Plural Hetero Atoms In The Hetero Ring Patents (Class 540/202)
  • Patent number: 6248733
    Abstract: This invention relates to the use of compounds having the general structure: wherein: Z1 and Z2 each independently represent an arene nucleus, which has from 5 to 14 ring atoms; G1 and G2 each independently represent a metal ligating group; R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfoxyl group, an arylsulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido group, a carbamoyl group, a suffamoyl group, a formyl group, an acyl group, a ureido group, an aryloxycarbonyl group, a silyl group, or a sulfoalkoxy group; L1 represents a nitrogen heterocycle; L2 represents a monodentate or polydentate (e.g.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: June 19, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Kevin D. Landgrebe, Charles E. Shelburne, Terrance P. Smith, Gregory D. Cuny
  • Patent number: 6191181
    Abstract: The present invention relates to urethane acrylates, which may be cured with high-energy radiation, in which the urethane acrylates are the reaction product of a) a polyisocyanate component containing 20 to 100 mole %, based on the moles of the polyisocyanate component a), of iminooxadiazine dione group-containing polyisocyanate trimers corresponding to formula A  wherein R1, R2and R3 are the same or different and represent linear or branched, C4-C20 (cyclo)alkyl groups and X is the same or different and represents isocyanate groups or isocyanate group-containing radicals that also contain iminooxadiazine dione, isocyanurate, uretdione, urethane, allophanate, biuret or oxadiazine trione groups, wherein R1, R2 and R3 are attached to a nitrogen atom, with b) an alcohol component containing at least one monobasic, hydroxy-functional, linear or branched C1-C12 alkyl ester of (meth)acrylic acid.
    Type: Grant
    Filed: November 4, 1999
    Date of Patent: February 20, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jan Weikard, Wolfgang Fischer, Frank Richter, Christian Zwiener
  • Patent number: 6184216
    Abstract: Compounds selected from the group consisting of formulae III, IV, VI and VIII wherein R is H is NH2, or a pharmacologically acceptable salt thereof, are suitable for use in methods for treating non-insulin-dependent diabetes mellitus (NIDDM) or obesity in a patient susceptible to or experiencing NIDDM or obesity by the systemic administration of such a compound in an amount effective to treat the NIDDM or obesity.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: February 6, 2001
    Assignee: Pharmacia & Upjohn Company
    Inventors: Scott D. Larsen, Martin D. Meglasson, Valerie A. Vaillancourt, Paul D. May
  • Patent number: 6180745
    Abstract: The present invention relates to moisture-curable compositions which have a) a content of (cyclo)aliphatically-bound isocyanate groups (calculated as NCO, MW 42) of 0.2 to 22% by weight and b) a content of succinyl urea groups (calculated as —NH—CO—N—, MW 57) of 0.1 to 14% by weight, and c) an equivalent ratio of (cyclo)aliphatically-bound isocyanate groups to succinyl urea groups of 4:1 to 1:1, wherein the preceding percentages are based on resin solids content of the moisture-curable compositions. The present invention also relates to coating, adhesive or sealing compositions containing these moisture-curable compounds as the binder.
    Type: Grant
    Filed: November 8, 1999
    Date of Patent: January 30, 2001
    Assignee: Bayer Corporation
    Inventor: Richard R. Roesler
  • Patent number: 6156863
    Abstract: A urea- and uretdione-functional polyaddition compound having free, partially or totally blocked isocyanate groups and having the following structure: ##STR1## wherein the substituents are defined as follows: ##STR2## n: 1-20; R.sub.1 is R or a linear, branched or cyclic alkylene or phenylene radicals having 2-16 carbon atoms;R.sub.2, R.sub.3 are each H, R.sub.4 or a ##STR3## R.sub.4, R.sub.5 are each identical or different hydrocarbon radicals having 1-14 carbon atoms;prepared by reacting isophorone diisocyanate-uretdione with diamine mixtures comprising 1-60 mol % diprimary diamines, 1-98 mol % primary/secondary diamines and 1-98 mol % disecondary diamines.
    Type: Grant
    Filed: April 15, 1999
    Date of Patent: December 5, 2000
    Assignee: Huels Aktiengesellschaft
    Inventor: Andreas Wenning
  • Patent number: 6150457
    Abstract: The present invention relates to compounds containing modified hydrazide groups and corresponding to formula I ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from a monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,X represents OR' or NHR' andR' represents a group which is inert to isocyanate groups under the conditions used to form the compound of formula I andn has a value of 2 to 6.The present invention also relates to one-component, thermoset coating compositions containing the compounds of formula I and a cross-linking component that is reactive with these compounds. Finally, the present invention relates coatings, sealants and adhesives prepared from these thermoset compositions.
