Phosphorus Atom Is Pentavalent Patents (Class 526/277)
  • Patent number: 5177121
    Abstract: Organic esters of chlorine-containing of bromine-containing phosphorus acids and BIS-GMA, and organic esters of phosphorus acids having chlorine or bromine bonded directly to phosphorus, the organic radical of said esters containing at least one polymerizable functional group. Also described are dental liner, 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: March 28, 1990
    Date of Patent: January 5, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: James E. Bunker
  • Patent number: 5160740
    Abstract: The present invention relates to a micromolecular endoplasmic reticulum which comprises a polymer obtained by polymerization of a mixture containing one or more polymerizable phospholipids, cholesterol and one or more polymerizable fatty acid. The macromolecular endoplasmic reticulum in which surface charge is fixed to negative can be used as a carrier of medicine, enzyme, hemoglobin, etc. in industrial fields or medical fields.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: November 3, 1992
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Etsuo Hasegawa, Shinji Takeoka, Hiroyuki Ohno, Hiroyuki Nishide, Eishun Tsuchida
  • Patent number: 5151479
    Abstract: This invention provides dental adhesive compositions consisting essentially of(a) an aliphatic amine salt of a polymerizable phosphoric ester, as represented by the formula ##STR1## where R and R' are specific radicals; (b) at least one radical-polymerizable unsaturated monomer; and(c) a radical polymerization initiator. These compositions are useful in bonding living dental tissue restoration materials to living tooth tissues, particularly to dentin.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: September 29, 1992
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Nobuhiro Mukai, Hitoshi Ige, Takayuki Makino, Junko Atarashi
  • Patent number: 5116882
    Abstract: A process for making thermoplastic copolymer beads from vinyl aromatic monomers and vinyl phosphonic acid derivatives is disclosed. A process for making foamed articles from the beads is also disclosed. The foamed articles are useful for packaging and construction applications.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: May 26, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Roger A. Grey, Laurel E. Schock, Diandre Armstead
  • Patent number: 5109033
    Abstract: Copolymer compositions based on vinyl aromatic monomers and derivatives of vinyl phosphonic acids are disclosed. The copolymer beads of the invention are advantageously used to make foamed articles useful for packaging and construction applications.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: April 28, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Roger A. Grey, Laurel E. Schock, Diandre Armstead
  • Patent number: 5032295
    Abstract: A polymer for use as a deflocculant in drilling muds comprising at least one unsaturated carboxylic acid or its anhydride or salt, at least one unsaturated sulfonic acid or its salt, at least one unsaturated cationic-containing monomer, and optionally, one or more unsaturated non-ionic monomer and/or one mono or di phosphate ester of an unsaturated alcohol.
    Type: Grant
    Filed: April 25, 1989
    Date of Patent: July 16, 1991
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Gary F. Matz, James C. Long
  • Patent number: 5028676
    Abstract: A resin used for magnetic recording media, comprising a vinyl chloride copolymer containing vinyl monomers with hydroxyl groups and vinyl monomers with quaternary ammonium salt groups as component units. The resin is made by a method which comprises polymerizing an organic solvent solution containing vinyl chloride, vinyl monomers with hydroxyl groups and vinyl monomers with quanternary ammonium salt groups in a reacting apparatus to thereby precipitate a vinyl chloride copolymer, the interior surface of said reactin apparatus, which comes into contact with said organic solvent solution being coated with a fluororesin.
    Type: Grant
    Filed: June 26, 1989
    Date of Patent: July 2, 1991
    Assignee: Sekisui Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takeshi Nakachi, Akio Hata, Yoshihisa Watanabe
  • 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: 4891401
    Abstract: Acrylic polymers with carboxylic acid and small amounts of phosphorus-containing strong acids are good pigment dispersants for use in water-based coating compositions.
