Preparing Directly From Ester, Organic Acid Or Salt, Other Than By Reduction Of Nitrile Patents (Class 564/468)
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Patent number: 6258976Abstract: Disclosed are processes for the preparation of compounds of the formula (I): H2N—(CH2)n—A—(CH2)m—NH2, or (II): H2N—(CH2)n—NH—C(═NR1)—NH—(CH2)m—NH2, wherein n and m are each independently an integer from 2 to 8; A is selected from the group consisting of —NR1—, —NR1—(CH2)r—NR1— and —NR1—(CH2)r—NR1—(CH2)z—NR1—, wherein r and z are an integer ranging from 2 to 8; and R1 is hydrogen or a protecting group having a carbonyl group.Type: GrantFiled: March 19, 1999Date of Patent: July 10, 2001Inventors: Francis Johnson, Ramesh C. Gupta
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Patent number: 6235940Abstract: In a process for preparing alkoxylated amines or alcohols in which a reaction mixture comprising an amine or an alcohol or a mixture of two or more amines and/or alcohols and an alkylene oxide, or a mixture of two or more different alkylene oxides, is reacted in one or more successive reaction steps, at least one of the reaction steps is carried out in the presence of a basic catalyst and, in at least one of the reaction steps, formic acid or a salt of formic acid or a mixture of two or more thereof is present in the reaction mixture or the reaction mixture is admixed with formic acid or a salt of formic acid, or a mixture of two or more thereof, after the alkoxylation is complete. The alkoxylates prepared by the process of the present invention have a light color and a low odor.Type: GrantFiled: September 11, 2000Date of Patent: May 22, 2001Assignee: BASF AktiengesellschaftInventors: Juergen Mohr, Toni Dockner
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Process for the preparation of protected 3-amino-1,2-dihydroxypropane acetal and derivatives thereof
Patent number: 6040464Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.Type: GrantFiled: May 27, 1999Date of Patent: March 21, 2000Assignee: Board of Trustees operating Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang -
Patent number: 6005146Abstract: The present invention provides improved adhesion promoters for latex paints. The adhesion promoters are enamines of acetoacetate esters, or substituted acetoacetate esters. The invention also provides two new compounds which are useful as adhesion promoters: 2-butyl-2-ethyl-1,3-propanediol bis(3-amino-2-butenoate) and trimethyl propane tris(3-amino-2-butenoate), and which are stable to hydrolysis on prolonged storage.Type: GrantFiled: November 20, 1998Date of Patent: December 21, 1999Assignee: Eastman Chemical CompanyInventors: Douglas Grant Atkins, Jonathan Stewart Witzeman
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Patent number: 5981802Abstract: The subject invention provides a method of preparing an allylic amine having the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently hydrogen, halogen, cyano, nitro, linear or branched chain alkyl, aryl, etc.; wherein each alkyl or arylalkyl if present is independently unsubstituted or substituted by fluoro, cyano, nitro, linear or branched chain acyl, dialkylamino, etc.; wherein each aryl if present is independently unsubstituted or substituted by fluoro, cyano, nitro, linear or branched chain alkyl, arylmercapto, etc.; and wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 optionally is covalently bonded linking pairwise a suitable atom from each to form from 0 to about 10 rings, wherein each ring contains between about four and about twelve atoms, using disubstituted sulfur diimides prepared in situ. Also provided are methods of preparing cyclic allylic amines in which allylic double bonds are endocyclic and exocyclic.Type: GrantFiled: December 14, 1995Date of Patent: November 9, 1999Assignee: The Trustees of Columbia University in the City of New YorkInventor: Thomas J. Katz
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Patent number: 5925792Abstract: A process for preparing an optically active dihydrosphingosine derivative is disclosed, comprising reducing a (2R,3R)-2-amino-3-hydroxyalkanoic acid derivative represented by formula (III): ##STR1## wherein R.sup.3 represents a straight-chain alkyl group having 7 to 21 carbon atoms; and R.sup.4 represents an amino group protecting group, (e.g., (2R,3R)-2-benzylamino-3-hydroxyoctadecanoic acid) with sodium tetrahydroborate in the presence of an acid. The process makes it feasible to produce an optically active dihydrosphingosine at high optical purity and through a simple process that is safe and easy to industrialize.Type: GrantFiled: August 13, 1996Date of Patent: July 20, 1999Assignee: Takasago International CorporationInventors: Kazutoshi Sakurai, Kenya Ishida
