Triethylene Diamines Patents (Class 544/351)
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Patent number: 5741906Abstract: A process for preparing triethylenediamine by passing an ethanolamine, ethyleneamine, piperazine or morpholine over a pentasil-type zeolite at elevated temperature characterized by employing a ZSM-5 zeolite in the hydrogen or ammonium form which has been pretreated with an aqueous solution of a chelating agent capable of forming a chelate-aluminum complex.Type: GrantFiled: November 15, 1996Date of Patent: April 21, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Jose Guadalupe Santiesteban, Hong-Xin Li, John Nelson Armor
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Patent number: 5716993Abstract: The present invention provides an anthranilic acid derivative having a cGMP-PDE inhibitory activity.An anthranilic acid derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof: ##STR1## ?wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent the same or different from each other, a hydrogen atom, a halogen atom, a hydroxy group, an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group, a nitro group, a hydroxyalkyl group, a cyano group or the like; R.sup.5 and R.sup.6 represent the same or different from each other, a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group or the like;W represents a group of the formula: --N.dbd. or --CH.dbd.; R.sup.7 and R.sup.Type: GrantFiled: September 14, 1995Date of Patent: February 10, 1998Assignee: Eisai Co., Ltd.Inventors: Fumihiro Ozaki, Keiji Ishibashi, Hironori Ikuta, Hiroki Ishihara, Shigeru Souda
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Patent number: 5663173Abstract: An optically active isomer or a racemate of a compound of general formula (I) ##STR1## in which either R.sub.1 represents a methoxy or cyclopropylmethoxy group andR.sub.2 represents a hydrogen, chlorine or bromine atom, orR.sub.1 and R.sub.2 together form, and in this order, a group of formula --O--CH.sub.2 --O--, --O--(CH.sub.2).sub.2 --, --O--(CH.sub.2).sub.2 --O-- or --O--(CH.sub.2).sub.3 --O--,R.sub.3 represents a hydrogen atom or an amino group, andR.sub.4 represents a hydrogen, chlorine or bromine atom,in the form of a free base or of a pharmaceutically acceptable acid addition salt.Type: GrantFiled: June 12, 1996Date of Patent: September 2, 1997Assignee: SynthelaboInventors: Samir Jegham, Jean Jacques Koenig, Alistair Lochead, Alain Nedelec, Yves Guminski
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Patent number: 5473065Abstract: The present invention relates to novel N,N'-difluorinated diazabicycloalkane derivatives which are useful as electrophilic fluorinating agents, processes for preparing such N,N'-difluorinated diazabicycloalkane derivatives and methods of using such compounds as fluorinating agents. The invention also presents novel N-fluorinated azaazoniabicycloalkane-Lewis acid adduct intermediates which are formed in the processes for preparing such N,N'-difluorinated diazabicycloalkane derivatives.Type: GrantFiled: December 7, 1993Date of Patent: December 5, 1995Assignee: Air Products and Chemicals, Inc.Inventor: Ronald E. Banks
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Patent number: 5459267Abstract: SUBSTITUTED-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS AND THEIR APPLICATION AS FLUORINATING AGENTS The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.Type: GrantFiled: December 23, 1993Date of Patent: October 17, 1995Assignee: AlliedSignal Inc.Inventors: Andrew J. Poss, George Shia
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Patent number: 5367071Abstract: The invention is a process for preparing 1,4-diazoniabicycloalkanes of Formula I wherein the corresponding 1-hydro-4-aza-1-azoniabi-cycloalkane salt of the 1,4-diazabicycloalkane is fluorinated in the presence of an alkali metal salt under reaction conditions sufficient to form the desired 1,4-diazoniabicycloalkane. ##STR1## wherein n represents 0, 1 or 2;each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl; andeach X.sup.- represents a counterion or 2X.sup.- represents a single divalent counterion.Type: GrantFiled: December 7, 1993Date of Patent: November 22, 1994Assignee: Air Products and Chemicals, Inc.Inventor: Robert G. Syvret
