Sulfur, Oxygen, Halogen Or Group Ia Or Iia Light Metal Containing Patents (Class 568/6)
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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: 5935944Abstract: A process and product formulated by complexing boronophenylalanine (BPA) and related compounds with a saccharide in an aqueous solution are disclosed. Formation of the complex is facilitated by raising the pH of the solution to a higher pH of about 10 or by lowering the pH of the solution to a lower pH of about 2 and then readjusting the pH to a body physiological pH of about 7.4. This BPA saccharide complex can then be delivered by i.v. or other injection or administered orally as a key component of the BNCT cancer treatment process The pH manipulation causes a much higher solubility of BPA or related compounds and thus a higher boron concentration in the tumor, thereby improving the therapy.Type: GrantFiled: February 20, 1996Date of Patent: August 10, 1999Assignee: Neutron Technology CorporationInventor: Thomas R. LaHann
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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: 5919983Abstract: A catalyst activator, comprising a cation which is a Bronsted acid capable of donating a proton, and an inert, compatible, noncoordinating, anion, characterized by a solubility constant at 25.degree. C. in hexane, cyclohexane or methylcyclohexane of at least 5 weight percent.Type: GrantFiled: March 14, 1997Date of Patent: July 6, 1999Assignee: The Dow Chemical CompanyInventors: Robert K. Rosen, Daniel D. VanderLende
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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: 5852191Abstract: Boron complexes of certain bis-heterocyclic compounds are provided. The complexes resemble monomethine cyanines and are useful for imparting fluorescent properties to materials by covalent and noncovalent association. The compounds have the following general formula: ##STR1## wherein the dotted lines Z.sub.1 and Z.sub.2 represent the atoms necessary to complete a structure selected from the group consisting of one ring, two fused rings, and three fused rings, each said ring having five or six atoms, and each said ring comprising carbon atoms and, optionally, no more than two atoms selected from oxygen, nitrogen and sulfur, and R.sub.1 through R.sub.5 represent various atoms or groups and M is Cl or F.Type: GrantFiled: June 7, 1995Date of Patent: December 22, 1998Assignee: Carnegie Mellon UniversityInventors: Bhalchandra M. Karandikar, Alan S. Waggoner, Ratnakar B. Mujumdar
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Patent number: 5698499Abstract: A composition of matter having the structure ##STR1## wherein R.sup.1, R.sup.2, R.sup.4, and R.sup.5 are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl, and R.sup.3 is alkylene. Lubricants and lubricant additives comprising the composition are also disclosed. The lubricants are preferably lubricating oils.Type: GrantFiled: February 3, 1997Date of Patent: December 16, 1997Assignee: Uniroyal Chemical Company, Inc.Inventors: John R. Baranski, Cyril A. Migdal
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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: 5698742Abstract: The present invention relates to a method for producing optically active alcohol derivatives, which are useful as fungicides, herbicides or plant growth regulators, represented by the formula, ##STR1## by carrying out the asymmetric reduction of a ketone compound represented by the formula, ##STR2## with a boron hydride-reducing agent modified with an optically active amino alcohol represented by the formula, ##STR3## and also relates to the boron hydride type compound obtained by reacting the above optically active amino alcohol with a boron hydride compound and its production method.Type: GrantFiled: July 8, 1993Date of Patent: December 16, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito, Toshio Nishioka