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Patent number: 5874623Abstract: Disclosed herein is a method of preparing polyether aminoalcohol by reacting a primary aminoalcohol with a polyether terminated with a good leaving group.Type: GrantFiled: August 2, 1993Date of Patent: February 23, 1999Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5874520Abstract: Substantially anhydrous nylon salts are made in a solid state process in which solid diamine carbamates are contacted and mixed with solid dicarboxylic acids in a near instantaneous reaction to produce the salt, and preferably are prepared by mixing the solid diamine carbamates and the solid dicarboxylic acids under conditions of high shear.Type: GrantFiled: September 15, 1997Date of Patent: February 23, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: John Harry Orth
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Patent number: 5801278Abstract: The invention provides a process for directly manufacturing a diamine/dicarboxylic acid salt with a low water content. The process includes reacting a diamine with a dicarboxylic acid to form a diamine/dicarboxylic acid salt. The reaction of the diamine and the dicarboxylic acid is carried out in the presence of about 0.5% to about 25% by weight water, based on the weight of the reaction mixture, while providing conditions in the reaction mixture such that the reaction mixture is in substantially solid particulate form.Type: GrantFiled: March 7, 1997Date of Patent: September 1, 1998Assignee: E. I. du Pont de Nemours and CompanhInventors: Ioannis V. Bletsos, Constantine D. Papaspyrides
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Patent number: 5763737Abstract: A method for the reduction of toxicity of S-(2-diisopropylamino)ethyl methylphosphonothioate ions in a medium or mixture by reaction with hydrogen peroxide and a strong inorganic acid.Type: GrantFiled: June 27, 1997Date of Patent: June 9, 1998Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Yu-Chu Yang, George W. Wagner
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Patent number: 5728884Abstract: The invention relates to a process for the work-up of a liquid complex hydrofluoride of a tertiary amine of the formula (I) ?R.sup.1 R.sup.2 R.sup.3 N.multidot.n HF!, where the radicals R.sup.1, R.sup.2 and R.sup.3 are C.sub.1 -C.sub.8 -alkyl groups which together have at least 7 carbon atoms and n is an integer or fractional number where 1.5<n<3, which, for the purpose of molecular addition of HF to a halogenated alkene, is reacted with the latter. In the reaction of the halogenated alkene with the complex amine hydrofluoride of the formula (I), the molar ratio HF:R.sup.1 R.sup.2 R.sup.3 N is allowed to fall until amine separates out as a further liquid phase, and the amine is separated off.Type: GrantFiled: December 18, 1995Date of Patent: March 17, 1998Assignee: SolvayInventors: Ulrich Hahn, Raimund Franz, Gunter Siegemund
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Patent number: 5672753Abstract: .alpha.-oximino carboxylic acids or their esters are reduced with an alkali boron hydride and hydrogen chloride or sulfuric acid to yield racemic amino alcohols (e.g. (RS)-tert-leucinol).Type: GrantFiled: February 21, 1996Date of Patent: September 30, 1997Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Wilfried Jahn, Michael Schwarm
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Patent number: 5648544Abstract: A process for the preparation of 2-aminoalkane-1,3-diols by a single step reduction of alkyl 2-oximino-3-oxoalkanoates. The reduction is carried out in the presence of at least one hydride, in a solvent, under inert atmosphere and at a controlled initial temperature.Synthetic yields are markedly improved.Type: GrantFiled: November 29, 1995Date of Patent: July 15, 1997Assignee: L'OrealInventors: Didier Semeria, Michel Philippe
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Patent number: 5639895Abstract: Disclosed is a process for producing .beta.-nitroenamine represented by the formula I: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and independently indicate a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkoxy group, an aryloxy group, a hydroxyl group or an aryl group, or an aryl group which may be optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group, a nitro group, a cyano group, an acylamino group, a di-lower alkylamino group, an arylamino group, a hydroxyl group, an arylsulfonyl group, a mercapto group, a lower alkylthio group or an arylthio group, R.sub.1 and R.sub.2 may bond together to form a cycloalkyl or bicycloalkyl and R.sub.3 is a hydrogen atom, a lower alkyl group, a cycloalkyl group or an aralkyl group; and an intermediate for producing the .beta.