Boron Attached Directly To Amino Nitrogen By Nonionic Bonding Patents (Class 564/9)
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Patent number: 6762260Abstract: The invention is a two part polymerizable composition comprising in one part an organoborane amine complex and one or more compounds containing ring opening heterocyclic moieties, and in a second part, compounds capable of being polymerized by free radical polymerization, a catalyst capable of polymerizing compounds containing ring opening heterocyclic moieties and optionally a component that will decomplex the organoborane amine complex. In one embodiment the invention is a two phase system comprising a first phase containing one or more polymers prepared from the compounds which polymerize by free radical polymerization and a second phase comprising polymerized or partially polymerized compounds derived from one or more compounds containing ring opening heterocyclic moieties.Type: GrantFiled: March 5, 2002Date of Patent: July 13, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel D. Harrington
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Patent number: 6730759Abstract: The invention is polymerizable composition comprising a) an organoborane/amine complex wherein the organoborane is a trialkyl borane or an alkyl cycloalkyl borane and the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; and, b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and optionally c) an effective amount of a compound which causes the complex to disassociate wherein the compound which causes disassociation of the complex is kept separate from the complex until initiation of polymerizatType: GrantFiled: June 15, 2001Date of Patent: May 4, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6713579Abstract: A method of modifying the surface of a low surface energy polymer by contacting the surface with a composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and optionally, c) an effective amount of a compound which causes the complex to disassociate.Type: GrantFiled: June 15, 2001Date of Patent: March 30, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6713578Abstract: A method of bonding two or more substrates together which comprises I. contacting the components of the composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and, c) optionally an effective amount of a compound which causes the complex to disassociate or heating the composition to a temperature at which the complex dissassociates; II.Type: GrantFiled: June 15, 2001Date of Patent: March 30, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6710145Abstract: A method of coating a substrate which comprises coating a substrate with the composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation, and c) an effective amount of a compound which causes the complex to disassociate; together under conditions such that polymerization is initiated.Type: GrantFiled: June 15, 2001Date of Patent: March 23, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6706831Abstract: The invention is a method of polymerization comprising contacting the components of the polymerizable composition of a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group; and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and c) in the presence of an effective amount of a compound which causes the complex to disassociate or at a temperature at which causes the complex to disassociate.Type: GrantFiled: June 15, 2001Date of Patent: March 16, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6600066Abstract: A novel process for preparing perhalogenated monoorganoboranes or diorganoboranes which makes it possible to obtain these compounds under conditions which can readily be implemented in the industry is described.Type: GrantFiled: June 14, 2001Date of Patent: July 29, 2003Assignee: Basell Polyolefine GmbHInventors: Jörg Schottek, Patricia Becker, Iris Küllmer
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Publication number: 20030100792Abstract: Process for preparing arylboron and alkylboron compounds of the formulae (II) and (III) by reacting arylmagnesium and alkylmagnesium halides of the formula (I) with boron compounds in microreactors in accordance with equation I or equation II, 1Type: ApplicationFiled: August 1, 2002Publication date: May 29, 2003Applicant: Clariant GmbHInventors: Manfred Koch, Detlef Wehle, Stefan Scherer, Klaus Forstinger, Andreas Meudt, Volker Hessel, Bernd Werner, Holger Lowe
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Patent number: 6384165Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: GrantFiled: February 15, 2001Date of Patent: May 7, 2002Assignee: 3M Innovative Properties Co.Inventor: Dean M. Moren
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Publication number: 20020040116Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: ApplicationFiled: February 15, 2001Publication date: April 4, 2002Applicant: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6335466Abstract: This invention provides a compound comprising fluorinated aminoborate monoanion of the formula: [R1R2R3N—BaHbFc]−1 I methods for preparing the same, and uses thereof, where R1, R2, R3, a, b, and c are those defined herein.Type: GrantFiled: October 31, 2000Date of Patent: January 1, 2002Assignee: Colorado State University Research FoundationInventors: Steven H. Strauss, Sergei V. Ivanov