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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: 5600005Abstract: A process for preparing a tetrakisfluorophenylborate which is useful as a catalyst component for the polymerization of olefins or as a raw material for synthesizing the same, efficiently at a high productivity per unit amount of a solvent and at a high yield. A mixed solvent of ether and an aliphatic hydrocarbon is used as a reaction solvent for preparing tetrakisphenylborate according to the following reaction formula,4M.sup.4 --C.sub.6 Y.sup.3.sub.5 +BCl.sub.3 .fwdarw.M.sup.4 B(C.sub.6 Y.sup.3.sub.5).sub.4wherein M.sup.4 is an alkali or alkaline earth metal, or represents R.sup.6.sub.2 Al, wherein R.sup.6 is an alkyl group, and Y.sup.3 is a hydrogen atom or a halogen atom.Type: GrantFiled: June 6, 1995Date of Patent: February 4, 1997Assignee: Idemitsu Kosan Co., Ltd.Inventors: Shoji Naganuma, Masami Watanabe, Norio Tomotsu
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Patent number: 5597663Abstract: An electrochemical cell (10) including a positive electrode (20), a negative electrode (30) and a low temperature organic, liquid lithium salt electrolyte (40) is provided. The low temperature lithium salt electrolyte includes a central atom selected from the group of aluminum, boron, gallium, indium, or thallium and at least four substituent groups which are organic, alkoxy groups. A unique characteristic of the electrolyte is that it remains liquid at ambient temperatures, as compared to most lithium salt electrolytes which are solid at room temperatures.Type: GrantFiled: May 30, 1995Date of Patent: January 28, 1997Assignee: Motorola, Inc.Inventors: Shekhar L. Pendalwar, Frank R. Denton, III
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Patent number: 5567849Abstract: A borane-sulfide represented by the formulaBH.sub.3.SR.sup.1 R.sup.2wherein B is boron, H is hydrogen, R.sup.1 and R.sup.2 each are straight or branched chain alkyl or alkoxy with at least one R being a branched chain when both R.sup.1 and R.sup.2 are alkyl, and S is sulfur. The compounds are hydroboration agents.Type: GrantFiled: May 9, 1995Date of Patent: October 22, 1996Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5545758Abstract: The present invention relates to an improved process for the in situ preparation of diisopinocampheylchloroborane which comprises reacting sodium borohydride and boron trichloride with .alpha.-pinene. The diisopinocampheylchloroborane thus obtained may be used, without isolation, to reduce prochiral ketones to their corresponding alcohols in high optical purity.Type: GrantFiled: August 11, 1994Date of Patent: August 13, 1996Assignee: Merck & Co., Inc.Inventors: Anthony O. King, Robert D. Larsen, Thomas R. Verhoeven, Mangzhu Zhao
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Patent number: 5545759Abstract: The invention relates to a production method, wherein, with 1 equivalent of pentafluorobenzene of the formula C.sub.6 HF.sub.5 M, 0.5 to 1.5 equivalents of an organometallic compound of the formula RM, wherein R is a hydrocarbon group of 1 to 10 carbon atoms and m is an alkali metal ion, are reacted at -120.degree. to 80.degree. C. in an ether type solvent, a hydrocarbon type solvent or a mixed solvent of the ether type solvent with the hydrocarbon type solvent to generate a pentafluorophenyl alkali metal salt of the formula C.sub.6 F.sub.5 M. Next, 1 equivalent of a boron compound of the formula BX.sub.3, where X is halogen, OR or NR'R" is reacted with 2.1 to 3.9 equivalents of a pentafluorophenyl alkali metal salt of the formula C.sub.6 F.sub.5 M within a temperature range from -120.degree. to 80.degree. C. to produce tris(pentafluorophenyl)borane of the formula (C.sub.6 F.sub.5).sub.3 B or a complex of tris(pentafluorophenyl)borane coordinated with the ether type solvent.Type: GrantFiled: January 27, 1995Date of Patent: August 13, 1996Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5534557Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 2, 1995Date of Patent: July 9, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5516441Abstract: A metal salt or boron compound of a hydrocarbyl-substituted aromatic hydroxy compound having at least two hydroxy-substituted aromatic rings bridged by sulfur, where at least one aromatic ring bears a substituent ortho to a hydroxy group, provides a useful lubricant additive. The substituent on the aromatic ring is an .alpha.-hydroxy aliphatic hydrocarbyl group or a --C(O)R.sup.2 group, where R.sup.2 is hydrogen or aliphatic hydrocarbyl. Preferred salts are magnesium.Type: GrantFiled: April 26, 1994Date of Patent: May 14, 1996Assignee: The Lubrizol CorporationInventor: Richard A. Denis