-nitroenamine.Type: GrantFiled: September 13, 1996Date of Patent: June 17, 1997Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5563288Abstract: The invention relates to processes for producing di-(tertiary aminoalkyl) carbonate including the step of reacting a tertiary alkanolamine with methyl alkyl carbonate in the presence of a transesterification catalyst to form tertiary aminoalkyl alkyl carbonate, wherein some of the tertiary alkanolamine reacts with the tertiary aminoalkyl alkyl carbonate to form di-(tertiary aminoalkyl) carbonate. The invention also relates to processes for producing di-(tertiary aminoalkyl) carbonate including the steps of (i) reacting dimethyl carbonate with an alcohol in the presence of a transesterification catalyst to form a methyl alkyl carbonate, and (ii) reacting a tertiary alkanolamine with the methyl alkyl carbonate formed in step i) in the presence of a transesterification catalyst to form tertiary aminoalkyl alkyl carbonate, wherein some of the tertiary alkanolamine reacts with the tertiary aminoalkyl alkyl carbonate to form di-(tertiary aminoalkyl) carbonate.Type: GrantFiled: June 7, 1995Date of Patent: October 8, 1996Assignee: OSi Specialties, Inc.Inventor: Victor C. Bastron
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Patent number: 5536888Abstract: A diol compound, for example, hexanediol, is produced with a high efficiency by esterifying a carboxylic acid mixture, collected from a reaction product mixture of a liquid phase oxidation of cyclohexane, with an esterifying agent and hydrogenate-decomposing the resultant esterification product mixture with hydrogen.Type: GrantFiled: December 27, 1994Date of Patent: July 16, 1996Assignee: UBE Industries, Ltd.Inventors: Yasushi Shiomi, Hiroyuki Fukushima, Toshihiko Sumida, Shinichi Furusaki
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Patent number: 5527949Abstract: A method for making an amine includes the steps of heating a reaction mixture including a nitrile, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; treating the first reaction intermediate with an acid in the presence of a primary alkanol to form a second reaction intermediate and an alkyl ester; separating the alkyl ester from the second reaction intermediate; and treating the second reaction intermediate with a base to form the amine.Type: GrantFiled: August 23, 1994Date of Patent: June 18, 1996Assignee: Rohm and Haas CompanyInventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
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Patent number: 5523478Abstract: A method for the manufacture of N,N dialkylglycamine compounds of general formula R.sub.2 NR.sub.1 R.sub.3 (I) by reacting a secondary amine of general formula R.sub.2 NHR.sub.3 (II) in which R.sub.2 is a straight or branched chain alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms and R.sub.3 is a residue from a monosaccharide, with an alkali metal or alkaline earth metal aliphatic sulphate, R.sub.1 SO.sub.4 M, in which R.sub.1 is a straight or branched chain alkyl or alkenyl group having from 8 to 24 carbon atoms.The betaine, suphobetaine and N-oxidised derivatives of (I) are provided for use as mild surfactants.Type: GrantFiled: November 16, 1994Date of Patent: June 4, 1996Assignee: Albright & Wilson LimitedInventors: Brynley M. Phillips, Ajit Kumar, Alan Smithson
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Patent number: 5442121Abstract: A process for producing N,N-disubstituted aminophenol which comprises the steps of:obtaining a reaction mixture containing N-substituted aminophenol by reacting a dihydric phenol and an amine;subjecting said reaction mixture to heat treatment so as to thermally decompose quaternary ammonia salt contained in said reaction mixture into a dihydric phenol and an amine, and removing at least said amine by distillation;separating high-boiling impurities by distillation to separate N-substituted aminophenol; andsubjecting said separated N-substituted aminophenol to reduction alkylation using an aldehyde compound.According to the present invention, high-purity N,N-disubstituted aminophenol can be obtained in a high yield at high selectivity, and a reduction catalyst can be used repeatedly because its activity can be maintained at a high level and yet it can retain high activity for a long period of time.Type: GrantFiled: November 15, 1994Date of Patent: August 15, 1995Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Shigeki Nagamatsu, Tomohiro Arase, Masaaki Yasuda