    Type: Grant
    Filed: November 23, 1998
    Date of Patent: November 21, 2000
    Assignees: Bayer Corporation, Bayer Aktiengesellscaft
    Inventors: Sze-Ming Lee, Douglas A. Wicks, Eberhard Koenig, Carol L. Kinney, Karen M. Henderson
  • Patent number: 6043332
    Abstract: The present invention relates to a process for the production of polyisocyanates containing uretdione groups bya) oligomerizing a portion of the isocyanate groups of diisocyanates having aliphatically and/or cycloaliphatically bound isocyanate groups in the presence of catalysts or catalyst systems which accelerate the dimerization of isocyanate groups and in the presence of trisubstituted phosphite stabilizers corresponding to formula (I) ##STR1## b) optionally termination of the oligomerization reaction at a degree of oligomerization of 10 to 60% by adding a catalyst poison andc) optionally removing unreacted diisocyanate by extraction or thin-layer distillation.The present invention also relates to the use of the resulting uretdione polyisocyanates as a starting component for polyurethane plastics, particularly as an isocyanate component for the production of uretdione hardeners for powder coating compositions.
    Type: Grant
    Filed: August 5, 1998
    Date of Patent: March 28, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Laas, Reinhard Halpaap, Hans-Ulrich Meier-Westhues, Ulrich Freudenberg
  • Patent number: 5961878
    Abstract: The invention relates to non-crystallising, amine-blocked polyisocyanates, to the preparation thereof and to their in one-component polyurethane stoving compositions, in particular for coil-coating applications.
    Type: Grant
    Filed: September 2, 1998
    Date of Patent: October 5, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Konig, Karl-Ludwig Noble, Christian Fussel
  • Patent number: 5945531
    Abstract: A polyisocyanate composition, comprising:A) from 55 to 87% by weight of a polyisocyanate which contains uretdione groups;B) from 10 to 30% by weight of blocking agent,C) from 3 to 30% by weight of polyol having more than two hydroxyl groups and/or chain extender having more than two hydroxyl groups, wherein the polyisocyanate contains more than two terminal, partially or fully blocked isocyanate groups and has a molecular weight of from 1000 to 10,000.
    Type: Grant
    Filed: December 8, 1997
    Date of Patent: August 31, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Rainer Gras
  • Patent number: 5919887
    Abstract: A process for decoloring polyisocyanates containing isocyanurate and uretdione groups comprises treating the demonomerized polyisocyanates containing isocyanurate and uretdione groups with oxygen.
    Type: Grant
    Filed: May 19, 1997
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Graf, Ernst Deuker, Stefan Wolff, Ludwig Schuster, Serge Wack, Richard Hardt
  • Patent number: 5914383
    Abstract: The present invention relates to a polyisocyanate mixture containing isocyanate trimers provided thati) 30 to 100 mole percent of the trimers are iminooxadiazine diones B and ##STR1## ii) 0 to 70 mole percent of the trimers are isocyanurates A iii) less than 10 mole percent of the polyisocyanate mixture is of the uretone imine structural type, andiv) the ratio of the sum of the mole percents of trimers A and B to the mole percent of uretdiones is greater than 4:1whereinR.sup.1, R.sup.2 and R.sup.3 are the same or different and represent the groups obtained by removing an isocyanate group from an aliphatic, cycloaliphatic, aromatic and/or araliphatic isocyanate having an NCO content of less than 70% and/or their oligomers.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: June 22, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frank Richter, Josef Pedain, Harald Mertes, Carl-Gerd Dieris
  • Patent number: 5912314
    Abstract: A Polyaddition product, containing uretdione groups, which is obtainable by reaction of (A) a diisocyanate mixture which contains uretdione groups and comprises (1) at least 40 mol % to not more than 80 mol % of isophorone diisocyanate containing uretdione groups and (2) not more than 60 mol % and not less than 20 mol % of hexamethylene diisocyanate containing uretdione groups, with (B) a disecondary diamine, in an NCO/NH ratio of 1:0.5 to 1:0.9 at room temperature to 60.degree. C. in a solvent which is inert towards isocyanates.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: June 15, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Elmar Wolf
  • Patent number: 5889022
    Abstract: Novel indole, indoline and quinoline derivatives of formula (I) processes for their preparation, pharmaceutical compositions containing them, and their use in medicine is disclosed. A structurally distinct class of compounds have now been discovered and have been found to exhibit 5HT.sub.1-D antagonist activity. In a first aspect, the present invention therefore provides a compound of formula (I) or a salt thereof, in which P is a 5-7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulphur, A, B, m, R.sup.1 -R.sup.8 are defined in the application.
