And Reactant Having Alcoholic Or Phenolic -xh Group, Wherein X Is Chalcogen (and Wherein H Of -xh May Be Replaced By Substituted Or Unsubstituted Ammonium, Or By A Group Ia Or Iia Light Metal) Patents (Class 558/110)
  • Patent number: 10836898
    Abstract: The present invention relates to a non-halogen flame retardant resin composition. More particularly, the present invention provides a non-halogen flame retardant resin composition capable of simultaneously exhibiting superior flame retardancy, whiteness, and gloss by addressing problems of a flame retardant resin such as difficulties in realizing V-1 grade or higher flame retardancy when a non-halogen flame retardant is used and poor colorability due to low gloss and whiteness.
    Type: Grant
    Filed: October 26, 2017
    Date of Patent: November 17, 2020
    Assignee: LG CHEM, LTD.
    Inventors: Je Sun Yoo, Ki Young Nam, Yong Yeon Hwang, Jae Young Sim, Seon Hyeong Bae, Jae Yeon Bae, In Seok Kim
  • Patent number: 9181487
    Abstract: A process for preparing ethylenedialkylphosphinic acids, ethylenedialkylphosphinic esters and ethylenedialkylphosphinic salts, wherein a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with an acetylenic compound (V) in the presence of a catalyst B, to give the ethylenedialkylphosphinic acid derivative (III), and the catalyst A comprises transition metals, transition-metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition-metal compound and at least one ligand, and the catalyst B comprises peroxide-forming compounds, peroxo compounds and/or azo compounds.
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: November 10, 2015
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Patent number: 9024054
    Abstract: A process for producing a purified O-(2,6-dichloro-4-methylphenyl)-O,O-dimethyl phosphorothioate, the process comprising: the first step of bringing a crude O-(2,6-dichloro-4-methylphenyl)-O,O-dimethyl phosphorothioate into contact with an acid; and the second step of recovering the purified O-(2,6-dichloro-4-methylphenyl)-O,O-dimethyl phosphorothioate from the mixture obtained in the first step.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: May 5, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiji Yamauchi, Ryuhei Wakita
  • Patent number: 9018413
    Abstract: The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition met
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: April 28, 2015
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Patent number: 8877957
    Abstract: Shown is the preparation and subsequent elaboration of P-chiral compounds that can be used as a building block for many P-chiral ligands used, for example, in asymmetric catalytic reactions. Specifically, a synthesis is shown for RP(O)(OR*)CH2OH, with R=H, Ph, aryl, alkyl, and R*=menthol (and other chiral alcohol-derived moieties), especially HP(O)(OMen)CH2OH (Men=L-menthol). This versatile building block is easily synthesized via reaction of inexpensive starting materials, H3PO2, menthol as the chiral auxiliary, and paraformaldehyde.
    Type: Grant
    Filed: June 7, 2013
    Date of Patent: November 4, 2014
    Assignee: Texas Christian University
    Inventors: Jean-Luc Montchamp, Olivier Berger
  • Publication number: 20140046076
    Abstract: The present invention relates to a process that is useful for surface functionalization of a substrate comprising at least one hydroxyl function, in which one or more point regions of said surface are brought into contact with an ionic liquid matrix containing at least one reactive molecule, as it is known, that carries at least one reactive function, under conditions that are suitable for the creation of a covalent bond between said reactive function of the molecule and a hydroxyl function of said surface.
    Type: Application
    Filed: March 2, 2012
    Publication date: February 13, 2014
    Inventors: Gilles Marchand, Antoine Hoang, Olivier Zaouak, Carole Sauer
  • Publication number: 20130331594
    Abstract: Shown is the preparation and subsequent elaboration of P-chiral compounds that can be used as a building block for many P-chiral ligands used, for example, in asymmetric catalytic reactions. Specifically, a synthesis is shown for RP(O)(OR*)CH2OH, with R=H, Ph, aryl, alkyl, and R*=menthol (and other chiral alcohol-derived moieties), especially HP(O)(OMen)CH2OH (Men=L-menthol). This versatile building block is easily synthesized via reaction of inexpensive starting materials, H3PO2, menthol as the chiral auxiliary, and paraformaldehyde.
