Patents Represented by Attorney, Agent or Law Firm E. E. Spielman, Jr.
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Patent number: 6281176Abstract: This invention provides a process for producing a betaine/amine oxide mixture. This process comprises reacting, in a liquid medium, an alkali metal &ohgr;-halocarboxylate with a first tertiary amine of the formula Ra2RbN, wherein each Ra group is a hydrocarbyl group which independently has from 1 to about 4 carbon atoms, and wherein the Rb group is a hydrocarbyl group which has from about 8 to about 24 carbon atoms, to produce a betaine product solution. To the betaine product solution is added a second tertiary amine of the formula Ra2RbN, wherein each Ra group is a hydrocarbyl group which independently has from 1 to about 4 carbon atoms, and wherein the Rb group is a hydrocarbyl group which has from about 8 to about 24 carbon atoms, to produce an amine/betaine mixture. The first and second tertiary amines can be separate portions of the same amine. Preferably, however, the first and second tertiary amines differ from each other.Type: GrantFiled: December 3, 1999Date of Patent: August 28, 2001Assignee: Albemarle CorporationInventors: Rebecca S. Cochran, Patrick C. Hu, Michael S. McCaig, Edmund F. Perkins, Jr., Joe D. Sauer, Dustin H. Thomas
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Patent number: 6258770Abstract: When certain weight ratios of certain flammable additive components (an ether and an epoxyalkane) are blended in n-propyl bromide, the components can actually function as flame retardants or flame suppressants when the resulting cleaning composition is used in aerosol applications. The proportions of the additives used are small; yet suitably effective stabilization against metallic corrosion is achieved even at mildly elevated temperatures.Type: GrantFiled: September 11, 1998Date of Patent: July 10, 2001Assignee: Albemarle CorporationInventors: Ronald L. Shubkin, Eric W. Liimatta
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Patent number: 6235844Abstract: These novel brominated styrenic polymers have a bromine content in the range of about 60 to about 66 wt % bromine; a total chlorine content, if any, of less than 700 ppm; a GPC weight average molecular weight in the range of about 500,000 to about 800,000; a DSC glass transition temperature of less than 175° C.; and a thermal stability in the Thermal Stability Test of 250 ppm HBr or less. Such flame retardant polymers exhibit superior performance qualities during use, especially in thermoplastics, including improved melt flow characteristics and improved thermal stability.Type: GrantFiled: October 13, 1998Date of Patent: May 22, 2001Assignee: Albemarle CorporationInventors: Billie B. Dadgar, Donald E. Balhoff, Charles H. Kolich, Meng-Sheng Ao, Homer C. Lin
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Patent number: 6235831Abstract: A polyalkylene terephthalate polymer, such as polyethylene terephthalate, polybutylene terephthalate, blends or copolymers thereof, and analogous polyester-type engineering thermoplastics, with which has been blended a flame retardant amount of brominated styrenic polymer, such as brominated polystyrene, that, prior to blending, is characterized by (a) containing less than 700 ppm Cl and having a TGA temperature for 1% weight loss of 340° C. or higher; and/or (b) having an actual Mw which is within about 20%, and preferably within about 10%, of its calculated theoretical Mw, the theoretical Mw being based upon the actual bromine content of the brominated styrenic polymer and the Mw of the styrenic polymer reactant used to produce the brominated styrenic polymer; and/or (c) being essentially free of each of the following impurities: (1) ethylene dichloride, (2) bromodichloroethane, (3) dibromochloroethane, (4) dibromodichloroethane, and (5) tribrormochloroethane.Type: GrantFiled: September 10, 1998Date of Patent: May 22, 2001Assignee: Albemarle CorporationInventors: Jon S. Reed, Susan D. Landry, Daniel A. De Schryver, Billie B. Dadgar, Donald E. Balhoff, Charles H. Kolich, Meng-Sheng Ao, Homer C. Lin
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Patent number: 6235946Abstract: Tetrabromobisphenol-A is produced in a bromination process where no bromine or only a very small proportion of bromine is fed to the reactor. In the process aqueous hydrobromic acid, is the sole source or a major source of the bromine. In the process there are at least three concurrent continuous feeds to the reactor. One is composed of bisphenol-A and/or underbrominated bisphenol-A and a water-miscible organic solvent. The second is gaseous hydrogen bromide or preferably, aqueous hydrobromic acid, and the third is aqueous hydrogen peroxide. Optionally a small additional continuous feed of bromine can be employed. The feeds are proportioned to maintain a liquid phase containing (i) from above about 15 to about 85 wt % water, based upon the amount of water and water-miscible organic solvent in such liquid phase, and (ii) an amount of unreacted bromine that is in excess over the stoichiometric amount theoretically required to convert the bisphenol-A and/or underbrominated bisphenol-A to tetrabromobisphenol-A.Type: GrantFiled: October 12, 1999Date of Patent: May 22, 2001Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