    Type: Grant
    Filed: June 20, 1996
    Date of Patent: March 30, 1999
    Assignee: SmithKline Beecham, p.l.c.
    Inventors: Laramie Mary Gaster, Paul Adrian Wyman
  • Patent number: 5859164
    Abstract: Uretdione-functional polyaddition compounds of the formula: ##STR1## where: ##STR2## R.sup.1 is R or linear, branched or cyclic alkylene radicals of 2-16 carbon atoms,R.sup.2 and R.sup.3 are identical or different hydrocarbon radicals of 1-14 carbon atoms,R.sup.4 is R.sup.
    Type: Grant
    Filed: September 15, 1997
    Date of Patent: January 12, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Joern Volker Weiss, Elmar Wolf, Felix Schmitt
  • Patent number: 5847067
    Abstract: Urea- and uretdione-functional polyisocyanates having the following formula (I): ##STR1## where ##STR2## n is an integer of from 1 to 20; R.sup.1, R.sup.3 =not more than one linear or branched (cyclo)alkyl radical having 1-14 carbon atoms or H and at least one of the formula: ##STR3## R.sup.2 =R, linear or branched (cyclo)alkyl radical having 6 carbon atoms; R.sup.4, R.sup.5 =identical or different hydrocarbon radicals having 1 to 14 carbon atoms.
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: December 8, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Rainer Gras
  • Patent number: 5795950
    Abstract: The present invention provides straight-chain crystalline polyuretdione which has a structure represented by formula (1): ##STR1## wherein Y represents ##STR2## X represents ##STR3## or --NCO; R.sub.1 is R.sub.2 or ##STR4## R.sub.2 is a residual group other than diol; R.sub.3 is a residual group obtained by removing an active hydrogen from a compound having one active hydrogen; R.sub.4 is a residual group obtained by removing two NCO groups from diisocyanate; and n is 1 or more,in formula (1), Y being replaced with a triazine ring represented by ##STR5## in the range of 0 to 15%, the polyuretdione having a latent NCO group content of 12 to 21% by weight, a weight-average molecular weight of 2000 to 20000 and a melting point of 60.degree. to 140.degree. C., and being not blocked at 40.degree. C. or less. The straight-chain crystalline polyuretdione of the present invention can be used as a hardener for powder coatings and does not cause a bad smell due to a blocking agent during baking of coating.
    Type: Grant
    Filed: November 18, 1996
    Date of Patent: August 18, 1998
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kenshi Sugimoto, Shinji Suzuki, Ichiro Ibuki
  • Patent number: 5773550
    Abstract: Isocyanurate- and uretdione-group-containing polyaddition product of an isophorone diisocyanate comprising the reaction product of:i) an isophorone diisocyanate which contains isocyanurate groups and uretdione groups; andii) a diol component selected from the group consisting of a diol, a disecondary diamine, a linear hydroxyl-containing polyester and a mixture thereof,wherein said isophorone diisocyanate comprises not more than 2% by weight of free isophorone diisocyanate and .gtoreq.5 wt. % of isophorone diisocyanate isocyanurate,wherein said isophorone diisocyanate is reacted with said diol component in an NCO/OH ratio of 1:0.5-1:0.95 and/or an NCO/NH ratio of 0.5:1 0.95:1.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: June 30, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Elmar Wolf
  • Patent number: 5750629
    Abstract: The present invention relates to a process for preparing pure bis(isocyanatoalkyl)monouretdiones corresponding to formula (I) ##STR1## wherein R represents identical or different, linear or branched alkyl groups having 4 to 9 carbon atoms,by oligomerizing at least a portion of the isocyanate groups of aliphatic diisocyanates in the presence of catalysts which accelerate the dimerization of isocyanate groups, terminating the reaction at the desired degree of oligomerization, removing unreacted excess diisocyanate by extraction or thin film distillation to obtain a distillation residue, subjecting the distillation residue to thin film distillation at a temperature of 160.degree. to 220.degree. C. and a pressure of 0.01 to 1.0 mbar and obtaining bis(isocyanato-alkyl)monouretdiones corresponding to formula (I) as the distillate.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: May 12, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Laas, Reinhard Halpaap, Josef Pedain, Klaus Konig
