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 558/92)
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Patent number: 11489201Abstract: The present disclosure is directed to a phosphorus-modified ionic liquid compound, the synthesis thereof and an electrochemical cell electrolyte containing the phosphorus-modified ionic liquid compound.Type: GrantFiled: October 9, 2020Date of Patent: November 1, 2022Assignee: NOHMS Technologies, Inc.Inventors: Surya Moganty, John Sinicropi, Gabriel Torres, Luigi Abbate, Yue Wu
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Patent number: 9290527Abstract: The invention relates to a method for producing 6-chlorodibenzo[d,f][1,3,2]-dioxaphosphepin (formula 1), comprising the following steps: a) addition of 2,2?-dihydroxybiphenyl, which is suspended in an inert solvant. into a reactor to an excess of phosphorous trichloride under inert gas and stirring; b) discharge and neutralization of the resulting gases from the reaction mixture; c) separation of the excess phosphorous trichloride and the solvant; d) obtention of 6-chlorodibenzo[d,f][1,3,2]-dioxaphosphepin.Type: GrantFiled: March 19, 2014Date of Patent: March 22, 2016Assignee: EVONIK DEGUSSA GMBHInventors: Dirk Fridag, Robert Franke, Bernhard Schemmer, Burkard Kreidler, Bjoern Wechsler
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Patent number: 9108988Abstract: A method of purifying an organic diphosphite of general formula (I) The method comprises providing a crude organic diphosphite of general formula (I) that is at least partly dissolved in a first solvent (L1), wherein (L1) is selected from the group consisting of alkylbenzenes, aryl alkyl ethers, chlorobenzene, and mixtures thereof, and precipitating by admixing with a second solvent (L2) selected from the group consisting of linear C1-C4-alkanols, ethylene glycol di(C1-C4-alkyl) ethers, and mixtures thereof, and separating off the precipitated organic diphosphite from the solvents.Type: GrantFiled: December 31, 2012Date of Patent: August 18, 2015Assignee: BASF SEInventors: Ulrich Berens, Holger Ganz, Franz Niklaus Windlin, Walid Al-Akhdar
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Patent number: 8822715Abstract: A method for producing an aromatic diphosphate comprising: Step 1 which is a step where a specific aromatic monohydroxy compound having a steric hindrance group at ortho-positions is made to react with phosphorus oxyhalide in the presence of a Lewis acid catalyst and then the unreacted phosphorus oxyhalide is removed under a reduced pressure to give a specific; and Step 2 which is a step where the reaction product obtained in the above step is made to react with a specific aromatic dihydroxy compound in an amount of 0.5 mol to 1 mol of halogen contained in the reaction product in the presence of a Lewis acid catalyst to give a specific aromatic diphosphate.Type: GrantFiled: June 21, 2011Date of Patent: September 2, 2014Assignee: Daihachi Chemical Industry Co., Ltd.Inventors: Kiyoharu Hirao, Katsuichi Ohtsuki, Hiroshi Tsuji, Hiroki Sato
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Patent number: 8735620Abstract: Processes for preparing (E)-2,4,6-(Trimethoxystyryl)-3-O-Phosphate Disodium-4-Methoxybenzyl Sulfones and uses thereof as antiproliferative agents, including, for example, anticancer agents, and as radioprotective and chemoprotective agents.Type: GrantFiled: December 17, 2008Date of Patent: May 27, 2014Assignee: EPR Pharmaceuticals PVT. LtdInventor: Reddy Sirigireddy
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Patent number: 8729287Abstract: The invention relates to a method for producing 6-chlorodibenzo[d,f][1,3,2]dioxaphosphepin (formula 1), comprising the following steps: a) addition of 2,2?-dihydroxybiphenyl, which is suspended in an inert solvant. into a reactor to an excess of phosphorous trichloride under inert gas and stirring; b) discharge and neutralization of the resulting gases from the reaction mixture; c) separation of the excess phosphorous trichloride and the solvant; d) obtention of 6-chlorodibenzo[d,f][1,3,2]dioxaphosphepin.Type: GrantFiled: October 9, 2009Date of Patent: May 20, 2014Assignee: Evonik Oxeno GmbHInventors: Dirk Fridag, Robert Franke, Bernhard Schemmer, Burkard Kreidler, Bjoern Wechsler
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Publication number: 20140123876Abstract: The invention relates to a hydroxy compound of formula (I) wherein n is an integer equal to or higher than 1 as an intermediate for the preparation of compounds of formulae (IIa) and (IIIb) as defined in the specification that can be used as water and oil resistance agents. The invention further relates to water and oil resistance compositions containing compounds (IIa) and (IIb).Type: ApplicationFiled: June 1, 2012Publication date: May 8, 2014Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Simonetta Antonella Fontana, Claudio Adolfo Pietro Tonelli, Piero Gavezotti