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Patent number: 6232408Abstract: Novel brominated styrenic polymers have an ionic bromine content of 2000 ppm or less, and one or more of the following additional characteristics: (a) a TGA temperature for 1% weight loss which is 340° C. or higher, and a chlorine content, if any, of less than about 700 ppm Cl (b) an actual Mw which is within about 20% of the calculated theoretical Mw, the theoretical Mw being based upon the actual bromine content of the brominated styrenic polymer and the Mw of the styrenic polymer reactant used to produce the brominated styrenic polymer; and (c) essentially no content of impurities selected from the group consisting of ethylene dichloride, bromodichloroethane, dibromochloroethane, dibromodichloroethane, and tribromochloroethane. Such flame retardant polymers exhibit superior performance qualities during use, especially in thermoplastics such as glass-filled polyesters and glass-filled nylons.Type: GrantFiled: September 10, 1998Date of Patent: May 15, 2001Assignee: Albemarle CorporationInventors: Billie B. Dadgar, Donald E. Balhoff, Charles H. Kolich, Meng-Sheng Ao, Homer C. Lin
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Patent number: 6232393Abstract: Flame retarded thermoplastic polymer compositions are formed by blending together a thermoplastic polymer and at least a flame retardant amount of a brominated styrenic polymer having, prior to blending, a total bromine content of at least about 50 wt % and in addition specified characteristics pertaining to such properties as (i) TGA temperature for 1% weight loss, (ii) hydrolyzable bromine content, (iii) chlorine content (if any), and/or (iv) thermal stability using a described Thermal Stability Test. Blends made with prior art brominated polystyrenes do not possess the enhanced thermal stability and reduced metal corrosiveness provided by these brominated styrenic polymers.Type: GrantFiled: September 10, 1998Date of Patent: May 15, 2001Assignee: Albemarle CorporationInventors: Billie B. Dadgar, Donald E. Balhoff, Charles H. Kolich, Meng-Sheng Ao, Homer C. Lin
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Patent number: 6221835Abstract: Novel synthetic zeolite compositions of extremely small particle sizes that have increased loading capability, and process technology for producing such compositions are described. So far as is presently known, it has never been possible to form such compositions heretofore. The process technology involves, inter alia, contacting the zeolite cake formed in its production with a specified type of treating agent and then subjecting the treated zeolite to physical subdivision.Type: GrantFiled: June 25, 1999Date of Patent: April 24, 2001Assignee: Albemarle CorporationInventors: Patrick C. Hu, Conrad J. Langlois, Jr., Dixie E. Goins, Joseph E. Coury
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Patent number: 6218584Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bis-phenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.Type: GrantFiled: June 10, 1999Date of Patent: April 17, 2001Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
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Patent number: 6207838Abstract: Electrolysis of organic disulfides in liquid sulfur dioxide is used to obtain organothiating agents, which can then be reacted with appropriate substrates to effect the synthesis of organothioaromatic compounds efficiently and in high yields. With appropriate phenolic compounds, regioselective substitution occurs in which para substitution greatly exceeds ortho substitution.Type: GrantFiled: April 30, 1999Date of Patent: March 27, 2001Assignee: The University of ArizonaInventors: Richard S. Glass, Viatcheslav V. Jouikov
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Patent number: 6207765Abstract: This invention relates to the bromination of styrenic polymers by contacting same with a brominating agent in the presence of a bromination catalyst and, as a reaction solvent, bromochloro-methane.Type: GrantFiled: April 13, 1999Date of Patent: March 27, 2001Assignee: Albemarle CorporationInventors: Meng-Sheng Ao, Billie B. Dadgar, Charles H. Kolich, Donald E. Balhoff, Homer C. Lin, David R. Brackenridge, Thorsten W. Brockman
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Patent number: 6166255Abstract: Exothermic oxidation of tertiary amine with aqueous hydrogen peroxide in an aqueous reaction medium formed or being formed from tertiary amine, aqueous hydrogen peroxide, carbon dioxide, and optionally chelating agent and/or additional water, is initiated at about 15 to about 25.degree. C., and while agitating the reaction mixture, the temperature is allowed to rise adiabatically to a temperature in the range of about 50 to about 100.degree. C. In this way, it is possible to produce tertiary amine oxides with very low levels, if any, of nitrosamine impurity, without addition of metal and/or phosphorus-containing components recommended in the prior art. Even though a substantial portion of the reaction is performed at temperatures in the range of about 50-100.degree. C., nitrosamine content, if any, in the resultant tertiary amine oxide product can be well below 30 ppb, and the free amine content, if any, can be well below 0.3 wt %.Type: GrantFiled: September 11, 1998Date of Patent: December 26, 2000Assignee: Albemarle CorporationInventors: Rebecca S. Cochran, Andrea P. Wight, Douglas H. Krzystowczyk, Dustin H. Thomas
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Patent number: 6165284Abstract: Silver tarnishing is inhibited when using ether stabilized, n-propyl bromide based cleaning compositions by including a saturated aliphatic alcohol in the compositions.Type: GrantFiled: June 25, 1998Date of Patent: December 26, 2000Assignee: Albemarle CorporationInventor: Ronald L. Shubkin