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Patent number: 6252023Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: GrantFiled: March 19, 1999Date of Patent: June 26, 2001Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6090950Abstract: Novel chiral boron and aluminum hydride complexes, compositions comprising the chiral hydride complexes, and methods for their synthesis and use are described. The novel chiral hydride complexes are of the formulas:MBH.sub.4-n-a (R*).sub.n (R').sub.a ;MBH.sub.2-b (R**) (R').sub.b ;MBH(R***);MBH(R*) (R");MAlH.sub.4-n-a (R*).sub.n (R').sub.a ;MAlH.sub.2-b (R**)(R').sub.b ;MAlH(R***); andMAlH(R*) (R"),whereinM is Na.sup.+, Li.sup.+ or K.sup.+ ;each R* is independently a monodentate chiral ligand;R** is a bidentate chiral ligand;R*** is a tridentate chiral ligand;R' is a monodentate achiral ligand;R" is a bidentate achiral ligand;n is 1-3;a is 0-2; andb is 0-1,with the proviso that n+a.ltoreq.3, and with the further proviso that when R** is S-BINOL, M is not Li.sup.+.Type: GrantFiled: August 23, 1996Date of Patent: July 18, 2000Assignee: Zeeland Chemicals, Inc.Inventor: Glenn L. Heise
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Patent number: 5935711Abstract: A composition comprises organoborane amine complex and aziridine-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: GrantFiled: October 23, 1996Date of Patent: August 10, 1999Assignee: 3M Innovative Properties CompanyInventors: Alphonsus V. Pocius, E. John Deviny
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Patent number: 5808070Abstract: A process is disclosed for preparing a compound of the FormulaM (R.sup.1 R.sup.2 N.BH.sub.3)or a complex thereof of the FormulaM (R.sup.1 R.sup.2 N.BH.sub.3).xLwhereinM is Li, Na, K, Rb or Cs;R.sup.1 is H, an aliphatic C.sub.1 to C.sub.5 residue, an aromatic residue, or a cycloaliphatic residue;R.sup.2 is H, an aliphatic C.sub.1 to C.sub.5 residue, an aromatic residue, or a cycloaliphatic residue; orR.sup.1 and R.sup.2 form a common cyclic residue;L is a dipolar aprotic solvent; andx is a numerical value from 0.1 to 5, which comprises the steps of:(a) where the compound of the Formula M(R.sup.1 R.sup.2 N.BH.sub.3) is prepared, reacting a compound of the FormulaR.sup.1 R.sup.2 NH.BH.sub.3with an alkali metal or an alkali metal amide in a non-polar aliphatic or aromatic solvent; or(b) where the complex of the Formula M(R.sup.1 R.sup.2 N.BH.sub.3).xL is prepared, reacting the compound of the FormulaR.sup.1 R.sup.2 NH.BH.sub.Type: GrantFiled: June 25, 1997Date of Patent: September 15, 1998Assignee: Metallgesellschaft AktiengesellschaftInventors: Heinrich Noth, Steffen Thomas, Peter Rittmeyer, Ulrich Wietelmann
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Patent number: 5731470Abstract: Substituted borate and carborate anions having unusual properties of being exceptionally weakly nucleophilic and being soluble in non-polar solvents. One-electron oxidation of the anions yields the corresponding radicals. The compounds are useful, e.g., as electrolytes, catalysts, and electrochromic materials.Type: GrantFiled: April 5, 1996Date of Patent: March 24, 1998Assignee: Board of Regents of the University of ColoradoInventors: Josef Michl, Benjamin T. King, Zbynek Janousek
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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: 5616796Abstract: A complex comprises organoborane and polyamine. The polyamine is the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine. The complexes are useful in systems for initiating the polymerization of acrylic monomer, which systems further include a material reactive with amine. Polymerizable acrylic monomer compositions useful as adhesives can be prepared.Type: GrantFiled: April 14, 1995Date of Patent: April 1, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alphonsus V. Pocius, Tadesse G. Nigatu
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Patent number: 5565615Abstract: In the preparation of dimethylamine-borane by reacting an alkali metal or alkaline earth metal borohydride with a dimethylammonium salt, the improvement which comprises effecting the reaction in a liquid mixture comprising dimethylamine as a solvent and an additional organic solvent.Type: GrantFiled: March 30, 1995Date of Patent: October 15, 1996Assignee: Bayer AktiengesellschaftInventors: Christoph Holzner, Alfred Wagner, Dietrich Pantke, Hans-Dieter Block, Hans-Heinrich Moretto, Wolfgang Ohlendorf