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Patent number: 5399763Abstract: A process for preparing an optically active 2-aminopropanal through oxidative cleavage of the corresponding optically active 3-amino-1,2-butanediol of the following formula (2): ##STR1## wherein R1 is a hydrocarbon group having 3 to 6 carbon atoms; R2 and R3 are each a hydrogen atom, or separately or together represent an N-protecting group; and the configuration at the *1 position is S or R. An optically active 2-aminopropanal of high purity can be obtained in a high yield by the process.Type: GrantFiled: January 14, 1994Date of Patent: March 21, 1995Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hisao Satoh, Taichi Koshigoe
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Patent number: 5331100Abstract: Self-building laundry detergents are organic polyamine amides, which contain a plurality of carboxylate radicals and an amide ester. These compounds are useful individually as detergents or as components in detergent compositions.Type: GrantFiled: November 27, 1987Date of Patent: July 19, 1994Assignee: Dowbrands Inc.Inventors: Harry A. Smith, Donald A. Tomalia
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Patent number: 5326911Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.Type: GrantFiled: July 20, 1992Date of Patent: July 5, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
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Patent number: 5283364Abstract: Polyamines containing primary amino groups are made by hydrolyzing an isocyanate with water in the presence of a solvent which is a carboxylic acid amide. The solvent must be used in a quantity of at least 10% by weight solvent based on 100% by weight of isocyanate. The weight ratio of solvent to water must be from 3 to 200. A homogeneous phase is maintained during the hydrolysis which is carried out at temperatures of from 20.degree. to 210.degree. C. A not incorporable basic and/or metal catalyst particularly alkali metal hydroxides may be employed. The polyamines produced by this process are particularly useful for the production of polyurethanes.Type: GrantFiled: January 15, 1993Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Klaus Konig, Hans-Joachim Meiners, Gerhard Grogler
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Patent number: 5231217Abstract: The present invention is directed to a novel solvent-free process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of an acidic catalyst selected from the group consisting of (i) boron trifluoride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8.Type: GrantFiled: March 20, 1991Date of Patent: July 27, 1993Assignee: Miles Inc.Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
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Patent number: 5220069Abstract: A process for preparing nitrogen-containing compounds which comprises contacting a carboxylated N-monosubstituted nitrogen-containing compound or a carboxylated N,N-disubstituted nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: June 15, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Bernard C. Ream
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Patent number: 5208379Abstract: Waste or scrap polyurethane may be conveniently and economically converted to useful active-hydrogen containing polyethers and polyamines by contacting the polyurethane with water, strong base, and an activating agent such as a quaternary ammonium compound containing at least 15 carbon atoms or an organic sulfonate containing at least 7 carbon atoms. The activating agent helps to accelerate the rate of base catalyzed hydrolysis.Type: GrantFiled: May 14, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Macarevich
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Patent number: 5164497Abstract: A decarboxylation process which comprises contacting a carboxylated compound with a metal oxide catalyst under conditions effective to decarboxylate the carboxylated compound.Type: GrantFiled: September 20, 1990Date of Patent: November 17, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson, Bernard C. Ream
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Patent number: 5149861Abstract: Trialkylamines and methyl formate are recovered from reaction mixtures obtained in the preparation of trimethylolalkanes by reaction of n-alkanals with from 2.2 to 4.5 moles of formaldehyde in aqueous solution in the presence of from 0.6 to 3 mole of trialkylamine, each quantity based on 1 mole of alkanal, and subsequent hydrogenation in a process wherein the crude reaction mixturea) is heated to from 100.degree. to 200.degree. C.Type: GrantFiled: March 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch, Heribert Deck, Heinz Auer, Erwin Brunner