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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: 20130090490Abstract: A method for producing an aromatic diphosphate comprising: Step 1 which is a step where a specific aromatic monohydroxy compound having a steric hindrance group at ortho-positions is made to react with phosphorus oxyhalide in the presence of a Lewis acid catalyst and then the unreacted phosphorus oxyhalide is removed under a reduced pressure to give a specific; and Step 2 which is a step where the reaction product obtained in the above step is made to react with a specific aromatic dihydroxy compound in an amount of 0.5 mol to 1 mol of halogen contained in the reaction product in the presence of a Lewis acid catalyst to give a specific aromatic diphosphate.Type: ApplicationFiled: June 21, 2011Publication date: April 11, 2013Applicant: DAIHACHI CHEMICAL INDUSTRY CO., LTD.Inventors: Kiyoharu Hirao, Katsuichi Ohtsuki, Hiroshi Tsuji, Hiroki Sato
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Publication number: 20130090489Abstract: A process for manufacturing a polyfluroalkanoyl phosphorodichloridate comprising reacting a polyfluoroalkanol having the general formula Rf—CH2—OH, wherein Rf is a linear or branched C1-C8 perfluoroalkyl group optionally interrupted by O, with at least 4 moles of POCl3 per mole of Rf—CH2—OH in the presence of 0.1 to 0.2 moles of LiCl catalyst per mole of Rf—CH2—OH at a temperature between 95° C. and 110° C. to form a phosphorodichloridate of the general formula Rf—CH2—O—P(O)Cl2.Type: ApplicationFiled: October 6, 2011Publication date: April 11, 2013Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: MING-HONG HUNG
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Publication number: 20120165444Abstract: Disclosed herein is a phosphorus compound represented by Formula 1: wherein each R is the same or different and is independently hydrogen, C1-C6 alkyl or C6-C12 aryl.Type: ApplicationFiled: October 12, 2011Publication date: June 28, 2012Applicant: CHEIL INDUSTRIES INC.Inventors: Min Soo LEE, Im Hyuck BAE, Seon Ae LEE, Sang Hyun HONG, Chang Hong KO, Beom Jun JOO, Jin Hwan KIM, Ik Hyun YU, Thi Hai VO, Thanh Kieu GIANG, Thi Thuy Hang NGUYEN
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Publication number: 20120004438Abstract: The present invention relates to low triphenyl phosphate, high phosphorous content aryl phosphates with high ortho alkylation that are suitable for use as flame retardant compositions, processes for their preparation, and their use as flame retardants.Type: ApplicationFiled: September 14, 2011Publication date: January 5, 2012Applicant: Albemarle CorporationInventors: William J. Layman, Arthur G. Mack, Techen Tsao, Jeffrey Todd Aplin, Hoover Chew, Douglas W. Luther
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Publication number: 20100004364Abstract: Disclosed herein is a flame retardant and impact modifier represented by the following Chemical Formula 1. The flame retardant and impact modifier may improve heat resistance and flowability as well as flame retardancy and impact strength of a thermoplastic resin composition. The present invention also provides a method of preparing the foregoing flame retardant and impact modifier and a thermoplastic resin composition including the flame retardant and impact modifier.Type: ApplicationFiled: July 2, 2009Publication date: January 7, 2010Applicant: Cheil Industries Inc.Inventors: Min Soo LEE, Beom Jun JOO
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Patent number: 6909010Abstract: A facile synthesis of symmetric esters of C1-C10 alkylenebisphopsphonic acids is disclosed in which a C1-C10 alkylenebis(phosphonic dichloride) is reacted with an alcohol in the presence of a catalytic amount of 1H-tetrazole and a base in an aprotic solvent to form a first reaction mixture. The first reaction mixture is maintained for a time period sufficient to form a C1-C10 alkylenebis(chloro ester phosphonate) that is reacted under basic conditions with an excess of a hydroxylated compound to form a second reaction mixture that is itself maintained for a time period sufficient to form a C1-C10 alkylenebis(ester phosphonate) partial ester, homoleptic tetraester or mixed tetraester. The material so formed can be recovered or used as is.Type: GrantFiled: April 5, 2002Date of Patent: June 21, 2005Assignee: Loyola University of ChicagoInventors: Albert W. Herlinger, Dominique C. Stepinski
