Preparing By Reacting Carbonyl Containing Compound With Amino Nitrogen Containing Compound Patents (Class 564/331)
  • Patent number: 8986825
    Abstract: The invention relates to a resin curing agent having the formula (I), wherein R1 to R4 are each individually selected from linear or branched C1 to C5 alkyl, a process for its manufacture, blends of the reaction products, and two-component curable resin systems.
    Type: Grant
    Filed: March 1, 2011
    Date of Patent: March 24, 2015
    Assignee: Hexcel Composites Limited
    Inventors: Steve Mortimer, Neal Patel, John Cawse
  • Patent number: 8759585
    Abstract: The invention provides a process for preparing diphenylmethanediamine, comprising the steps of: a) reacting aniline with formaldehyde in the presence of an acid, b) neutralizing the predominant part of the acid with ammonia and/or aqueous ammonia solution, c) separating the reaction mixture from step b) into an aqueous phase and an organic phase, d) neutralizing the other part of the acid, present in the organic phase, with aqueous alkali metal hydroxide solution, e) separating the reaction mixture from step d) into an aqueous phase and an organic phase, f) treating the aqueous phase obtained in step c) or optionally the combined aqueous phases from steps c) and e) with at least one oxide or hydroxide of an alkaline earth metal, g) removing the ammonia obtained in step f).
    Type: Grant
    Filed: December 13, 2010
    Date of Patent: June 24, 2014
    Assignee: BASF SE
    Inventors: Markus Siegert, Torsten Mattke, Tilmann Steinmetz, Hans-Juergen Pallasch, Filip Nevejans
  • Patent number: 8558027
    Abstract: The present disclosure relates to compositions, systems, and methods of forming an amine (e.g., methylenedianiline (MDA)) using an acid catalyst including, for example, a metal oxide-silica catalyst calcined at temperature(s) of about ?500° C. to form a solid acid silica-metal oxide catalyst. A metal oxide of a solid acid silica-metal oxide catalyst may comprise alumina. A process for making a solid acid silica-metal oxide catalyst may comprise calcining an amorphous alumina-silica material at temperature(s) of about ?500° C. and/or under an anhydrous and/or inert atmosphere. A rearrangement reaction of the condensation product of aniline and formaldehyde in the presence of a solid acid silica-metal oxide catalyst may yield more MDA and/or more desirable isomer(s) of MDA than reactions performed with a corresponding catalyst calcined at temperature(s) of less than 500° C.
    Type: Grant
    Filed: August 14, 2009
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies Inc.
    Inventors: Heiko Weiner, David C. Molzahn, Robert J. Gulotty, Jr.
  • Publication number: 20120316262
    Abstract: The invention relates to a resin curing agent having the formula (I), wherein R1 to R4 are each individually selected from linear or branched C1 to C5 alkyl, a process for its manufacture, blends of the reaction products, and two-component curable resin systems.
    Type: Application
    Filed: March 1, 2011
    Publication date: December 13, 2012
    Applicant: HEXCEL COMPOSITES LIMITED
    Inventors: Steve Mortimer, Neal Patel, John Cawse
  • Publication number: 20120232307
    Abstract: The invention provides a process for preparing diphenylmethanediamine, comprising the steps of: a) reacting aniline with formaldehyde in the presence of an acid, b) neutralizing the predominant part of the acid with ammonia and/or aqueous ammonia solution, c) separating the reaction mixture from step b) into an aqueous phase and an organic phase, d) neutralizing the other part of the acid, present in the organic phase, with aqueous alkali metal hydroxide solution, e) separating the reaction mixture from step d) into an aqueous phase and an organic phase, f) treating the aqueous phase obtained in step c) or optionally the combined aqueous phases from steps c) and e) with at least one oxide or hydroxide of an alkaline earth metal, g) removing the ammonia obtained in step f).
