Carbonyl Dihalide Reactant (e.g., Phosgene, Etc.) Patents (Class 560/347)
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Patent number: 4948917Abstract: Process for the preparation of .beta.-chloroethylsulfonylaryl isocyanates of the formula (1)Cl--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NCO (1)wherein A is a phenylene radical, which can contain substituents from the series comprising alkyl(C.sub.1 -C.sub.6), alkoxy(C.sub.1 -C.sub.6), chlorine, bromine and nitro, or a naphthylene radical, by allowing at least 2 moles of phosgene to act on 1 mole of .beta.-hydroxyethylsulfonyl-arylamine of the formula (2)HO--H.sub.2 C--H.sub.2 C--O.sub.2 S--A--NH.sub.2 (2)wherein A has the abovementioned meaning, in the presence of a catalyst at temperatures of about 100.degree. to 200.degree. C., if appropriate in an inert solvent.Type: GrantFiled: February 14, 1990Date of Patent: August 14, 1990Assignee: Hoechst AktiengesellschaftInventor: Hans H. Steuernagel
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Patent number: 4922005Abstract: Hexamethylene diisocyanate (HDI) is prepared by introducing a hexamethylenediamine (HDA) solution and an equivalent amount or more of hydrogen chloride gas simultaneously into a turbulent zone in the vicinity of an agitating blade in an inert organic solvent held under agitation within a tank-shaped reactor and allowing them to undergo a successive salt-forming reaction so as to obtain a high-concentration slurry of hexamethylenediamine hydrochloride (HDA.multidot.HCl) and then reacting the slurry with phosgene. The phosgenation is effected by charging an HDA.multidot.HCl slurry of a high concentration, such as that obtained by the above process, into a tank-shaped reactor held under a pressure above the atmosphere pressure but below 5 kg/cm.sup.2 G and controlling the amount of phosgene, which is to be blown into the reactor, at a level 1-18 molar times per hour the total amount of HDA.multidot.HCl and HDI in the reaction mixture.Type: GrantFiled: November 13, 1985Date of Patent: May 1, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masanobu Ajioka, Makoto Aiga, Masafumi Kataita, Akihiro Tamaki
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Patent number: 4918220Abstract: Toluene diisocyanate (TDI) is separated and recovered from the residues of the production thereof, e.g., from the tars of phosgenation of an aromatic diamine, by extracting such residues with an extractant which comprises an inert gas, e.g., CO.sub.2, in either the liquid or supercritical state, optionally in the presence of a coextractant diluent, for example an ester, aromatic hydrocarbon or chlorinated aromatic hydrocarbon, or chlorinated aliphatic hydrocarbon.Type: GrantFiled: January 13, 1989Date of Patent: April 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Gerard Collas, Georges Gros, Ferenc Sagi
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Patent number: 4851570Abstract: This invention relates to a process for the continuous production of an organic monoisocyanate or polyisocyanate in a single stage reaction. A reaction mixture is formed by continuously mixing, at a temperature elevated above room temperature but not exceeding about 150.degree. C., a solution in a substantially inert organic solvent of a monoamine or polyamine corresponding to the monoisocyanate or polyisocyanate and a solution in a substantially inert organic solvent of phosgene. The reaction mixture is continuously passed upwards from below through a reaction column comprising at least 10 separate chambers separated by perforated plates, wherein each perforation of said perforated plates has a diameter of less than about 20 mm.Type: GrantFiled: October 27, 1988Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Gottfried Zaby, Helmut Judat, Siegbert Humburger, Stefaan de Vos, Rolf W. Eckermann
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Patent number: 4851571Abstract: The present invention is directed to a process for the production of a mono- and/or polyisocyanate by the phosgenation of a mono- and/or polyamine in a mixer which comprises(a) a casing having at least two inlets and at least one outlet,(b) a rotatable shaft extending through the casing,(c) at least one rotor disc attached to the shaft such that the rotor disc is perpendicular to the shaft,(d) at least one stator disc attached to the casing such that the stator disc is parallel to the rotor disc and has an opening such that the shaft can pass through the stator disc,(e) optionally at least one running wheel attached to the shaft and containing openings such that when the shaft is rotating the running wheel provides a pumping effect to the reaction mixture passing through the mixer,(f) at least one inlet through the casing for introducing a phosgene solution axially to the shaft and against the rotor disc,(g) at least one inlet through the casing for introducing a mono- and/or polyamine amine solution or suspeType: GrantFiled: May 5, 1988Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz Sauer, Hermann Dallmeyer, Uwe J. Zarnack, Berthold Keggenhoff, Bernd Weber
