Boron Containing Patents (Class 568/1)
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Patent number: 6306555Abstract: Radiation-sensitive compositions comprising (a1) a cationically or acid-catalytically polymerisable or crosslinkable compound or (a2) a compound that increases its solubility in a developer under the action of acid; and (b) at least one diaryliodonium salt of formula I X is branched C3-C20alkyl or C3-C8cycloalkyl; X1 is hydrogen, linear C1-C20alkyl, branched C3-C20alkyl or C3-C8cycloalkyl; with the proviso that the sum of the carbon atoms in X and X1 is at least 4; Y is linear C1-C10alkyl, branched C3-C10alkyl or C3-C8cycloalkyl; A− is a non-nucleophilic anion, selected from the group (BF4)−, (SbF6)−, (PF6)−, (B(C6F5))4−, C1-C20alkylsulfonate, C2-C20haloalkylsulfonate, unsubstituted C6-C10arylsulfonate, camphorsulfonate, and C6-C10arylsulfonate substituted by halogen, NO2, C1-C12alkyl, C1-C12halo-alkyl, C1-C12alkoxy or by COOR1; and R1 is C1-C20alkyl, phenyl, benzyl; or phenyl mono- or poly-substituted by C1-C12alkyl, C1-C12alkoxy or by halogen; with theType: GrantFiled: December 18, 2000Date of Patent: October 23, 2001Assignee: CIBA Specialty Chemicals Corp.Inventors: Reinhard Schulz, Jean-Luc Birbaum, Jean-Pierre Wolf, Stephan Ilg, Hitoshi Yamato, Toshikage Asakura
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Patent number: 6281389Abstract: A solution containing an organic solvent and a compound including impurities, represented by, for example, general formula (1) (wherein R1 to R10 independently represent H, F, a hydrocarbon group or an alkoxy group, at least one of R1 to R5 is F, at least one of R6 to R10 is F, M is H, alkali metal, alkaline earth metal or alkaline earth metal halide, n is 3 or 4, and m is 2 when M is an alkaline earth metal, or m is 1 when M is the other) is mixed with water. The purified compound is reacted with a compound which forms a monovalent cation seed to prepare a derivative. Thus, a purifying method capable of efficiently and easily separating and removing colored components contained in tetrakis(fluoroaryl)borate compounds can be provided. Moreover, it is possible to provide a method capable of preparing a highly-pure tetrakis(fluoroaryl)borate derivative efficiently and at low costs.Type: GrantFiled: September 7, 1999Date of Patent: August 28, 2001Assignee: Nippon Shokubai Co., Ltd.Inventors: Hitoshi Mitsui, Toshiya Iida, Ikuyo Ikeno, Naoko Hirano, Yukiko Ariyoshi
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Publication number: 20010014739Abstract: Tetrakis(fluoroaryl)borate•magnesium halide (Ar4BMgX) expressed by General Formula (1): 1Type: ApplicationFiled: February 9, 2001Publication date: August 16, 2001Applicant: NIPPON SHOKUBAI CO., LTD.Inventors: Hitoshi Mitsui, Tsunemasa Ueno, Ikuyo Ikeno, Naoko Yamamoto
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Patent number: 6268537Abstract: A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.Type: GrantFiled: May 25, 1999Date of Patent: July 31, 2001Assignee: Mine Safety Appliances CompanyInventors: Elizabeth R. Burkhardt, Christopher P. Sutton, Joerg Bruening, David F. Rouda
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Publication number: 20010007044Abstract: Fluorohydrocarbyl substituted boratabenzene compounds, especially perfluorophenyl substituted boratabenzene compounds, are useful olefin polymerization cocatalysts with metallocenes.Type: ApplicationFiled: February 20, 2001Publication date: July 5, 2001Inventors: David D. Devore, Francis J. Timmers, David R. Neithamer
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Patent number: 6248265Abstract: Fluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and fluoroaromatic compounds via separate additions of different fluoroaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired fluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The fluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(fluoroaryl)boranes or tetrakis(fluoroaryl)borates.Type: GrantFiled: June 16, 2000Date of Patent: June 19, 2001Assignee: Albemarle CorporationInventors: John Y. Lee, David W. Owens, Charles R. Everly, Ronny W. Lin, John M. Power, Steven P. Diefenbach, Niomi L. Krzystowczyk