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Patent number: 5280120Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a carboxylated cyclic nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: December 2, 1992Date of Patent: January 18, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5274166Abstract: The present invention provides a dithiocarbamic acid salt which can be converted, at a very high yield, to an isothiocyanate suitable for use as an intermediate for production of thiazabicyclononane derivative or monothiourazole derivative; a process for producing said dithiocarbamic acid salt at a high yield without using thiophosgene having a toxicity problem; and a process for producing an isothiocyanate using said dithiocarbamic acid salt.The dithiocarbamic acid salt of the present invention is represented by general formula (2), and the process for producing said dithiocarbamic acid salt (2) comprises reacting an aniline represented by general formula (5) with carbon disulfide in the presence of 1,4-diazabicyclo[2.2.2]octane (3) or 4-pyrrolidinopyridine (4).The process for producing an isothiocyanate (1) according to the present invention comprises reacting the above dithiocarbamic acid salt (2) with a halogen compound.Type: GrantFiled: September 30, 1992Date of Patent: December 28, 1993Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Mikio Yamaguchi, Hideo Ohi
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Patent number: 5212312Abstract: Dyes of the formula ##STR1## in which F is the radical of an indigoid dye, of a benzothioxanthene or of an aromatic dye which contains at least 4 alicyclic and/or heterocyclic, fused six-membered rings and at least two ring keto groups and is not water-soluble, R.sub.1 is a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted cycloalkyl radical, a substituted or unsubstituted aryl radical or a radical of the formula--A--Qwhere A is a substituted or unsubstituted C.sub.1-4 -alkylene radical and Q is a basic radical, which may be quaternised, and R.sub.2 is hydrogen or a substituted or unsubstituted C.sub.1-4 -alkyl radical, or in which R.sub.1 and R.sub.2 together with the ##STR2## group are a phthalimide radical, and R.sub.3 is hydrogen, a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted aryl radical, a C.sub.1-4 -alkoxycarbonyl radical or a N,N-di-C.sub.1-4 -alkylcarboxamide radical and n is 1, 2, 3 or 4.Type: GrantFiled: September 22, 1986Date of Patent: May 18, 1993Assignee: Ciba-Geigy AGInventors: Jean-Marie Adam, Athanassios Tzikas
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Patent number: 5194613Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a carboxylated cyclic nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: March 16, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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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: 5162531Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a cyclic nitrogen-containing compound reactant with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: November 10, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5124378Abstract: N--OR.sub.1 substituted hindered amine light stabilizers impart outstanding stabilization properties to ambient cured coatings based on a variety of resins, the stabilized coatings exhibiting improved durability, weatherability, and the like.Type: GrantFiled: October 19, 1988Date of Patent: June 23, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf A. Behrens, Andrew Mar
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Patent number: 5113617Abstract: The present invention relates to a method for inducing male sterility in plants which comprises treating seeds of a plant receptive to said treatment by application of an effective amount of a compound of the formula: ##STR1## wherein R and R.sup.1 are hydrogen, alkyl, alkenl, alkynl, allyl, aryl, halogen or boron and may be the same or different;X and X.sup.1 are fluorine, chlorine, bromine or iodine; nitrate, sulfate, sulfonate, phosphate, citrate, or maleate;n and n.sup.1 are the integers 0 or 1, and may be the same or different;m and m.sup.1 are integers from 0 to 4, and may be the same or different;for a period of time and under conditions sufficient to induce male sterility in adult plants which are grown from said treated seeds.Type: GrantFiled: March 27, 1990Date of Patent: May 19, 1992Assignee: Arizona Board of Regents on behalf of University of ArizonaInventor: Robert G. McDaniel