    Type: Application
    Filed: June 7, 2013
    Publication date: December 12, 2013
    Inventors: Jean-Luc Montchamp, Olivier Berger
  • Publication number: 20130194364
    Abstract: Anti-kogation agents and ink compositions containing it. Such anti-kogation agent has the formula (I) or (II) wherein R is an alkyl group having from 1 to 10 carbon atoms and n is an integer ranging from 3 to 10. A disclosed ink composition includes an ink vehicle, from about 0.1 to about 10 weight percentage of colorants and from about 0.01 to about 10 weight percentage of the anti-kogation agents.
    Type: Application
    Filed: September 24, 2010
    Publication date: August 1, 2013
    Applicant: Hewlett-Packard Developement Company, L.P.
    Inventors: Paul Tyrell, Robert A. Brunck, Kevin P. DeKam, Garry Hinch
  • Publication number: 20130158284
    Abstract: The invention relates to a method for producing phosphoric acid triesters of formula (I). According to said method, phosphoric acid or a phosphoric acid derivative selected from orthophosphoric acid, tetraphosphoric decaoxide and polyphosphoric acid is reacted with alkoxylated alcohols of formulae (II) R1—(OA1)x—OH, (III) R2—(OA2)y—OH, and (IV) R3—(OA3)z—OH, in the molar ratio phosphoric acid or phosphoric acid derivative to alkoxylated alcohol of 1:2.5 to 1:3.3, at between 200 and 240° C.
    Type: Application
    Filed: February 5, 2013
    Publication date: June 20, 2013
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventor: Clariant Finance (BVI) Limited
  • Publication number: 20120289636
    Abstract: A method for preparation of secondary alcohols with a high proportion of hydroxyl group at the C2 position is disclosed. Alkyl carboxylates, high in alpha-methylcarboxylate content, are produced via reaction of an alpha-olefin and a carboxylic acid in the presence of a cerium catalyst. The resultant alkyl carboxylate is hydrolyzed to yield a secondary alcohol with a high 2-hydroxyl content. The secondary alcohol may be used to prepare esters, especially phthalate esters or cyclohexanoate diesters, which are useful as plasticizers. These esters are more effective as plasticizers than esters derived from other secondary alcohols due to their high C2 point of attachment.
    Type: Application
    Filed: November 16, 2010
    Publication date: November 15, 2012
    Inventors: Karla S. Colle, Allen D. Godwin
  • Patent number: 8293938
    Abstract: The invention relates to alkylphosphonous acids, salts and esters of formula (I) A-P(?O)(OX)—H (I) wherein A is C2-C20alkyl, C2-C20alkylene, and C8-C20 alkaryl are optionally substituted, and X is H, alkyl, aryl, alkylaryl, alkenyl, substituted alkyl, aryl, alkaryl, alkenyl, ammonium, primary, secondary, tertiary, quaternary alkyl and/or aryl ammonium, an alkali metal, an alkaline earth metal, a metal of the third and fourth main group and the second, fourth and eight sub-group or a metal of the lanthanoid group. The invention also relates to methods for producing same and to the uses of said compounds.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 23, 2012
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause
  • Publication number: 20110281983
    Abstract: The invention relates to a method for producing monohydroxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, b) the, obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with alkylene oxides of formula (V) in the presence of a catalyst B to obtain a monofunctionalized dialkylphosphinic acid derivative (III), wherein R1, R2, R3, R4, R5, R6, R7, R8 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, and X represents H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, catalyst A represents transition metals and/or transition metal compounds and/or catalyst systems composed of a transiti
    Type: Application
    Filed: October 6, 2009
    Publication date: November 17, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110275744
    Abstract: The invention relates to a method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ether.