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Patent number: 6235222Abstract: In order to provide a method of safely, efficiently, and industrially manufacturing fluoroaryl magnesium halide containing no impurities, such as coloring components, by a relatively gradual reaction compared with the conventional reactions, and a method of readily and efficiently manufacturing a highly-pure fluoroaryl borane derivative, fluoroaryl magnesium halide expressed by General Formula (1): where each of R1-R5 independently represents H, F, a hydrocarbon group, or an alkoxy group, provided that at least three of R1-R5 are fluorine atoms, and Xa represents Cl, Br, or I; is manufactured by reacting, in a solvent containing a chain ether solvent, hydrocarbon magnesium halide expressed by General Formula (2): R6MgXa (2) where R6 represents a hydrocarbon group, and Xa represents Cl, Br, or I; with fluoroaryl halide expressed by General Formula (3): where each of R1-R5 independently represents H, F, a hydrocarbon group, or an alkoxy group, provided that atType: GrantFiled: October 22, 1999Date of Patent: May 22, 2001Assignee: Nippon Shokubai Co., Ltd.Inventors: Hitoshi Mitsui, Toshiya Iida, Ikuyo Ikeno, Naoko Hirano, Yukiko Ariyoshi
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Patent number: 6231790Abstract: Pentafluorophenyl Grignard reagents are reacted with a boron trihalide in a non-ethereal solvent such as toluene to produce a tetrakis pentafluorophenyl borate magnesium halide.Type: GrantFiled: November 19, 1996Date of Patent: May 15, 2001Assignee: Boulder Scientific CompanyInventor: Fredric Askham
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Patent number: 6215025Abstract: Tetrakis(fluoroaryl)borate.magnesium halide (Ar4BMgX) expressed by General Formula (1): where each of R1-R10 represents a hydrogen atom, a fluorine atom, a hydrocarbon group, or an alkoxy group, provided that at least one of R1-R5 represents a fluorine atom and at least one of R6-R10 represents a fluorine atom, X represents a chlorine atom, a bromine atom, or an iodide atom, and n represents 2 or 3, is treated with alkali metal salts of carboxylic acid and/or alkali earth metal salts of carboxylic acid. Then, a tetrakis(fluoroaryl)borate derivative (Ar4BZ) is produced by reacting treated Ar4BMgX with a compound generating monovalent cation seeds (for example, N,N-dimethylaniline.hydrochloride). Consequently, it has become possible to provide a purifying process of separating/removing impurities from Ar4BMgX readily and efficiently, and a process of producing inexpensive Ar4BX efficiently.Type: GrantFiled: October 26, 1998Date of Patent: April 10, 2001Assignee: Nippon Shokubai Co., Ltd.Inventors: Hitoshi Mitsui, Tsunemasa Ueno, Ikuyo Ikeno, Naoko Yamamoto
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Patent number: 6210863Abstract: Compounds of the formula I or I′ in which R1 and R2 independently of one another, for example, are an aromatic hydrocarbon, with the proviso that the aromatic hydrocarbon radical is substituted in at least one o-position, or R1 and R2, for example, independently of one another are C1-C20alkyl, which is substituted by R9R10R11Si; R2a is, for example, a divalent aromatic hydrocarbon radical; R3 is C1-C20alkyl which is substituted by R9R10R11Si or is an aromatic hydrocarbon; R4 is, for example, C1-C20alkyl, C3-C12cycloalkyl or phenyl-C1-C6alkyl; E is R14R15R16P or R8R8aR7N; R7, R8 and R8a and R9, R10 and R11 independently of one another are, for example, C1-C12alkyl; R14, R15 and R16 independently of one another are substituted phenyl and G is a radical which is able to form positive ions, with the proviso that, if R1, R2 and R3 are 2,4,6-trimethylphenyl, R4 is not C2-C20alkyl or C2-C8alkenyl, are suitable for use as particularly reactive photoinitiators.Type: GrantFiled: May 19, 1999Date of Patent: April 3, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6169208Abstract: A solution comprising a halomagnesium tetrakis(Faryl)borate in a liquid organic medium, wherein the liquid organic medium is comprised of one or more liquid dihydrocarbyl ethers, one or more liquid hydrocarbons, one or more liquid halogenated hydrocarbons, or mixtures thereof, is contacted with water. This produces magnesium di[tetrakis(Faryl)borate] in the organic phase of a two-phase water/liquid organic medium. The magnesium di[tetrakis(Faryl)borate] can be, but need not be, isolated. A protic ammonium salt, an onium salt, or a triarylmethyl salt can be reacted with the magnesium di[tetrakis(Faryl)borate] to produce the corresponding protic ammonium, onium, or triarylmethyl tetrakis(Faryl)borate. The magnesium di[tetrakis(Faryl)borate] can instead be reacted with a metal salt to form a metal tetrakis(Faryl)borate.Type: GrantFiled: December 3, 1999Date of Patent: January 2, 2001Assignee: Albemarle CorporationInventor: John Y. Lee
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Patent number: 6162950Abstract: An alkali metal fluoride is reacted with a halomagnesium tetrakis(.sup.F aryl)borate to form an alkali metal tetrakis(.sup.F aryl)borate. The alkali metal tetrakis(.sup.F aryl)borate can be isolated, or the alkali metal cation can be replaced by an organic cation.Type: GrantFiled: December 3, 1999Date of Patent: December 19, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, Jamie R. Strickler
