Monoether Patents (Class 564/508)
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Patent number: 4788339Abstract: Perfluoroaminoethers are provided. The perfluoroaminoethers have two or more tertiary amino nitrogen atoms each of which is connected to the other(s) adjacent thereto by (1) a catenary, ether oxygen-containing, perfluoroalkylene linking group the catenary carbon atoms of which are in the form of segments of vicinal carbon atoms that are 2 to 4 in number, said segments having up to 5 carbon atoms, a catenary ether oxygen-containing perfluorocyclohexylene linking group, or (3) a catenary ether oxygen-containing linking group having perfluoroalkylene and perfluorocyclohexylene moieties, the sum of the catenary ether oxygen atoms being 1 to 6.Type: GrantFiled: August 14, 1986Date of Patent: November 29, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: George G. I. Moore, John C. Hansen
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Patent number: 4748226Abstract: This invention relates to novel 2-(alkoxymethyl) pentane-1,5-diisocyanates, 2-(alkoxymethyl)-pentane-1,5-diurethanes, and 2-(alkoxymethyl)-pentane 1,5-dicarbamic acid chlorides having the structure: ##STR1## in which R is a straight chain or branched C.sub.1 -C.sub.20 -alkyl radical, a straight chain or branched C.sub.2 -C.sub.20 -alkenyl radical, a straight chain or branched C.sub.3 -C.sub.20 -oxaalkyl radical, an optionally substituted C.sub.5 -C.sub.12 -cycloalkyl radical, or an optionally substituted C.sub.7 -C.sub.20 -aralkyl radical and X is a --NCO--, --NH--CO.sub.2 R.sup.1 --, --NHCO.sub.2 R.sup.2 -- OR - NHCOCl-group whereby R.sup.1 and R.sup.2 can be the same or different and are a straight chain or branched C.sub.1 -C.sub.20 -alkyl radical or a C.sub.5 -C.sub.12 cycloalkyl radical, as well as a process for their preparation.Type: GrantFiled: September 16, 1987Date of Patent: May 31, 1988Assignee: BASF AktiengesellschaftInventors: Franz Merger, Wolfgang Schwarz
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Patent number: 4696771Abstract: Novel aminopolyols are the products of the reaction of an N-substituted ethanolamine with a terminal epoxy-containing compound. The epoxy-containing compounds may be:I. terminal mono-epoxy-containing aliphatic hydrocarbons,II. mono-glycidyl ethers of aliphatic hydrocarbons,III. mono-glycidyl esters of fatty acids, andIV. di-glycidyl ethers of bisphenols.The novel aminopolyols are useful in the preparation of novel polyurethanes by reaction with polyisocyanates.Type: GrantFiled: December 3, 1985Date of Patent: September 29, 1987Assignee: Henkel CorporationInventor: Don E. Floyd
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Patent number: 4665234Abstract: A novel class of severely sterically hindered secondary aminoether alcohols of the general formula: ##STR1## are prepared wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl and hydroxylalkyl radicals R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals, with the proviso that at least one of R.sub.4 or R.sub.5 bonded to the carbon atom directly bonded to the nitrogen atom is an alkyl or hydroxyalkyl radical when R.sub.3 is hydrogen, x and y are each positive integers ranging from 2-4 and z is a positive integer ranging from 1-4. The compounds are useful in the selective removal of H.sub.2 S from mixtures containing H.sub.2 S and CO.sub.2.Type: GrantFiled: August 15, 1983Date of Patent: May 12, 1987Assignee: Exxon Research and Engineering CompanyInventor: Eugene L. Stogryn
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Patent number: 4650865Abstract: The invention relates to a process for preparing tertiary ether amines corresponding to the following general formula: ##STR1## by reacting in the presence of a strong base a tertiary amine corresponding to the following formula: ##STR2## with a sulfuric acid semi-ester salt corresponding to the following formula:R.sup.1 --(OC.sub.n H.sub.2n).sub.x --OSO.sub.3 M. (III)Preferably, each mole of the tertiary amine corresponding to formula (II) is reacted under substantially anhydrous conditions at a temperature of 140.degree. to 230.degree. C. with from about 0.2 to 3.0 moles of the sulfuric acid semi-ester salt of formula (III) in the presence of from about 1 to 1.5 moles of a strong base preferably an alkali metal hydroxide or an alkali metal alcoholate.Type: GrantFiled: February 7, 1986Date of Patent: March 17, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Fritz Lange, Alfred Meffert