    Type: Application
    Filed: October 6, 2009
    Publication date: November 10, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Mathias Dietz, Werner Krause, Martin Sicken
  • Publication number: 20110251314
    Abstract: The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition met
    Type: Application
    Filed: October 6, 2009
    Publication date: October 13, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110251315
    Abstract: The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C?C, C?O, or C?N double bonds to obtain compounds of type (III), wherein R1, R2, R3, R4, R5, R6 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, X represents, inter alia, H, C1-C18-alkyl, C6-C18-aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH2, NHR, NR2, or O—CO—R8, and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents transition metals and/or transition metal compo
    Type: Application
    Filed: October 6, 2009
    Publication date: October 13, 2011
    Applicant: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
  • Publication number: 20110251312
    Abstract: The invention relates to a process for preparing ethylenedialkylphosphinic acids, ethylenedialkylphosphinic esters and ethylenedialkylphosphinic salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with an acetylenic compound (V) in the presence of a catalyst B, to give the ethylenedialkylphosphinic acid derivative (III), where R1, R2, R3, R4, R5, R6, R11, R12, R13 and R14 are identical or different and independently of one another inter alia are H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl and X is H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalyst A comprises transition metals and/or transition-metal compounds and/or catalyst systems which are composed of
    Type: Application
    Filed: December 15, 2009
    Publication date: October 13, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110237818
    Abstract: A process for producing a purified O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate, the process comprising: the first step of bringing a crude O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate into contact with an acid; and the second step of recovering the purified O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate from the mixture obtained in the first step.
    Type: Application
    Filed: December 18, 2009
    Publication date: September 29, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Eiji Yamauchi, Ryuhei Wakita
  • Publication number: 20110237722
    Abstract: The invention relates to a method for producing mono-hydroxy-functionalized dialkylphosphinic acids, esters and salts.
    Type: Application
    Filed: October 6, 2009
    Publication date: September 29, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110237721
    Abstract: The invention relates to a method for producing mono-carboxy-functionalized dialkyiphosphinic acids, esters and salts using a vinyl ester of a carboxylic acid.
    Type: Application
    Filed: October 6, 2009
    Publication date: September 29, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Mathias Dietz, Werner Krause, Martin Sicken
  • Publication number: 20110237720
    Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof by means of vinyl compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with carbon monoxide to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R1, R2, R3, R4, R5, R6 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X and Y are the same or different and stand indepe
    Type: Application
    Filed: October 6, 2009
    Publication date: September 29, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110224340
    Abstract: The invention relates to a method for producing mono-vinylfunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is converted with olefins (IV) to an alkylphosphonic acid, salt, or ester (II) in the presence of a catalyst A, b) the alkylphosphonic acid, salt, or ester (II) thus created is converted with acetylenic compounds of formula (V) into a mono-vinylfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, where R1, R2, R3, R4, R5, R6 are the same or different and are independent of each other, among other things, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems comprised of a transition metal and/or a transitio
    Type: Application
    Filed: October 6, 2009
    Publication date: September 15, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110213062
    Abstract: The invention relates to a method for producing mono-hydroxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with carbon monoxide to yield a mono-functionalized dialkylphosphinic acid derivative (VII) in the presence of a catalyst C, and d) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VII); is reacted to yield a mono-hydroxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst D, wherein R1, R2, R3, R4, R5, R6 are the same or different and stan
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110040116
    Abstract: The invention relates to a method for producing phosphoric acid triesters of formula (I). According to said method, phosphoric acid or a phosphoric acid derivative selected from orthophosphoric acid, tetraphosphoric decaoxide and polyphosphoric acid is reacted with alkoxylated alcohols of formulae (II) R1—(OA1)x-OH, (Ill) R2—(OA2)y-OH, and (IV) R3—(OA3)z-OH, in the molar ratio phosphoric acid or phosphoric acid derivative to alkoxylated alcohol of 1:2.5 to 1:3.3, at between 200 and 240° C.
    Type: Application
    Filed: July 29, 2008
    Publication date: February 17, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Peter Klug, Franz-Xaver Scherl, Waltraud Simsch, Adelgunde Oberhauser
  • Publication number: 20100063311
    Abstract: This invention provides oligomeric hydrogen phosphonates represented by the formula (I) where R is an alkyl group having one to about six carbon atoms; R? is a linear or branched hydrocarbylene group or an oxygen-containing hydrocarbylene group having two to about twenty carbon atoms or a hydrocarbylene group having at least one cycloaliphatic or aromatic ring, where at least one of R? is a linear or branched hydrocarbylene group or an oxygen-containing hydrocarbylene group and at least one of R? is a hydrocarbylene group having at least one cycloaliphatic or aromatic ring; and n is a number from 2 to about 20. Also provided are processes for making these oligomeric hydrogen phosphonates, oligomeric organophosphonate compositions, and processes for making these oligomeric organophosphonate compositions.