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Patent number: 6162953Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features the addition of bisphenol-A to a reaction mass containing unreacted Br.sub.2 and 30 to 85 wt % water and an alcohol solvent, the reaction mass being at a relatively high temperature.Type: GrantFiled: September 28, 1999Date of Patent: December 19, 2000Assignee: Albemarle CorporationInventors: Bonnie G. McKinnie, Richard A. Holub, Hassan Y. Elnagar
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Patent number: 6147264Abstract: Bisphenol-A or preferably, a mixture of bisphenol-A and underbrominated bisphenol-A, is brominated in a liquid phase reaction medium in which tetrabromobisphenol-A is relatively insoluble, using a stoichiometric deficiency of bromine to thereby form in the reaction mass a precipitate (i.e., a solids phase) composed of 50-95 wt % of tetrabromobisphenol-A and 50-5 wt % of underbrominated bisphenol-A. The precipitate is separated from the reaction mass, preferably during the bromination, and tetrabromobisphenol-A is recovered from the precipitate. Preferably underbrominated bisphenol-A is recycled as feed to the bromination. The process technology of this invention has the capability of producing high quality tetrabromobisphenol-A (high purity, good color, low ionic halide content) with efficient raw material utilization, minimized waste product formation, and minimized waste disposal costs.Type: GrantFiled: April 8, 1999Date of Patent: November 14, 2000Assignee: Albemarle CorporationInventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
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Patent number: 6133381Abstract: This invention relates to a thermally stable brominated polystyrene composition which contains alkali metal base (e.g., NaOH) in an amount less than about 1 wt % such that if the flame retardant is dissolved in bromochloromethane and the resultant solution is extracted with water, the resultant water extract exhibits a pH of at least about 9.0. A preferred composition of this type even when heated to 315.degree. C. for one hour did not undergo darkening--the color remained tan. Comparative samples not containing the base turned black under these same conditions. Especially useful compositions additionally have less than 500 ppm, and better still, less than 100 ppm total Cl, and at least about 67 wt % bromine. Processes for producing the compositions are also described.Type: GrantFiled: April 24, 1998Date of Patent: October 17, 2000Assignee: Albelmarle CorporationInventors: Jon S. Reed, Charles H. Kolich, Billie B. Dadgar, Donald E. Balhoff, Meng-Sheng Ao, Homer C. Lin, Thorsten W. Brockmann, David R. Brackenridge
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Patent number: 6133221Abstract: A cleaning process suitable for both mild and aggressive applications employs non-flammable, non-corrosive and environmentally friendly, fluorinated hydrobromocarbon solvent based cleaning compositions.Type: GrantFiled: January 13, 1999Date of Patent: October 17, 2000Assignee: Albemarle CorporationInventors: Phillip R. Beaver, James E. Boone, Dixie E. Goins, Eric W. Liimatta, David L. Shelton, Ronald L. Shubkin
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Patent number: 6121490Abstract: A process for producing tertiary amine oxide having two methyl or ethyl groups and one long chain primary aliphatic group in a stable, solid form is described. Aqueous 65-90% hydrogen peroxide and tertiary amine having two methyl or ethyl groups and one primary aliphatic hydrocarbyl group of 8-24 carbon atoms are mixed in proportions of ca. 1.1-1.3 moles of hydrogen peroxide per mole of tertiary amine in the presence of carbon dioxide and in the absence of organic solvent. When the conversion of the tertiary amine to tertiary amine oxide in the reaction mass has reached ca. 60-90%, the reaction mass is transferred to a separate vessel and the reaction mass is then allowed to solidify at a temperature of ca. 20-60.degree. C. The process makes possible the production of highly pure solid product without formation of any appreciable amounts of undesirable by-products.Type: GrantFiled: April 14, 1999Date of Patent: September 19, 2000Assignee: Albemarle CorporationInventor: Hassan Y. Elnagar
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Patent number: 6121500Abstract: A mixture of water and a glycol, such as ethylene glycol, is employed as the solvent for the reaction between 1,6-dibromo-2-naphthol and an alkali metal sulfite in the preparation of 6-bromo-2-naphthol and its derivatives to effect a substantial reduction in reaction time. The glycol/water mol ratio is ordinarily in the range of 0.1-0.5/1, preferably 0.3/0.5/1.Type: GrantFiled: March 4, 1999Date of Patent: September 19, 2000Assignee: Albemarle CorporationInventor: Mahmood Sabahi
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Patent number: 6114293Abstract: A process for cleaning movie film, and especially cellulose acetate based polymer film, without causing film damage, comprises immersing the film into a cleaning solvent composition which comprises one or more halogenated hydrobromocarbons having from 1 to 3 carbons, from 1 to 3 bromine atoms and at least one chlorine or fluorine atom, such as 3-bromo-1,1,1-trifluoropropane, removing the film from the solvent and drying the film.Type: GrantFiled: January 13, 1999Date of Patent: September 5, 2000Assignee: Albemarle CorporationInventors: Phillip R. Beaver, James E. Boone, Dixie E. Goins, Eric W. Liimatta, David L. Shelton, Ronald L. Shubkin