    Type: Grant
    Filed: March 22, 1989
    Date of Patent: January 2, 1990
    Assignee: E. I. Du Pont De Nemours and Company
    Inventors: Jozef T. Huybrechts, Guido R. Louis van den Bosch, Rudolf F. Landriette Verhaegen
  • Patent number: 4859756
    Abstract: Polymers are obtained by polymerization of water-soluble monomers which contain one or more polymerizable olefinic double bonds and a quaternary nitrogen atom which is substituted by one or more hydroxyalkyl groups and are present in the form of halide-free salts, with or without further comonomers.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: August 22, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Helmut Goertz, Alfred Oftring, Friedrich Vogel
  • 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: 4782120
    Abstract: Non-polluting thinning adjuvant for sea-water and/or fresh-water based drilling muds.Non-polluting thinning adjuvant for sea-water and/or fresh-water based drilling muds, with the aim to maintain their rheological characteristics in the extreme conditions of temperature and pressure which prevail in wells drilled at great depths. This thinning adjuvant is characterized by the fact that it is a hydrosoluble copolymer resulting from the copolymerization of ethylenic acids, acrylamides and ethylenic esters of phosphoric acid.Its general formula is: ##STR1## in which the indices m,n,p -expressed in % in mole- are chosen from the following intervals:0%<m<90%2%<n<100%0%<p<90%and where radicals R.sub.1, R.sub.2 and R.sub.4 are chosen from the group consisting of H and the alkyles, and radical R.sub.3 is chosen from the group consisting of alkylenes and alkylene-oxides and/or polyalkylene oxides.
    Type: Grant
    Filed: April 13, 1987
    Date of Patent: November 1, 1988
    Assignee: Coatex, S.A.
    Inventors: Jacky Rousset, Jean-Bernard Egraz, Gilles Letetour
  • Patent number: 4732698
    Abstract: A water soluble polymer composition is disclosed. The polymer has repeat units characterized by the structural formulae: ##STR1## wherein R.sub.1 is H or lower alkyl (C.sub.1 -C.sub.3)b; R.sub.2 is OH, OM, or NH.sub.2 ; M is a water soluble cation; R.sub.3 is a hydroxy substituted alkyl or alkylene radical having from 1 to about 6 carbon atoms or a non-substituted alkyl or alkylene radical having from 1 to 6 carbon atoms; X is an anionic radical; Z is H or hydrogens or a water soluble cation or cations which together counterbalance the valence of X, and D is 0 or 1. The copolymer is effective in inhibiting the precipitation of certain scale forming salts, and also acts to inhibit corrosion of metal parts in contact with water systems.
    Type: Grant
    Filed: February 10, 1987
    Date of Patent: March 22, 1988
    Assignee: Betz Laboratories, Inc.
    Inventor: Fu Chen
  • Patent number: 4708815
    Abstract: Scale control polymers and methods of use are disclosed. The polymers are water soluble and are composed of repeat units formed from an .alpha.,.beta. ethylenically unsaturated compound, and repeat units formed from allyl alkylene phosphite ethers.
    Type: Grant
    Filed: February 10, 1987
    Date of Patent: November 24, 1987
    Assignee: Betz Laboratories, Inc.
    Inventors: Fu Chen, Keith A. Bair
  • Patent number: 4681686
    Abstract: New cotelomer compounds having the formula I ##STR1## and salts thereof wherein A is a random polymeric residue comprising at least one unit of formula II ##STR2## and at least one unit of formula III, different from a unit of formula II, ##STR3## and B is hydrogen or a residue A; wherein m and n are integers such that the sum of m+n is an integer of from 3 to 100, the ratio of n:m being from 99 to 1:1 to 99, provided that the resulting telomers are water-soluble and wherein m and/or n in a residue A may be the same as or different from m and/or n in a residue B; R is hydrogen, methyl or ethyl;R.sub.1 is a residue -OX, wherein X is hydrogen, an alkali- or alkaline earth metal, ammonium or an amine residue;R.sub.2 is hydrogen, methyl or a residue --CO.sub.2 R.sub.5, wherein R.sub.5 is hydrogen or a straight- or branched chain alkyl residue having 1 to 8 carbon atoms;R.sub.3 is hydrogen, a straight- or branched chain alkyl residue having 1 to 4 carbon atoms, hydroxymethyl or a residue --CO.sub.2 R.sub.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: July 21, 1987
    Inventors: Norman Richardson, Brian Holt, Barry Cook
  • 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: 4650847
    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: April 4, 1985
    Date of Patent: March 17, 1987
    Assignee: Kuraray Co., Ltd.
    Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
  • Patent number: 4647638
    Abstract: Novel organophosphates of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents H or CH.sub.3, m is a numeral of 1-5 and n is a numeral of 1-2, and adhesives comprising them.
    Type: Grant
    Filed: November 18, 1985
    Date of Patent: March 3, 1987
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Minoru Yokoshima, Tetsuo Ohkubo
  • Patent number: 4626577
    Abstract: A process for preparing a methanolic solution of poly(allylamine) is disclosed, wherein an inorganic acid salt of polyallylamine (e.g. hydrochloride, phosphate or sulfate) is ground into a fine powder, which powder is dispersed in a methanolic solution of caustic alkali (e.g. NaOH or KOH) or ammonia and treated at the temperature of 0.degree. to 65.degree. C. for a period of 10 hours or less.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: December 2, 1986
    Assignee: Nitto Boseki Co., Ltd.