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Patent number: 5510536Abstract: A method of producing tris(pentafluorophenyl)borane or its ether complex, using pentafluorobenzene as the source of the pentafluorophenyl group. The process comprises reacting pentafluorobenzene with an organo metallic compound (II) of the formula R.sub.2-n MgX.sub.n, wherein n denotes a real number of 0 or 1, X denotes a halogen atom and R denotes a hydrocarbon group of 1 to 10 carbon atoms. The reaction is carried out in an ether solvent at a temperature not less than 25.degree. C. The resulting pentafluorophenylmagnesium compound has the formula (C.sub.6 F.sub.5).sub.2-n MgX.sub.n (III), wherein n denotes a real number of 0 or 1 and X denotes a halogen atom. The pentafluorophenylmagnesium compound of the formula (III) is next reacted with a borane compound of the formula BX.sub.3, wherein X denotes a halogen atom. The reaction is carried out at a temperature in the range of 0.degree. C. to 250.degree. C., preferably 60.degree. C. to 250.degree. C.Type: GrantFiled: December 22, 1993Date of Patent: April 23, 1996Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5500453Abstract: A sulfonium complex or oxosulfonium complex of the formula (1), ##STR1## wherein R.sup.1 is a benzyl group, a substituted benzyl group, a phenacyl group, a substituted phenacyl group, an aryloxy group, a substituted aryloxy group, an alkenyl group or a substituted alkenyl group, each of R.sup.2 and R.sup.3 is independently any one of groups defined as R.sup.1, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, an alkynyl group, a substituted alkynyl group, an alicyclic group, a substituted alicyclic group, an alkoxyl group, a substituted alkoxyl group, an alkylthio group, a substituted alkylthio group, an amino group or a substituted amino group, or R.sup.2 and R.sup.3 may bond together forming a ring structure, R.sup.4 is an oxygen atom or lone pair, and each of R.sup.5, R.sup.6, R.sup.7 and R.sup.Type: GrantFiled: August 4, 1994Date of Patent: March 19, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yasumasa Toba, Madoka Yasuike, Yamaguchi Takeo
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Patent number: 5493056Abstract: The invention relates to a method for producing tetrakis(pentafluorophenyl)borate derivatives of the formula (C.sub.6 F.sub.5).sub.4 BM which comprises reacting 1 equivalent of pentafluorobenzene with 0.5 to 1.5 equivalents of an organometallic compound RM at -120.degree. to 80.degree. C., in an ether type solvent, a hydrocarbon type solvent or a mixture thereof, to generate pentafluorophenyl alkali metal salt represented by the formula C.sub.6 F.sub.5 M, and then reacting either (1) not less than 3.7 equivalents of said pentafluorophenyl alkali metal salt with 1 equivalent of a boron compound BX.sub.3, or (2) not less than 0.8 equivalents of said pentafluorophenyl alkali metal salt with 1 equivalent of tris(pentafluorophenyl)borane.Type: GrantFiled: December 22, 1993Date of Patent: February 20, 1996Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5488169Abstract: A method of producing tetrakis(pentafluorophenyl)borate derivatives of the formula [(C.sub.6 F.sub.5).sub.4 B].sub.2-n MgX.sub.n wherein n denotes an integer of 0 or 1 and X denotes a halogen atom, using pentafluorophenylmagnesium derivatives of the formula (C.sub.6 F.sub.5).sub.2-n MgX.sub.n, wherein n denotes an integer of 0 or 1 and X denotes a halogen atom, as a source of the pentafluorophenyl group.Type: GrantFiled: December 21, 1993Date of Patent: January 30, 1996Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5481039Abstract: Compositions comprisinga) a functional liquid or an internal combustion engine fuel andb) at least one compound of the general formula I ##STR1## wherein R.sub.1 is --(CH.sub.2 --X).sub.n R, where X=--S-- or --O--, n=0 or 1 to 18 carbon atoms, a phenyl group, a phenyl group which is substituted by at least one C.sub.1 -C.sub.18 alkyl group, a phenyl-C.sub.1 -C.sub.4 alkyl group or a phenyl-C.sub.1 -C.sub.4 alkyl group which is substituted by at least one C.sub.1 -C.sub.4 alkyl group, or R.sub.1 is an alkyl group of 1 to 18 carbon atoms which is substituted by at least one OH group, or R.sub.1 is a ##STR2## group in which the alkyl moiety contains 1 to 18 carbon atoms, and R.sub.2 and R.sub.3 are the same or different and are --H or, independently of R.sub.1, have the same meanings as R.sub.1, and M is B, Al, Fe, Cr, Sb or Bi, or M is a group M'--R' or a group M'--OR", where M' is Ti, Zr or Sn, and R' and R" is C.sub.1 -C.sub.18 alkyl or R' is ##STR3## wherein M' is defined above, and R.sub.1 ', R.sub.Type: GrantFiled: October 21, 1994Date of Patent: January 2, 1996Assignee: Ciba-Geigy Corp.Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