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Patent number: 5128471Abstract: The present invention relates to a process for the production of primary amines containing aliphatically or cycloaliphatically bound amino groups, characterized in that the isocyanate groups of organic isocyanates containing aliphatically and/or cycloaliphatically bound isocyanate groups are formylated with formic acid in a first reaction step and the N-formyl groups are subsequently converted into amino groups.The present invention also relates to polyamine mixtures obtained by this process and containinga) about 40 to 90% by weight, based on the total weight of components a) and b), of N,N',N"-tris-(6-aminohexyl)-isocyanurate andb) about 10 to 60% by weight, based on the total weight of components a) and b), of higher homologs of this triamine containing more than one isocyanurate ring.Finally, the present invention relates to the use of these polyamine mixtures as hardeners for polymer precursors containing epoxide or isocyanate groups.Type: GrantFiled: April 10, 1990Date of Patent: July 7, 1992Assignee: Bayer AktiengesellschaftInventor: Hans J. Scholl
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Patent number: 5066824Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.Type: GrantFiled: August 3, 1990Date of Patent: November 19, 1991Assignee: Mobay CorporationInventors: Robson Mafoti, Josef Sanders
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Patent number: 4985556Abstract: Perfluorocarboxylic acid fluorides represented by the formula A-B, wherein A is either ##STR1## and B stands for a perfluoro-di-substituted amino group, and perfluoro(dialkylaminopropenes) represented by the formula A"-B", wherein A" stands for ##STR2## and B" has the same meaning as B defined above, are novel compounds. Methods for the production of these novel compounds are also disclosed.Type: GrantFiled: September 9, 1988Date of Patent: January 15, 1991Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Takashi Abe, Eiji Hayashi
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Patent number: 4935546Abstract: A process for the production of a primary alkylamine or a dimethylalkylamine in a single stage comprising heating a reaction medium comprising a long chain carboxylic acid ester with ammonia and hydrogen in the presence of a mixed catalyst of the oxide-metal type; said oxide being titanium dioxide and the metal being a combination of copper and cobalt or of copper, chromium, and cobalt; and the mixed oxide-metal catalyst.Type: GrantFiled: October 9, 1987Date of Patent: June 19, 1990Assignee: Ceca, S.A.Inventors: Joel Barrault, Mongi Seffen, Christian Forquy
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Patent number: 4931595Abstract: Polyamines containing primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a catalyst incorporable through an NCO reactive group and a water-miscible aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material has an NCO content of from 0.5 to 40% by weight. The catalyst is used in a quantity of at least 0.0001% by weight, based on 100% by weight of isocyanate compound. The water-miscible solvent is used in a quantity of at least 10% by weight, based on 100% by weight of isocyanate compound. The polyamines thus produced are particularly useful in the production of polyurethanes.Type: GrantFiled: August 2, 1989Date of Patent: June 5, 1990Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4912216Abstract: A perfluoro-(N-vinylamine) compound containing a >NCF.dbd.CF.sub.2 group is produced from a perfluoro-compound containing a group of the general formula: ##STR1## (wherein X stands for a fluorine atom or a --OM group having an alkali or alkaline earth metal ion for M) and having connected to the group of the general formula a perfluoro-alkyl group having a total of 2 to 6 carbon atoms contained in the main carbon chain thereof by heating the perfluoro-compound at a temperature in the range of 100.degree. C. to 500.degree. C. thereby effecting conversion of the group of the foregoing general formula into the aforementioned >NCF.dbd.CF.sub.2 group.Type: GrantFiled: July 10, 1987Date of Patent: March 27, 1990Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventor: Takashi Abe
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Patent number: 4683337Abstract: In the recovery of ethylene amines from aqueous solutions by alcohol extraction the alcoholic extract is treated with carbon dioxide so as to convert the extracted amines into carbamates, which are then back extracted with water and recovered by conventional decarbonation and dehydration. The double extraction technique results in an aqueous concentrate of at least twice the original amine concentration.Type: GrantFiled: November 21, 1983Date of Patent: July 28, 1987Assignee: Akzo nvInventor: Frederik J. Budde