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Patent number: 6150487Abstract: This invention relates to a multifunctional organic alkali metal initiator for the preparation of various kinds of star polymers by anionic polymerization, a process for making the initiator, a process using said initiator for making star polymers and the polymers obtained. The initiator can be represented by the formula: M.sub.a (RMe).sub.b, wherein M is selected from Sn, Ti, Al, Si and/or B; R is a hydrocarbyl group containing 8-100 carbon atoms, a=1-3, b=2.5-6.5, Me is an alkali metal which may be selected from Na and Li. The initiator was synthesized by reacting an organic alkali metal with a conjugated diene and/or a mono-olefin monomer, and then adding hetero-atom containing halide. The star polymer obtained has a radial molecular structure consisting of several macromolecular chain arms radiating from the initiator core, and its molecular weight distribution expressed by GPC presents a uniform singlet.Type: GrantFiled: June 29, 1998Date of Patent: November 21, 2000Assignee: China Petrochemical CorporationInventors: Xingying Zhang, Guantai Jin, Suhe Zhao
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Patent number: 6150560Abstract: This invention relates to methods for separating tris(aryl)boranes from tris(aryl)boranetetrahydrofuran complexes in hydrocarbon solvents via distillation.Type: GrantFiled: April 22, 1999Date of Patent: November 21, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, Jamie R. Strickler
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Patent number: 6140537Abstract: A method of producing a boron-based compound represented by general formula (1) including a first step of reacting lithium, magnesium or a compound containing lithium, a compound represented by general formula (2), and a compound represented by general formula (3): R.sup.2 --Y to produce a borate metal salt represented by general formula (4), and a second step of adding to the borate metal salt an onium halide represented by general formula (5): Z.sup.+ .multidot.X.sup.- to effect ion exchange reaction (the symbols in the formulae have the same meanings as described in the specification).According to the production method of the present invention, a high purity boron-based compound represented by the general formula (1) above useful as a photopolymerization initiator and a light-absorbing decolorizing agent can be obtained in a short time and a high yield as compared with the conventional method.Type: GrantFiled: August 5, 1999Date of Patent: October 31, 2000Assignee: Showa Denko K.K.Inventors: Tsuyoshi Katoh, Morihiko Yamada
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Patent number: 6129863Abstract: Perfluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and polyhaloaromatic compounds via separate additions of different polyhaloaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired perfluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The perfluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(perfluoroaryl)boranes or tetrakis(perfluoroaryl)borates.Type: GrantFiled: December 18, 1998Date of Patent: October 10, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, David W. Owens, Charles R. Everly, Ronny W. Lin, John M. Power, Steven P. Diefenbach, Niomi L. Krzystowczyk
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Patent number: 6118026Abstract: A (fluoroaryl)borane compound expressed by General Formula (1): ##STR1## where each of R.sub.1 -R.sub.5 represents a hydrogen atom, a fluorine atom, a hydrocarbon group, or an alkoxy group, provided that at least one of R.sub.1 -R.sub.5 represents a fluorine atom, X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and n represents 2 or 3, is stabilized by letting inorganic metal salts having a fluorine atom coexist with the (fluoroaryl)borane compound in a hydrocarbon solution. After the hydrocarbon solution is concentrated in the presence of the inorganic metal salts, the inorganic metal salts are removed and the fluoroaryl)borane compound is crystallized.Type: GrantFiled: June 25, 1998Date of Patent: September 12, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Hitoshi Mitsui, Tsunemasa Ueno, Ikuyo Ikeno, Naoko Yamamoto