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Patent number: 5473036Abstract: Bromomagnesium tetrakis(fluorophenyl) borate reactible intermediates can be formed by reacting at least four equivalents of fluorophenyl magnesium bromide with every one equivalent of boron trifluoride in ether solvent using a sufficient amount of heat to drive the reaction to completion. This type of reactible intermediate can then be reacted with a salt containing a suitable cation, such as ammonium, trityl or onium, preferably substituted with phenyl or alkyl, such as lower alkyl, to form the desired combination of weakly coordinating boron anion and activating cation.Type: GrantFiled: March 3, 1995Date of Patent: December 5, 1995Assignee: Akzo Nobel N.V.Inventors: Andrzej M. Piotrowski, Dennis F. Taylor, Dietmar Seyferth
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Patent number: 5468890Abstract: The invention concerns iodonium salts of the general formula A-I.sup.+ --B X.sup.-, in which A is a group of the general formula ##STR1## in which C is a monovalent aromatic hydrocarbon group with 6 to 14 carbon atoms or a monovalent aromatic hydrocarbon group containing at least one oxygen and/or sulphur atom and with 5 to 14 atoms in the aromatic ring, D, E and F are each substituents of C, D being a group of the formula --(O).sub.x --(R).sub.y --SiR1/3, E being a group of the formula --OR.sup.2, F being a group of the formula --R.sup.3, a being 1, 2, or 3, b being 0, 1 or 2, c being 0, 1 or 2, x being 0 or 1 and y being 0 or 1, and R, R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1; B is a group of the formula ##STR2## in which E and F, which are as defined above, may each be bound to the 2, 3, 4, 5 or 6 position in the benzene ring, d is 0, 1 or 2, e is 0, 1 or 2 and X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group comprising CF.sub.Type: GrantFiled: June 8, 1994Date of Patent: November 21, 1995Assignee: Wacker-Chemie GmbHInventors: Christian Herzig, Silke Scheiding
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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: 5466845Abstract: The present invention provides photoactive sulfonium salts which can be employed as photoinitiators for the polymerization of cationically polymerized organic substances and are soluble in these substances.Type: GrantFiled: October 20, 1994Date of Patent: November 14, 1995Assignee: Wacker-Chemie GmbHInventor: Christian Herzig
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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: 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: 5426222Abstract: The present invention relates to an improved method for the preparation of iodonium salts. More specifically, the present invention relates to an improved method for the production of symmetric or asymmetric diaryliodonium triflate (trifluoromethane sulfonate) salts. The diaryliodonium salts of the present invention are useful as photoacid catalysts for use in acid-sensitive polymerization and in curing systems such as radiation curable release coating compositions.Type: GrantFiled: August 17, 1994Date of Patent: June 20, 1995Assignee: Dow Corning CorporationInventors: Scott E. Wargo, John P. Cannady
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Patent number: 5420355Abstract: A highly pure borate complex of a trialkylborane with an alkylated or arylated alkali metal is obtained by reacting an aryl magnesium halide with a boron trihalide to produce a triarylborane product. The triarylborane product is then subjected to thorough removal of magnesium salts produced as by-products and removal of unreacted aryl magnesium halide. A solution of alkylated or arylated alkali metal in a hydrocarbon solvent, a straight chain ether solvent or a mixed solvent thereof is then added dropwise to the solution of triarylborane product in a hydrocarbon solvent, straight chain ether solvent or mixed solvent thereof, while keeping the temperature range from -80.degree. to 25.degree. C.Type: GrantFiled: October 27, 1993Date of Patent: May 30, 1995Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5412143Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.Type: GrantFiled: December 30, 1993Date of Patent: May 2, 1995Assignee: Zambon Group S.p.A.Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