    Type: Application
    Filed: December 13, 2010
    Publication date: September 13, 2012
    Applicant: BASF SE
    Inventors: Markus Siegert, Torsten Mattke, Tilmann Steinmetz, Hans-Juergen Pallasch, Filip Nevejans
  • Publication number: 20120046497
    Abstract: The invention relates to a process for preparing methylenediphenyldiamine (MDA) by reacting formaldehyde and aniline in the presence of an acidic catalyst, wherein the oxygen content in the process for preparing MDA is <10 000 ppm, based on all compounds present in the process. The invention further relates to the phosgenation of MDA to methylenediphenyl diisocyanate (MDI).
    Type: Application
    Filed: April 20, 2010
    Publication date: February 23, 2012
    Applicant: BASF SE
    Inventors: Eckhard Stroefer, Heiner Schelling, Robert Reinhardt, Michael Zoellinger, Daniel Breuninger, Markus Kraemer, Kai Thiele, Peter Van Den Abeel
  • Publication number: 20120035396
    Abstract: The invention relates to a process for preparing methylenediphenyldiamine (MDA), comprising the following steps a) to c): a) converting formaldehyde and aniline to aminal b) removing water from the aminal obtained in step a) to establish a water content of 0 to 5% by weight based on the aminal, and c) adding an acidic catalyst to the aminal having a water content of 0 to 5% by weight, which comprises using formaldehyde in step a) in the form of highly concentrated formaldehyde with a CH2O content of >50% by weight and preparing the formaldehyde by oxidative dehydrogenation from methanol.
    Type: Application
    Filed: April 19, 2010
    Publication date: February 9, 2012
    Applicant: BASF SE
    Inventors: Eckhard Stroefer, Kai Thiele, Michael Zoellinger, Johnny Moors, Jon S. Speier
  • Patent number: 7893301
    Abstract: The present invention provides a method of preparing polymethylene-polyphenyl-polyamine (briefly referred to as polyamine, DAM), in which a high gravity rotating bed is used as the mixing reactor of formaldehyde and aniline hydrochloride, the mixing solution of aniline hydrochloride and circulation solution and the formaldehyde are fed into the high gravity rotating bed reactor proportionally to carry out mixing and condensation reaction under a condition of a very high gravity; the materials leaving the high gravity rotating bed reactor is introduced into a stirred vessel to proceed with the pre-condensation reaction and obtain a condensation solution; and the process steps of heating, molecular rearrangement, neutralization, water washing and purification, etc. are completed to obtain the refined DAM.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: February 22, 2011
    Assignees: Ningbo Wanhua Polyurethanes Co., Ltd., Beijing University of Chemical Technology
    Inventors: Jiansheng Ding, Jianfeng Chen, Hongke Zhang, Haikui Zou, Weiqi Hua, Pengyuan Zhang, Shuchang Sun, Guangwen Chu, Limin Xu
  • Publication number: 20100105951
    Abstract: The invention provides a process for preparing diphenylmethanediamine, comprising the steps of a) reacting aniline with formaldehyde in the presence of an acid, b) neutralizing the acid with ammonia, c) separating the reaction mixture from step b) into an aqueous phase and an organic phase, d) treating the aqueous phase obtained in step c) with an oxide or hydroxide of an alkaline earth metal, e) separating off the ammonia obtained in step d).
    Type: Application
    Filed: January 2, 2008
    Publication date: April 29, 2010
    Applicant: BASF SE
    Inventors: Veronika Wloka, Torsten Mattke, Daniel Breuninger
  • Publication number: 20090240077
    Abstract: The present invention relates to a process for producing diamines and polyamines of the diphenylmethane series (MDA) by reacting aniline and formaldehyde in the presence of an acid catalyst, wherein the aniline contains in total less than 0.5 wt. %, based on the total weight of aniline, of one or more compounds which contain at least one carbonyl group or of one or more compounds that are formed by reaction of these compounds which contain at least one carbonyl group with aniline.