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Patent number: 5543569Abstract: Borane-N,N-dialkylanilines represented by the formulaH.sub.3 B. C.sub.6 H.sub.5 NRR'wherein N is nitrogen, R is isobutyl or isopropyl and R' is straight or branched chain lower alkyl. The compounds are useful as hydroboration agents and for generating diborane.Type: GrantFiled: May 9, 1995Date of Patent: August 6, 1996Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5516909Abstract: A method for producing amine-boranes, specifically pyridine-borane which is highly stable and of good color is described.Type: GrantFiled: February 15, 1994Date of Patent: May 14, 1996Assignee: Boulder Scientific CompanyInventor: Jeffrey M. Sullivan
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Patent number: 5489707Abstract: Novel poly(B-alkenyl-borazines), such as poly(B-vinyl borazine), are useful as precursors to BN ceramics. The poly alkenylborazines, which may advantageously be soluble and easily processed, are prepared by heat treatment of corresponding B-alkenylborazines, which are themselves novel compounds.Type: GrantFiled: October 11, 1994Date of Patent: February 6, 1996Assignee: The Trustees of the University of PennsylvaniaInventors: Larry G. Sneddon, Anne T. Lynch
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Patent number: 5466798Abstract: The present invention relates to novel, powerful reducing agents, lithium aminoborohydrides which are prepared by addition of BH.sub.3 .cndot.THF to the corresponding dialkylamine at 25.degree. C. to give the intermediate amineborane complex. Subsequent deprotonation by strong base, e.g. n-BuLi, yields the aminoborohydride quantitatively. Lithium aminoborohydrides are powerful reducing agents, comparable in strength to lithium aluminum hydride. The activity is determined by the dialkylamine. Lithium pyrrolidinoborohydride has unique activity and selectivity in its reducing properties. Esters, lactones and anhydrides are reduced cleanly at 25.degree. C. to give the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that lithium pyrrolidinoborohydride is also capable of reducing a wide range of functional groups including amides, epoxides, oximes, nitriles and halides.Type: GrantFiled: October 15, 1993Date of Patent: November 14, 1995Assignee: The Regents of the University of CaliforniaInventors: Bakthan Singaram, Gary B. Fisher, Joseph C. Fuller, John Harrison, Christian T. Goralski
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Patent number: 5376746Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one part a stable organoboron amine complex and in the second part an aldehyde destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides room temperature, relatively slow curing systems with good adhesive properties making them useful in applications where longer open times are required.Type: GrantFiled: October 15, 1993Date of Patent: December 27, 1994Assignee: National Starch and Chemical Investment Holding CorporationInventor: Martin M. Skoultchi
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Patent number: 5284976Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.Type: GrantFiled: July 19, 1993Date of Patent: February 8, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5276195Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.Type: GrantFiled: July 14, 1993Date of Patent: January 4, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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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: 5214209Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 25, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5210310Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 11, 1993Assignee: Aldrich Chemical Co., Inc.Inventor: Herbert C. Brown
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Patent number: 5169547Abstract: Borated or partially borated, amine-contained hindered phenols provide effective antioxidant properties to compositions comprising lubricants and liquid fuels.Type: GrantFiled: September 29, 1988Date of Patent: December 8, 1992Assignee: Mobil Oil CorporationInventors: Liehpao O. Farng, Andrew G. Horodysky
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Patent number: 5145998Abstract: A method for producing an optically active amine which is an important compound as a resolving agent for medicines, agricultural chemicals, intermediates thereof, etc is disclosed.Type: GrantFiled: October 2, 1990Date of Patent: September 8, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yoji Sakito, Gohfu Suzukamo, Yukio Yoneyoshi
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Patent number: 5144071Abstract: Alkenecarboxylic esters of the formula I ##STR1## where R.sup.1 is alkyl of 1 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl or 1 to 4 carbon atoms, the substituents being identical or different, and n is 1, 2 or 3 are prepared by reacting lactones of the formula II ##STR2## where R.sup.2 has the same meanings as in the formula I, R.sub.3 is hydrogen or methyl and m is 0, 1 or 2, with the proviso that n and m differ by 1 when R.sub.3 is hydrogen and by 2 when R.sub.3 is methyl, with alkanols having 1 to 6 carbon atoms at from 50.degree. to 450.degree. C. in the presence of zeolites and/or phosphates as catalysts.Type: GrantFiled: December 22, 1989Date of Patent: September 1, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito, Toshio Nishioka