  • Patent number: 5593827
    Abstract: The compound N-(.beta.-ketocaproyl)L-homoserine lactone is shown to be an autoinducer that enhances gene expression in a wide variety of microorganisms. Use can be made of this property for diagnostic purposes, e.g., when gene expression causes bioluminescence or antibiotic production, or to promote bacterial growth. The invention claims use for these purposes of the compound and analogs of formula (I) where n is 2 or 3, each of X and Y is O, S or NH, and R is optionally-substituted C1-C12 alkyl or acyl. Some of these are also claimed as new compounds.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: January 14, 1997
    Assignee: The University of Nottingham
    Inventors: Barrie W. Bycroft, Paul Williams, Gordon S. A. B. Stewart, Siri R. Chhabra, Paul Stead, Michael K. Winson, Philip J. Hill, Catherine E. D. Rees, Nigel J. Bainton
  • Patent number: 5591846
    Abstract: New nonionic radiographic contrast agents having the formula ##STR1## wherein Y is a single bond, ##STR2## R.sub.1, R.sub.1 ' and R.sub.2 are the same or different and are hydrogen, alkyl or hydroxyalkyl.Hydroxyalkyl refers to such alkyl groups having 1 or more hydroxy groups. Preferred hydroxyalkyl groups include: ##STR3## R.sub.3 and R.sub.4 are the same or different and are hydrogen, methyl or --CH.sub.2 CH.sub.2 OH; R.sub.5 is hydrogen, alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH or OH and R.sub.6 is alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH, OH or hydrogen and may be the same or different than R.sub.5 and m is zero or one, with the proviso that no methylene or methine carbon atom of the heterocyclic ring is attached to both a nitrogen and an oxygen atom with the additional proviso that when Y is a single bond, m is not zero. These new contrast agents are water soluble and have desirable low osmolality and anticoagulant properties.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: January 7, 1997
    Assignee: Bracco International B.V.
    Inventors: Ramachandran S. Ranganathan, Thangavel Arunchalam, Edmund R. Marinelli, Radhakrishna K. Pillai
  • Patent number: 5565527
    Abstract: Polymeric, catalytically active compounds comprising polymer chains to which imidazole groups are linked terminally or laterally are used as catalysts for the dimerization of isocyanates.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Roland Minges, Christian Schade, Konrad Stiefenhoefer
  • Patent number: 5552507
    Abstract: Diisocyanates containing carboxylic acid ester groups corresponding to the formula: ##STR1## in which R and R.sup.1 represent specified groups are produced by phosgenation of the corresponding diamines, optionally present in the form of an ammonium salt. These diisocyanates are useful as starting materials in the production of plastics containing urethane and/or urea groups and as starting materials for the production of intermediate products used for the production of such plastics.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: September 3, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Wamprecht, Klaus Jost, Stefan Penninger
  • Patent number: 5532228
    Abstract: The invention discloses side-chain homologous vitamin D derivatives of formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, B, and D have the meanings defined in the specification and either (1) A is a direct bond between carbon atoms 20 and 22 and X is an oxy alkylene radical, --(CH.sub.2).sub.n O-- where n is 1 to 3; (2) A is a methylene bridge, --CH.sub.2 --, between carbon atoms 20 and 22 and X is either an alkylene radical, --(CH.sub.2).sub.n -- or an oxy alkylene radical, --(CH.sub.2).sub.n O--, where n is 1 to 3; or (3) if A is a direct bond and B and D together form a second bond, then X(R.sup.5) (R.sup.6) is ##STR2## The compounds possess proliferation-inhibiting and cell-differentiating activity.