    Type: Application
    Filed: March 17, 2009
    Publication date: September 24, 2009
    Applicant: Bayer MaterialScience AG
    Inventors: Stefan Wershofen, Heinz-Herbert Muller, Richard Adamson, Fritz Pohl, Knut Sommer
  • Patent number: 7528283
    Abstract: The invention provides an improved process for preparing diamines and polyamines from the diphenylmethane series by reacting aniline and formaldehyde in the presence of an acid catalyst, the improvement involving the aniline containing less than about 3 wt. % of diamines and polyamines from the diphenylmethane series, based on the weight of the aniline.
    Type: Grant
    Filed: January 24, 2007
    Date of Patent: May 5, 2009
    Assignee: Bayer MeterialScience AG
    Inventors: Fritz Pohl, Jeffrey Bolton, Richard Adamson, Heinz-Herbert Muller, Rudolf Uchdorf
  • Patent number: 7435853
    Abstract: Di- and polyamines of the diphenylmethane series are produced by a) converting nitrobenzene and methanol in the presence of a catalyst to aniline, formaldehyde and carbon monoxide, and then b) converting the aniline and formaldehyde produced in step a) in the presence of an acid catalyst to di- and polyamines of the diphenylmethane series, and c) converting the carbon monoxide produced in step a) with chlorine to phosgene.
    Type: Grant
    Filed: February 9, 2006
    Date of Patent: October 14, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Stefan Grabowski, Markus Dugal, Aurel Wolf
  • Patent number: 7408083
    Abstract: A process is described for preparing diaminodiarylmethanes comprising the steps a) reacting an aromatic amine with a methylene-donating agent in the presence of homogeneous acid catalysts, b) removing the homogeneous acid catalyst from the reaction product, c) working up and purifying the reaction product, which comprises removing the homogeneous acid catalyst from the reaction mixture by adsorption to a solid adsorbent.
    Type: Grant
    Filed: June 25, 2004
    Date of Patent: August 5, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Steinbrenner, Eckhard Stroefer, Martin Sohn, Veronika Quaschning, Helmut Moehwald, Kai Thiele, Filip Deberdt, Jan D. Jacobs, Rolf Pinkos
  • Patent number: 7247749
    Abstract: Novel monoamidine, monoamidoxime and bisamidine curatives, co-curatives and cure accelerators are provided for use with perfluoroelastomeric compositions as well as novel synthesis methods for making monoamidine- and monoamidoxime-based curatives, co-curatives and cure accelerators. Also provided are diphenyl-based curatives, co-curatives and cure accelerators having sufficiently high molecular weight such that the melting temperature of the curatives, co-curatives and cure accelerators is no greater than about 240° C., and more preferably no greater than about 230° C.
    Type: Grant
    Filed: January 29, 2004
    Date of Patent: July 24, 2007
    Assignees: Greene, Tweed of Delaware, Inc., Federal State Unitary Enterprise S.V. Lebedev Institute of Synthetic Rubber
    Inventors: Carl A. Aufdermarsh, Harshad P. Amin, Anestis Logothetis, Victor Gubanov, Margarita Volkova, Lioudmila Karmanova, Alexandr Kollar, Polina Troichanskaia, Gennady Emelianov, Vsevolod Berenblit
  • Patent number: 7041776
    Abstract: The invention relates to a method of producing polyisocyanates of the diphenylmethane series including the steps of a) reacting aniline and formaldehyde in the presence of HCl to provide a product mixture containing polyamines of the diphenylmethane series, HCl, aniline and water; b) removing excess aniline and water by distillation to provide a product mixture comprising polyamines of the diphenylmethane series, HCl, no more than 10 wt. % aniline based on the polyamines, and no more than 5 wt. % water based on the polyamines; and c) phosgenating the product mixture in (b).
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: May 9, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Daniel Koch, Hans-Georg Pirkl, Torsten Hagen, Stefan Wershofen
  • Patent number: 6846956
    Abstract: Described is a triarylmethane dye of the formula I where R1 and R2 are independently methyl, ethyl or hydroxyethyl, Q is substituted or unsubstituited phenyl or naphthyl and A? is the equivalent of an anion. It does not detach carcinogenic Michler's ketone.