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Patent number: 4680360Abstract: Poly(allylamine salts) of high polymerization degree is obtained in high yield by the polymerization of monoallylamine salt with a specified radical-polymerization initiator having in the molecule an azo group. Various poly(allylamine) derivatives are obtained by reacting said poly(allylamine salt) with acrylic compounds, or formic acid and formaldehyde.Type: GrantFiled: November 13, 1984Date of Patent: July 14, 1987Assignee: Nitto Boseki Co., LtdInventors: Toshio Ueda, Yoshinori Sato, Susumu Harada
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Patent number: 4658062Abstract: Novel amine terminated polybutadiene compounds of the formula: ##STR1## wherein R is hydrogen, a straight or branched chain alkyl group containing from 1 to 10 carbon atoms or a substituted or unsubstituted aryl or aralkyl group containing one or more benzenoid rings which may be fused or joined by single valency bonds, and n is an integer of from about 5 to 1500 and a process for the preparation thereof.Type: GrantFiled: June 24, 1985Date of Patent: April 14, 1987Assignee: Atlantic Richfield CompanyInventors: Harry R. Hinney, Jamil Baghdadchi
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Patent number: 4624937Abstract: An improved process is provided for the selective production of secondary amines and primary amines by bringing together under reaction conditions a tertiary amine or a secondary amine with oxygen or an oxygen-containing gas in the presence of an activated carbon catalyst, the improvement which comprises using an activated carbon catalyst wherein oxides have been removed from the surface of the carbon.Type: GrantFiled: February 28, 1985Date of Patent: November 25, 1986Assignee: Monsanto CompanyInventor: Shine K. Chou
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Patent number: 4625064Abstract: An improved process for preparing a bis [.beta.-(N,N-dimethylamino)ethyl]ether by reacting a bismethohalide of bis [.beta.-(N,N-dimethylamino)ethyl]ether represented by the following general formula: ##STR1## (wherein X denotes a halogen atom), with an aliphatic amine having a boiling point of not lower than 220.degree. C. at atmospheric pressure and having a primary amino group in the molecule thereof. The process comprises the following two steps (a) and (b): (a) a step of distilling out water at a temperature of not more than 130.degree. C. under reduced pressure from a mixture of said bismethohalide aqueous solution and said aliphatic amine to provide a concentration of said bismethohalide to water of not less than 85% by weight, and (b) a step of reacting said bismethohalide and amine in a solid-liquid phase at a temperature of not lower than 140.degree. C.Type: GrantFiled: April 6, 1984Date of Patent: November 25, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4558120Abstract: Dense star polymers having terminal group densities greater than conventional star polymers exhibit greater and more uniform reactivity than their corresponding conventional star polymers. For example, a third generation, amine-terminated polyamidoamine dense star polymer prepared from ammonia, methyl acrylate and ethylenediamine has 1.24.times.10.sup.-4 amine moieties per unit volume (cubic Angstrom units) in contrast to the 1.58.times.10.sup.-6 amine moieties per unit volume contained by a conventional star polymer. Such dense star polymers are useful as demulsifiers for oil/water emulsions, wet strength agents in the manufacture of paper, and agents for modifying viscosity in aqueous formulations such as paints.Type: GrantFiled: December 27, 1983Date of Patent: December 10, 1985Assignee: The Dow Chemical CompanyInventors: Donald A. Tomalia, James R. Dewald
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Patent number: 4540720Abstract: The invention relates to a simplified, economic process for the production of polyamines by the alkaline hydrolysis of compounds containing terminal aromatic and/or aliphatic isocyanate groups (including modified isocyanates or NCO-prepolymers and semi-prepolymers with NCO-contents of from 0.5 to 40% by weight), with strong aqueous bases, direct isolation of the polyamines from the carbamate stage being possible by thermal carbamate decomposition and/or solvent extraction.The invention also relates to the use of the aromatic and/or aliphatic polyamines containing primary NH.sub.2 -groups obtainable by the process according to the invention for the production of polyurethanes, such as optionally cellular polyurethane plastics and polyurethane foams.Type: GrantFiled: July 26, 1982Date of Patent: September 10, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Grogler, Klaus Konig, Dieter Dieterich