    Inventor: Susumu Harada
  • 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: 4560599
    Abstract: A method for the direct stepwise coating of a solid substrate with a polyfunctional polymerizable surfactant to provide a multilayer assembly of a plurality of oriented monolayers of polymerized surfactant on a surface of the solid substrate comprising depositing and polymerizing sequential layers of polymerizable surfactant on the substrate from a polymerization system comprising:(a) a polyfunctional polymerizable surfactant in an aqueous or other polar solvent system; and(b) a polyfunctional polymerizable surfactant in a non-polar organic solvent systemand wherein the sequential coatings are alternately effected from the (a) and (b) polymerization systems and the polymerizable surfactant utilized is the same or different for each sequential coating,and multilayered surfactant coated solid substrate products produced by this method.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: December 24, 1985
    Assignee: Marquette University
    Inventor: Steven L. Regen
  • Patent number: 4540722
    Abstract: Dental liner and primer compositions having improved adhesion to dentin and containing a metal dissolved in a polar organic solvent, said metal being selected from Fe, Cu, Mn, Co, Sn, Cr, Ni, and Zn.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: September 10, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: James E. Bunker
  • 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: 4533708
    Abstract: The instant invention is directed to a polyampholyte polymer, having an intrinsic viscosity of 0.05 to 4.5 dl/g in 1.0 M NaCl, prepared from 32.5 to 90 percent acrylic acid and/or methacrylic acid, 1.5 to 65 percent, by weight, of acrylamide and 0.5 to 25 percent, by weight, of dimethyldiallyl ammonium chloride and/or diethyldiallyl ammonium chloride.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: August 6, 1985
    Assignee: Calgon Corporation
    Inventor: Christine A. Costello
  • 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: 4487859
    Abstract: A self-curing water dispersed emulsion or solution polymerized polymer comprises copolymerizing ethylenically unsaturated monomers including (i) alkylol acrylamide monomer, (ii) functional monomer such as carboxyl, hydroxyl, amine, or amide functional monomer, (iii) phosphated monomer, and (iv) other ethylenically unsaturated monomer.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: December 11, 1984
    Assignee: SCM Corporation
    Inventor: Phillip C. Martino
  • Patent number: 4480080
    Abstract: Photographic assemblages, elements, receiving elements and cover sheets are described employing a novel timing layer comprising the following recurring units: ##STR1## wherein R.sup.1 is a straight or branched chain alkyl group of from 1 to about 10 carbon atoms or aralkyl group of from about 7 to about 10 carbon atoms;R.sup.2 is a substituted or unsubstituted aryl group of from 6 to about 12 carbon atoms;R.sup.3 is a straight or branched aliphatic group having from 1 to about 20 carbon atoms or an aromatic group having from about 6 to about 20 carbon atoms, the group being substituted with at least one free carboxylic acid group, free sulfonic acid group, free phosphoric acid group or salt thereof;x is from about 1 to about 30 weight percent; andy+z is from about 99 to about 70 weight percent, the ratio of y:z ranging from about 15:85 to about 70:30.The timing layer has a high activation energy and provides improved processing temperature latitude.
    Type: Grant
    Filed: October 24, 1983
    Date of Patent: October 30, 1984
    Assignee: Eastman Kodak Company
    Inventors: David B. Bailey, Edward P. Abel
  • Patent number: 4452957
    Abstract: Homo- and copolymers of quaternary ammonium monomers are prepared directly in dry form by a process which comprises forming a solution of the monomer(s), solvent and a free-radical initiator and simultaneously polymerizing the monomers and drying the solution at a temperature above the boiling point of the solvent.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: June 5, 1984
    Assignee: National Starch and Chemical Corporation
    Inventor: Dennis Neigel
  • Patent number: 4442239
    Abstract: Phosphate derivatives represented by the formula ##STR1## wherein R represents a group containing at least one reactive double bond and A represents a group which may optionally contain reactive double bonds are disclosed. The phosphate derivatives of the present invention have at least two reactive double bonds, and polymers prepared from these phosphate derivatives in the presence or absence of other polymerizable monomers are useful as fillers for human hard tissues such as bones and teeth.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: April 10, 1984
    Assignee: Sankin Industry Co., Ltd.
