopolymers, copolymers and terpolymers of a styrene based monomer are prepared by:(1) polymerizing at least one oxidized styrylphosphine monomer selected from the group of:(C.sub.6 H.sub.5).sub.2 P(O)N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2,(c.sub.6 h.sub.5 o).sub.2 p(o)n.dbd.p(c.sub.6 h.sub.5).sub.2 c.sub.6 h.sub.4 ch.dbd.ch.sub.2,(c.sub.6 h.sub.5).sub.2 c.sub.3 n.sub.3 n.dbd.p(c.sub.6 h.sub.5).sub.2 c.sub.6 h.sub.4 ch.dbd.ch.sub.2 and(C.sub.6 H.sub.5) C.sub.3 N.sub.3 [N.dbd.P(C.sub.6 H.sub.5).sub.2 C.sub.6 H.sub.4 CH.dbd.CH.sub.2 ].sub.2 ; or(2) polymerizing p-diphenylphosphinestyrene and then oxidizing said polymerized p-diphenylphosphinestyrene monomer with an organoazide selected from the group of (C.sub.6 H.sub.5).sub.2 P(O)N.sub.3,(C.sub.6 H.sub.5 O).sub.2 P(O)N.sub.3,(C.sub.6 H.sub.5).sub.2 C.sub.3 N.sub.3 (N.sub.3) and C.sub.6 H.sub.5 C.sub.3 N.sub.3 (N.sub.3).sub.2.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: May 30, 1978
    Inventors: James C. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Fletcher, Kazimiera Jola Liliana Paciorek
  • Patent number: 3972841
    Abstract: The low temperature physical properties of copolymers and terpolymers containing fluoroalkoxy groups such as are described in U.S. Pat. Nos. 3,515,699 and 3,700,629 are improved by the incorporation of up to 35 mol % of non-fluorinated alkoxy groups in the polymers in place of some of the fluoroalkoxy groups. The polyphosphazenes of this invention also preferably contain a small amount of unsaturated substituent on the phosphazene backbone to enhance curability.
    Type: Grant
    Filed: January 29, 1975
    Date of Patent: August 3, 1976
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Tai Chun Cheng, Gary S. Kyker, Thomas A. Antkowiak