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)
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Patent number: 10836898Abstract: 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: GrantFiled: October 26, 2017Date of Patent: November 17, 2020Assignee: 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
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Patent number: 9181487Abstract: 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: GrantFiled: December 15, 2009Date of Patent: November 10, 2015Assignee: Clariant Finance (BVI) LimitedInventors: Michael Hill, Werner Krause, Martin Sicken
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Patent number: 9024054Abstract: 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: GrantFiled: December 18, 2009Date of Patent: May 5, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Eiji Yamauchi, Ryuhei Wakita
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Patent number: 9018413Abstract: 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 metType: GrantFiled: October 6, 2009Date of Patent: April 28, 2015Assignee: Clariant Finance (BVI) LimitedInventors: Michael Hill, Werner Krause, Martin Sicken
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Patent number: 8877957Abstract: 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: GrantFiled: June 7, 2013Date of Patent: November 4, 2014Assignee: Texas Christian UniversityInventors: Jean-Luc Montchamp, Olivier Berger
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Publication number: 20140046076Abstract: 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: ApplicationFiled: March 2, 2012Publication date: February 13, 2014Inventors: Gilles Marchand, Antoine Hoang, Olivier Zaouak, Carole Sauer
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Publication number: 20130331594Abstract: 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: ApplicationFiled: June 7, 2013Publication date: December 12, 2013Inventors: Jean-Luc Montchamp, Olivier Berger
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Publication number: 20130194364Abstract: 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: ApplicationFiled: September 24, 2010Publication date: August 1, 2013Applicant: Hewlett-Packard Developement Company, L.P.Inventors: Paul Tyrell, Robert A. Brunck, Kevin P. DeKam, Garry Hinch
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Publication number: 20130158284Abstract: 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: ApplicationFiled: February 5, 2013Publication date: June 20, 2013Applicant: CLARIANT FINANCE (BVI) LIMITEDInventor: Clariant Finance (BVI) Limited
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Publication number: 20120289636Abstract: 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: ApplicationFiled: November 16, 2010Publication date: November 15, 2012Inventors: Karla S. Colle, Allen D. Godwin
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Patent number: 8293938Abstract: 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: GrantFiled: July 2, 2008Date of Patent: October 23, 2012Assignee: Clariant Finance (BVI) LimitedInventors: Michael Hill, Harald Bauer, Werner Krause
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Publication number: 20110281983Abstract: 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 transitiType: ApplicationFiled: October 6, 2009Publication date: November 17, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110275744Abstract: The invention relates to a method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ether.Type: ApplicationFiled: October 6, 2009Publication date: November 10, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Mathias Dietz, Werner Krause, Martin Sicken
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Publication number: 20110251312Abstract: 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 ofType: ApplicationFiled: December 15, 2009Publication date: October 13, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110251314Abstract: 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 metType: ApplicationFiled: October 6, 2009Publication date: October 13, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110251315Abstract: 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 compoType: ApplicationFiled: October 6, 2009Publication date: October 13, 2011Applicant: Clariant Finance (BVI) LimitedInventors: Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
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Publication number: 20110237721Abstract: 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: ApplicationFiled: October 6, 2009Publication date: September 29, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Mathias Dietz, Werner Krause, Martin Sicken
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Publication number: 20110237818Abstract: 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: ApplicationFiled: December 18, 2009Publication date: September 29, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Eiji Yamauchi, Ryuhei Wakita
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Publication number: 20110237720Abstract: 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 indepeType: ApplicationFiled: October 6, 2009Publication date: September 29, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110237722Abstract: The invention relates to a method for producing mono-hydroxy-functionalized dialkylphosphinic acids, esters and salts.Type: ApplicationFiled: October 6, 2009Publication date: September 29, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110224340Abstract: 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 transitioType: ApplicationFiled: October 6, 2009Publication date: September 15, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110213062Abstract: 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 stanType: ApplicationFiled: October 6, 2009Publication date: September 1, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Michael Hill, Werner Krause, Martin Sicken
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Publication number: 20110040116Abstract: 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: ApplicationFiled: July 29, 2008Publication date: February 17, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Peter Klug, Franz-Xaver Scherl, Waltraud Simsch, Adelgunde Oberhauser
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Publication number: 20100063311Abstract: 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: ApplicationFiled: April 30, 2008Publication date: March 11, 2010Applicant: ALBEMARLE CORPORATIONInventors: Arthur G. Mack, Techen Tsao, Anne M. Sauer
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Patent number: 7541484Abstract: 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: GrantFiled: December 14, 2005Date of Patent: June 2, 2009Assignee: Kao CorporationInventors: Norio Ueyama, Yoshifumi Nishimoto