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Patent number: 5405598Abstract: Compounds of formula I and II ##STR1## in which B contains a carboranyl group and one of R.sub.3 and R.sub.4 is a carboranyl group or a boronic acid or ester are useful sensitizing agents for boron neutron capture therapy.Type: GrantFiled: February 24, 1992Date of Patent: April 11, 1995Inventors: Raymond F. Schinazi, Dennis C. Liotta
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Patent number: 5399781Abstract: A method for producing Ph.sub.3 C[B(C.sub.6 F.sub.5).sub.4 ] in an improved yield by reacting LiB(C.sub.6 F.sub.5).sub.4, which has not been isolated between production and use, with Ph.sub.3 CCl preferably in a molar ratio of LiB(C.sub.6 F.sub.5).sub.4 to Ph.sub.3 CCl of 1:(1.+-.0.05), and preferably in the presence of a hydrocarbon solvent such as an aliphatic hydrocarbon containing from 5 to 8 carbon atoms, to give a Ph.sub.3 C[B(C.sub.6 F.sub.5).sub.4 ] product; optionally evaporating the hydrocarbon solvent; extracting the resulting Ph.sub.3 C[B(C.sub.6 F.sub.5).sub.4 ] product; separating insoluble LiCl, and isolating the product. The product may be isolated, for example, by freeing it of solvent, thereafter dissolving the product in toluene to form a toluene solution, introducing the toluene solution into a hydrocarbon solvent to form crystals of the product, and recovering the crystals. In the method, the LiB(C.sub.6 F.sub.5).sub.Type: GrantFiled: October 12, 1993Date of Patent: March 21, 1995Assignee: Solvay Deutschland GmbHInventor: Guenther Doellein
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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
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Patent number: 5382672Abstract: Derivatives of benzeneborinic acid, preparation thereof and use thereof as synthetic intermediates.Type: GrantFiled: November 19, 1993Date of Patent: January 17, 1995Assignee: SynthelaboInventors: Isaac Chekroun, Jose Ruiz-Montes, Manuel Bedoya-Zurita, Guy Rossey
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Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
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Patent number: 5344948Abstract: Neutral single-source molecular organic precursors containing tetradentate tripodal chelating ligands are provided that are useful for the preparation of films using chemical vapor deposition. These complexes can be generally represented by the formula ##STR1## wherein "M" is selected from the group consisting of a lanthanide, an actinide, a Group IIIA metal, a Group IIIA metalloid, a Group IVA metal, a Group IVA metalloid, a Group VA metal, a Group VA metalloid, a Group IIIB metal, a Group IVB metal, a Group VB metal, a Group VIB metal, a Group VIIB metal, and a Group VIIIB metal. The ligand "Z" can be present or absent, i.e., k=0-1, and is selected from the group consisting of hydrogen, halide, and a group bonded to "M" through N, O, P, S, As, Si, or C. In the tetradentate tripodal chelating ligand "E.sub.c " is N, P, or As, and m=0-1. When "E.sub.t " is N, P, or As, m=1, and when "E.sub.t " is O, S, or Se, m=0. Each "R.sup.1 " is independently selected from the group consisting of hydrogen, (C.sub.1 -C.Type: GrantFiled: July 10, 1992Date of Patent: September 6, 1994Assignee: Iowa State University Research Foundation, Inc.Inventor: John G. Verkade
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Patent number: 5296433Abstract: Tris(pentafluorophenyl)borane complexes having the general formula (C.sub.6 F.sub.5).sub.3 B.(YXH).sub.q wherein X is oxygen, or sulfur; q is 1 to 3; Y is a hydrogen atom, R.sup.1 --, (R.sup.2).sub.3 Si--, or (R.sup.3 ).sub.2 C.dbd.N--; R.sup.1 is a hydrocarbyl group containing 1 to 500 carbon atoms, and may contain a divalent oxygen and further may be a fluorine-containing hydrocarbyl group; R.sup.2 is independently a linear or branched alkyl group containing 1 to 25 carbon atoms, or a phenyl group, further R.sup.2 may contain a SiO-- group; and R.sup.3 is independently a hydrocarbyl group containing 1 to 25 carbon atoms, R.sup.3 may be a hydrogen atom provided both R.sup.3 groups selected are not hydrogen atoms; and to complexes containing the borane complexes with an organometallic compound, either as a neutral compound or as an acidic salt that are useful as catalysts for polymerization and copolymerization of olefins and to polymeric products prepared using these catalysts.Type: GrantFiled: April 14, 1992Date of Patent: March 22, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Allen R. Siedle, William M. Lamanna