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Patent number: 5086178Abstract: Fluorinated diazabicycloalkane derivative of the following Formula I: ##STR1## wherein n represents 0, 1 or 2; R represents a quaternizing organic group; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl and each X.sup.- independently represents a conterion or 2X.sup.- represents a single divalent counterion, are electrophilic fluorinating agents.Type: GrantFiled: September 20, 1990Date of Patent: February 4, 1992Assignee: Air Products and Chemicals, Inc.Inventor: Ronald E. Banks
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Patent number: 5006577Abstract: N-hydroxy-substituted hindered amine light stabilizers impart outstanding stabilization properties to ambient cured coatings based on a variety of resins, the stabilized coatings exhibiting improved durability, weatherability, and the like.Type: GrantFiled: October 19, 1988Date of Patent: April 9, 1991Assignee: Ciba-Geigy CorporationInventors: Rudolf A. Behrens, Andrew Mar
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Patent number: 4990616Abstract: A flowable triethylenediamine composition containing 200 to 1,000 ppm zinc stearate. Aqueous solutions containing such flowable triethylenediamine in amounts suitable for making polyurethane foam are clear and colorless without foam formation on the solution surface.Type: GrantFiled: March 17, 1989Date of Patent: February 5, 1991Assignee: Air Products and Chemicals, Inc.Inventor: Thomas W. Panunto
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Patent number: 4966969Abstract: The present invention relates to a process for preparing triethylenediamines which comprises contacting an amine compound having, in the molecule, a group represented by the general formula: ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and X is nitrogen or oxygen) with a catalyst comprising crystalline metallosilicate having a silica (SiO.sub.2)/metal oxide (M.sub.2 O.sub.3) molar ratio of 12/1 or more under a pressure of not less than 4 kg/cm.sup.2 (absolute pressure).According to the present invention, the conversion of the amine compound can be greatly increased and thus the desired triethylenediamines can be produced in a high yield.Type: GrantFiled: February 14, 1990Date of Patent: October 30, 1990Assignee: Idemitsu Kosan Company LimitedInventors: Haruhito Sato, Masanori Tsuzuki
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Patent number: 4918190Abstract: Disclosed are a crystalline complex compound of a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each otherand a tertiary diamine represented by Formula (II): ##STR2## wherein A represents a group having two carbon atoms as a chain member which may be branched; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and A, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be bonded to each other,and a process of separation and purification of the propargyl alcohol using the crystalline complex compound described above.Type: GrantFiled: July 30, 1987Date of Patent: April 17, 1990Assignee: Ube Industries, Ltd.Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
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Patent number: 4814446Abstract: Fluorinated triethylenediamine compounds such as perfluorotriethylenediamine and the novel compounds undecafluorotriethylenediamine and decafluorotriethylenediamine, prepared by indirect fluorination of triethylenediamine by passing triethylenediamine over, e.g., cobalt trifluoride (CoF.sub.3), is useful as a material capable of carrying oxygen in an aqueous emulsion for lifesaving a patient suffering from massive hemorrhage and for preserving internal organs in transplantation. The compounds undergo rapid biological elimination due to their low molecular weight.Type: GrantFiled: January 6, 1987Date of Patent: March 21, 1989Assignee: Biomed-Technology, Inc.Inventor: William E. Erner
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Patent number: 4804758Abstract: 1,4-Diazabicyclo[2.2.2]octane and C-substituted 1,4-diazabicyclo[2.2.2]octanes of the formula (I) ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl or alkenyl, each of 1 to 4 carbon atoms, are prepared from a heterocyclic amine of the formula (II) ##STR2## where R.sup.1 and R.sup.2 have the above meanings, R.sup.3 is hydrogen, hydroxyethyl or aminoethyl and X is hydroxyl or amino, in the presence of borosilicate and/or iron silicate zeolites as catalysts. Particularly suitable catalysts are the borosilicate and iron silicate zeolites of the pentasil type.Type: GrantFiled: October 8, 1987Date of Patent: February 14, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Kurt Schneider, Walter Best
