Phosphorus Atom Is Pentavalent Patents (Class 526/277)
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Patent number: 5177121Abstract: 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: GrantFiled: March 28, 1990Date of Patent: January 5, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventor: James E. Bunker
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Patent number: 5160740Abstract: 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: GrantFiled: April 27, 1990Date of Patent: November 3, 1992Assignee: Nippon Oil & Fats Co., Ltd.Inventors: Etsuo Hasegawa, Shinji Takeoka, Hiroyuki Ohno, Hiroyuki Nishide, Eishun Tsuchida
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Patent number: 5151479Abstract: 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: GrantFiled: April 20, 1990Date of Patent: September 29, 1992Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Nobuhiro Mukai, Hitoshi Ige, Takayuki Makino, Junko Atarashi
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Patent number: 5116882Abstract: 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: GrantFiled: May 16, 1991Date of Patent: May 26, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Roger A. Grey, Laurel E. Schock, Diandre Armstead
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Patent number: 5109033Abstract: 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: GrantFiled: May 16, 1991Date of Patent: April 28, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Roger A. Grey, Laurel E. Schock, Diandre Armstead
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Patent number: 5032295Abstract: 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: GrantFiled: April 25, 1989Date of Patent: July 16, 1991Assignee: National Starch and Chemical Investment Holding CorporationInventors: Gary F. Matz, James C. Long
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Patent number: 5028676Abstract: 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: GrantFiled: June 26, 1989Date of Patent: July 2, 1991Assignee: Sekisui Kagaku Kogyo Kabushiki KaishaInventors: Takeshi Nakachi, Akio Hata, Yoshihisa Watanabe
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Patent number: 4980433Abstract: 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: GrantFiled: October 5, 1989Date of Patent: December 25, 1990Assignee: Betz Laboratories, Inc.Inventors: Fu Chen, William S. Carey
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Patent number: 4891401Abstract: 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: GrantFiled: March 22, 1989Date of Patent: January 2, 1990Assignee: E. I. Du Pont De Nemours and CompanyInventors: Jozef T. Huybrechts, Guido R. Louis van den Bosch, Rudolf F. Landriette Verhaegen
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Patent number: 4859756Abstract: 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: GrantFiled: July 29, 1988Date of Patent: August 22, 1989Assignee: BASF AktiengesellschaftInventors: Hans-Helmut Goertz, Alfred Oftring, Friedrich Vogel
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Patent number: 4816495Abstract: 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: GrantFiled: December 9, 1986Date of Patent: March 28, 1989Assignee: Dentsply Research & Development Corp.Inventors: Gordon B. Blackwell, Chin-Teh Huang
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Patent number: 4782120Abstract: 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: GrantFiled: April 13, 1987Date of Patent: November 1, 1988Assignee: Coatex, S.A.Inventors: Jacky Rousset, Jean-Bernard Egraz, Gilles Letetour
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Patent number: 4732698Abstract: 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: GrantFiled: February 10, 1987Date of Patent: March 22, 1988Assignee: Betz Laboratories, Inc.Inventor: Fu Chen
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Patent number: 4708815Abstract: 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: GrantFiled: February 10, 1987Date of Patent: November 24, 1987Assignee: Betz Laboratories, Inc.Inventors: Fu Chen, Keith A. Bair
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Patent number: 4681686Abstract: 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: GrantFiled: July 10, 1985Date of Patent: July 21, 1987Inventors: Norman Richardson, Brian Holt, Barry Cook
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Patent number: 4657941Abstract: 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: GrantFiled: November 29, 1984Date of Patent: April 14, 1987Assignee: Dentsply Research & Development Corp.Inventors: Gordon B. Blackwell, Chin-Teh Huang
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Patent number: 4650847Abstract: 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: GrantFiled: April 4, 1985Date of Patent: March 17, 1987Assignee: Kuraray Co., Ltd.Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
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Patent number: 4647638Abstract: 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: GrantFiled: November 18, 1985Date of Patent: March 3, 1987Assignee: Nippon Kayaku Kabushiki KaishaInventors: Minoru Yokoshima, Tetsuo Ohkubo
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Patent number: 4626577Abstract: 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: GrantFiled: January 6, 1986Date of Patent: December 2, 1986Assignee: Nitto Boseki Co., Ltd.Inventor: Susumu Harada
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Patent number: 4619965Abstract: 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: GrantFiled: February 21, 1986Date of Patent: October 28, 1986Assignee: Nippon Paint Co., Ltd.Inventors: Keizou Ishii, Takeo Kurauchi, Jun Nozue, Shinichi Ishikura
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Patent number: 4560599Abstract: 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: GrantFiled: January 28, 1985Date of Patent: December 24, 1985Assignee: Marquette UniversityInventor: Steven L. Regen
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Patent number: 4540722Abstract: 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: GrantFiled: January 15, 1982Date of Patent: September 10, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventor: James E. Bunker
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Patent number: 4539382Abstract: 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: GrantFiled: August 22, 1983Date of Patent: September 3, 1985Assignee: Kuraray Co., Ltd.Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
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Patent number: 4537940Abstract: 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: GrantFiled: October 10, 1984Date of Patent: August 27, 1985Assignee: Kuraray Co., Ltd.Inventors: Ikuo Omura, Junichi Yamauchi, Yoshinori Nagase, Fumiko Uemura
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Patent number: 4533708Abstract: 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: GrantFiled: May 17, 1982Date of Patent: August 6, 1985Assignee: Calgon CorporationInventor: Christine A. Costello