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Patent number: 5283359Abstract: The preparation of arylethanolamines, and in particular albuterol (salbutamol), together with their novel boron, acetal and hemi-acetal intermediates is described.Type: GrantFiled: March 1, 1993Date of Patent: February 1, 1994Assignee: Schering Corp.Inventors: Chou-Hong Tann, T. K. Thiruvengadam, John Chiu, Michael Green, Timothy L. McAllister, Cesar Colon, Junning Lee
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Patent number: 5273686Abstract: Organic-solvent soluble magnesium hydrides or formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine, ##STR2## is a chelating ligand, E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: August 28, 1991Date of Patent: December 28, 1993Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5266224Abstract: A cross-linking system using boron alpha-hydroxy carboxylic acid salts is shown for use in a water based well treating fluid. The cross-linker will gel the water based fluid usually after a delay at a relatively neutral pH. The cross-linker is provided as a concentrated stable solution containing borate ion as boric acid in a concentration of from less than 1% up to 25% by weight. The cross-linking solution additionally may contain from 1% to 10% of EDTA and/or Glycerine, however, without these additives the cross-linking solution is stable through temperature changes and freeze-and-thaw cycles. Water based fracturing fluid is shown using galactomannan guar polymers, hydroxypropyl guar polymers or derivatives thereof.Type: GrantFiled: August 11, 1992Date of Patent: November 30, 1993Assignee: Zirconium Technology CorporationInventor: Sharif Sharif
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Patent number: 5252234Abstract: A cross-linking system using boron alpha-hydroxy carboxylic acid salts is shown for use in a water based well treating fluid. The cross-linker will gel the water based fluid usually after a delay at a relatively neutral pH. The cross-linker is provided as a concentrated stable solution containing borate ion as boric acid in a concentration of from less than 1% up to 25% by weight. The cross-linking solution additionally may contain from 1% to 10% of EDTA and/or Glycerine, however, without these additives the cross-linking solution is stable through temperature changes and freeze-and-thaw cycles. Water based fracturing fluid is shown using galactomannan guar polymers, hydroxypropyl guar polymers or derivatives thereof.Type: GrantFiled: August 11, 1992Date of Patent: October 12, 1993Assignee: Zirconium Technology CorporationInventor: Sharif Sharif
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Patent number: 5239121Abstract: Process for the production of 2-aryl-1,3-propanediols from a tropate ester and novel intermediate compounds produced thereby.Type: GrantFiled: September 16, 1992Date of Patent: August 24, 1993Assignee: Ganes Chemicals Inc.Inventors: Francis Johnson, Richard Miller
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Patent number: 5220072Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo and a process for preparing.Type: GrantFiled: March 23, 1992Date of Patent: June 15, 1993Assignee: Aldrich Chemical Co., Inc.Inventor: Herbert C. Brown
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Patent number: 5218138Abstract: This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one and a sterically hindered dialkylated borane to form a complex at about -50.degree. C. to about 0.degree. C., and reducing the complex with hydride at about -25.degree. C. to about 50.degree. C.Type: GrantFiled: September 2, 1992Date of Patent: June 8, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Fang-Ting Chiu, William L. Studt
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Patent number: 5157149Abstract: A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-.alpha.-benzoylamino-4-boronocinnamic acid, asymmetrically hydrogenating the z-.alpha.Type: GrantFiled: June 4, 1991Date of Patent: October 20, 1992Assignee: The United States of America as represented by the United States Department of EnergyInventor: Edward G. Samsel