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Patent number: 5144032Abstract: An improved curing agent for use in coatings, laminates, moldings, castings and adhesives comprising the use of an amine-boron adduct component along with anhydride and epoxy component mixtures. Also provided is an improved process for the preparation of tertiary amine borane curing agents.Type: GrantFiled: April 19, 1991Date of Patent: September 1, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Anthony J. Arduengo
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Patent number: 5141676Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##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,--E D.fwdarw. 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 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: April 17, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5106928Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one-part a stable organoboron amine complex and in the second part an organic acid destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides a fast, room temperature cure with good stability and exhibiting both high tensile strength and high peel strength.Type: GrantFiled: April 29, 1991Date of Patent: April 21, 1992Assignee: National Starch and Chemical Investment Holding CorporationInventors: Martin M. Skoultchi, Nicholas V. Merlo
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Patent number: 5091536Abstract: Organic-solvent soluble magnesium hydrides of the 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, dialkylamide, aralkyl, aryl or diarylamide 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,--E D.fwdarw. 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 dialkylamide, diarylamide 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: February 9, 1988Date of Patent: February 25, 1992Assignee: Studiengesellschaft Kohle mbhInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5055231Abstract: This invention is directed to a product formed by reacting under condensation conditions, in effective molar ratios, an orthoboric acid and an alkanoletheramine having the formulaH(OCHR-CH.sub.2).sub.n --OR.sub.1 NH.sub.2whereinR is hydrogen or lower alkyl, R.sub.1 is lower alkylene andn is 1-5.Type: GrantFiled: March 10, 1989Date of Patent: October 8, 1991Assignee: REWO Chemische Werke GmbHInventors: Franz-Josef Hadamik, Wilfried Kappa, George F. Urban
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Patent number: 5051514Abstract: Organoborane imidazole compounds having the formula: ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and X are defined in the description, and intermediates therefor are disclosed.The compounds of formula I are especially useful as agricultural fungicides.Type: GrantFiled: September 25, 1990Date of Patent: September 24, 1991Assignee: Chevron Research and Technology CompanyInventors: Tsze H. Tsang, Patricia Pomidor
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Patent number: 5041651Abstract: The present invention relates to an asymmetrically modified borohydride type compound obtained by reacting an optically active amino alcohol represented by the formula, ##STR1## or its salt with an acid with a borohydride compound; its production method; and a method for producing an optically active alcohol derivative useful as fungicides, herbicides or plant growth regulators and represented by the formula, ##STR2## which comprises asymmetrically reducing a ketone compound represented by the formula, ##STR3## with the asymmetrically modified borohydride type compound.Type: GrantFiled: May 2, 1988Date of Patent: August 20, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Kazuhiko Hamada, Toshio Nishioka
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Patent number: 5023513Abstract: Novel amine-alkylborane derivatives are disclosed which exhibit significant antineoplastic and antihyperlipidemic activities. Methods for preparing the compounds are disclosed as well as methods for utilizing the compounds to induce antineoplastic and antihyperlipidemic activity.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: Boron Biologicals, Inc.Inventors: Bernard F. Spielvogel, Anup Sood
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Patent number: 5011989Abstract: The optically active benzylamine derivatives of the present invention are very useful for use as the asymmetric ligand of an asymmetric reducing agent. By using the optically active amine-boron complex prepared from the compound of the present invention, optically active products can be obtained in a specifically high optical yield. Moreover, the separation and recovery of the reaction products and asymmetric ligand can be easily achieved.Type: GrantFiled: October 3, 1988Date of Patent: April 30, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito
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Patent number: 4913830Abstract: Poly (C.sub.5 -C.sub.9 lactone) modified Mannich base adducts are made by reacting a C.sub.5 -C.sub.9 lactone, an amine, an aldehyde, and a hydrocarbyl substituted, hydroxy aromatic compound, e.g. a polyisobutenyl phenol which, in turn, preferably is made by reacting a polymer of a C.sub.2 to C.sub.10 monoolefin, preferably polyisobutylene, having a molecular weight of about 700 to 10,000 with a hydroxy aromatic compound. The resulting adducts are useful per se as oil soluble dispersant additives. They are also useful in fuel and lubricating oil compositions, as well as in concentrates and additive packages.Type: GrantFiled: January 9, 1989Date of Patent: April 3, 1990Assignee: Exxon Chemical Patents Inc.Inventors: Robert D. Lundberg, Antonio Gutierrez
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Patent number: 4865830Abstract: Admixing an aluminum alkyl, and optionally a boron compound, with a hydride of nitrogen in the gas phase and maintaining a gas phase temperature, optionally in the presence of a carrier gas, and producing aluminum nitride alone or in admixture with a precursor thereof or boron nitride or both.Type: GrantFiled: January 27, 1988Date of Patent: September 12, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ulrich Klabunde, Edward J. Newitt, Frederick N. Tebbe
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Patent number: 4801439Abstract: A process for preparing tractable preceramic precursors of Group IIIA metal/Group VA nonmetal compounds, such as BN, in which a first reactant containing a Group VA nonmetal to hydrogen bond, such as ammonia or an amine is reacted with a second reactant containing a Group IIIA metal to hydrogen bond, such as a metal hydride, in the presence of a metal catalyst that catalyzes dehydrocoupling of the bonds to form the precursor. Further reaction of the precursor in the presence of the catalyst forms oligomeric/polymeric forms of the precursor.Type: GrantFiled: September 15, 1986Date of Patent: January 31, 1989Assignee: SRI InternationalInventors: Yigal D. Blum, Richard M. Laine
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Patent number: 4760149Abstract: The present invention relates to an asymmetrically modified borohydride type compound obtained by reacting an optically active amino alcohol represented by the formula, ##STR1## or its salt with an acid with a borohydride compound; its production method; and a method for producing an optically active alcohol derivative useful as fungicides, herbicides or plant growth regulators and represented by the formula, ##STR2## which comprises asymmetrically reducing a ketone compound represented by the formula, ##STR3## with the asymmetrically modified borohydride type compound.Type: GrantFiled: September 30, 1985Date of Patent: July 26, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Kazuhiko Hamada, Toshio Nishioka
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Patent number: 4749809Abstract: The present invention relates to an optically active borane complex represented by the general formula, ##STR1## wherein R.sup.1 represents an aryl group, R.sup.2 represents an alkyl group and a mark * means an asymmetric carbon, and a method for producing optically active alcohol derivatives by the reduction of prochiral ketones with said borane complex. The optically active alcohol derivative is useful for fungicides, herbicides or plant growth regulators.Type: GrantFiled: July 1, 1985Date of Patent: June 7, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Kazuhiko Hamada, Toshio Nishioka
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Patent number: 4713190Abstract: Carboxylic amide dispersants are reacted with a fluorine-containing acid reagent selected from fluorophosphoric acid, boron trifluoride, fluoboric acid and the ammonium salts thereof. The reaction of the dispersant with the fluorine-containing acid passivates the dispersant to fluorocarbon compositions used as seals, for example in automobile engines.Type: GrantFiled: October 23, 1985Date of Patent: December 15, 1987Assignee: Chevron Research CompanyInventor: Timothy R. Erdman
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Patent number: 4659817Abstract: Compounds and methods featuring, in one aspect, compositions containing an organic boronic acid and one or more reporter groups.Type: GrantFiled: August 8, 1984Date of Patent: April 21, 1987Assignee: The Children's Medical Center CorporationInventors: Paul M. Gallop, Mercedes Paz
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Patent number: 4600520Abstract: Borated adducts of alkyl diamines and alkoxides impart effective multifunctional friction reducing and high temperature stabilizing characteristics to compositions comprising hydrocarbyl lubricants and fuels.Type: GrantFiled: December 27, 1983Date of Patent: July 15, 1986Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: RE36115Abstract: A method for producing amine-boranes, specifically pyridine-borane which is highly stable and of good color is described.Type: GrantFiled: February 14, 1997Date of Patent: February 23, 1999Assignee: Boulder Scientific CompanyInventor: Jeffrey M. Sullivan