    Type: Grant
    Filed: June 1, 1993
    Date of Patent: July 2, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Gunter Neef, Gerald Kirsch, Andreas Stein-Eyer, Katica Schwarz, Matthias Brautigam, Ruth Thieroff-Ekerdt, Petra Rach
  • Patent number: 5484916
    Abstract: In a process for the preparation of polyisocyanates containing uretdione groups by catalytic dimerization of monomeric isocyanates, the catalysts employed are polymers carrying imidazole groups.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: January 16, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Roland Minges, Christian Schade
  • Patent number: 5461135
    Abstract: Disclosed herein is a liquid, monoallophanate-containing, monouretidione-containing polyisocyanate composition characterized by having (i) an isocyanate functionality of between 2.8 and 6.5, (ii) a free NCO content of 10% to 47% by weight, (iii) a viscosity of less than 1000 cp (25.degree. C.), and (iv) the presence of monouretidione and monoallophanate groups in a molar ratio of said monouretidione groups to said monoallophanate groups of between about 20:1 and about 1:5. Also disclosed is a process for producing the above compositions, as well as their use, optionally in blocked form in one or two component coating compositions.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: October 24, 1995
    Assignee: Olin Corporation
    Inventors: Adam G. Malofsky, Stephen L. Goldstein
  • Patent number: 5449775
    Abstract: Polymeric, catalytically active compounds comprising polymer chains to which imidazole groups are linked terminally or laterally are used as catalysts for the dimerization of isocyanates.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Roland Minges, Christian Schade, Konrad Stiefenhoefer
  • Patent number: 5409921
    Abstract: Compounds characterized generally as thiazetidinyl-terminated alkylamino ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; wherein X is selected from oxygen atom and methylene; wherein B is a thiazetidinyl group; wherein R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; wherein R.sub.2 is phenylmethyl; wherein each of R.sub.3 and R.sub.5 is hydrido; wherein R.sub.4 is selected from--(CH.sub.2).sub.q --C.tbd.C-Vwherein V is selected from hydrido and methyl; wherein R.sub.6 is cyclohexylmethyl; wherein R.sub.7 is selected from isobutyl, cyclopropyl and cyclopropylmethyl; wherein q is a number selected from zero through three, inclusive; and wherein n is a number selected from zero through three, inclusive; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: April 25, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, Robert E. Manning
  • Patent number: 5329003
    Abstract: The invention deals with a process for the preparation of uretdione group containing polyisocyanates comprising reacting monomeric aromatic diisocyanates in the presence of a catalyst whereby imidazoles or benzimidazoles having general structure formulas I or II are used as catalysts ##STR1## or their mixtures are used whereby R.sup.1 through R.sup.7 have the meaning cited in claim 1.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: July 12, 1994
    Assignee: BASF Aktiengesellschaft
    Inventor: Bernd Bruchmann
  • Patent number: 5315004
    Abstract: This invention relates to a process for preparing a dimer by the steps of: (a) cyclodimerizing a polyisocyanate in the presence of a dimerization catalyst which is covalently bound to an insoluble inorganic matrix by contacting said polyisocyanate with said catalyst at a temperature of between about 20 and about 135.degree. C. in a reaction to form an uretidione-containing cyclodimerized isocyanate wherein a portion of the isocyanate moieties comprising said polyisocyanate are converted to uretidione groups, and (b) separating said catalyst from said cyclodimerized isocyanate in order to stop said reaction after a desired amount of isocyanate moieties in said polyisocyanate have been converted to uretidione moieties.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: May 24, 1994
    Assignee: Olin Corporation
    Inventors: Stephen L. Goldstein, Anthony D. Hamer, Lawrence E. Katz, Michael J. McGeary, Curtis P. Smith
  • Patent number: 5283355
    Abstract: Compounds of the Formula (5) and processes for their preparation and use, particularly in the manufacture of unsymmetrical triphenodioxazine dyes: ##STR1## wherein: Y is H, alkyl, substituted alkyl, alkoxy, Cl or Br;R is a group of Formula (3) ##STR2## R.sup.1 and R.sup.2 are each independently alkyl, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an optionally substituted 4, 5 or 6 membered alicyclic or heterocyclic ring;R.sup.3 is H;Z is Cl, Br or A--NH; andA is H or the residue of a primary amine.