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Patent number: 6673955Abstract: The invention relates to a process for preparing triethyl phosphate by reacting phosphorus oxychloride with a greater than stoichiometric quantity of ethanol under reduced pressure at temperatures of from 0 to 50° C. in a reaction vessel, wherein a) the volatile components resulting from the reaction are predominantly condensed by means of a reflux condenser and the remaining volatile components are passed into a scrubber filled with water, b) after the end of the reaction, the reaction mixture is separated distillatively in an outgassing column into a top product and a bottom product which predominantly comprises triethyl phosphate, c) the top product of the outgassing column is combined with the contents of the scrubber and d) the contents of the scrubber are separated distillatively in an azeotropic distillation to obtain water and ethanol as top product and the ethanol, preferably after dewatering, is preferably returned to the reaction.Type: GrantFiled: November 22, 2002Date of Patent: January 6, 2004Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Mitschke, Kaspar Hallenberger, Ottfried Schlak, Johannes Kaulen
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Patent number: 6660696Abstract: Phosphorothionate derivatives derived from cashew nut shell liquid (CNSL) for use as an thermally stable antioxidant, antiwear, friction reducing and extreme pressure additive in a lubricant composition are synthesized by the steps of (a) partially hydrogenating distilled technical cashew nut shell liquid with palladium or nickel or platinum catalyst; to hydrogenate the olefinic chain; (b) reacting partially hydrogenated technical cashew nut shell liquid with phosphorus trihalide and sulphur, the reaction being carried out at a temperature ranging from 20 to 220° C. A lubricant containing a major proportion of a material selected from the group consisting of an oil of lubricating viscosity or a grease; and remainder an additive including CNSL phosphorothionate derivative, prepared by the foregoing process.Type: GrantFiled: June 20, 2002Date of Patent: December 9, 2003Assignee: Indian Oil Corporation LimitedInventors: Rajeev Ranjan, Ajay Kumar Arora, Rakesh Sarin, Deepak Kumar Tuli, Ram Prakash Verma, Akhilesh Kumar Bhatnagar
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Patent number: 6613928Abstract: A condensed phosphoric ester having a very low content of isopropenyl phenyl diphenyl phosphate, which reduces heat resistance and causes the contamination of molds during the molding when the condensed phosphoric ester is used as an additive for a resin, is provided by a process including a first step of reacting a phosphorus oxytrihalide with a bisphenol A derivative at a specific ratio to prepare a phosphorohalidate; a second step of removing unreacted phosphorus oxytrihalide; a third step of reacting the reaction product obtained in the second step with a monophenol-based compound at a temperature equal to or lower than 120° C.; and a fourth step of reacting the phosphorohalidate with the monophenol-based compound at a temperature equal to or higher than 120° C.Type: GrantFiled: April 15, 2002Date of Patent: September 2, 2003Assignee: Daihachi Chemical Industry Co., Ltd.Inventors: Shin Nakamura, Kazuo Noguchi, Taku Fujisawa, Takafumi Ohkawa
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Patent number: 6605736Abstract: A condensed phosphoric ester having a very low content of volatile components is provided by a process including a first step of reacting a phosphorus oxytrihalide with a bisphenol-based compound to prepare a phosphorohalidate; a second step of removing unreacted phosphorus oxytrihalide; and a third step of reacting the phosphorohalidate with a monophenol-based compound at a specific ratio.Type: GrantFiled: April 15, 2002Date of Patent: August 12, 2003Assignee: Daihachi Chemical Industry Co., Inc.Inventors: Shin Nakamura, Kazuo Noguchi, Taku Fujisawa, Takafumi Ohkawa
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Patent number: 6605737Abstract: An objective of the present invention is to provide a method for preparing a high-purity, condensed phosphoric ester made of a bisphenol A derivative and having a very low content of monomer-type phosphoric ester that causes reduction in the heat resistance and the contamination of the molds during the molding when the condensed phosphoric ester is used as an additive for a resin. According to the present invention, a bisphenol A derivative, a phosphorus oxytrihalide and a hydroxy compound are reacted in the presence of a decomposition retardant, whereby the above problems can be solved.Type: GrantFiled: May 3, 2002Date of Patent: August 12, 2003Assignee: Daihachi Chemical Industry Co., Ltd.Inventors: Shin Nakamura, Taku Fujisawa, Takafumi Okawa