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Patent number: 4803205Abstract: A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.Type: GrantFiled: June 7, 1988Date of Patent: February 7, 1989Assignee: Warner-Lambert CompanyInventors: Alexander J. Bridges, John M. Domagala
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Patent number: 4780468Abstract: A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.Type: GrantFiled: August 7, 1987Date of Patent: October 25, 1988Assignee: Warner-Lambert CompanyInventors: Alexander J. Bridges, John M. Domagala
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Patent number: 4772706Abstract: An improved process for the preparation of 7-substituted amino-1-alkyl- or cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids is described where tetrafluorobenzoyl chloride is converted in three operations via 1-alkyl or 1-cycloalkyl-1,4-dihydro-6,7,8-trifluoro-4-oxoquinoline-3-carbonitrile which in a separate step or in situ is displaced and hydrolyzed to the desired product.Type: GrantFiled: January 13, 1986Date of Patent: September 20, 1988Assignee: Warner-Lambert CompanyInventors: James N. Wemple, James R. Zeller, John M. Domagala
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Patent number: 4757143Abstract: Cyclic and acyclic hydroxyethyl ethylenepolyamines are converted to triethylenediamine when using a catalyst composed of zirconia or titania to which from about 0.5 to about 7 wt. % of phosphorous has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: July 12, 1988Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Walter H. Brader, Jr., Ernest L. Yeakey, Edward C. Nieh, Thomas T. McConnell
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Patent number: 4754036Abstract: N-(hydroxypropyl) piperazine and/or N,N'-(dihydroxypropyl) piperazine can conjointly be converted to C-methyl-triethylenediamine and allyl piperazine with excellent conjoint yield and selectivity when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: June 28, 1988Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Thomas T. McConnell
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Patent number: 4742168Abstract: The use of certain oxyalkyl amines as anti-caking agents for triethylenediamine (TEDA) is disclosed. The anti-caking agent comprises polyoxypropylene amines or their amides, the amines having the formula: ##STR1## wherein X is hydrogen, a methyl radical or an ethyl radical, Z is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 external ether linkages; n is a number from 1 to about 40 and r is a number from 2 to 4.Type: GrantFiled: July 31, 1986Date of Patent: May 3, 1988Assignee: Texaco Inc.Inventor: Robert L. Zimmerman
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Patent number: 4691015Abstract: Hydroxylamines derived from hindered amines are effective in stabilizing polyolefin compositions containing a stabilizer or mixture of stabilizers selected from the group consisting of the phenolic antioxidants, the hindered amine light stabilizers, the alkylated hydroxybenzoate light stabilizers, the ultraviolet light absorbers, the organic phosphorus compounds, the alkaline metal salts of fatty acids and the thiosynergists, against degradation upon high temperature extrusion, exposure to the combustion products of natural gas, gamma irradiation or upon storage for extended periods.Type: GrantFiled: March 21, 1985Date of Patent: September 1, 1987Assignee: Ciba-Geigy CorporationInventors: Rudolf A. Behrens, Raymond Seltzer
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Patent number: 4656268Abstract: There are described novel cationic quinophthalone compounds of the formula I ##STR1## wherein the symbols have the meanings defined in claim 1, and also processes for producing them. These novel quinophthalone compounds can be used in particular as dyes for dyeing and printing paper, greenish-yellow dyeings having good fastness to water and to light being obtained.Type: GrantFiled: October 18, 1985Date of Patent: April 7, 1987Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4628092Abstract: The flowability of stored triethylenediamine is improved by admixing with a flow promoting amount of a C.sub.5 -C.sub.28 acetylenic alcohol. Especially suitable as a flow promoting additive for triethylenediamine is a mixture of 3,6-dimethyl-1-heptyne-3-ol and 3,5,8,10-tetramethyl-6-dodecyn-5,8-diol.Type: GrantFiled: June 21, 1985Date of Patent: December 9, 1986Assignee: Air Products and Chemicals, Inc.Inventors: Akio Takahashi, Robert G. Petrella