    Type: Grant
    Filed: October 22, 1991
    Date of Patent: February 1, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventor: William J. E. Norris
  • Patent number: 5258508
    Abstract: The present invention relates to a process for the preparation of oligomeric polyisocyanates in which(a) a portion of the isocyanate groups of organic polyisocyanates is oligomerized in the presence of catalysts that accelerate the dimerization of isocyanate groups, and(b) the oligomerization reaction is terminated after reaction of about 5 to about 45% of the isocyanate groups present in said organic polyisocyanates by the addition of a catalyst poison comprising a silylated acid corresponding to the formulaX--[Si(CH.sub.3).sub.3 ].sub.nwhereinX represents the neutral acid residue obtained by removal of the acidic hydrogen atoms from an n-basic acid having a pK.sub.a value of at most 3, other than a hydrohalic acid, andn is an integer of 1 to 3.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: November 2, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Scholl
  • Patent number: 5237058
    Abstract: The present invention relates to a process for the production of polyisocyanates containing uretdione and/or isocyanurate groups bya) partially oligomerizing the isocyanate groups of organic diisocyanates to form uretdione and/or isocyanurate groups in the presence of catalysts containing trivalent phosphorus,b) terminating the oligomerization reaction at the desired degree of oligomerization by converting the catalyst into a catalytically inactive oxidized form by the addition of an oxidizing agent andc) subsequently removing unreacted diisocyanate by thin-layer distillation.The present invention also relates to the polyisocyanates containing uretdione and/or isocyanurate groups obtained by this process.Finally, the present invention also relates to the use of these polyisocyanates, optionally blocked with blocking agents for isocyanate groups, as the isocyanate component in polyurethane coating compositions.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: August 17, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans J. Laas, Reinhard Halpaap, Josef Pedain
  • Patent number: 5218111
    Abstract: The present invention relates to dimerization catalysts which are suitable for the dimerization of organic isocyanates by heterogeneous catalysis, wherein the catalysts contain tertiary phosphines adsorbed onto adsorbent, porous carrier materials having a particle size (90%) of 0.1 to 10 mm, a pore volume of 0.4 to 1.4 ml/g, an average pore diameter of 5 to 50 nm and a specific surface area (BET) of 100 to 700 m.sup.2 /g.The present invention also relates to a process for the preparation of these catalysts by the adsorption of tertiary phosphines onto these carrier materials, optionally in the presence of inert solvents.Finally, the present invention relates to the use of these catalysts for the preparation of polyisocyanates containing uretdione and isocyanurate groups by the dimerization and trimerization of a proportion of the isocyanate groups of organic diisocyanates.
    Type: Grant
    Filed: August 9, 1991
    Date of Patent: June 8, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Scholl
  • Patent number: 5216107
    Abstract: The present invention relates to a binder composition containinga) 20 to 70% by weight of oligomerization products of 1,6-diisocyanatohexane, the oligomerization products having isocyanate groups at least partially blocked with blocking agents for isocyanate groups and containing at least 50% by weight, based on the weight of the oligomerization products, of blocked uretdione diisocyanates corresponding to formula (I) ##STR1## wherein R represents the residue formed by removal of the active hydrogen atom from a monofunctional blocking agent, andb) 30 to 80% by weight of a polyol component containing a mixture ofb1) 100 parts by weight of an alkoxylation product of bisphenol A corresponding to formula (II) ##STR2## wherein R' is hydrogen or a methyl group and n is a whole or fractional number from 1 to 2,b2) 20 to 200 parts by weight castor oil andb3) 0 to 40 parts by weight of other organic polyhydroxyl compounds.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: June 1, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Pedain, Friedrich Schrader, Dieter Mager, Hans-Heribert Burgdorfer
  • Patent number: 5202358
    Abstract: The present invention relates to liquid storable organic isocyanates containing carbodiimide and/or uretone imine groups prepared by(a) partially carbodiimidizing isocyanate groups of an organic isocyanate with catalysts of the phospholine type, and(b) terminating the carbodiimidization reaction by the addition of a silylated acid corresponding to the formulaX--[Si(CH.sub.3).sub.3 ].sub.nin whichX represents the neutral acid residue obtained by removal of the acidic hydrogen atoms from an n-basic acid having a pK.sub.a value of at most 3, other than a hydrohalic acid, andn is an integer of 1 to 3.The invention further relates to the use of the liquid polyisocyanate mixtures according to the invention for the preparation of polyurethane plastics, preferably polyurethane foams, having improved burning behavior.