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Publication number: 20030100787Abstract: A one pot process for the preparation of sterically hindered triaryl phosphite is provided. The triaryl phosphite is of the formula P(OR)3 and is produced by reacting a hydroxyl-substituted aryl compound of formula ROH with phosphorus trihalide in a presence of a Lewis base, wherein R represents an aryl compound of a formula C6H3R1R2, wherein each R1 and R2 is an organic substituent. The process preferably comprises of mixing a substantial stoichiometric amount of 2,4-dialkyl phenol with phosphorous trihalide in methylene chloride with stoichiometric amount of pyridine. The reaction is preferably carried out at 0-5° C. and takes only 1 hr for the completion, followed by a precipitation out of isopropanol.Type: ApplicationFiled: August 2, 2002Publication date: May 29, 2003Applicant: Strides Inc.Inventors: P.M. Akbarali, K.K. Vijay Raj, Karabasana T. Gouda, Ramachandran Radhakrishnan
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Publication number: 20030060648Abstract: A facile synthesis of symmetric esters of C1-C10 alkylenebisphopsphonic acids is disclosed in which a C1-C10 alkylenebis(phosphonic dichloride) is reacted with an alcohol in the presence of a catalytic amount of 1H-tetrazole and a base in an aprotic solvent to form a first reaction mixture. The first reaction mixture is maintained for a time period sufficient to form a C1-C10 alkylenebis(chloro ester phosphonate) that is reacted under basic conditions with an excess of a hydroxylated compound to form a second reaction mixture that is itself maintained for a time period sufficient to form a C1-C10 alkylenebis(ester phosphonate) partial ester, homoleptic tetraester or mixed tetraester. The material so formed can be recovered or used as is.Type: ApplicationFiled: April 5, 2002Publication date: March 27, 2003Inventors: Albert W. Herlinger, Dominique C. Stepinski
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Patent number: 6528559Abstract: This invention provides a halogen-free flame retardant which advantageously has a high melting point and a low volatility and does not impair the inherent properties of resins. The flame retardant of the invention is a phosphazene compound crosslinked with a crosslinking group such as a phenylene group, wherein each of the crosslinking groups is interposed between the two oxygen groups left after the elimination of phenyl groups from the phosphazene compound; the crosslinked phenoxyphosphazene compound does not have any free hydroxyl groups (derived from crosslinking groups); and the amount of the phenyl groups in the crosslinked compound is 50 to 99.9%, based on the total number of the phenyl groups in the phosphazene compound.Type: GrantFiled: February 12, 2001Date of Patent: March 4, 2003Assignee: Otsuka Chemical Co., Ltd.Inventors: Yoshifumi Nakacho, Tadao Yabuhara, Yuji Tada, Yoichi Nishioka
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Patent number: 6489502Abstract: The present invention relates to a process for preparing phosphoric acid esters, in particular a process for preparing monomeric bridged bisaryl diphosphates, wherein a water-binding agent is added to the reaction solution.Type: GrantFiled: December 4, 2000Date of Patent: December 3, 2002Assignee: Bayer AktiengesellschaftInventors: Nikolaus Janke, Manfred Pieroth, Dieter Heinz, Werner Bäcker
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Patent number: 6486339Abstract: The isomerization of an alkylated phenol composition that contains an ortho-alkyl substituted phenol component to isomerize and reduce the level of ortho-alkyl substituted phenol component therein can be accomplished by heating that composition in the presence of a catalytically effective amount of a solid acid catalyst to carry out such isomerization and reduction in the level of ortho-alkyl substituted phenol. Examples of suitable solid acid catalysts can be selected from the H-form zeolites, the supported sulfonic acids, and the heteropoly acids. The resulting isomerized product can be subsequently phosphorylated.Type: GrantFiled: April 26, 2001Date of Patent: November 26, 2002Assignee: Akzo Nobel NVInventors: Anantha N. Desikan, George E. Whitwell
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Patent number: 6462216Abstract: The present invention provides a process for producing phosphorohalidate characterized in that a crude reaction product obtained by reacting a phosphorus oxyhalide with an aromatic hydroxy compound in the presence of a Lewis acid catalyst is purified by distillation in the presence of an alkali metal salt. The process of the invention produces a high-purity phosphorohalidate in high yield which contains no impurities such as the phosphorus oxihalidate and aromatic hydroxy compound used as starting materials and the catalyst.Type: GrantFiled: August 8, 2001Date of Patent: October 8, 2002Assignee: Daihachi Chemical Industry Co., Ltd.Inventor: Yasunori Fujita