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Patent number: 4847408Abstract: The present invention relates to a process for the preparation of diisocyanates corresponding to the formulaOCN--R--NCOwhereinR denotes a (cyclo)aliphatic hydrocarbon group with up to 15 carbon atomsby phosgenation of the corresponding diamines represented by the formulaH.sub.2 N--R--NH.sub.2in the gas phase, characterized in that(a) the diamines in vapor form, optionally diluted with an inert gas or with the vapors of an inert solvent, and phosgene are separately heated to temperatures of about 200.degree. to 600.degree. C. and continuously reacted together in a cylindrical reaction chamber which is free from moving parts and heated to about 200.degree. to 600.degree. C., while a turbulent flow is maintained in the reaction chamber.Type: GrantFiled: April 25, 1988Date of Patent: July 11, 1989Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Frosch, Heinrich Grave, Herbert Stutz, Eckart Waldau, Peter Fuhrmann
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Patent number: 4820866Abstract: Diisocyanates corresponding to a specified formula are produced by reacting an alcohol corresponding to a specified formula with a nitrochlorobenzene in the presence of NaOH and/or KOH in powder form and a strongly polar, aprotic solvent to produce a dinitro compound corresponding to a specified formula. This dinitro compound is hydrogenated to form the corresponding diamine which diamine is phosgenated to produce the corresponding diisocyanate. The resultant diisocyanates may then be used as starting materials in polyisocyanate addition processes.Type: GrantFiled: August 12, 1987Date of Patent: April 11, 1989Assignee: Bayer AktiengesellschaftInventor: Josef Sanders
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Patent number: 4777283Abstract: Alkoxycarbonyl isocyanates are prepared from carbamic acid esters by reacting these with phosgene and adding a catalyst.Type: GrantFiled: December 31, 1986Date of Patent: October 11, 1988Assignee: Bayer AktiengesellschaftInventors: Andreas Krebs, Hermann Hagemann
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Patent number: 4745216Abstract: Polyisocyanates are produced by reacting a polyamide solution with a phosgene solution. After the product polyisocyanate has been recovered, the solvent or a portion of the solvent employed is treated with crosslinked polymers insoluble in the solvent which polymers contain primary and/or secondary alcoholic hydroxyl groups and/or primary and/or secondary amino groups. After treatment, the polymer and any reaction products are removed. The solvent may then be reused. Preferred solvents are chlorobenzene and o-dichlorobenzene. The preferred polymers are bead polymers or bead copolymers of (meth)acrylic acid or styrene/divinyl benzene copolymer.Type: GrantFiled: March 25, 1985Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Berthold Keggenhoff, Gunther Ellendt, Marcel Petinaux, Alfred Mitschker, Peter M. Lange
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Patent number: 4675437Abstract: Cycloaliphatic triisocyanates or isomer mixtures of such triisocyanates corresponding to the formula ##STR1## in which R represents hydrogen or a C.sub.1 -C.sub.4 alkyl group are produced by phosgenating the corresponding cycloaliphatic triamines or isomer mixtures of such triamines or a salt thereof.These triisocyanates are useful in the production of polyisocyanate addition products, particularly polyurethane coatings and lacquers.Type: GrantFiled: April 29, 1985Date of Patent: June 23, 1987Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Stefan Penninger, Michael Brockelt, Gunter Hammen, Herbert Stutz
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Patent number: 4657940Abstract: The present invention is directed to 4,4'-diisocyanato phenylbenzylether, its method of production by reaction of the corresponding diamine with phosgene and the use of the diisocyanate for the production of polyisocyanate polyaddition products, preferably polyurethane plastics.Type: GrantFiled: February 13, 1986Date of Patent: April 14, 1987Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Peter Heitkamper
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Patent number: 4650899Abstract: A liquid composition comprising a mixture of isomers of essentially diisocyanates having the diphenylmethane structure, the distribution by weight of isomers in the composition for each 100 parts by weight of the composition being:32 to 55% of the 4,4' isomer,30 to 45% of the 2,4' isomer,5 to 12% of the 3,4' isomer,4 to 10% of the 2,2' isomer, and2 to 5% of the 2,3' isomer;and the method of making the composition by first reacting a benzyl halide with benzene, followed by nitration, hydrogenation, and phosgenation.Type: GrantFiled: April 26, 1984Date of Patent: March 17, 1987Assignee: AtochemInventors: Jacques Kervennal, Henri Mathais, Raymond Commandeur