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Patent number: 6057480Abstract: A fluoroaryl magnesium derivative is produced by reacting aryl fluoride, hydrocarbon halide, and magnesium with one another in an ether solvent or a mixed solvent of the ether solvent and a hydrocarbon solvent. Also, a (fluoroaryl)borane compound is produced by mixing both a solution prepared by dissolving the fluoroaryl magnesium derivative into the ether solvent and another solvent prepared by dissolving the boron halide in the ether solvent with a hydrocarbon solvent having a higher boiling point than the ether solvent, so that the fluoroaryl magnesium derivative and boron halide react with each other while the ether solvent is being distilled out.Type: GrantFiled: October 16, 1997Date of Patent: May 2, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Tsunemasa Ueno, Ikuyo Katsumi, Naoko Yamamoto, Hitoshi Mitsui
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Patent number: 6048985Abstract: A method of stabilizing borane-tetrahydrofuran complex comprises the step of maintaining the temperature of the borane-tetrahydrofuran complex at or below 20.degree. C. A method of reacting a borane reagent with a substrate comprises the steps of heating the borane reagent and the substrate in a reaction vessel and preventing escape of evolved diborane from the reaction vessel. Preferably, a reaction vessel containing a borane reagent and a substrate is maintained under at greater than atmospheric pressure with back-pressure regulation.Type: GrantFiled: December 22, 1998Date of Patent: April 11, 2000Assignee: Mine Safety Appliances CompanyInventors: Elizabeth R. Burkhardt, Joseph A. Corella, II
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Patent number: 6020511Abstract: A method of forming a film on a substrate using, Group III metal complexes, including Group IIIA metals and Group IIIB metals, which include the lanthanides. The complexes and methods are particularly suitable for the preparation of semiconductor structures using chemical vapor deposition techniques and systems.Type: GrantFiled: August 25, 1998Date of Patent: February 1, 2000Assignee: Micron Technology, Inc.Inventors: Brian A. Vaartstra, Brenda D. Wanner
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Patent number: 6011180Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is, for example, C.sub.1 -C.sub.20 alkyl or phenyl-C.sub.1 -C.sub.6 alkyl which radicals are unsubstitutedor substituted; R.sub.2, R.sub.3 and R.sub.4 independently of one another are phenyl or biphenyl, which radicals are unsubstituted or substituted; wherein the sum of the Hammett .sigma. constants (.SIGMA..sub..sigma.) of the substitutents on the aromatic radicals R.sub.2, R.sub.3 and R.sub.4 is between +0.36 and +2.58; R.sub.8, R.sub.9, R.sub.14, R.sub.15 and R.sub.16 are, for example, C.sub.1 -C.sub.12 alkyl, phenyl-C.sub.1 -C.sub.6 alkyl or phenyl, and G is a radical which is able to form positive ions. These compounds are suitable as photoinitiators for photopolymerizable compositions which contain acid groups, in the presence of a coinitiator if desired.Type: GrantFiled: November 21, 1996Date of Patent: January 4, 2000Inventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6008414Abstract: Highly reactive hydroborating agents dioxane-monochloroborane and dioxane-dichloroborane are provided. Also provided by this invention are methods for producing dioxane-monochloroborane, dioxane-dichloroborane and methods for hydroborating olefins with these reagents.Type: GrantFiled: February 16, 1999Date of Patent: December 28, 1999Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 6005133Abstract: The enantioselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the presence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulae (I) and (II). The compounds of formulae (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulae (I) and (II) may be generated in situ.Type: GrantFiled: October 10, 1995Date of Patent: December 21, 1999Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 6002044Abstract: A method for producing a borate compound represented by formula (1) is disclosed, comprising a first step of reacting lithium or magnesium or a compound containing lithium or magnesium, a halide represented by formula (2) and a compound represented by formula (3) in a solvent to produce a boronate compound precursor, a second step of reacting lithium or magnesium or a compound containing lithium or magnesium, a halide represented by formula (4) and the boronate compound precursor obtained in the first step in a solvent to produce a borate metal salt, and a third step of adding an onium halide represented by formula (5) to the borate metal salt obtained in the second step to effect ion-exchange reaction (the formulae are as described in the specification).Type: GrantFiled: November 10, 1998Date of Patent: December 14, 1999Assignee: Showa Denko K.K.Inventors: Morihiko Yamada, Tsuyoshi Katoh, Norihide Arai