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Patent number: 4621036Abstract: Certain solid organic depolarizers are disclosed for use in non-aqueous active metal cells which allow such cells to achieve both high voltage and high capacity with greater enhanced stability. The depolarizers include halogen adducts of triethylenediamine, also known as 1,4 diazabicyclo [2.2.2] octane such as N,N'-tetrachloro triethylenediamine.Type: GrantFiled: September 6, 1985Date of Patent: November 4, 1986Assignee: Honeywell Inc.Inventor: Narayan Doddapaneni
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Patent number: 4588811Abstract: There are described novel cationic quinophthalone compounds of the formula I ##STR1## wherein the symbols have the meanings defined in claim 1, and also processes for producing them. These novel quinophthalone compounds can be used in particular as dyes for dyeing and printing paper, greenish-yellow dyeings having good fastness to water and to light being obtained.Type: GrantFiled: November 19, 1984Date of Patent: May 13, 1986Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4474959Abstract: Formate salts of nitrogenous bases containing tertiary nitrogen are prepared by reacting the nitrogenous base with carbon dioxide and hydrogen using a soluble transition metal catalyst. For example triethylamine is reacted with carbon dioxide and hydrogen using ruthenium trichloride as catalyst and an isopropanol/water mixture as solvent to yield triethylammonium formate which was separated from the reaction mixture by distillation.Type: GrantFiled: May 16, 1983Date of Patent: October 2, 1984Assignee: BP Chemicals LimitedInventors: David J. Drury, John E. Hamlin
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Patent number: 4467089Abstract: Novel carbamic and carbonic acid derivatives are provided by simultaneous reaction of a secondary amine and a tertiary amine with carbon dioxide. These derivatives correspond in general to the formula ##STR1## in which R.sub.1 and R.sub.2 may be individual substituents attached to the N or together form with N a heterocyclic moiety; R.sub.3, R.sub.4, R.sub.5 may be individual short chain alkyl or hydroxyalkyl substituents on the N or form therewith a monocyclic or bicyclic heterocyclic moiety. These described compounds find particular use as heat activatable delayed action catalysts especially for use in polyurethane formulations.Type: GrantFiled: March 4, 1982Date of Patent: August 21, 1984Assignee: Air Products and Chemicals, Inc.Inventor: Ibrahim S. Bechara
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Patent number: 4435334Abstract: Compounds which contain ammonium groups and sulphonic acid groups and which, in the betaine form, correspond to the formula ##STR1## wherein X denotes --CO-- or --SO.sub.2 --,R.sub.1 denotes hydrogen or alkyl,R.sub.2, R.sub.3 and R.sub.4, independently of one another denote alkyl, alkenyl or aralkyl, orR.sub.4 denotes ##STR2## Y denotes alkylene or xylylene, m denotes 1 or 2,n denotes 0 or 1, andR.sub.5 and R.sub.6, independently of one another, denote hydrogen, alkyl, alkoxy or halogen,and in addition, if n=1,R.sub.2 or R.sub.4 denotes amino, alkylamino, dialkylamino, aryl or cycloalkyl,R.sub.2 and R.sub.3, together with the nitrogen atom which is bonded to them, denote a 5-membered or 6-membered ring,R.sub.2, R.sub.3 and R.sub.4, together with the nitrogen atom which is bonded to them, denote a pyridinium ring, a group of the formula ##STR3## or hydrogen, Y denotes arylene, benzylene or a radical of the formula ##STR4## Z denotes a direct bond, --(CH.sub.2).sub.p --, --O--, --O--(CH.sub.2).sub.Type: GrantFiled: December 28, 1981Date of Patent: March 6, 1984Assignee: Bayer AktiengesellschaftInventors: Frank-Michael Stohr, Peter Wild, Horst Nickel
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Patent number: 4383021Abstract: Nickel complexes of diazabicyclooctane derivatives of one of the following formulae I and II are useful metallizing agents for the formation of metal complexed image dyes in image receiving elements for the dye diffusion transfer process ##STR1## In these formulae R.sup.1 represents an n-functional aliphatic hydrocarbon radical optionally containing carbocyclic or heterocyclic groups, carbonyl groups, sulphonyl groups and/or heteroatoms (O, S, N) as intermediate members;R.sup.2 and R.sup.3 represent hydrogen or alkyl;A.sup..crclbar. represents an anion; andn represents a number of from 1 to 5.Type: GrantFiled: February 10, 1982Date of Patent: May 10, 1983Assignee: Agfa-Gevaert AktiengesellschaftInventors: Peter Bergthaller, Guenter Helling, Jurgen Strauss