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Patent number: 6420465Abstract: The present invention relates to a process for preparing phosphoric acid esters, in particular monomeric bisaryl diphosphates, or bridged phosphates.Type: GrantFiled: December 4, 2000Date of Patent: July 16, 2002Assignee: Bayer AktiengesellschaftInventors: Nikolaus Janke, Reinhard Pech, Andreas Chrisochoou, Dieter Heinz, Werner Bäcker, Kaspar Hallenberger
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Publication number: 20020068835Abstract: The present invention relates to a process for preparing phosphoric acid esters, in particular monomeric bisaryl diphosphates, or bridged phosphates.Type: ApplicationFiled: December 4, 2000Publication date: June 6, 2002Inventors: Nikolaus Janke, Reinhard Pech, Andreas Chrisochoou, Dieter Heinz, Werner Backer, Kaspar Hallenberger
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Patent number: 6399685Abstract: Emulsion formation is minimized or prevented and hydrolytic product degradation is suppressed during purification of impure bisphenol-A bis(diphenylphosphate). This is accomplished by forming a hydrocarbon solution of bisphenol-A bis(diphenylphosphate) plus impurities in a solvent comprising at least one aromatic hydrocarbon and at least one paraffinic hydrocarbon. Optionally, but preferably, this solution is washed with water or an aqueous buffer solution. Next, the hydrocarbon solution is washed one or more times with an aqueous alkaline washing solution that has a specific gravity that differs from the specific gravity of the hydrocarbon solution by at least about 0.05 gram per cubic centimeter. After each washing the mixture settles into a purified organic phase and a separate aqueous phase, and these phases are separated from each other.Type: GrantFiled: December 11, 2000Date of Patent: June 4, 2002Assignee: Albemarle CorporationInventors: W. Dirk Klobucar, William B. Harrod, Billie B. Dadgar, Joseph D. McLean, Gary D. Heidebrecht, Hao V. Phan, Thomas R. Nicholas, Jeffrey L. Broeker
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Patent number: 6388120Abstract: A method of making phosphoric acid esters by continuously reacting a phosphorus oxyhalide with a polyol to produce at least about 60% normalized monomeric halophosphate intermediate, and then reacting the monomeric halophosphate intermediate with an alcohol to produce a desired phosphoric acid ester is provided. In other embodiments, the reaction of the monomeric halophosphate intermediate with the alcohol can also be carried out continuously. Another aspect of the invention provides a method of making phosphoric acid esters by continuously reacting a phosphorus oxyhalide with a monohydric alcohol to produce at least about 60% normalized monohalomonophosphate diester intermediate, and then reacting the monohalomonophosphate diester intermediate with a polyol to produce a phosphoric acid ester. In other embodiments, the reaction of the monohalomonophosphate diester intermediate with the polyol may also be carried out continuously.Type: GrantFiled: April 28, 1999Date of Patent: May 14, 2002Assignee: PABU Services, Inc.Inventors: Robert M. Farner, David W. Bartley, Jon D. Lehmkuhler
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Publication number: 20020038044Abstract: The present invention relates to a process for preparing phosphoric acid esters, in particular a process for preparing monomeric bridged bisaryl diphosphates, wherein a water-binding agent is added to the reaction solution.Type: ApplicationFiled: December 4, 2000Publication date: March 28, 2002Inventors: Nikolaus Janke, Manfred Pieroth, Dieter Heinz, Werner Backer
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Publication number: 20020013488Abstract: High purity sterically hindered diaryl chlorophosphates, having a purity of at least 98% by weight and a proportion of the corresponding aryl dichlorophosphate less than 1.5% by weight, are prepared by a method including the steps of gradually introducing POCl3 into a mixture of a sterically hindered hydroxyaromatic compound such as 2,6-xylenol and a catalyst such as magnesium chloride, and gradually increasing the temperature of the reaction mixture to a final level in the range of about 135-150° C. The products are capable of reaction with amines such as piperazine to produce sterically hindered phosphoramidates.Type: ApplicationFiled: August 22, 2001Publication date: January 31, 2002Applicant: General Electric CompanyInventors: John Robert Campbell, Paul Edward Howson, Matthew Ladd Reitz
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Publication number: 20020010356Abstract: A novel process is described for preparing phosphonites or phosphinites by reacting a product of a Friedel-Crafts reaction with alcohols or phenols and separating off the byproducts formed. The novelty is the aftertreatment with a protic compound, or with an oxide, hydroxide, (hydrogen)carbonate resp. (hydrogen)phosphate of a metal or with a nitrogen containing compound (as defined in claim 1), or with any combination of one or more substances of the above mentioned compound classes. Products having a low halide and aluminium content are obtained which are distinguished by an improved clear solubility and an improved action as stabilizer for polymeric materials.Type: ApplicationFiled: June 29, 2001Publication date: January 24, 2002Inventors: Ernst Gronmaier, Peter` Staniek