    Type: Grant
    Filed: May 18, 1992
    Date of Patent: April 13, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Rainer Welte
  • Patent number: 5149766
    Abstract: The present invention relates to a process for the preparation of uretdione group containing polyisocyanates comprising reacting monomeric aromatic diisocyanates in the presence of 1,2-dimethylimidazole used as a catalyst in an inert organic solvent whereby the weight ratio of solvent to diisocyanate lies in a range of from 0.1:1 to 2:1.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: September 22, 1992
    Assignee: BASF Aktiengesellschaft
    Inventor: Bernd Bruchmann
  • Patent number: 5143994
    Abstract: The present invention relates to polyisocyanate mixtures prepared from 1,6-diisocyanatohexane (HDI) and 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl cyclohexane (IPDI), which have a uretdione content (calculated as C.sub.2 N.sub.2 O.sub.2) of 8 to 25% by weight and an isocyanurate content (calculated as C.sub.3 N.sub.3.sub.O.sub.3) of not more than 24% by weight and containa) 20 to 60% by weight of uretdione diisocyanatesb) 0 to 40% by weight of isocyanurate triisocyanatesc) 15 to 60% by weight of higher homologues of the polyisocyanates of components a) and b) containing more than one uretdione ring and/or isocyanurate ring andd) a total of not more than 1% by weight of (HDI) and (IPDI).The present invention also relates to a process for the preparation of these polyisocyanate mixtures and to their use, optionally blocked with blocking agents for isocyanate groups, as the isocyanate component in polyurethane coating compositions.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: September 1, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans J. Laas, Reinhard Halpaap, Josef Pedain, Jurgen Mosbach
  • Patent number: 5122609
    Abstract: Novel cyclic N,N,N' and N,N,N',N'-substituted organyloxysilyl-functional silanes are prepared by reacting an aminopropyl silane with carbon disulfide and heating the dithiocarbamate.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: June 16, 1992
    Assignee: Degussa Aktiengesellschaft
    Inventors: Ulrich Deschler, Peter Kleinschmit
  • Patent number: 5100998
    Abstract: The invention relates to a process for improving the flowability and preventing the agglomeration of finely divided dimerized 2,4-toluene diisocyanate in which a precipitated silicas and/or pyrogenic silica having a hydrophobic surface is added to the finely divided dimerized 2,4-toluene diisocyanate. The invention also relates to the finely divided dimerized 2,4-toluene diisocyanate prepared by this process.
    Type: Grant
    Filed: January 8, 1991
    Date of Patent: March 31, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Richard Kopp, Gerhard Grogler, Heinrich Hess, Lutz Georgias, Helmut Hurnik, Hans D. Thomas
  • Patent number: 5073550
    Abstract: Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di-(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: December 17, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Erwin Gotschi
  • Patent number: 5010203
    Abstract: Novel cyclic N,N,N' and N,N,N',N'-substituted organyloxysilyl-functional silanes are prepared by reacting an aminopropyl silane with carbon disulfide and heating the dithiocarbamate.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: April 23, 1991
    Assignee: Degussa Aktiengesellschaft
    Inventors: Ulrich Deschler, Peter Kleinschmit
  • Patent number: 4988723
    Abstract: Benzopyran derivatives of formula (I) wherein the substituents are as defined herein are provided. The compounds possess vasodilating activity and are useful in the treatment of hypertension. Pharmaceutical compositions and methods of treating hypertension are also provided.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: January 29, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Youichi Shiokawa, Koichi Takimoto, Kohei Takenaka, Takeshi Kato
  • Patent number: 4987137
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof; ##STR1## wherein: R.sub.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen;R.sub.2 and R.sub.3 are both hydrogen or together represent a bond;R.sub.4 is hydrogen and R.sub.5 is hydrogen or R.sub.4 and R.sub.5 together represent an oxo group;R.sub.6 is C.sub.1-7 alkyl substituted by NR.sub.8 R.sub.9 where R.sub.8 and R.sub.9 are independently hydrogen or C.sub.1-4 alkyl or together are C.sub.3-7 polymethylene optionally containing a further heteroatom which is oxygen, sulphur or nitrogen substituted by R.sub.10 where R.sub.10 is hydrogen, C.sub.1-4 alkyl or benzyl, and optionally substituted by one or two C.sub.1-4 alkyl, C.sub.2-5 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminocarbonyl optionally substituted by one or two C.sub.1-6 alkyl groups or by a benzyl group, cyano, phenyl or benzyl and wherein any phenyl or benzyl group is optionally substituted in the phenyl ring by one or two halo, CF.sub.3, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: January 22, 1991
    Assignee: Beecham Wuelfing GmbH & Co., KG
    Inventors: Dagmar Hoeltje, Dietrich Thielke
  • Patent number: 4946837