    Inventors: Masayoshi Tsunekawa, Shinzo Yoshida, Tamotsu Komura
  • Patent number: 4433124
    Abstract: There is provided a one-part structural adhesive composition having satisfactory adhesive to plane surfaces and oily surface-adhesion properties. The adhesive composition comprises substantial amounts of a hydroxyl-containing polymerizable methacrylate represented by a certain general formula and a polymerizable methacrylate having 2 or more methacrylic groups as well as small amounts of a polymerizable organic phosphate represented by a certain general formula, tetrahydroquinoline salt of o-benzoic sulfimide, an organic hydroperoxide and water; the amounts of the above-mentioned components in the composition being within defined ranges.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: February 21, 1984
    Assignee: Okura Kogyo Kabushiki Kaisha
    Inventors: Takanori Okamoto, Hisakazu Mori, Hideaki Matsuda
  • Patent number: 4424310
    Abstract: Poly(allyl)poly(alkenylphenols) are prepared by the transcarbonation of poly(alkenylphenols).
    Type: Grant
    Filed: October 28, 1982
    Date of Patent: January 3, 1984
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Garnet E. McConchie
  • Patent number: 4420587
    Abstract: Phosphonopolyester oligomers are prepared from hydroxyalkylated 2,2',-bis(3-allylphenyl-4-hydroxy) alkanes and phosphonyl dihalides. The oligomers are useful in the preparation of polyester resins, epoxy resins, and polyurethanes.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: December 13, 1983
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4351881
    Abstract: A coating composition comprising a polyfunctional monomer (a) having at least 3 (meth)acryloyloxy groups, a (meth)acrylic acid mono or diester of polyethyleneglycol (b), a sulfonic acid (c), a phosphoric acid ester (d), an ethanolamine (e), organic solvent, and a photosensitizer.
    Type: Grant
    Filed: November 13, 1980
    Date of Patent: September 28, 1982
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kazumasa Kamada, Isao Sasaki, Kenji Kushi
  • Patent number: 4348329
    Abstract: New phospholipids containing a conjugated di-yne system have the formula: ##STR1## wherein at least one of B.sub.1 and B.sub.2 is a group of the formula--(CO).sub.p --X.sub.1 --C.tbd.C--C.tbd.C--Y.sub.1wherein p is 0 or 1, X.sub.1 is a direct bond or a divalent aliphatic or cycloaliphatic group, Y.sub.1 is H or a monovalent aliphatic or cycloaliphatic group, the total number of carbon atoms in X.sub.1 and Y.sub.1 in each of B.sub.1 and/or B.sub.2 being 8 to 26; and the other of B.sub.1 and B.sub.2 is either (a) the same or a different group of the formula:--(CO).sub.p --X.sub.1 --C.tbd.C--C.tbd.C--Y.sub.1where X.sub.1, Y.sub.1 or p are as defined above;or (b) is an aliphatic or cycloaliphatic group containing at least 8 carbon atoms; n is 0 or 1, m is 2, 3 or 4 and each R independently represents an alkyl group containing 1 to 4 carbon atoms, and are prepared by esterification and/or etherification of glycerol by conventional techniques.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: September 7, 1982
    Inventor: Dennis Chapman
  • Patent number: 4321335
    Abstract: A powder coating resin composition comprising (A) a phosphorus-containing vinyl polymer containing a curable functional group and having a softening point, determined by the ring and ball method, of 70.degree. to 150.degree. C. and a number average molecular weight of 1500 to 30000, and (B) a curing agent.
    Type: Grant
    Filed: June 11, 1980
    Date of Patent: March 23, 1982
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Shunji Arimoto, Akio Shoji, Shoichiro Takezawa, Noboru Ishikawa, Hirofumi Takeda
  • Patent number: 4291097
    Abstract: Coating compositions comprising a polyfunctional monomer of a mono or polypentaerythritol poly(meth)acrylate, a bifunctional (meth)acrylate having specific monomer structure, an additional (meth)acrylate containing not more than 2 (meth)acryloyloxy groups, a phosphoric acid ester and an ethanolamine all blended together in a suitable organic solvent system together with a photosensitizer are disclosed. The compositions provide a scratch-resistant, hard cross-linked film surface that is dyeable and resists static and fogging to a synthetic resin article, such as polymethyl methacrylate, to which they are applied.