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Patent number: 5998496Abstract: A compound of the general formula:A-L.sup.+ D.sup.-where A is a moiety which absorbs radiation and enters an excited state in which it accepts an electron; D.sup.- is a moiety which donates an electron to the excited state A and releases a free radical; and L.sup.+ is a cationic linking group which tethers electron acceptor moiety A to electron donor moiety D.sup.-. Cationic linking moiety L.sup.+ has the formula:-L'-G-where L' is a moiety which forms a stable radical with acceptor moiety A upon transfer of an electron from donor moiety D.sup.- to electron acceptor moiety A, and G is a moiety which forms a leaving group upon transfer of the electron from donor moiety D.sup.- to acceptor moiety A.Type: GrantFiled: August 19, 1996Date of Patent: December 7, 1999Assignee: Spectra Group Limited, Inc.Inventors: Salah A. Hassoon, Ananda M. Sarker, Douglas C. Neckers
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Patent number: 5962742Abstract: A process is disclosed for the preparation of 5-bromo-2-fluorobenzeneboronic acid, which is useful as an intermediate in the preparation of a non-ester pyrethroid compound. The compound can be, for example, a fluoroolefin, which is useful as a pesticide.Type: GrantFiled: June 6, 1997Date of Patent: October 5, 1999Assignee: American Cyanamid CompanyInventor: Keith D. Barnes
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Patent number: 5959151Abstract: One aspect of the invention is a process for purifying a pentafluorophenyl boron compound from a crude mixture comprised of the pentafluorophenyl boron compound and impurities, the impurities at least comprised of an ether and water, the process comprising: (a) mixing the crude mixture with an azeotropic organic solvent which (i) is capable of azeotrope formation with the water and (ii) has a boiling point above the boiling point of the ether; (b) distilling the resulting solution to remove at least a portion of the impurities; and (c) cooling the distilled solution so that a precipitate comprised of the pentafluorophenyl boron compound is formed. Processes are also described for producing pentafluorophenyl boron compounds which are particularly pure, dry and fine.Type: GrantFiled: April 9, 1998Date of Patent: September 28, 1999Assignee: Albemarle CorporationInventors: John Y. Lee, Steven P. Diefenbach, John M. Power, Ronny W. Lin
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Patent number: 5932393Abstract: The invention relates to photopolymerizable compositions comprising as photoinitiator a borate of the formula I or I' ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are, for example and independently of one another, phenyl or another aromatic hydrocarbon, with or without any heteroatoms, which radicals are unsubstituted or are substituted, or the radicals R.sub.1 and R.sub.2 form bridges to produce structures of the formulae II, IIa or IIb ##STR2## with the provisos that not more than two of the radicals R.sub.1, R.sub.2 and R.sub.3 are identical and either at least two of the radicals R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or phenyl radicals which are substituted in both ortho-positions or at least one radical R.sub.1, R.sub.2 or R.sub.3 is a sterically bulky aryl radical and the remaining radicals of R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or are phenyl radicals which are substituted in at least one ortho-position; R.sub.4 is, for example, phenyl or C.sub.1 -C.Type: GrantFiled: November 21, 1996Date of Patent: August 3, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5886229Abstract: Synthetic routes for forming alkali metal substituted borohydride compounds include the step of reacting an alkali metal reagent, a hydrogen donor, and a substituted borane. The reactions proceed without the requirement of specialized handling of alkali metal hydrides associated with prior synthetic processes for the production of alkali metal trisubstituted borohydride compounds. A chemical composition comprises solid potassium tri-sec-butyl borohydride.Type: GrantFiled: May 29, 1998Date of Patent: March 23, 1999Assignee: Mine Safety Appliances CompanyInventors: Joseph A. Corella, II, David H. Ellenberger, Joerg Bruening