    Type: Grant
    Filed: August 14, 2001
    Date of Patent: January 25, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Hellmut Kast, Thomas Gessner, Rainer Tresch
  • Patent number: 6831192
    Abstract: A process for preparing methylenedianiline by reacting aniline with formaldehyde in the presence of acid catalysts comprising, in a semicontinuous process, introducing aniline with or without acid catalyst, feeding formaldehyde with or without acid catalyst through a mixing element into a circuit in which aniline with or without acid catalyst and with or without previously added formaldehyde is circulated and, after feeding in at least 50% of the total amount of formaldehyde to be fed in, heating the reaction mixture to a temperature above 75° C. In addition, the invention relates to a process for preparing polyisocyanates by phosgenation of amines obtainable in this manner and to the polyisocyanates obtainable by this process.
    Type: Grant
    Filed: May 21, 2002
    Date of Patent: December 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Ströfer, Jan Jacobs, Wilfried Seyfert, Hans Volkmar Schwarz, Olaf Schweers, Volker Scharr, Ulrich Penzel
  • Patent number: 6818795
    Abstract: Process for the production of methylenedianiline and its higher homologous products which comprises reacting aniline, or one of its derivatives, and formaldehyde, or one of its precursors, in one or two reactors in the presence of a solid acid catalyst selected from a zeolite or a silico-alumina, distilling off the reaction water or the water added with the reagents.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: November 16, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Carlo Perego, Alberto De Angelis, Aldo Bosetti
  • Patent number: 6765079
    Abstract: Novel cross linked polymer films prepared from poly4-[(4-cardanylazo]benzoic acid and poly4-[(4-acryloylcardanylazo]benzoic acid are disclosed. The invention also relates to novel monomers 4-[(4-cardanylazo] benzoic acid and 4-[(4-acryloylcardanylazo] benzoic acid and polymers thereof as well processes for the preparation thereof.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: July 20, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Muthusamy Saminathan, Chennakkattu Krishna Sadasivan Pillai
  • Patent number: 6649798
    Abstract: The present invention concerns a process for the production of methylenedianiline (MDA) having a high monomer content.
    Type: Grant
    Filed: August 7, 2002
    Date of Patent: November 18, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Klein, Dirk Grotjohann, Christine Mendoza-Frohn, Daniel Koch, Heinz-Herbert Müller, Hans-Georg Pirkl, Rudolf Uchdorf, Gerhard Wegener
  • Patent number: 6639102
    Abstract: Polyisocyanates of the diphenyl methane series having reduced color values are obtained by a) reacting aniline and formaldehyde in the presence of an acid catalyst to form a polyamine, b) neutralizing the reaction mixture containing polyamine with a base, c) separating the neutralized mixture into the aqueous and the organic phases, d) adding a base to the organic phase and then e) phosgenating the resulting polyamine to produce the corresponding polyisocyanate.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: October 28, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Hagen, Friedhelm Kämper, Daniel Koch, Rudolf Uchdorf, Stefan Wershofen
  • Publication number: 20030171619
    Abstract: Process for the production of methylenedianiline and its higher homologous products which comprises reacting aniline or one of its derivatives, and formaldehyde, or one of its precursors in one or two reactors in the presence of a solid acid catalyst selected from a zeolite or a silico-alumina, distilling the reaction water or the water added with the reagents.
    Type: Application
    Filed: March 24, 2003
    Publication date: September 11, 2003
    Inventors: Carlo Perego, Alberto De Angelis, Carlo Perego
  • Patent number: 6610888
    Abstract: A method of reacting a solution comprising a mixture of chemical compounds which are in chemical equilibrium with one another with at least one further chemical compound (9) is provided. The method comprises the following steps: fractionation of the solution by means of a separation method to give at least two fractions (5, 6) which are enriched in different chemical compounds of the mixture; and reaction of a fraction (5) with the further chemical compound or compounds (9). The fractionation is advantageously carried out using a film evaporator (1). Unreacted fractions (6) can be recirculated via a residence time vessel (3) back to the fractionation step. The method is particularly suitable for reactions of an aqueous formaldehyde solution in which various components of the solution (formaldehyde, methylene glycol, polyoxymethylene glycols) react in different ways.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: August 26, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Ströfer, Stephan Scholl, Hans Hasse
  • Publication number: 20030045745
    Abstract: Polyisocyanates of the diphenylmethane series are produced by a) reacting aniline and formaldehyde in the presence of an acidic catalyst to produce a polyamine, b) neutralizing the reaction mixture from step a) with a base at a temperature of more than 110° C. or neutralizing the reaction mixture from step a) with a base and heating the neutralized mixture to a temperature of more than 110° C., and c) phosgenating the polyamine from step b) to convert it to the corresponding polyisocyanate.