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Patent number: 4525493Abstract: 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: GrantFiled: January 25, 1984Date of Patent: June 25, 1985Assignee: Kuraray Co., Ltd.Inventors: Ikuo Omura, Junichi Yamauchi
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Patent number: 4515930Abstract: 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: GrantFiled: January 20, 1984Date of Patent: May 7, 1985Assignee: Kuraray Co., Ltd.Inventors: Ikuo Omura, Junichi Yamauchi
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Patent number: 4487859Abstract: 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: GrantFiled: November 21, 1983Date of Patent: December 11, 1984Assignee: SCM CorporationInventor: Phillip C. Martino
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Patent number: 4480080Abstract: 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: GrantFiled: October 24, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: David B. Bailey, Edward P. Abel
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Patent number: 4452957Abstract: 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: GrantFiled: August 11, 1982Date of Patent: June 5, 1984Assignee: National Starch and Chemical CorporationInventor: Dennis Neigel
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Patent number: 4442239Abstract: 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: GrantFiled: February 10, 1982Date of Patent: April 10, 1984Assignee: Sankin Industry Co., Ltd.Inventors: Masayoshi Tsunekawa, Shinzo Yoshida, Tamotsu Komura
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Patent number: 4433124Abstract: 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: GrantFiled: November 23, 1981Date of Patent: February 21, 1984Assignee: Okura Kogyo Kabushiki KaishaInventors: Takanori Okamoto, Hisakazu Mori, Hideaki Matsuda
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Patent number: 4424310Abstract: Poly(allyl)poly(alkenylphenols) are prepared by the transcarbonation of poly(alkenylphenols).Type: GrantFiled: October 28, 1982Date of Patent: January 3, 1984Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Garnet E. McConchie
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Patent number: 4420587Abstract: 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: GrantFiled: September 27, 1982Date of Patent: December 13, 1983Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4351881Abstract: 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: GrantFiled: November 13, 1980Date of Patent: September 28, 1982Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kazumasa Kamada, Isao Sasaki, Kenji Kushi
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Patent number: 4348329Abstract: 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: GrantFiled: December 22, 1980Date of Patent: September 7, 1982Inventor: Dennis Chapman
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Patent number: 4321335Abstract: 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: GrantFiled: June 11, 1980Date of Patent: March 23, 1982Assignee: Dainippon Ink & Chemicals, Inc.Inventors: Shunji Arimoto, Akio Shoji, Shoichiro Takezawa, Noboru Ishikawa, Hirofumi Takeda
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Patent number: 4291097Abstract: 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: GrantFiled: December 14, 1979Date of Patent: September 22, 1981Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Kazumasa Kamada, Isao Sasaki, Kenji Kushi
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Patent number: 4279718Abstract: 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: GrantFiled: October 1, 1979Date of Patent: July 21, 1981Assignee: Bayer AktiengesellschaftInventors: Karl-Ernst Schuster, Hans Rudolph, Wolfram Mayer, Hans J. Rosenkranz
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Patent number: 4277565Abstract: 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: GrantFiled: March 29, 1979Date of Patent: July 7, 1981Assignee: Asahi Glass Company, Ltd.Inventors: Yoshio Oda, Masaaki Yamabe, Masao Kato
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Patent number: 4259117Abstract: 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: GrantFiled: August 25, 1978Date of Patent: March 31, 1981Assignee: Kuraray Co., Ltd.Inventors: Junichi Yamauchi, Eiichi Masuhara, Nobuo Nakabayashi, Kyoichiro Shibatani, Tooru Wada
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Patent number: 4250007Abstract: 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: GrantFiled: March 14, 1979Date of Patent: February 10, 1981Assignee: Ube Industries, Ltd.Inventors: Hiroshi Yasuno, Toshimune Yoshinaga, Tsunetomo Nakano
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Patent number: 4247672Abstract: 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: GrantFiled: July 16, 1979Date of Patent: January 27, 1981Assignee: Ciba-Geigy CorporationInventors: Theobald Haug, Jurg Kiefer
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Patent number: 4222780Abstract: 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: GrantFiled: April 21, 1978Date of Patent: September 16, 1980Assignee: Kuraray Co., Ltd.Inventors: Kyoichiro Shibatani, Ikuo Omura, Junichi Yamauchi
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Patent number: 4212953Abstract: 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: GrantFiled: September 1, 1978Date of Patent: July 15, 1980Assignee: McDonnell Douglas CorporationInventors: Martin B. Sheratte, Lydia H. Simanyi
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Patent number: 4177179Abstract: 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: GrantFiled: August 3, 1978Date of Patent: December 4, 1979Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kenji Kurihara, Shigekazu Kasahara, Takashi Suzuki
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Patent number: 4100140Abstract: 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: GrantFiled: June 18, 1976Date of Patent: July 11, 1978Assignee: Ciba-Geigy CorporationInventors: Abdul-Cader Zahir, Alfred Renner
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Patent number: 4071508Abstract: 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: GrantFiled: February 11, 1975Date of Patent: January 31, 1978Assignee: Plastomedical Sciences, Inc.Inventor: Robert Steckler
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Patent number: 4031299Abstract: 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: GrantFiled: April 11, 1975Date of Patent: June 21, 1977Assignee: Stauffer Chemical CompanyInventor: Chung H. Wei
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Patent number: 4031037Abstract: 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: GrantFiled: February 20, 1975Date of Patent: June 21, 1977Inventors: Jaroslav Kalal, Jiri Coupek, Svatopluk Pokorny, Frantisek Svec, Karel Bouchal