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Patent number: 5869723Abstract: Ionic compounds represented by general formula (I), method of their production, olefin polymerization catalyst components, and olefin polymerization catalysts containing the components are provided.?M(R.sup.1).sub.k (R.sup.2).sub.1 (R.sup.3).sub.m (R.sup.4 -L).sub.n !.sup.- ?D!.sup.+ (I)(wherein, M is an element belonging to the Group 13; R.sup.1, R.sup.2 and R.sup.3 are pentafluorophenyl, etc., R.sup.4 is a substituted phenylene group, etc., k, l and m being each 0 or an integer of 1 to 3, and n being an integer of 1 to 4 such that k+l+m+n=4; L is trichlorosilyl, methyldichlorosilyl, dimethylchlorosilyl group, etc.; and D is a monovalent cation).Type: GrantFiled: February 10, 1997Date of Patent: February 9, 1999Assignee: Showa Denko K.K.Inventors: Shinji Hinokuma, Shigenobu Miyake, Michio Ono, Shintaro Inazawa
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Patent number: 5744646Abstract: A process for preparing tris(pentafluorophenyl)borane, the steps of the process comprising:a) forming a pentafluorophenyl metal compound wherein the metal is selected from Group 11 or 12;contacting the (pentafluorophenyl) metal compound from step a) with a boron halide compound to form tris (pentafluorophenyl)borane; andc) recovering the resulting tris(pentafluorophenyl)borane.Type: GrantFiled: April 2, 1997Date of Patent: April 28, 1998Assignee: The Dow Chemical CompanyInventors: David R. Wilson, Robert E. LaPointe
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Patent number: 5698538Abstract: Novel boronic acid and ester and carboxyl-modified amino acid compounds of the Formula I, which are inhibitors of trypsin-like enzymes, are disclosed :R.sup.1 --Z--CHR.sup.2 --A,where R.sup.1, Z, R.sup.2 arid A are defined within.Type: GrantFiled: July 26, 1996Date of Patent: December 16, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Eugene Cruz Amparo, William Henry Miller, Gregory James Pacofsky, John Wityak, Patricia Carol Weber, John Jonas Vytautas Duncia, Joseph Basil Santella, III
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Patent number: 5693261Abstract: Pentafluorophenylmagnesium halides are prepared by a Grignard exchange reaction of hydrocarbylmagnesium halide with pentafluorochlorobenzene. The pentafluorophenylmagnesium halides are converted to pentafluorophenyl metal or metalloid derivatives by reacting them with metal or metalloid halides such as BF.sub.3.Type: GrantFiled: August 9, 1995Date of Patent: December 2, 1997Assignee: Albemarle CorporationInventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
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Patent number: 5693867Abstract: Tetraphenylborates are obtained in an industrially advantageous grade by spray drying an organic, aqueous or organic-aqueous extract of the tetraphenylborates obtainable in the tetraphenylborates synthesis. It is advantageous to treat the specified extract prior to spray drying with pH-controlling auxiliaries and adsorbents to remove byproducts or to limit their formation. The process gives tetraphenylborates in a homogeneous technical grade, i.e. in a narrow particle size distribution and in a particular particle shape, which improves the dispersibility in the medium to be used.Type: GrantFiled: August 29, 1996Date of Patent: December 2, 1997Assignee: Hoechst AktiengesellschaftInventors: Rudiger Baur, Hermann Fuchs, Hans-Tobias Macholdt, Jorg Gitzel, Wilfried Theiss
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Patent number: 5679289Abstract: Procedures are disclosed which preclude significant safety hazards in the production of bulk quantities pentafluorophenyl lithium. A pentafluorophenyl compound is reacted with an alkyl lithium compound in a reaction zone, preferably temperature controlled, under conditions such that only a small amount of a predetermined quantity of pentafluorophenyl lithium product is present in the reaction zone at any time. The product may be directly discharged from the reaction zone for combination with another reactant.Type: GrantFiled: October 23, 1996Date of Patent: October 21, 1997Assignee: Boulder Scientific CompanyInventor: Terry E. Krafft
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Patent number: 5668192Abstract: Novel onium borates of an element of Groups 15 to 17 of the Periodic Table, or borates of an organometallic complex of an element of Groups 4 to 10 of the Periodic Table, well suited for the photochemical/electron beam cationic initiation of polymerization/crosslinking, the anionic borate moiety of which having the formula:[BX.sub.a R.sub.b ].sup.-in which a and b are integers ranging from 0 to 4 and a+b=4; the symbols X are each a halogen atom when a ranges up to 3 and an OH functional group when a ranges up to 2; and the symbols R, which may be identical or different, are each a phenyl radical substituted by at least one element or electron-withdrawing substituent or by at least two halogen atoms, or an aryl radical containing at least two aromatic ring members, or such aryl radical bearing at least one electron-withdrawing substituent.Type: GrantFiled: April 18, 1996Date of Patent: September 16, 1997Assignee: Rhone-Poulenc ChimieInventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