    Type: Application
    Filed: April 30, 2008
    Publication date: March 11, 2010
    Applicant: ALBEMARLE CORPORATION
    Inventors: Arthur G. Mack, Techen Tsao, Anne M. Sauer
  • Patent number: 7541484
    Abstract: The invention relates to a process for producing a phosphate, which includes reacting a phosphorus pentaoxide-containing phosphorylating agent with an organic hydroxy compound, the reaction being carried out at a reaction temperature of 50 to 70° C. until the degree (w) of remaining phosphorus pentaoxide undissolved in a reaction solution, defined by the following equation (1), is reduced to 15 wt % or less: W=[1?(AVt?AVp)/AV0]×100??(1) wherein W is the degree [wt %] of remaining phosphorus pentaoxide undissolved in a reaction solution; AVt is the acid value [mg KOH/g] of the reaction solution excluding undissolved phosphorus pentaoxide in an arbitrary time; AVp is the theoretical acid value [mg KOH/g] of the phosphorylating agent excluding undissolved phosphorus pentaoxide; and AV0 is the theoretical acid value [mg KOH/g] of phosphorus pentaoxide.
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: June 2, 2009
    Assignee: Kao Corporation
    Inventors: Norio Ueyama, Yoshifumi Nishimoto
  • Patent number: 7196213
    Abstract: Provided are a process for producing a phosphate and a process for stabilizing a phosphate, the phosphate being an acid-form phosphate wherein an organic hydroxy compound is an alkylene oxide adduct. A production process of a phosphate and a stabilization process of a phosphate, including the step 1 of reacting an organic hydroxy compound represented by the following general formula (I) with a phosphorylating agent: R1—O—(AO)n—H??(I) wherein R1 represents a straight or branched alkyl group or alkenyl group having 6 to 36 carbon atoms, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n is a number of 0.1 to 100 on the average; the step 2 of purifying the reaction product obtained in the step 1 until the content of the organic hydroxy compound that has not yet reacted becomes 2% or less by weight; and the step 3 of adding water to the purified product obtained in the step 2 at such a ratio that the content of water in the final product is from 0.5 to 10% by weight.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: March 27, 2007
    Assignee: Kao Corporation
    Inventors: Akira Matsunaga, Satoru Kijima
  • Patent number: 6855757
    Abstract: The invention relates to a process of preparing glycol carboxyethylmethylphosphinate, which comprises a) reacting elemental yellow phosphorus with methyl chloride in the presence of an alkali or alkaline earth metal hydroxide to form a mixture which includes the alkali and/or alkaline earth metal salts of methylphosphonous, phosphorous and hypophosphorous acids as main constituents, b) esterifying the methylphosphonous acid from the mixture obtained by a), c) removing the methylphosphonous ester from the mixture, d) adding the thus obtained methylphosphonous ester to an acrylic ester, e) hydrolyzing the diester thus obtained, f) esterifying the resulting carboxyethylmethylphosphinic acid with ethylene glycol directly to the glycol carboxyethylmethylphosphinate. The invention also relates to the use of the glycol carboxyethylmethylphosphinates prepared according to the invention as reactive flame retardants for polymers.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: February 15, 2005
    Assignee: Clariant GmbH
    Inventors: Sebastian Hörold, Heinz-Peter Breuer, Elisabeth Jung
  • Publication number: 20040138182
    Abstract: This invention discloses and claims processes for preparing colchicine derivatives, products obtained by these processes, and use thereof. More specifically, the invention relates essentially to a process for preparing organophosphorus compounds and their salts, having therapeutic activity, in particular in oncology.
    Type: Application
    Filed: December 5, 2003
    Publication date: July 15, 2004
    Applicant: AVENTIS PHARMA S.A.