    Type: Application
    Filed: August 20, 2002
    Publication date: March 6, 2003
    Inventors: Torsten Hagen, Friedhelm Kamper, Daniel Koch, Heinz-Herbert Muller
  • Patent number: 6433219
    Abstract: A process for preparing methylenedianiline by reacting aniline with formaldehyde in the presence of acid catalysts comprising, in a semicontinuous process, introducing aniline with or without acid catalyst, feeding formaldehyde with or without acid catalyst through a mixing element into a circuit in which aniline with or without acid catalyst and with or without previously added formaldehyde is circulated and, after feeding in at least 50% of the total amount of formaldehyde to be fed in, heating the reaction mixture to a temperature above 75° C. In addition, the invention relates to a process for preparing polyisocyanates by phosgenation of amines obtainable in this manner and to the polyisocyanates obtainable by this process.
    Type: Grant
    Filed: September 8, 2000
    Date of Patent: August 13, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Ströfer, Jan Jacobs, Wilfried Seyfert, Hans Volkmar Schwarz, Olaf Schweers, Volker Scharr, Ulrich Penzel
  • Patent number: 6329551
    Abstract: A phenylenediamine derivative represented by following formula (I) or (II): wherein R1 and R2 each represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; R3 represents a hydrogen atom or a methyl group; R4 represents a methyl group or an ethyl group; and n and m each is 1, 2, or 3; wherein R1 and R2 each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a cyano group; and n and m each is 1, 2, or 3, is disclosed. These phenylenediamine derivatives are effectively used as antioxidants for rubbers, which scarcely cause vanishing by evaporation or a thermal denaturation even under a high-temperature condition of 150° C. or higher.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: December 11, 2001
    Assignee: NOK Corporation
    Inventors: Seiji Nakagome, Akihiko Toda
  • Patent number: 5684180
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679840
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679841
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5675035
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5672737
    Abstract: The invention relates to a process for the fractionation and purification of mixtures of aromatic polyamines and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5663424
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648520
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648519
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5386059
    Abstract: The present invention encompasses an improved process for preparing polymethylene polyphenyl polyisocyanate comprising reacting phosgene with polymethylene polyphenyl polyamine, the improvement wherein the polymethylene polyphenyl polyamine is acidified prior to phosgenation.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: January 31, 1995
    Assignee: Miles Inc.
    Inventors: Jeffrey S. Bolton, Ramon Kalyanaraman, Steven L. Schilling, Clarence D. Blue
  • Patent number: 5359141
    Abstract: The invention relates to an improved process for the production of polynuclear aromatic polyamines by condensation of aniline with formaldehyde in the presence of water and acidic catalysts and working up of the reaction mixture by extraction with a hydrophobic solvent, the acid catalyst accumulating in the aqueous phase of the extraction step being reused.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: October 25, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt, Marcel Petinaux, Rudolf Uchdorf, Hans-Peter Schal
  • Patent number: 5310769
    Abstract: A process for production of polyamines of the diphenylmethane series through a condensation reaction of aniline with formaldehyde in the presence of an acid catalyst, neutralization of the acid catalyst after reaction completion, and distillation of the resultant polyamine mixture is described. The key feature of the process is the abrupt increase in reaction temperature after the condensation reaction or after the first rearrangement step.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: May 10, 1994
    Assignees: Bayer Aktiengesellschaft, Miles Inc.