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Patent number: 4650907Abstract: Novel nonaromatic fluoroallylamines are potent MAO inhibitors and at low dose selectively inhibit MAO-B. They are useful in the treatment of depression and coadministered with L-dopa, in the treatment of Parkinsonism.Type: GrantFiled: December 5, 1985Date of Patent: March 17, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Philippe Bey, Michael G. Palfreyman, Ian A. McDonald
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Patent number: 4636568Abstract: There are disclosed certain aminoether compounds which are useful as intermediates in the preparation of photographic image dye providing materials. The aminoethers are represented either by the formula ##STR1## wherein R is hydrogen or an alcohol protecting group and R.sub.1 is hydrogen, alkyl or aralkyl such as benzyl or phenethyl; or the formula ##STR2## wherein R.sub.2 and R.sub.3 are alkyl having from 1 to 6 carbon atoms or R.sub.2 and R.sub.3 together represent the carbon atoms necessary to form, together with the oxygen atoms to which they are bonded and >CH, a five or six member saturated heterocyclic moiety which may include substituted rings and fused rings.Type: GrantFiled: August 27, 1984Date of Patent: January 13, 1987Assignee: Polaroid CorporationInventors: Myron S. Simon, David P. Waller
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Patent number: 4618481Abstract: An alkaline absorbent composition comprising a severely hindered amino compound and an amine salt is provided. A process for the removal of H.sub.2 S from fluid mixtures using this absorbent composition to produce a very low level of H.sub.2 S in the treated fluid is also provided. The process is also suited for the selective removal of H.sub.2 S from fluid mixtures comprising H.sub.2 S and CO.sub.2.Type: GrantFiled: August 30, 1985Date of Patent: October 21, 1986Assignee: Exxon Research and Engineering Co.Inventors: Fred J. Heinzelmann, Noah S. Rothblatt, James P. Glass, Jr., Geoffrey R. Say, George R. Chludzinski, Guido Sartori, W. S. Winston Ho
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Patent number: 4588843Abstract: It has been discovered that when reaction is effected between an alkali metal omega-amino-alkoxide and an alkyl halide, nucleophilic attack of the alkoxide on the alkyl halide occurs so that an (alkoxyalkyl)amine is formed. The conventional Hofmann displacement reaction (elimination of CH.sub.3 Br) does not occur to any significant extent. Nor does the common olefin elimination reaction occur to any significant extent when using alkali metal omega-aminoalkoxides having one or two C.sub.2 or higher alkyl substituents on the nitrogen atom.Type: GrantFiled: April 26, 1984Date of Patent: May 13, 1986Assignee: Ethyl CorporationInventor: Everett M. Marlett
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Patent number: 4582938Abstract: This invention relates to a polyamine composition suited for catalytically effecting reaction between organic polyisocyanate and an active hydrogen compound as measured by the Zerewitinoff method e.g. a polyol, a polyester polyol of polyether in the manufacture of urethane compositions.Type: GrantFiled: October 24, 1983Date of Patent: April 15, 1986Assignee: Air Products and Chemicals, Inc.Inventor: Howard L. Harwell
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Patent number: 4578462Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: August 22, 1983Date of Patent: March 25, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4504279Abstract: A novel fuel composition contains ethanol methanol or gasohol plus, as a corrosion inhibitor, a reaction product of isatoic anhydride and a t-alkyl primary amine which has been further reacted with an alkoxyalkylaminoalkyl amine.Type: GrantFiled: July 9, 1984Date of Patent: March 12, 1985Inventor: Rodney L. Sung