    Type: Grant
    Filed: December 14, 1979
    Date of Patent: September 22, 1981
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Kazumasa Kamada, Isao Sasaki, Kenji Kushi
  • Patent number: 4279718
    Abstract: Compounds added to initiate photopolymerization of monomers to produce polymeric coatings include compounds of the formula ##STR1## wherein Ar is phenyl or naphthyl,R is hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogen, dialkylamino with 1-4 carbon atoms in each alkyl group, carboxyl, or alkoxycarbonyl with 1-4 carbon atoms in the alkoxy group,X is alkylene having 3 to 6 carbon atoms or alkylene having 6 to 72 carbon atoms interrupted by at least one member selected from the group consisting of ##STR2## and the precursor of X being a polyol having 3 to 6 hydroxyls and having a hydroxyl number of from 100 to 1850,R.sub.1 is hydrogen or methyl,n is a number with a value from about 2 to about 5, andn+m is a number with a value from about 3 to about 6.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: July 21, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Ernst Schuster, Hans Rudolph, Wolfram Mayer, Hans J. Rosenkranz
  • Patent number: 4277565
    Abstract: A macromolecular adsorbent is suitable for recovering heavy metal ions such as uranium ions from a dilute solution such as sea water and is a polymer having pendant groups having the formula ##STR1## wherein R.sup.1 represent a C.sub.1 -C.sub.8 divalent organic group; R.sup.2 and R.sup.3 respectively represents a C.sub.1 -C.sub.5 divalent organic group; p, q, r and l respectively represent 0 or 1; R.sub.f represents a C.sub.1 -C.sub.10 divalent perfluoro group; X.sup.1 and X.sup.2 respectively represent hydroxyl group or a hydroxyl convertible group or atom.
    Type: Grant
    Filed: March 29, 1979
    Date of Patent: July 7, 1981
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Yoshio Oda, Masaaki Yamabe, Masao Kato
  • Patent number: 4259117
    Abstract: A dental filling agent is provided, which contains a phosphoric or phosphonic acid ester compound containing at least one polymerizable functional group and either a group of the formula ##STR1## or a group of the formula ##STR2## or a high molecular weight compound obtainable by polymerizing the compound either alone or as a comonomer unit. This agent has a high bonding affinity for the tooth and enjoys prolonged stability in wet environments.
    Type: Grant
    Filed: August 25, 1978
    Date of Patent: March 31, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Junichi Yamauchi, Eiichi Masuhara, Nobuo Nakabayashi, Kyoichiro Shibatani, Tooru Wada
  • Patent number: 4250007
    Abstract: A photosetting composition useful as a coating varnish comprising a modified, epoxidized butadiene polymer, at least one photopolymerizable monomer and a photosensitizer, the modified, epoxidized butadiene polymer comprising (1) an epoxidized butadiene polymer backbone group, (2) 5 to 50 aromatic or cyclocyclic polybasic carboxylic ester side chain groups per 100 butadiene units, each having at least one acryloyl or methacryloyl terminal group and a linking group formed by a reaction between a carboxylic acid radical in the polybasic carboxylic ester and an epoxy radical in the epoxidized butadiene polymer and, optionally, (3) 0 to 50 phosphoric ester additional side chain groups per 100 butadiene units, each having a linking group formed by a reaction between a hydroxyl radical attached to a P atom in the phosphoric ester and an epoxy radical in the epoxidized butadiene polymer.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: February 10, 1981
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Yasuno, Toshimune Yoshinaga, Tsunetomo Nakano
  • Patent number: 4247672
    Abstract: Heat-curable mixtures which are stable on storage and consist of (a) poly-imides of specific unsaturated dicarboxylic acids of the general formula I ##STR1## in which A is a x-valent organic radical having at least 2 and not more than 30 carbon atoms, Z is a radical of the formulae ##STR2## and x is the number 2 or 3, and (b) poly-(.beta.-iminocrotononitriles) of the formula II, III and/or IV ##STR3## in which Y is a m-valent organic radical having at least 2 and at most 30 carbon atoms, R' is a hydrogen atom or an alkyl having 1 to 6 carbon atoms, cycloalkyl having 5 or 6 carbon atoms or aryl having 6 to 10 carbon atoms, R is an aliphatic or aromatic radical having not more than 30 carbon atoms, E, together with the two nitrogen atoms, is a five-membered or six-membered ring, m is 2 or 3 and n is 1 or 2, are suitable for the production of moulded materials, preferably by casting the resin mixture or by laminating or bonding substrates.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: January 27, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Theobald Haug, Jurg Kiefer
  • Patent number: 4222780
    Abstract: An adhesive composition is provided for hard human tissues which contains 0.1 to 10 weight percent as phosphorus of a phosphinic acid compound having the ##STR1## structure. This adhesive composition provides an intimate bond with hard human tissues such as tooth, bone, etc. and has prolonged stability under wet conditions.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: September 16, 1980
    Assignee: Kuraray Co., Ltd.