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Patent number: 4345079Abstract: Scoopability of triethylene diamine (TEDA) is improved by admixture therewith of a minor quantity (about 0.5 up to 2% by weight) of an additive in liquid form. The types of additives described are liquid glycol compounds selected from among polyethylene glycols, glycol esters, glycol ethers and amino alcohols. Preferred additives are: Carbowax polyethylene glycols having the general formulaHOCH.sub.2 (CH.sub.2 OCH.sub.2).sub.x CH.sub.2 OHwherein x is about 3 to about 13, glycol diacetate and triethylene glycol diacetate.Type: GrantFiled: April 21, 1980Date of Patent: August 17, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Floyd L. Hyman, Martin H. Ziv
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Patent number: 4303791Abstract: New compounds 1-alkyl, 4-aza, 1-azonia-bicyclo (2,2,2)octane, 4-oxide, halides useful as templates for the formation of crystalline zeolites and process for preparing said new compounds from diazobicyclooctane.Type: GrantFiled: September 10, 1979Date of Patent: December 1, 1981Assignee: Mobil Oil CorporationInventor: Costandi A. Audeh
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Patent number: 4284775Abstract: There is disclosed a novel process for the preparation of 1,4-diazabicyclooctane dihydrohalides having the formula ##STR1## wherein each R is independently selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl, and cycloalkyl, and X is chlorine or bromine, said process comprising heating at a temperature of at least about 100.degree. C. and in a dipolar aprotic solvent certain novel dihaloalkylene diamines. Neutralization of the dihydrohalides provides the corresponding 1,4-diazabicyclooctane free bases.Also disclosed are certain novel 1,4-diazabicyclooctane diammonium dihalides formed as intermediates in the above process and a process for their conversion to the 1,4-diazabicyclooctane dihydrohalides and free bases thereof.The 1,4-diazabicyclo compounds produced in accordance with the invention find particular utility as catalysts in the preparation of polyurethanes from organic polyols and polyisocyanates.Type: GrantFiled: February 4, 1980Date of Patent: August 18, 1981Assignee: The Upjohn CompanyInventor: George H. Temme
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Patent number: 4232152Abstract: Amine salts of tertiary amino acids have been found to be effective as catalysts for polyurethane synthesis and they have been found to exhibit delayed action, in many instances, in the polymerization of urethanes. Typically, the amine salts of tertiary amino acids are formed by initially reacting a primary or secondary amine with an aldehyde and disubstituted acid to form a Mannich adduct and then reacting the resulting Mannich acid adduct with an amine.Type: GrantFiled: October 23, 1978Date of Patent: November 4, 1980Assignee: Air Products and Chemicals, Inc.Inventors: Ibrahim S. Bechara, Rocco L. Mascioli, Philip J. Zaluska
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Patent number: 4216322Abstract: There is disclosed a novel process for the preparation of 1,4-diazabicyclooctane dihydrohalides having the formula ##STR1## wherein each R is independently selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl, and cycloalkyl, and X is chlorine or bromine, said process comprising heating at a temperature of at least about 100.degree. C. and in a dipolar aprotic solvent certain novel dihaloalkylene diamines. Neutralization of the dihydrohalides provides the corresponding 1,4-diazabicyclooctane free bases.Also disclosed are certain novel 1,4-diazabicyclooctane diammonium dihalides formed as intermediates in the above process and a process for their conversion to the 1,4-diazabicyclooctane dihydrohalides and free bases thereof.The 1,4-diazabicyclo compounds produced in accordance with the invention find particular utility as catalysts in the preparation of polyurethanes from organic polyols and polyisocyanates.Type: GrantFiled: October 30, 1978Date of Patent: August 5, 1980Assignee: The Upjohn CompanyInventor: George H. Temme