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Patent number: 4490556Abstract: A method for preparing bis[.beta.-(N,N-dimethylamino)ethyl]ether characterized by performing a one stage reaction at a temperature of below 100.degree. C. wherein vapor of sulfuric anhydride is being introduced into a mixed solution consisting of sodium N,N-dimethylaminoethoxide, N,N-dimethylethanolamine and dioxane.Type: GrantFiled: October 18, 1983Date of Patent: December 25, 1984Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Hideo Sakka, Yukihiro Tsutsumi
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Patent number: 4474988Abstract: Bis-(N,N-dialkylamino)alkyl ethers are produced by reacting a (N,N-dialkylamino) alkanol over a heterogeneous solid acid catalyst. The (N,N-dialkylamino) alkanol can optionally be accompanied by an inert carrier. The resulting bis-ethers are useful as catalysts in the production of polyurethanes, especially cellular polyurethanes.Type: GrantFiled: December 27, 1982Date of Patent: October 2, 1984Assignee: Union Carbide CorporationInventor: Steven W. Kaiser
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Patent number: 4471138Abstract: A novel class of severely sterically hindered secondary aminoether alcohols of the general formula: ##STR1## are prepared wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl and hydroxylalkyl radicals R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals, with the proviso that at least one of R.sub.4 or R.sub.5 bonded to the carbon atom directly bonded to the nitrogen atom is an alkyl or hydroxyalkyl radical when R.sub.3 is hydrogen, x and y are each positive integers ranging from 2-4 and z is a positive integer ranging from 1-4. The compounds are useful in the selective removal of H.sub.2 S from mixtures containing H.sub.2 S and CO.sub.2.Type: GrantFiled: December 27, 1982Date of Patent: September 11, 1984Assignee: Exxon Research and Engineering Co.Inventor: Eugene L. Stogryn
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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: 4464488Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce compounds of the formula ##STR1## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and R" is methyl or ##STR2## where R is as above. Monocarboxylic acid salts of these compounds show unexpectedly high efficiency as polyurethane catalysts. Smaller amounts of this amine are required to produce foams having the same reaction profile as foams made with prior art amine salt catalysts.Type: GrantFiled: August 11, 1983Date of Patent: August 7, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Bruce W. Peterson
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Patent number: 4454297Abstract: Bis(aminoethyl) ether is reacted with an alkylene oxideto form a 2-[2-aminoethoxy-2-ethylamino]alkanol which is useful as an epoxy curative.The curative is cured with a polyepoxide to form an epoxy resin useful for such applications as decorative coatings, encapsulations, adhesives, laminates, potting compounds, etc.Type: GrantFiled: January 14, 1983Date of Patent: June 12, 1984Assignee: Texaco Inc.Inventors: Harold G. Waddill, Robert L. Zimmerman
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Patent number: 4433170Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydrogenation catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with piror art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: February 21, 1984Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4417075Abstract: A novel class of di-secondary aminoethers of the general formula: ##STR1## are disclosed wherein R.sub.1 and R.sub.8 are each independently selected from the group consisting of primary alkyl having 1 to 8 carbon atoms and primary hydroxyalkyl having 2 to 8 carbon atoms, secondary alkyl and secondary hydroxyalkyl radicals having 3 to 8 carbon atoms, tertiary alkyl and tertiary hydroxyalkyl radicals having 4 to 8 carbon atoms, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are each independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.3 alkyl and hydroxyalkyl radicals, with the proviso that R.sub.2, R.sub.3, R.sub.6, and R.sub.7 are C.sub.1 -C.sub.4 alkyl or hydroxyalkyl radicals when R.sub.1 and R.sub.8 are primary alkyl or hydroxyalkyl radicals, and at least one of R.sub.2 or R.sub.3 and R.sub.6 or R.sub.7 are C.sub.1 to C.sub.3 alkyl or hydroxyalkyl radicals when R.sub.1 and R.sub.Type: GrantFiled: January 18, 1982Date of Patent: November 22, 1983Assignee: Exxon Research and Engineering Co.Inventor: Eugene L. Stogryn