    Inventors: Christian Wehrey, Serge Droux
  • Patent number: 6440952
    Abstract: Therapeutic compounds and methods for modulating amyloid deposition in a subject, whatever its clinical setting, are described. Amyloid deposition is modulated by the administration to a subject of an effective amount of a therapeutic compound comprising a phosphonate group and a carboxylate group, a congener thereof, or a pharmaceutically acceptable salt or ester thereof. In preferred embodiments, an interaction between an amyloidogenic protein and a basement membrane constituent is modulated.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: August 27, 2002
    Assignee: Queen's University at Kingston
    Inventors: Walter A. Szarek, Xianqi Kong, Gregory R. J. Thatcher, Boris Gorine
  • Patent number: 6441223
    Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: August 27, 2002
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6407277
    Abstract: An organic hydroxyl compound is reacted with a phosphorylating agent comprising phosphorus pentaoxide and at least one compound selected from the group consisting of water, phosphoric acid and polyphosphoric acid and having a value represented by formula (I) of from 0.5 to 1.0, under such a condition that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2; or alternatively, an organic hydroxyl compound is reacted with the above phosphorylating agent under such a condition that the ratio as defined by formula (II) has a value in the range of from exceeding 3.2 up to 6.4 and then phosphorus pentaoxide is added to the reaction product in such an amount that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2 with respect to the total feeds of the starting materials to conduct further reaction.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: June 18, 2002
    Assignee: Kao Corporation
    Inventors: Akira Matsunaga, Akira Fujiu, Shinji Tsuyutani, Toshio Nozaki, Masayuki Ueda
  • Patent number: 6319432
    Abstract: Disclosed is a flame retardant comprising bisphenol A bis(diphenyl phosphate) and its dimer, the former having an HPLC determined 78 to 87 area % and an 85 to less than 90 normalized area %, the normalized area % being based on the total HPLC area % of the bisphenol A bis(diphenyl phosphate) and the dimer. The flame retardant also has a low isopropenylphenyl diphenyl phosphate and a low triphenylphosphate content.
    Type: Grant
    Filed: June 11, 1999
    Date of Patent: November 20, 2001
    Assignee: Albemarle Corporation
    Inventors: William B. Harrod, W. Dirk Klobucar
  • Patent number: 6278012
    Abstract: The present invention relates to a process for the preparation of phosphinic acid esters, which comprises a) reacting elemental yellow phosphorus with alkylating agents in the presence of a base to give a mixture which comprises, as principal constituents, the (metal) salts of alkylphosphonous, phosphorous and hypophosphorous acids, b) esterifying the principal constituents of the mixture from a) to give an ester mixture, c) isolating the ester of the alkylphosphonous acid from the ester mixture, d) adding the resultant ester of the alkylphosphonous acid onto an olefin containing a functional group. The invention likewise relates to the use of the phosphinic acid esters prepared by this process, inter alia as flame retardants and precursors for further syntheses.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: August 21, 2001
    Assignee: Clariant GmbH
    Inventors: Sebastian Hörold, Norbert Weferling, Heinz-Peter Breuer, Martin Sicken
  • Patent number: 6191253
    Abstract: A dispersant for aqueous mill-bases obtainable by reacting a polyethylene glycol with a molar excess of a hydroxycarboxylic acid containing from 4 to 17 carbon atoms or lactone thereof and/or with a C3-4-alkylene oxide to form a polymeric diol and phosphating the diol. The preferred hydroxycarboxylic acid or lactone is &egr;-caprolactone.
    Type: Grant
    Filed: June 9, 1998
    Date of Patent: February 20, 2001
    Assignee: Zeneca Limited
    Inventors: John David Schofield, Dean Thetford
  • Patent number: 6090968
    Abstract: The present invention relates to a process for preparing phosphinic esters which comprisesa) reacting elemental yellow phosphorus with alkyl halides in the presence of alkali metal hydroxide or alkaline earth metal hydroxide to form a mixture which comprises as main constituents the alkali metal salts and/or alkaline earth metal salts of alkylphosphonous acid, phosphorous acid and hypophosphorous acidb) removing the alkylphosphonous acid from the mixture obtained as described in a),c) esterifying the alkylphosphonous acid,d) adding the resultant ester of the alkylphosphonous acid to a compound having at least one C.dbd.C double bond.The invention likewise relates to the use of the phosphinic esters prepared by this process inter alia as flame retardants and as precursor for further syntheses.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: July 18, 2000
    Assignee: Clariant GmbH
    Inventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
  • Patent number: 6090967
    Abstract: The present invention relates to a process for preparing phosphonous esters which comprisesa) reacting elemental yellow phosphorus with alkyl halides in the presence of alkali metal hydroxides and/or alkaline earth metal hydroxides to form a mixture which comprises, as main components, the alkali metal salts and/or alkaline earth metal salts of the alkylphosphonous, phosphorous and hypophosphorous acids,b) removing the alkylphosphonous acid from the mixture obtained by a)c) esterifying the alkylphosphonous acid.The invention likewise relates to the use of the phosphonous esters prepared by this process.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: July 18, 2000
    Assignee: Clariant GmbH
    Inventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
  • Patent number: 6034261
    Abstract: An organic hydroxyl compound is reacted with a phosphorylating agent comprising phosphorus pentaoxide and at least one compound selected from the group consisting of water, phosphoric acid and polyphosphoric acid and having a value represented by formula (I) of from 0.5 to 1.0, under such a condition that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2; or alternatively, an organic hydroxyl compound is reacted with the above phosphorylating agent under such a condition that the ratio as defined by formula (II) has a value in the range of from exceeding 3.2 up to 6.4 and then phosphorus pentaoxide is added to the reaction product in such an amount that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.