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Patent number: 4204062Abstract: Amine salts of tertiary amino acids have been found to be effective as catalysts for polyurethane synthesis and they have been found to exhibit delayed action, in many instances, in the polymerization of urethanes. Typically, the amine salts of tertiary amino acids are formed by initially reacting a primary or secondary amine with an aldehyde and disubstituted acid to form a Mannich adduct and then reacting the resulting Mannich acid adduct with an amine.Type: GrantFiled: October 23, 1978Date of Patent: May 20, 1980Assignee: Air Products & Chemicals, Inc.Inventors: Ibrahim S. Bechara, Rocco L. Mascioli, Philip J. Zaluska
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Patent number: 4163055Abstract: New 2,9-dioxatricyclo[4,3,1,0.sup.3,7 ] decane derivatives are disclosed which are substituted by an amino methyl group in the C.sub.3 position, and which exhibit sedative, especially sleep improving properties, and which have the formula ##STR1## wherein R.sub.1 represents an amino group ONE OF R.sub.2 and R.sub.3 is hydrogen and the other represents hydroxy acyloxy or carbamyloxy or R.sub.2 and R.sub.3 jointly represent oxygenOne of R.sub.4 and R.sub.5 is hydrogen and the other represents alkyloxy or aralkyloxyY and y' each represent hydrogen or jointly form a bond and their pharmacologically acceptable salts, as well as pharmaceutical formulations thereof.Type: GrantFiled: February 18, 1977Date of Patent: July 31, 1979Assignee: Kali-Chemie Pharma GmbHInventors: Peter W. Thies, Akiji Asai
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Patent number: 4160099Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein ##STR2## represents a tertiary aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.Type: GrantFiled: September 20, 1976Date of Patent: July 3, 1979Assignee: Interx Research CorporationInventor: Nicolae S. Bodor
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Patent number: 4150145Abstract: Disclosed are N-alkylated derivatives of thienamycin sulfoxide (I, n=1) and sulfone (I, n=2): ##STR1## wherein n=1 or 2; and R.sup.5, R.sup.6, and R.sup.7 are, inter alia, hydrogen or alkyl. Such compounds the their pharmaceutically acceptable O- and carboxyl- derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.Type: GrantFiled: September 15, 1977Date of Patent: April 17, 1979Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Raymond A. Firestone, William J. Leanza
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Patent number: 4136033Abstract: Compounds of the formula ##STR1## wherein K.sup..sym. is a cationic group, preferably heterocyclic,R is hydrogen or an organic radical, preferably alkyl, phenyl or acyl,R.sub.1 is hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl, amino or substituted amino, andA.sup..crclbar. is an anion,Are useful as intermediates in the synthesis of azo dyes of the formula ##STR2## wherein D is an aromatic carbocyclic or heterocyclic diazo component radical, andK.sup..sym., r, r.sub.1 and A.sup..crclbar. are as defined above.Type: GrantFiled: June 25, 1974Date of Patent: January 23, 1979Assignee: Sandoz Ltd.Inventor: Willy Steinemann
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Patent number: 4093663Abstract: Novel onium surfactants are described which correspond to the formula X[(CH.sub.2 CH.sub.2 O).sub.m CH.sub.2 --R--CHR'--Q.sup..sym. A.sup..crclbar. ].sub.n, wherein X is an n-valent hydrophobic radical derived by the removal of n-atoms of active hydrogen from an organic compound; m is one or more; R is a divalent aromatic radical of from 6 to about 14 carbon atoms, the chain-length of which may be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q.sup.+ is a quaternized atom of nitrogen or phosphorus or a tertiary atom of sulfur; A.sup.- is a compatible anion; and n is from 1 to 5. The following compound is an example C.sub.9 H.sub.19 --C.sub.6 H.sub.4 --O--CH.sub.2 CH.sub.2 O--.sub.15 CH.sub.2 --C.sub.6 H.sub.4 --CH.sub.2 --S.sup..sym. --(CH.sub.3).sub.2 Cl.sup..crclbar. . The novel surfactants are prepared in two steps.Type: GrantFiled: November 15, 1973Date of Patent: June 6, 1978Assignee: The Dow Chemical CompanyInventors: Robert F. Harris, Earl H. Wagener
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Patent number: 4092316Abstract: A liquid phase synthesis of C-alkyl-triethylenediamines involves heating to elevated temperatures of from about 200.degree. C to 300.degree. C a suitable N-(2-hydroxyalkyl) piperazine feedstock in the presence of a catalytic amount of a pentavalent acidic phosphorus compound and then recovering the C-alkyl-triethylenediamine product from the resulting reaction product mixture.Type: GrantFiled: December 23, 1976Date of Patent: May 30, 1978Assignee: Texaco Development CorporationInventor: Edward C. Y. Nieh