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Patent number: 4409000Abstract: Combinations of certain hydroxy amines, particularly the "Ethomeens," and hydrocarbon-soluble carboxylic dispersants are useful as engine and carburetor detergents for normally liquid fuels. The preferred compositions are those in which the carboxylic dispersants are the reaction products of substituted succinic acids with polar compounds, especially with amines such as ethylene polyamines.Type: GrantFiled: December 14, 1981Date of Patent: October 11, 1983Assignee: The Lubrizol CorporationInventor: William M. LeSuer
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Patent number: 4405811Abstract: A novel class of severely sterically hindered tertiary amino compounds having a pK.sub.a value at 20.degree. C. greater than 8.6, preferably ranging from 9.3 to about 10.6, and a cumulative -E.sub.s value of at least 1.9 are found to be useful in selective removal of H.sub.2 S from a normally gaseous mixture containing H.sub.2 S and CO.sub.2.Type: GrantFiled: January 18, 1982Date of Patent: September 20, 1983Assignee: Exxon Research and Engineering Co.Inventors: Eugene L. Stogryn, Guido Sartori
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Patent number: 4392867Abstract: Alcohols may be inhibited against corrosion by addition thereto of an amine [R(OR').sub.n ].sub.a --NH.sub.3-a typically dodecyloxy-(isopropoxy)-isopropylamine.Type: GrantFiled: December 14, 1981Date of Patent: July 12, 1983Assignee: Texaco Inc.Inventors: Rodney L. Sung, William M. Sweeney
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Patent number: 4392866Abstract: Alcohols may be inhibited against corrosion by addition thereto of an ether amine ##STR1## typically C.sub.12 H.sub.25 OCH.sub.2 CH.sub.2 CH.sub.2 NHCH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2.Type: GrantFiled: November 5, 1981Date of Patent: July 12, 1983Assignee: Texaco Inc.Inventors: Rodney L. Sung, George J. Sidote, William M. Sweeney
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Patent number: 4352920Abstract: Epoxy resin compositions are provided containing aminoalkoxy compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from H and ##STR2## and R.sub.3, R.sub.4 and R.sub.5 are all independently selected from H and a lower alkyl group having from 1 to about 6 carbon atoms. Also provided are methods for curing epoxy resins where aminoalkoxy curing agents may be employed.Type: GrantFiled: February 2, 1981Date of Patent: October 5, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4351934Abstract: Novel epoxy resin compositions are provided, comprising an epoxy resin and at least one aminoalkoxypropane of the formula: ##STR1## where R.sub.1, and R.sub.2 are independently selected from H and ##STR2## where R.sub.3 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms.Type: GrantFiled: February 2, 1981Date of Patent: September 28, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Calvin D. Welch
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Patent number: 4343745Abstract: The invention provides a process for solubilizing an organic or mineral salt in an organic solvent, said process comprising contacting an organic or mineral salt of the formula A.sup.- M.sup.+, wherein A.sup.- represents a mineral or organic anion and M.sup.+ represents a cation selected from the group consisting of the cation NH.sub.4.sup.+ and its derivatives and the cations derived from the metals of the groups I.sub.A, II.sub.A, III.sub.A, IV.sub.A, V.sub.A, VI.sub.A, VII.sub.A, VIII, I.sub.B, II.sub.B, III.sub.B, IV.sub.B and V.sub.B of the periodic table, with at least one sequestering agent which is soluble in said organic solvent, said sequestering agent having the formula:N[CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (I)wherein n is an integer from 0 to 10 inclusive; R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, are each a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms; R.sub.Type: GrantFiled: February 29, 1980Date of Patent: August 10, 1982Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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Patent number: 4338408Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with prior art amine catalysts.Type: GrantFiled: July 20, 1981Date of Patent: July 6, 1982Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Ernest L. Yeakey