    Type: Grant
    Filed: February 8, 1999
    Date of Patent: March 7, 2000
    Assignee: Kao Corporation
    Inventors: Akira Matsunaga, Akira Fujiu, Shinji Tsuyutani, Toshio Nozaki, Masayuki Ueda
  • Patent number: 5883280
    Abstract: An organic hydroxyl compound is reacted with polyphosphoric acid under such conditions that the ratio, as defined by formula (1), has a value exceeding 3.2; and phosphorus pentaoxide is added to the reaction product thus obtained in such an amount that the ratio, as defined by formula (1), has a value in the range of from 2.8 to 3.2: ##EQU1## If necessary, the obtained reaction product is deodorized by the removal of the organic hydroxyl compound unreacted therefrom. The process does not give any product of high-viscous gel and therefore enables the industrially easy manufacture of a phosphoric monoester having an extremely high purity, a lowered orthophosphoric acid content, and a good odor.
    Type: Grant
    Filed: March 20, 1997
    Date of Patent: March 16, 1999
    Assignee: Kao Corporation
    Inventors: Shinji Tsuyutani, Kengo Shibata, Kiyoshi Aimono
  • Patent number: 5785894
    Abstract: A dispersant for aqueous mill-bases obtainable by reacting a polyethylene glycol with a molar excess of a hydroxycarboxylic acid containing from 4 to 17 carbon atoms or lactone thereof and/or with a C.sub.3-4 -alkylene oxide to form a polymeric diol and phosphating the diol. The preferred hydroxycarboxylic acid or lactone is .epsilon.-caprolactone.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: July 28, 1998
    Assignee: Zeneca Limited
    Inventors: John David Schofield, Dean Thetford
  • Patent number: 5783690
    Abstract: A 2-N-amidoethyl protected nucleoside analog phosphoramidite of formula (1): ##STR1## is useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with phosphoramidite (1) in solution or solid phase oligonucleotide analog synthesis are high and the 2-N-amidoethyl protecting group can be removed easily under standard conditions.
    Type: Grant
    Filed: September 18, 1997
    Date of Patent: July 21, 1998
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Zacharia S. Cheruvallath, Daniel C. Capaldi, Vasulinga T. Ravikumar, Douglas L. Cole
  • Patent number: 5554781
    Abstract: The invention relates to a process for producing a unique phosphation reagent and to a simple, single-stage process utilizing this reagent to produce alkyl phosphate esters having high monoalkyl phosphate content in combination with low dialkyl phosphate, trialkyl phosphate, phosphoric acid and residual alcohol.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: September 10, 1996
    Inventor: Robert L. Reierson
  • Patent number: 5550274
    Abstract: The invention relates to a simple, single-stage process to produce alkyl phosphate esters having high monoalkyl phosphate content in combination with low dialkyl phosphate, trialkyl phosphate, phosphoric acid and other nonionic (usually residual alcohol) components in which a unique phosphation reagent having a preferred effective equivalent polyphosphoric acid concentration of 121-123% is produced and utilized in-situ.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: August 27, 1996
    Inventor: Robert L. Reierson
  • Patent number: 5502231
    Abstract: The present invention relates to a process for the preparation of compounds of the general formula I ##STR1## in which R.sup.1 and R.sup.2 are defined as stated in claim 1, characterized in that a 1,1,1-tris(hydroxymethyl)-(C.sub.2 -C.sub.5)-alkane or 2,2-bis(hydroxymethyl)-1,3-propanediol is reacted with vinylphosphonic anhydride.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: March 26, 1996
    Assignee: Cassella Aktiengesellschaft
    Inventors: Fritz Engelhardt, Ulrich Riegel, Hans-Jerg Kleiner
  • Patent number: 5463101
    Abstract: This invention relates to first stage phosphation processes which utilize a unique phosphation reagent that esterifies ethoxylated alcohols under mild reaction conditions, thus realizing reduced initial 1,4-dioxane production followed by formation of a dioxane-water azeotrope and the vacuum stripping at above about 100 torr of the azeotrope. This easily achieves product 1,4-dioxane levels below about 15 ppm based on the total ester weight.