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Patent number: 5646098Abstract: The invention relates to novel compositions comprising ene and free radical adducts of unsaturated and saturated hydrocarbons, and acyclic and cyclic vicinal polycarbonyl compounds such as diethyl ketomalonate and indantrione. The adducts are reacted with nucleophiles such as amines, electrophiles such as anhydrides and esters, and metal ions. Post-products are obtained via reaction of said products with capping reagents such as boric acid. Compositions containing said adducts, products and post-products include oleaginous substances such as fuels and lube oils.Type: GrantFiled: May 13, 1994Date of Patent: July 8, 1997Assignee: Exxon Chemical Patents IncInventor: Stanley J. Brois
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Patent number: 5621143Abstract: A complex comprises organoborane and polyoxyalkylenepolyamine. The complexes are useful in systems for initiating the polymerization of acrylic monomer, which systems further include an amine reactive compound. Polymerizable acrylic monomer compositions useful as adhesives can be prepared.Type: GrantFiled: April 14, 1995Date of Patent: April 15, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventor: Alphonsus V. Pocius
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Patent number: 5600003Abstract: Tetraphenylborates are obtained in an industrially advantageous grade by spray drying an organic, aqueous or organic-aqueous extract of the tetraphenylborate obtainable in the tetraphenylborate synthesis. It is advantageous to treat the specified extract prior to spray drying with pH-controlling auxiliaries and adsorbents to remove byproducts or to limit their formation. The process gives tetraphenylborates in a homogeneous technical grade, i.e. in a narrow particle size distribution and in a particular particle shape, which improves the dispersibility in the medium to be used.Type: GrantFiled: January 10, 1995Date of Patent: February 4, 1997Assignee: Hoechst AktiengesellschaftInventors: R udiger Baur, Hermann Fuchs, Hans-Tobias Macholdt, J org Gitzel, Wilfried Theisse
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Patent number: 5600004Abstract: An improved process for recovering pentafluorophenyl metal or metalloid compounds prepared by reacting pentafluoromagnesium halides with a metal or metalloid halide in ether solutions uses a precipitating agent such as an ether to precipitate the by-products from the reaction mixture.Type: GrantFiled: February 21, 1995Date of Patent: February 4, 1997Assignee: Albemarle CorporationInventor: Steven P. Diefenbach
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Patent number: 5585507Abstract: A photoresist composition containing an alkylsulfonium salt compound represented by the following general formula (I): ##STR1## Wherein R.sup.1 and R.sup.2 may be the same or different, each being a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, R.sup.3 is a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, a C.sub.5 to C.sub.7 2-oxocycloalkyl radical, or a linear or branched C.sub.3 to C.sub.8 2-oxoalkyl radical, and Y.sup.- represents a counter ion. The photoresist composition has high transparency to deep U.V. light having wavelengths of 220 nm or less and is capable of forming good fine patterns with high sensitivity, thus being useful as chemically amplified type resist which is exposed to the deep U.V. light from an ArF excimer laser.Type: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Assignee: NEC CorporationInventors: Kaichiro Nakano, Katsumi Maeda, Shigeyuki Iwasa, Etsuo Hasegawa
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Patent number: 5541351Abstract: Processes are disclosed for preparing compounds of the formula Z--R--Z where each Z can be selected from cyclopentadienyl type radicals such as substituted or unsubstituted cyclopentadienyl, indenyl, fluorenyl or tetrahydroindenyl or where one Z is Cl, Br, or I by reacting specific Z precursors with a dihaloalkylene compound. Also new cyclopentadienyl-type compounds are disclosed.Type: GrantFiled: August 15, 1994Date of Patent: July 30, 1996Assignee: Phillips Petroleum CompanyInventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