    Inventors: Christian Konig, Manfred Gallus, Reinhold Wullner, Franz-Moritz Richter, Rudolf Uchdorf, William C. Forester
  • Patent number: 5286760
    Abstract: Disclosed herein is a process for preparing a reaction product containing methylene diphenylamine comprising reacting aniline with an aldehyde, in the presence of a low level of an acid wherein the acid level is reduced before digesting reaction mixture at a high temperature which is sufficient to effect a rearrangement of the intermediates to produce a reaction product containing methylene diphenylamines and low levels of impurities.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: February 15, 1994
    Assignee: Miles, Inc.
    Inventors: Jeffrey S. Bolton, Robert L. Mayen
  • Patent number: 5280100
    Abstract: The present invention relates to blocked polyisocyanates based on the reaction product ofi) an organic polyisocyanate comprising a member selected from the group consisting of bis-(4-isocyanatocyclohexyl)-methane, NCO prepolymers prepared from bis-(4-isocyanatocyclohexyl)-methane, polyisocyanate adducts prepared from bis-(4-isocyanatocyclohexyl)-methane, isocyanurate group-containing polyisocyanates prepared from 1,6-hexamethylene diisocyanate and isocyanurate and allophanate group-containing polyisocyanates prepared from 1,6-hexamethylene diisocyanate withii) methylamyl ketoxime.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: January 18, 1994
    Assignee: Miles Inc.
    Inventor: Lanny D. Venham
  • Patent number: 5208379
    Abstract: 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: Grant
    Filed: May 14, 1992
    Date of Patent: May 4, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Lau S. Yang, Diane A. Macarevich
  • Patent number: 5196591
    Abstract: The invention relates to an improved process for the production of polynuclear aromatic polyamines by condensation of aniline with formaldehyde in the presence of water and acidic catalysts and working up of the reaction mixture by extraction with a hydrophobic solvent, the acid catalyst accumulating in the aqueous phase of the extraction step being reused.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: March 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt, Marcel Petinaux, Rudolf Uchdorf, Hans-Peter Schal
  • Patent number: 5117061
    Abstract: Novel anilines of the 2,6-dialkyl-4-dialkylaminomethylaniline type are prepared by reacting a secondary amine and an aldehyde with a primary aniline reactant having a free para position and substituents in both ortho positions in the presence of an acid catalyst, the amounts of amine and acid employed being at least equimolar with respect to the amount of aldehyde, and the reaction being conducted by adding the primary aniline reactant to a preformed mixture of the secondary amine, aldehyde, and acid.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: May 26, 1992
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 5081251
    Abstract: Stilbene compounds of the general formula Ia, Ib or IcR.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.3 R.sup.4 R.sup.5 R.sup.6 (Ia)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 R.sup.4 R.sup.5 R.sup.6 --CH.dbd.CH--Ar.sup.3 R.sup.7 R.sup.8 R.sup.9 (Ib)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 (CH.sub.2).sub.n Ar.sup.3 --CH.dbd.CH--Ar.sup.4 R.sup.4 R.sup.5 R.sup.6 (Ic)where Ar.sup.1 to Ar.sup.4 are identical or different aromatic or quasi-aromatic radicals and n is from 0 to 20 and where either at least one of the radicals R.sup.1 to R.sup.6 or R.sup.9 is hydrocarbon-solubilizing alkyl, alkoxy, dialkylamino or diarylamino of 4 or more carbon atoms in the alkyl moiety or, if formula Ic contains no radicals R.sup.1 to R.sup.6, n is not less than 4, are prepared by metalating a toluene/xylene analog R.sup.1 R.sup.2 R.sup.3 ArCH.sub.3 or H.sub.3 CR.sup.4 R.sup.5 R.sup.6 ArCH.sub.