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Patent number: 4613687Abstract: A polyisocyanate or mixture of polyisocyanates in which the main component(s) correspond to the formula: ##STR1## in which R.sub.1, R.sub.2, and R.sub.3 each represent hydrogen or a saturated alkyl group containing from 1 to 12 carbon atoms, provided that at least two of these radicals represent hydrogen; andm, n, o and p each represent 0 or 1, provided that when m, n, o and/or p represent 0, the free valency is taken up by a hydrogen atom and that the sum of m+n+o+p is greater than 1 on a statistical average.Such polyisocyanate or mixture of polyisocyanates may be produced by first reacting a 4-nitrobenzyl halide, a 3-nitrobenzyl halide, a benzyl halide, a benzyl alcohol or a nitrobenzyl chloride isomer mixture with nitrobenzene, an alkyl-substituted nitrobenzene, an alkyl benzene or benzene in the presence of a Friedel-Crafts or an acid catalyst.Type: GrantFiled: August 17, 1981Date of Patent: September 23, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 4597909Abstract: The present invention is directed to a process for the production of polyamines of the diphenylmethane series having a high diamine content and a low 2,2'-diamino-diphenylmethane content by condensing aniline with formaldehyde in the presence of hydrochloric acid as catalyst, neutralizing the acid catalyst at the end of the condensation reaction and working up the polyamine mixture thus obtained by distillation, characterized in that(a) in a first reaction stage, from 2.0 to 3.5 moles of aniline are reacted with 1 mole of formaldehyde in the presence of hydrochloric acid or a condensation product produced from 2.0 to 3.5 moles of aniline and 1 mole of formaldehyde in the absence of acid catalyst is reacted in the presence of hydrochloric acid at a degree of protonation maintained at 40 to 60% at temperatures below 50.degree. C.Type: GrantFiled: February 21, 1985Date of Patent: July 1, 1986Assignee: Bayer AktiengesellschaftInventors: Berthold Keggenhoff, Enno Mahlmann, Willi Eifler, Gunther Ellendt
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Patent number: 4595744Abstract: Low melting point compositions, comprising a mixture of diisocyanate isomers having the diphenylethane structure, and containing by weight about:35 to 55% of 2,4' isomer,15 to 40% of 4,4' isomer,10 to 25% of 2,2' isomer,3 to 10% of 3,4' isomer, and3 to 8% of 2,3' isomer;to the method of making such compositions by the nitration of aromatic diphenylethane rings, followed by a hydrogenation and phosgenation; and polyurethanes formed utilizing such compositions.Type: GrantFiled: December 7, 1984Date of Patent: June 17, 1986Assignee: AtochemInventors: Jacques Kervennal, Henri Mathais
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Patent number: 4587058Abstract: A diisocyanate corresponding to the general formula: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 represent hydrogen or a C.sub.2 -C.sub.12 alkyl group provided that two of the radicals R.sub.1, R.sub.2 and R.sub.3 represent hydrogen and the third represents an alkyl group containing from 2 to 12 carbon atoms. Mixtures of diisocyanates in which the described diisocyanate is a major substituent are also within the scope of this disclosure. Such compounds and mixtures are made by reacting a nitrobenzyl halide, an unsubstituted benzyl halide or a benzyl alcohol in the presence of a Friedel-Crafts catalyst with an alkylbenzene or a nitroalkylbenzene and then converting the nitro groups to amino groups by hydrogenation or reduction. The thus-produced amino compound is then phosgenated to form the diisocyanate.The compounds and mixtures of the present invention are useful in the production of polyurethane plastics.Type: GrantFiled: August 7, 1981Date of Patent: May 6, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 4581174Abstract: The invention relates to a process for the continuous preparation of organic isocyanates, preferably polyisocyanates, through the reaction of organic amines, preferably polyamines, with phosgene in the presence of organic solvents under pressure, for example from 5 to 100 bar, at elevated temperatures, for example from 100 to 220.degree. C., whereby the reaction mixture is partially recycled, preferably using natural circulation, and the hydrogen chloride content in the reaction mixture prior to the addition of the amine is less than 0.5 percent by weight based on the total weight of the reaction mixture and the molar ratio of phosgene to NH.sub.2 group in the organic amines is from 12:1 to 200:1.Type: GrantFiled: January 25, 1985Date of Patent: April 8, 1986Assignee: BASF AktiengesellschaftInventors: Rainer Ohlinger, Harald Schnez, Ludwig Pfannenstiehl, Bernd Blumenberg, Hans J. Raabe
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Patent number: 4574059Abstract: Decane-1,10-diisocyanates corresponding to the formula ##STR1## wherein R.sub.1 is an alkyl or cycloalkyl radical, and R.sub.Type: GrantFiled: February 27, 1985Date of Patent: March 4, 1986Assignee: ATOCHEMInventors: Jacques Kervennal, Pierre Durual