    Abstract: A compound of the formula; ##STR1## wherein R.sup.0 stands for nitrogen-containing heterocyclic group, acyl group or amino-protecting group, Z stands for S, S.fwdarw.O, O or CH.sub.2, R.sup.4 stands for hydrogen atom, methoxy group or formamido group, R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted thiazol-3-yl group forming a fused ring at the 4,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof.This compound is novel and has excellent antibacterial activity.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: August 7, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
  • Patent number: 4929724
    Abstract: The invention is directed to a process for the production of uretdione group-containing compounds by dimerizing at least a part of the isocyanate groups of organic isocyanates in the presence of compounds containing phosphorus-nitrogen bonds as dimerization catalysts, characterized in that the reaction is carried out in the presence, as co-catalysts, of H-active organic compounds having a pKa-value of at least 6, which have at least one hydrogen atom bound to oxygen, sulphur or nitrogen.The invention also relates to the uretdione group-containing compounds obtained according to this process and to their use for the production of plastics materials according to the isocyanate-polyaddition process.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Theodor Engbert, Jurg Frohlich, Werner Kubitza, Peter Breidenbach, Gerhard Mennicken
  • Patent number: 4912210
    Abstract: A process for the preparation of a uretedione, comprising the steps of:(i) reacting at least one C.sub.6-15 (cyclo)aliphatic diisocyanate under substantially anhydrous conditions with a pyridine of the formula ##STR1## wherein R.sub.1 and R.sub.2 are, independent from one another, a C.sub.1-4 alkyl group or R.sub.1 and R.sub.2 taken together with the attached nitrogen form a pyrrolidine, piperidine or morpholine ring, to form a reaction mixture containing said uretedione, and(ii) isolating said uretedione from said reaction mixture by vacuum thin layer evaporation after the degree of dimerization in said reaction mixture has reached 10-80%.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: March 27, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Josef Disteldorf, Werner Huebel, Karl Schmitz
  • Patent number: 4868298
    Abstract: A continuous method for the high-yield, one-step, solvent-free manufacture of blocked polyisocyanurate compounds useful as curing agents in powder coating compositions. The preferred method of manufacture is to pre-mix a blocking agent and a polymerization catalyst (BAC mix) prior to injection with an organic isocyanate monomer having two or more isocyanate groups (herein termed a polyisocyanate) into a preheated reaction zone wherein the BAC mix and the polyisocyanate react to form the blocked polyisocyanurate compound that is obtained after discharge from the reaction zone and cooling.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: September 19, 1989
    Assignee: Cargill, Incorporated
    Inventor: Larry F. Brinkman
  • Patent number: 4835271
    Abstract: A compound of the formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: R.sub.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen;R.sub.2 and R.sub.3 are both hydrogen or together represent a bond;R.sub.4 is hydrogen and R.sub.5 is hydrogen or R.sub.4 and R.sub.5 together represent an oxo group;R.sub.6 is C.sub.1-7 alkyl substituted by NR.sub.8 R.sub.9 where R.sub.8 and R.sub.9 are independently hydrogen or C.sub.1-4 alkyl or together are C.sub.3-7 polymethylene optionally containing a further hetereoatom which is oxygen, sulphur or nitrogen substituted by R.sub.10 where R.sub.10 is hydrogen, C.sub.1-4 alkyl or benzyl, and optionally substituted by one or two C.sub.1-4 alkyl, C.sub.2-5 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminocarbonyl optionally substituted by one or two C.sub.1-6 alkyl groups or by a benzyl group, cyano, phenyl or benzyl and wherein any phenyl or benzyl group is optionally substituted in the phenyl ring by one or two halo, CF.sub.3, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: May 30, 1989
    Assignee: Beecham-Wuelfing GmbH & Co., KG
    Inventors: Dagmar Hoeltje, Dietrich Thielke
  • Patent number: 4831161
    Abstract: Prepare N-(amidoalkyl)imides by contacting an imide with a 2-oxazoline under reaction conditions, optionally in the presence of a solvent.
    Type: Grant
    Filed: June 24, 1987
    Date of Patent: May 16, 1989
    Assignee: The Dow Chemical Company
    Inventors: Pen-Chung Wang, Steven P. Crain
  • Patent number: 4826971
    Abstract: There are disclosed compounds having the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1-10 carbon atoms, phenyl or phenyl substituted with halo, lower alkyl, lower alkoxy, nitro, cyano or lower alkoxycarbonyl;R.sub.2 and R.sub.3 are phenyl or phenyl mono- or di- substituted with halo, lower alkyl, lower alkoxy, nitro, cyano, diloweralkylamino or lower alkoxycarbonyl and R.sub.2 and R.sub.3 may be the same or different; andR.sub.4 is alkyl of 1-10 carbon atoms, phenyl or phenyl mono- or di- substituted with halo, lower alkyl, lower alkoxy, cyano, nitro or lower alkoxycarbonyl;and their use as antifungal agents.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: May 2, 1989
    Assignee: American Home Products Corporation
    Inventor: Jerauld S. Skotnicki