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Patent number: 4331778Abstract: The present invention relates to a process for the production of polyurethane plastics by reacting compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight in the range of from 400 to 10,000, polyisocyanates and, optionally, chain extenders having a molecular weight of from 32 to 400, foam stabilizers, water and/or organic blowing agents in the presence of catalysts containing tertiary nitrogen. These catalysts are characterized in that mixtures of (a) one or more cross-linking catalysts corresponding to the following general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represent C.sub.1 -C.sub.5 -alkyl radicals, preferably CH.sub.3 -- or C.sub.2 H.sub.5 radicals,R' and R" represent hydrogen or the same or different C.sub.1 -C.sub.3 -alkyl radicals, preferably CH.sub.3 -- or C.sub.2 H.sub.Type: GrantFiled: December 10, 1979Date of Patent: May 25, 1982Assignee: Bayer AktiengesellschaftInventors: Claus-Dieter Sommerfeld, Peter Haas, Kuno Wagner, Manfred Kapps
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Patent number: 4324739Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: March 31, 1980Date of Patent: April 13, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4296231Abstract: The use of compounds of the formula ##STR1## in which m is a number from 3 to 10, X is a grouping of the formula in which R is an alkyl having 4 to 10 C atoms or a phenyl which is unsubstituted or substituted by chlorine, bromine or alkyl or alkoxy each having 1 to 3 C atoms, and Y is a hydrogen atom or has the meaning defined for X, which are obtained by adding on 1 or 2 mols of an aliphatic or aromatic monoglycidyl ether to 1 mol of a dimethylaminoalkylamine, as a curing catalyst for epoxide resins or as a curing accelerator in curable mixtures consisting of epoxide resins and polycarboxylic anhydrides or polyhydric phenols.Type: GrantFiled: May 1, 1980Date of Patent: October 20, 1981Assignee: Ciba-Geigy CorporationInventors: Ferdinand Gutekunst, Rolf Schmid
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Patent number: 4260748Abstract: Morpholine is produced by the catalytic hydrogenation of bis (cyanomethyl) ether.Type: GrantFiled: March 7, 1980Date of Patent: April 7, 1981Assignee: Air Products and Chemicals, Inc.Inventors: Dale D. Dixon, Randall J. Daughenbaugh
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Patent number: 4247482Abstract: A process is provided for producing bis-(N,N-dialkylamino)alkyl ethers of the formula (R.sub.2 NR').sub.2 O, wherein R is a methyl or ethyl group and R' is a bivalent alkylene group having from 2 to 3 carbon atoms. The novel process is effected by a two-step, preferably "one pot," reaction that utilizes SO.sub.3 vapor and R.sub.2 NR'ONa as reactants, wherein R and R' are defined above. The resulting bis-ethers are useful as catalysts in the production of polyurethanes, especially cellular polyurethanes.Type: GrantFiled: December 13, 1979Date of Patent: January 27, 1981Assignee: Union Carbide CorporationInventor: Fedor Poppelsdorf
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Patent number: RE32174Abstract: Combinations of certain hydroxy amines, particularly the "Ethomeens," and hydrocarbon-soluble carboxylic dispersants are useful as engine and carburetor detergents for normally liquid fuels. The preferred compositions are those in which the carboxylic dispersants are the reaction products of substituted succinic acids with polar compounds, especially with amines such as ethylene polyamines.Type: GrantFiled: October 25, 1984Date of Patent: June 10, 1986Assignee: The Lubrizol CorporationInventor: William M. LeSuer