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Patent number: 5496960Abstract: There is disclosed a new boron-containing compounds such as bis-(pentafluorophenyl)borane, (C.sub.6 F.sub.5).sub.2 BH and related compounds and a method for producing the compounds. The new borane is suitable for use as a hydroboration reagent for the rapid hydroboration of alkenes and alkynes. The borane is also suitable for use as a hydroboration reagent to produce useful boron reagents that can be used in Ziegler-Natta homogeneous olefin polymerization catalyst systems. Specifically, the borane reagent can be used to produce Cp.sub.2 Zr{.eta..sup.3 -CH(C.sub.6 H.sub.5)[(.mu.-H)B(C.sub.6 F.sub.5).sub.2 ]}, which exhibits an efficacy for polymerization of ethylene.Type: GrantFiled: January 20, 1995Date of Patent: March 5, 1996Assignee: University of GuelphInventors: Warren E. Piers, Rupert E. von Haken Spence
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Patent number: 5481038Abstract: Borane-N,N-diisopropylalkylamines as represented by the formula:H.sub.3 B.NPr.sup.i.sub.2 Rwherein Pr.sup.i is isopropyl, R is branched-chain alkyl or cycloalkyl having 3 to 6 carbon atoms and B is boron are provided. The compounds are new hydroboration agents.Type: GrantFiled: May 9, 1995Date of Patent: January 2, 1996Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5468902Abstract: Novel onium borates of an element of Groups 15 to 17 of the Periodic Table, or borates of an organometallic complex of an element of Groups 4 to 10 of the Periodic Table, well suited for the photochemical/electron beam cationic initiation of polymerization/crosslinking, the anionic borate moiety of which having the formula:[BX.sub.a R.sub.b ].sup.-in which a and b are integers ranging from 0 to 4 and a+b=4; the symbols X are each a halogen atom when a ranges up to 3 and an OH functional group when a ranges up to 2; and the symbols R, which may be identical or different, are each a phenyl radical substituted by at least one element or electron-withdrawing substituent or by at least two halogen atoms, or an aryl radical containing at least two aromatic ring members, or such aryl radical bearing at least one electron-withdrawing substituent.Type: GrantFiled: March 23, 1993Date of Patent: November 21, 1995Assignee: Rhone-Poulenc ChimieInventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
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Patent number: 5462692Abstract: Stable, solid acetyl peroxyborate compounds which are active oxygen-containing compounds derived from acetic acid and boron-oxygen compounds. The compounds of the invention have a peracetic acid content which can be liberated instantly and directly in water with only minor formation of hydrogen peroxide The acetyl peroxyborates of the invention are useful in washing, bleaching and cleaning agent and disinfectant applications and as oxidizing agents in organic synthesis.Type: GrantFiled: December 2, 1991Date of Patent: October 31, 1995Assignee: Peroxid-Chemie GmbHInventors: Richard Roesler, Siegfried Schelle, Michael Gnann, Werner Zeiss
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Patent number: 5463131Abstract: A one-step process is provided for the synthesis of organohaloboranes, including diisopinocampheylchloroborane, and alkoxyorganoboranes. The present process does not utilize a thermally unstable ether adduct or a malodorous dimethyl sulfide adduct as required in prior processes. In general, the organohaloboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with boron trihalide and diborane. Alkoxyorganoboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with alkylborate and diborane.Type: GrantFiled: June 30, 1994Date of Patent: October 31, 1995Assignee: Mine Safety Appliances CompanyInventor: Elizabeth R. Burkhardt
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Patent number: 5399780Abstract: A method of producing a high-purity triarylborane with high yield by reacting, in a solvent inert to the reaction product, a 1.0-8.0 mol/L boron halide solution with a 0.1-3.0 mol/L aryl magnesium halide solution in a straight chain ether solvent, where the molar ratio of aryl magnesium halide to boron trihalide is 3.1-3.5 to 1.0, respectively, and then the straight chain ether solvent is distilled from the reaction mixture. Distillation crystallizes out the halogenated magnesium salt which is produced as a by-product, increasing the recovery rate of the product.Type: GrantFiled: October 27, 1993Date of Patent: March 21, 1995Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5382697Abstract: Preparation of triarylborane from catalyst residues containing nickel complexes with triarylborane by heating the complexes at reduced pressure, and recovering the triarylborane by condensation.Type: GrantFiled: June 23, 1994Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Albert L. Casalnuovo, Thomas Foo