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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: 6235689Abstract: The degree of bonding of a perfluoro polyether lubricant topcoat to a magnetic recording medium is improved by forming a polymeric phosphate derivative thereof. In an embodiment of the present invention, a perfluoro polyether phosphate polymer is formed with a molecular weight of about 1000 to about 5000, and applied to a magnetic recording medium to achieve a bonded lube ratio in excess of 0.9.Type: GrantFiled: October 5, 1998Date of Patent: May 22, 2001Assignee: Seagate Technology LLCInventor: Samuel J. Falcone
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Patent number: 6232485Abstract: A process for the production of liquid meta-rich triaryl phosphate esters having low triphenyl phosphate content and low viscosity comprises (a) an alkylation stage wherein a phenol is reacted with an olefin having 2 to 12 carbon atoms in the presence of a strong acid catalyst to give a reaction product comprising a mixture of meta and para alkylated phenols; and (b) a transalkylation stage wherein the mixture of alkylated phenols from the alkylation stage is heated in the presence of a strong acid catalyst to increase the meta isomer content of the mixture to at least 25% whilst maintaining a phenol level below 22%; and (c) a phosphorylation stage wherein the mixture of alkylated phenols from the transalkylation stage is reacted with a phosphorylating agent; and wherein the strong acid catalyst used in stages (a) and (b) is a Bronsted acid having an acid strength of less than zero. Preferred catalysts are activated clays such as bentonite, montmorillonite or Fullers Earth clay.Type: GrantFiled: November 26, 1999Date of Patent: May 15, 2001Assignee: Great Lakes Chemical CorporationInventors: Tracy Anne Derbyshire, Hazel May Farrow, Jonathan Simon Hill
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Patent number: 6211396Abstract: A process for producing a halogen-containing phosphate ester includes the steps of: (i) reacting a phosphorus halide selected from the group consisting of phosphorus oxyhalides and phosphorus pentahalides with a halogen-containing hydroxy compound to obtain a reaction mixture including a halogen-containing phosphate ester, (ii) purifying the halogen-containing phosphate ester by adding an aqueous medium selected from the group consisting of water, neutral aqueous solutions, acidic aqueous solutions and basic aqueous solutions to the reaction mixture to crystallize the halogen-containing phosphate ester, and (iii) distilling waste water from the purification step.Type: GrantFiled: January 5, 2000Date of Patent: April 3, 2001Assignee: Daihachi Chemical Industry Co., Ltd.Inventor: Shin Nakamura
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Patent number: 6204404Abstract: A process for preparing an ester compound comprising reacting a halogen-substituted aliphatic hydroxy compound or aromatic hydroxy compound with a phosphorus oxyhalide or phosphorus pentahalide in the presence of 0.005 to 10 mol % of a phosphorus trihalide with respect to the hydroxy compound to obtain a phosphoric ester compound. Phosphoric ester compounds of high purity containing less coloring components can be prepared without using an antioxidant.Type: GrantFiled: December 3, 1999Date of Patent: March 20, 2001Assignee: Daihachi Chemical Industry Co., Ltd.Inventors: Noriaki Tokuyasu, Shin Nakamura
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Patent number: 6184275Abstract: A crystalline polymer composition comprising 100 parts by weight of a crystalline polymer and 0.005 to 5 parts by weight of a compound represented by formula (I): wherein R1 and R2 each independently represent an alkyl group having 1 to 9 carbon atoms; R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and M represents an alkali metal, the compound having a chlorine content of 500 ppm or less.Type: GrantFiled: August 13, 1999Date of Patent: February 6, 2001Assignee: Asahi Denka Kogyo Kabushiki KaishaInventors: Masayuki Takahashi, Etsuo Tobita