    Inventors: Kyoichiro Shibatani, Ikuo Omura, Junichi Yamauchi
  • Patent number: 4212953
    Abstract: Production of urethane foams of increased fire resistance by mixing an ethylenic, e.g. allyl or vinyl, phosphorus compound with a polyol and polymerizing the polyol with polyisocyanate while simultaneously polymerizing the ethylenic phosphorus compound with a suitable catalyst to form an interpenetrating network of urethane polymer and phosphorus-containing polymer.
    Type: Grant
    Filed: September 1, 1978
    Date of Patent: July 15, 1980
    Assignee: McDonnell Douglas Corporation
    Inventors: Martin B. Sheratte, Lydia H. Simanyi
  • Patent number: 4177179
    Abstract: In an aqueous cold setting paint, a specific copolymer and an epoxy resin being soluble in an alcoholic sovlent are incorporated.The specific copolymer is obtained by a solution polymerization of(a) a monomer having ethylenic unsaturated double bond and a nitrogen-containing base,(b) a monomer having ethylenic unsaturated double bond and a phosphoric acid group or a salt thereof or an ester thereof,(c) a monomer having ethylenic unsaturated double bond and carboxylic acid group or a salt thereof and(d) a monomer having ethylenic unsaturated double bond which is copolymerizable with a component (a), (b) or (c) or further treatment of the resulting copolymer with a base.
    Type: Grant
    Filed: August 3, 1978
    Date of Patent: December 4, 1979
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kenji Kurihara, Shigekazu Kasahara, Takashi Suzuki
  • Patent number: 4100140
    Abstract: The invention relates to the manufacture of crosslinked polymers which contain imide groups by reacting polymaleimides with alkenylphenols or alkenylphenol ethers, preferably at temperatures of 100.degree. to 250.degree. C. The reaction mixture optionally also contains polymerization catalysts. The manufacture of the polymers is as a rule carried out with simultaneous shaping. Shaped articles (for example castings), laminates, adhesive bonds and foams can be manufactured in this way. It is also possible to carry out the reaction in solution.
    Type: Grant
    Filed: June 18, 1976
    Date of Patent: July 11, 1978
    Assignee: Ciba-Geigy Corporation
    Inventors: Abdul-Cader Zahir, Alfred Renner
  • Patent number: 4071508
    Abstract: Novel anionic hydrogels, containing acidic groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and cross-linking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a polymerizable acidic monomer containing a sulfonic acid, sulfate or phosphate group in its molecular structure, such as sulfo-ethyl acrylate or methacrylate or a sulfate or phosphate derivative of a hydroxyalkyl- acrylate or methacrylate, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acryloid monomer such as an alkyl acrylate or methacrylate, acrylamides etc.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: January 31, 1978
    Assignee: Plastomedical Sciences, Inc.
    Inventor: Robert Steckler
  • Patent number: 4031299
    Abstract: A polyvinyl chloride extender resin having an average particle size of between about 5 microns and about 50 microns can be formed by using conventional suspension polymerization procedures if a prehomogenized solution comprising an effective amount of polyallyl compound and a low molecular weight propylene polymer are incorporated in the suspension polymerization medium to control the rheological properties of the resin.
    Type: Grant
    Filed: April 11, 1975
    Date of Patent: June 21, 1977
    Assignee: Stauffer Chemical Company
    Inventor: Chung H. Wei
  • Patent number: 4031037
    Abstract: Organic three-dimensional polymeric gel-like materials containing covalently bonded phosphoric acid or a derivative thereof and a method for their manufacture. The bonding is accomplished by the reaction of the free hydroxy or epoxide groups in the homogeneous or macroporous gel-like matrix with the H.sub.3 PO.sub.4, P.sub.2 O.sub.5, phosphorus pentahalide and oxyhalide. The halide containing groups may then be hydrolyzed to form acid groups which then may be modified to form complex compounds by reaction with Lewis acids. The gel material may serve as a strongly acidic cation exchanger, catalyst or polymer reagent.
    Type: Grant
    Filed: February 20, 1975
    Date of Patent: June 21, 1977
    Inventors: Jaroslav Kalal, Jiri Coupek, Svatopluk Pokorny, Frantisek Svec, Karel Bouchal