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Patent number: 4525590Abstract: The invention relates to an improved process for the production of polyamines containing urethane and/or urea and/or biuret and/or isocyanurate groups and, preferably, also alkylene ether, carbonate and/or acetal groups by the alkaline hydrolysis of corresponding compounds containing terminal aliphatic and/or aromatic isocyanate groups.To this end, the compounds containing terminal NCO-groups, preferably NCO-preadducts, are converted by means of selected bases into the carbamates and neutralized by introduction into equivalent quantities of acid or by the simultaneous introduction of the components in equivalent quantities into a reaction vessel, after which the polyamines are directly isolated by methods known per se.The invention also relates to the use of the polyamines obtained by the process for the production of polyurethanes.Type: GrantFiled: July 15, 1982Date of Patent: June 25, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Klaus Konig, Holger Meyborg, Walter Meckel, Armin Zenner
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Patent number: 4324724Abstract: A process for the manufacture of polyalkylenepolyamines by reacting a primary or secondary amine with a compound of the formula ##STR1## where X is --Cl, --Br, or --OSO.sub.3 H and R.sup.1 and R.sup.2 are H or saturated alkyl of 1 to 4 carbon atoms, and with at least the stoichiometric amount, based on the compound of the formula I, of an aqueous solution, of from 15 to 45 percent strength, of an alkali metal hydroxide or alkaline earth metal hydroxide, at from 60.degree. to 200.degree. C., cooling the reaction mixture to a temperature at which 2 aqueous phases form, and separating off the upper phase, containing polyalkylenepolyamnines. The rate of reaction can be increased by adding catalytic amounts of compounds which initiate the polymerization of alkyleneimines.Type: GrantFiled: October 2, 1978Date of Patent: April 13, 1982Assignee: BASF AktiengesellschaftInventors: Hans Mueller, Klaus Wulz, Karl-Heinz Beyer, Werner Streit
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Patent number: 4322537Abstract: Tertiary amines in which at least one group bonded directly to the nitrogen atom is alkyl of 2 to 20 carbon atoms or in which two or more groups bonded directly to the nitrogen atom together are alkylene of 4 to 7 carbon atoms, are oxidized by trihaloacetyl anhydride or trihaloacetyl halide to mono- and di-trihaloacetylated alpha, beta-enamines.Type: GrantFiled: June 2, 1980Date of Patent: March 30, 1982Assignee: President and Fellows of Harvard CollegeInventor: Stuart L. Schreiber
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Patent number: 4271318Abstract: An .omega.-lactam having 4-12 carbon atoms, an oligomer thereof or a ring-opened polymer or an .omega.-amino carboxylic acid corresponding thereto, is heated in the presence of water and a metallic carbonate compound to obtain a metallic salt of .omega.-amino carboxylic acid. Barium, calcium and lithium are the preferred metals. The resulting metal salt is converted to an amino Schiff base which may be used as a starting material for preparing an .alpha.,.omega.-diamino alkane which may or may not include an amino group as a side chain. This further produces a metallic carbonate compound. The metallic carbonate is returned and used again as a reagent for forming the metal salt of the .omega.-amino carboxylic acid to create a closed system.Type: GrantFiled: September 28, 1979Date of Patent: June 2, 1981Assignee: Toray Industries, Inc.Inventors: Tsutomu Setsuda, Hideyuki Aizawa, Takeshi Kimura
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Patent number: RE32677Abstract: The invention relates to a simplified, economic process for the production of polyamines by the alkaline hydrolysis of compounds containing terminal aromatic and/or aliphatic isocyanate groups (including modified isocyanates or NCO-prepolymers and semi-prepolymers with NCO-contents of from 0.5 to 40% by weight), with strong aqueous bases, direct isolation of the polyamines from the carbamate stage being possible by thermal carbamate decomposition and/or solvent extraction.The invention also relates to the use of the aromatic and/or aliphatic polyamines containing primary NH.sub.2 -groups obtainable by the process according to the invention for the production of polyurethanes, such as optionally cellular polyurethane plastics and polyurethane foams.Type: GrantFiled: April 7, 1986Date of Patent: May 24, 1988Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Grogler, Klaus Konig, Dieter Dieterich