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Patent number: 7196213Abstract: 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: GrantFiled: December 23, 2003Date of Patent: March 27, 2007Assignee: Kao CorporationInventors: Akira Matsunaga, Satoru Kijima
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Patent number: 6855757Abstract: 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: GrantFiled: October 30, 2002Date of Patent: February 15, 2005Assignee: Clariant GmbHInventors: Sebastian Hörold, Heinz-Peter Breuer, Elisabeth Jung
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Publication number: 20040138182Abstract: 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: ApplicationFiled: December 5, 2003Publication date: July 15, 2004Applicant: AVENTIS PHARMA S.A.Inventors: Christian Wehrey, Serge Droux
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Patent number: 6441223Abstract: 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: GrantFiled: November 30, 2000Date of Patent: August 27, 2002Assignee: Monsanto Technology LLCInventor: Thaddeus S. Franczyk, II
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Patent number: 6440952Abstract: 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: GrantFiled: May 17, 2001Date of Patent: August 27, 2002Assignee: Queen's University at KingstonInventors: Walter A. Szarek, Xianqi Kong, Gregory R. J. Thatcher, Boris Gorine
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Patent number: 6407277Abstract: 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: GrantFiled: June 9, 1997Date of Patent: June 18, 2002Assignee: Kao CorporationInventors: Akira Matsunaga, Akira Fujiu, Shinji Tsuyutani, Toshio Nozaki, Masayuki Ueda
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Patent number: 6319432Abstract: 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: GrantFiled: June 11, 1999Date of Patent: November 20, 2001Assignee: Albemarle CorporationInventors: William B. Harrod, W. Dirk Klobucar
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Patent number: 6278012Abstract: 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: GrantFiled: May 24, 2000Date of Patent: August 21, 2001Assignee: Clariant GmbHInventors: Sebastian Hörold, Norbert Weferling, Heinz-Peter Breuer, Martin Sicken
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Patent number: 6191253Abstract: 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: GrantFiled: June 9, 1998Date of Patent: February 20, 2001Assignee: Zeneca LimitedInventors: John David Schofield, Dean Thetford
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Patent number: 6090967Abstract: 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: GrantFiled: June 29, 1999Date of Patent: July 18, 2000Assignee: Clariant GmbHInventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
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Patent number: 6090968Abstract: 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: GrantFiled: June 29, 1999Date of Patent: July 18, 2000Assignee: Clariant GmbHInventors: Sebastian Horold, Norbert Weferling, Heinz-Peter Breuer
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Patent number: 6034261Abstract: 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: GrantFiled: February 8, 1999Date of Patent: March 7, 2000Assignee: Kao CorporationInventors: Akira Matsunaga, Akira Fujiu, Shinji Tsuyutani, Toshio Nozaki, Masayuki Ueda
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Patent number: 5883280Abstract: 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: GrantFiled: March 20, 1997Date of Patent: March 16, 1999Assignee: Kao CorporationInventors: Shinji Tsuyutani, Kengo Shibata, Kiyoshi Aimono
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Patent number: 5785894Abstract: 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: GrantFiled: December 13, 1996Date of Patent: July 28, 1998Assignee: Zeneca LimitedInventors: John David Schofield, Dean Thetford
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Patent number: 5783690Abstract: 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: GrantFiled: September 18, 1997Date of Patent: July 21, 1998Assignee: ISIS Pharmaceuticals, Inc.Inventors: Zacharia S. Cheruvallath, Daniel C. Capaldi, Vasulinga T. Ravikumar, Douglas L. Cole
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Patent number: 5554781Abstract: 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: GrantFiled: March 6, 1995Date of Patent: September 10, 1996Inventor: Robert L. Reierson
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Patent number: 5550274Abstract: 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: GrantFiled: March 7, 1995Date of Patent: August 27, 1996Inventor: Robert L. Reierson
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Patent number: 5502231Abstract: 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: GrantFiled: February 21, 1995Date of Patent: March 26, 1996Assignee: Cassella AktiengesellschaftInventors: Fritz Engelhardt, Ulrich Riegel, Hans-Jerg Kleiner
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Patent number: 5463101Abstract: 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: GrantFiled: December 1, 1994Date of Patent: October 31, 1995Assignee: Rhone-Poulenc Inc.Inventor: Robert L. Reierson
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Patent number: 5420328Abstract: 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: GrantFiled: September 9, 1993Date of Patent: May 30, 1995Assignee: Affymax Technologies, N.V.Inventor: David A. Campbell
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Patent number: 5359115Abstract: 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: GrantFiled: September 11, 1992Date of Patent: October 25, 1994Assignee: Affymax Technologies, N.V.Inventors: David A. Campbell, Jeffrey W. Jacobs
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Patent number: 5357037Abstract: This invention relates to new phosphorus-containing duromers of oligophosphites and epoxides or bisacrylates or unsaturated polyesters.Type: GrantFiled: April 8, 1994Date of Patent: October 18, 1994Assignee: Bayer AktiengesellschaftInventors: Burkhard Kohler, Wolfgang Ebert
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Patent number: 5344951Abstract: 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: GrantFiled: March 16, 1993Date of Patent: September 6, 1994Assignee: Ethyl Petroleum Additives, Inc.Inventor: Abbas Kadkhodayan
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Patent number: 5334741Abstract: 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: GrantFiled: July 20, 1992Date of Patent: August 2, 1994Assignee: Research Corporation Technologies, Inc.Inventors: Louis D. Quin, Stefan Jankowski
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Patent number: 5306840Abstract: 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: GrantFiled: August 5, 1992Date of Patent: April 26, 1994Assignee: Euticals S.p.A.Inventor: Giovanni Tronconi