    Type: Grant
    Filed: September 7, 1989
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Dietmar Bender, Klaus Bronstert
  • Patent number: 5047591
    Abstract: Bis-(amino-nitrophenyl)-methane can be produced in one stage with an approximately quantitative yield by condensing o-nitraniline and formaldehyde in water at a temperature of between 20.degree. and 40.degree. C. in the presence of sulfuric acid, and subsequently rearranging the formed methylene-bis-(o-nitraniline) by treatment of the reaction mixture at a temperature of between 90.degree. and 100.degree. C.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: September 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Werner Stegmann
  • Patent number: 5026815
    Abstract: Chain-lengthening agents based on chlorinated 4,4'-methylenebisanilines for p-phenylene-methylenediisocyanate prepolymer are used for the preparation of cast polyurethane elastomers.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: June 25, 1991
    Assignee: Lonza Ltd.
    Inventors: Theodor Volker, Hans Althaus, Andreas Schmidt
  • Patent number: 4992575
    Abstract: N,N'-dimethyl aromatic diamines are prepared from the corresponding diprimary amines via a two step synthesis forming first the corresponding di-succinylimidomethylamine and then reductively cleaving the succinylimido group. The products are useful, e.g., as epoxy curing agents.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: February 12, 1991
    Assignee: American Cyanamid Company
    Inventor: Dalip K. Kohli
  • Patent number: 4978791
    Abstract: 2,2'-Dichloro-6,6'-diethylmethylene-bis-aniline or mixtures thereof with compounds of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are straight-chained or branched alkyl radicals having 2 to 4 C atoms, or R.sub.1 and/or R.sub.3 are chlorine and the remaining R's have the above-mentioned significance, as chain-extension means or cross-linkage means for polyurethanes or epoxide resins. Process for the production of 2,2'-dichloro-6,6'-diethylmethylene-bis-aniline or such mixtures. 2-ethyl-6-chloroaniline is condensed with itself or an aniline having the formula: ##STR2## wherein R.sub.5 and R.sub.6 are the same or different and are straight-chained or branched having 2 to 4 C atoms, with the proviso that R.sub.5 can also be chlorine, in acidic medium with formaldehyde or compounds which form formaldehyde. The compounds in the mixture can be condensation products of two molecules of such aniline derivatives.
    Type: Grant
    Filed: June 25, 1985
    Date of Patent: December 18, 1990
    Assignee: Lonza Ltd.
    Inventors: Theodor Volker, Hans Althaus
  • Patent number: 4950792
    Abstract: New methylenebis(metachloro)anilines which are chain-lenghtening agents or cross-linking agents for polyurethanes.
    Type: Grant
    Filed: June 9, 1988
    Date of Patent: August 21, 1990
    Assignee: Lonza Ltd.
    Inventors: Hans Althaus, Theodor Volker, Andreas Schmidt
  • Patent number: 4924028
    Abstract: This invention relates to an improved process for the preparation of polynuclear aromatic polyamines in which the reaction product is prepared by condensing aniline with formaldehyde in the presence of water and acidic catalysts and is worked up by extraction with a hydrophobic solvent. The acid catalyst that accumulates in the aqueous phase during the extraction process is reused.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: May 8, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt, Marcel Petinaux, Rudolf Uchdorf
  • Patent number: 4792624
    Abstract: 'An improvement is described in the process of preparing polymethylene polyphenyl polyamines by condensing aniline and formaldehyde in the presence of an acid catalyst. The improvement entails adding a minor proportion of a polyamine mixture comprising di(aminophenyl)methanes and oligomeric polymethylene polyphenyl polyamines, collectively known as polymethylene polyphenyl polyamines or polymeric MDA, to an intermediate stage of the condensation reaction where the various intermediately formed aminobenzylamines are present. The process lends itself to either a batch or continuous method for preparing the polyamines.The improvement is actually observed in the polymethylene polyphenyl polyisocyanates derived from the polyamines which have substantially reduced color over those polyisocyanates prepared from polyamines prepared via a prior art method. Such color improvements invariably carry over to polyurethane products derived therefrom.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: December 20, 1988
    Assignee: The Dow Chemical Company
    Inventors: Richard Hatfield, Jr., Howard R. Steele, Nirad N. Shah