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Patent number: 6075159Abstract: A phosphite represented by the formula (I): ##STR1## wherein n repesents 1 or 2; A represents alkylene; B represents a direct bond or alkylene; one of Y and Z represents a hydroxyl group, alkoxy or aralkyloxy, and the other one represents a hydrogen atom or alkyl; X represents a group of formula (II): ##STR2## wherein R.sup.1 and R.sup.2 represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, an aralkyl group or a phenyl group; R.sup.3 represents a hydrogen atom or an alkyl group; and R.sup.4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, an aralkyl group or a phenyl group, or R.sup.4 may be combined to form a direct bond, a sulfur bond (--S--), or an unsubstituted or substituted methylene group; R.sup.5 and R.sup.6 independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, an aralkyl group or a phenyl group;R.sup.8 represents a hydrogen atom or an alkyl group; andR.sup.Type: GrantFiled: October 30, 1997Date of Patent: June 13, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Naoki Inui, Taketoshi Kikuchi, Kanako Fukuda, Takashi Sanada
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Patent number: 6069267Abstract: A process for the preparation of organodiphosphites of the formula (R.sup.1 O).sub.2 P(OZO)P(OR.sup.1).sub.2 wherein R.sup.1 and Z are different substituted or unsubstituted aryl groups.Type: GrantFiled: July 10, 1998Date of Patent: May 30, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Wilson Tam
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Patent number: 6034260Abstract: The present invention relates to a process for the preparation of symmetrically substituted phosphoric acid diesters of long-chain linear or branched alcohols of chain length C.sub.4 to C.sub.22.Type: GrantFiled: March 11, 1999Date of Patent: March 7, 2000Assignee: Bayer AGInventors: Karl-Heinz Mitschke, Christoph Holzner
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Patent number: 5948930Abstract: The invention relates to process for the preparation of an O-alkyl, O-alkyl phosphorochloridothioate by 1) reacting A) a thiophosphoryl halide with B) an alcohol, in the presence of C) a tertiary amine acid acceptor and D) a solvent, and 2) reacting the resultant product with a second alcohol, different from the alcohol used in step 1). In the preferred embodiment, the intermediate product is not isolated before reaction with the second alcohol.Type: GrantFiled: September 11, 1997Date of Patent: September 7, 1999Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: David M. Mayes, Daniel M. Wasleski, Gerd Grah, Hermann Seifert
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Patent number: 5891939Abstract: Phosphites inhibitors for organic material represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 independently represent hydrogen atom, an alkyl group, a cycloalkyl group, an alkylcycloalkyl group, an aralkyl group or a phenyl group; R.sup.3 is hydrogen atom or alkyl; X is a direct bond, sulfur atom, or methylene group which may optionally be substituted with alkyl or cycloalkyl; A represents a dihydric alcohol residue; B is a direct bond or alkylene; and one of Y and Z represents an alkoxy group or an aralkyloxy group, and the other one represents hydrogen atom or an alkyl group; and a process for producing the same are provided.Type: GrantFiled: August 6, 1997Date of Patent: April 6, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Taketoshi Kikuchi, Naoki Inui, Kanako Fukuda, Takashi Sanada
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Patent number: 5830936Abstract: Phosphites which are a deterioration inhibitors for organic material represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, or certain hydrocarbyl radicals; X represents a direct bond, a sulfur atom or a methylene group which may optionally be substituted; Z is --A.sup.1 --CO--O--Y.sup.1 or --A.sup.2 --O--CO--Y.sup.2 wherein A.sup.1 is a direct bond or an alkylene group; Y.sup.1 is aralkyl or aryl; A.sup.2 is a residue of a dihydric alcohol; and Y.sup.2 is alkyl, aralkyl or a phenyl group, and a process for producing the same are provided.Type: GrantFiled: August 22, 1997Date of Patent: November 3, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Taketoshi Kikuchi, Naoki Inui, Kanako Fukuda, Takashi Sanada
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Patent number: 5616767Abstract: A process is provided for making 2,2 bisphenyl phosphites and 2,2 biphenyl phosphites. The process provides pure product without requiring a recrystallization step. The process involves reacting phosphorous trichloride with either (a) an aromatic diphenol selected from the group of bisphenyl and biphenyls or (b) a monohydroxy hydrocarbon compound, to induce a first product, and then reacting the first product with the other of (a) and (b) in the presence of an amount of tri-n-alkylamine sufficient to neutralize the hydrochloric acid produced in the second reaction, and utilizing an aromatic liquid hydrocarbon medium and a minimum amount to facilitate precipitation of the resultant aromatic phosphite.Type: GrantFiled: February 28, 1995Date of Patent: April 1, 1997Assignee: General Electric CompanyInventors: William P. Enlow, James A. Mahood