    Type: Grant
    Filed: December 1, 1994
    Date of Patent: October 31, 1995
    Assignee: Rhone-Poulenc Inc.
    Inventor: Robert L. Reierson
  • Patent number: 5420328
    Abstract: Phsophonate esters can be synthesized in high yields by condensations of alcohols with methyl phosphonates followed by selective demethylation. The reaction is general, relativly insensitive to steric constraints of hindered phosphonic acids, and can also be carried out on a solid support to synthesize large collections of compounds to screen for pharmacological activity.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: May 30, 1995
    Assignee: Affymax Technologies, N.V.
    Inventor: David A. Campbell
  • Patent number: 5359115
    Abstract: Phosphonate esters can be synthesized in high yields by condensations of alcohols with methyl phosphonates followed by selective demethylation. The reaction is general, relatively insensitive to steric constraints of hindered phosphonic acids, and can also be carried out on a solid support to synthesize large collections of compounds to screen for pharmacological activity.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: October 25, 1994
    Assignee: Affymax Technologies, N.V.
    Inventors: David A. Campbell, Jeffrey W. Jacobs
  • Patent number: 5357037
    Abstract: This invention relates to new phosphorus-containing duromers of oligophosphites and epoxides or bisacrylates or unsaturated polyesters.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: October 18, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Burkhard Kohler, Wolfgang Ebert
  • Patent number: 5344951
    Abstract: This invention relates to an improved process for producing diesters of phosphorous acid. The process comprises (a) reacting phosphorous acid with monohydric alcohol in a petroleum distillate solvent while maintaining a reaction mass temperature within the range of from about 130.degree. to about 138.degree. C., and (b) refluxing the reaction mass during the reaction, wherein the phosphorous acid contains about 20 up to about 35 wt. % water, the molar ratio of alcohol to phosphorous acid used is within the range of from about 2.0:1 to about 4.0:1, and water is removed from the reaction mass essentially as it is formed during steps (b) and (c).
    Type: Grant
    Filed: March 16, 1993
    Date of Patent: September 6, 1994
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventor: Abbas Kadkhodayan
  • Patent number: 5334741
    Abstract: Solid substrates with free hydroxyl groups are phosphorylated by thermolysing a solution of phosphoramidate of the formula ##STR1## in the presence of the substrate, whereby metaphosphate is generated which phosphorylates the substrate.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: August 2, 1994
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis D. Quin, Stefan Jankowski
  • Patent number: 5306840
    Abstract: A process for preparing pure L-alpha-Glycerylphosphoryl-D-Myoinositol and its salts consists of a) preparing the crude Na+ or K+ salt of L-.alpha.-Glycerylphosphoryl-D-Myoinositol, passing an aqueous solution of the salt through an acid resin in H form whereby ion exchange occurs and the acid L-.alpha.-Glycerylphosphoryl-D-Myoinositol is eluted by washing the resin with water. Then the aqueous solution is passed through a basic resin whereby the L-.alpha.-Glycerylphosphoryl-D-Myoinositol is adsorbed on the resin as the anion. The resin is eluted first with a dilute solution of formic, acetic or propionic acid and then eluted with a more concentrated solution of the same acid. The preparation of severals salts is also described.
    Type: Grant
    Filed: August 5, 1992
    Date of Patent: April 26, 1994
    Assignee: Euticals S.p.A.
    Inventor: Giovanni Tronconi