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Patent number: 5414103Abstract: A polyalkylene glycol ether phosphate ester, or salt thereof, having the formula:R.sub.w --P(O)(OH).sub.3-w (I)wherein w is an integer from 1 to 3, andR is an oil-soluble polyether moiety having the formula:R.sup.1 X[(C.sub.x H.sub.2x O).sub.n (C.sub.y H.sub.2y O).sub.p ].sub.m(II)wherein R.sup.1 is either an alkyl or an alkyl phenyl group having from 7 to 30 carbon atoms,X is either O, S, or Nx is an integer from 2 to 4,y is an integer from 6 to 30,m is 1 when X is O or S and m is 2 when X is N,n and p are such that the polyether moiety contains between 1 and 35% by weight of (C.sub.y H.sub.2y O) units and between 35 and 80% by weight of (C.sub.x H.sub.2x O) units, and the molecular weight of the polyalkylene glycol moiety is between 500 and 5000 is disclosed,The phosphate ester can be prepared by reacting a polyether with a phosphating agent, e.g. phosphorus pentoxide and water. Lubricating oil compositions comprising the phosphate ester or salt thereof are also disclosed.Type: GrantFiled: December 28, 1992Date of Patent: May 9, 1995Assignee: Oceanfloor LimitedInventors: Robert B. Cracknell, Anthony J. Moore
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Patent number: 5401845Abstract: Compounds of the formula I ##STR1## in which x is 1, 2 or 3, and, if x=1, R.sup.1 is C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.18 alkyl substituted by halogen, --COOR.sup.2, --CN, --NR.sup.3 R.sup.4 or by --CONR.sup.3 R.sup.4, C.sub.2 -C.sub.18 alkyl which is interrupted by --NR.sup.5 --, --O-- or --S--, C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl-C.sub.1 -C.sub.4 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen, phenyl-C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or R.sub.1 is naphthyl, a radical of the formula ##STR2## R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl or phenyl-C.sub.1 -C.sub.4 alkyl, R.sup.6 is hydrogen, methyl, allyl or benzyl, R.sup.7 is hydrogen or --OR.sup.9, R.sup.8 is hydrogen or methyl, R.sup.9 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.10 and R.sup.11, independently of one another, are hydrogen or C.sub.1 -C.sub.Type: GrantFiled: March 11, 1994Date of Patent: March 28, 1995Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Peter Hofmann, Rudolf Maul, Volker Schenk, Eduard Troxler, Horst Zinke
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Patent number: 5281741Abstract: A process is provided for preparing an aryl diphosphate ester containing less than 5% by weight of triarylphosphate. The process reacts a solution of a dihydroxy aromatic compound and an excess of phosphorus oxychloride in a nonaqueous solvent having a boiling point greater than 110.degree. C. The excess phosphorus oxychloride and part of the solvent are distilled from the solution at atmospheric pressure and the intermediate, a diphosphotetrachloridate solution, is reacted with a monohydric aryl compound. After extracting with an aqueous, alkaline solution the product is recovered by distilling off the remaining solvent.Type: GrantFiled: November 13, 1990Date of Patent: January 25, 1994Assignee: FMC CorporationInventors: Louis T. Gunkel, Henry J. Barda
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Patent number: 4929746Abstract: Organic esters of chlorine-containing or bromine-containing phosphorus acids and BIS-GMA, as well as 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 23, 1989Date of Patent: May 29, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventor: James E. Bunker
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Patent number: 4824603Abstract: Amphoteric and zwitter-ionic phosphate surfactants corresponding to the following formula ##STR1## (a) in which R.sup.1 is a C.sub.6 -C.sub.22 alkyl group, a group R.sup.4 (OC.sub.n H.sub.2n).sub.x --, where n=2 to 4, x=1 to 6, and R.sup.4 is a C.sub.6 -C.sub.22 alkyl group, or a group R.sup.5 --CONH(CH.sub.2).sub.m, where R.sup.5 is a C.sub.5 -C.sub.21 group and m=2 to 4; R.sup.2 is hydrogen; and R.sup.3 is a C.sub.1 -C.sub.4 alkyl group or a group --(C.sub.n H.sub.2n O).sub.x --H or --(C.sub.n H.sub.2n O).sub.x --PO.sub.3 H.sub.2, where n=2 to 4 and x=1 to 6, or(b) in which R.sup.1 is a C.sub.1 -C.sub.4 alkyl group or a C.sub.2 -C.sub.4 2-hydroxyalkyl group; R.sup.2 is a C.sub.6 -C.sub.22 alkyl group; and R.sup.3 is as defined above.to mixtures thereof with correspondingly substituted phosphate surfactants corresponding to formula (I), in which the --PO.sub.3 H.sub.2 group or groups are replaced by hydrogen; and to neutral and basic salts of the foregoing.Type: GrantFiled: October 28, 1987Date of Patent: April 25, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hinrich Moller, Ulrich Zeidler