Polycarbamic Patents (Class 560/25)
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Patent number: 5705593Abstract: The present invention relates to polyisocyanates prepared from diphenylmethane diisocyanate wherein at least 95% of the isocyanate groups are blocked with diethyl malonate and wherein the polyisocyanates have, based on solids,A) a content of unblocked and blocked isocyanate groups (calculated as NCO) of 9% to 13%,B) a content of allophanate groups (calculated as C.sub.2 HN.sub.2 O.sub.3, molecular weight 101) of 3% to 9% andC) a calculated average functionality of 2.0 to 2.5.The present invention also relates to a process for the production of these polyisocyanates and to their use as crosslinking agents for organic polyhydroxyl compounds in polyurethane stoving lacquers.Type: GrantFiled: September 10, 1996Date of Patent: January 6, 1998Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Josef Pedain, Theodor Engbert, Holger Casselmann, Frank Kobelka
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Patent number: 5703193Abstract: A process for reducing the amount of residual organic diisocyanate monomer in a polyurethane prepolymer reaction product mixture which comprises distilling the polyurethane prepolymer reaction product mixture in the presence of a combination of at least one inert first solvent with a boiling point below the boiling point of the residual organic diisocyanate monomer and at least one inert second solvent with a boiling point above the boiling point of the residual organic diisocyanate monomer, at a temperature which exceeds the vaporization temperature of the residual organic diisocyanate monomer and which is below the decomposition temperature of the polyurethane prepolymer.Type: GrantFiled: June 3, 1996Date of Patent: December 30, 1997Assignee: Uniroyal Chemical Company, Inc.Inventors: Ronald Owen Rosenberg, Ajaib Singh, Christopher James Maupin, Brian Scott Lombardo
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Patent number: 5698731Abstract: A process is described for the preparation of aromatic carbamates in which an organic carbonate in a stoichiometric quantity or in a quantity higher than the stoichiometric value is reacted with an aromatic amine operating in the presence of a carbamation catalyst, wherein this catalyst is selected from N,N-substituted carbamate complexes of zinc or copper.The process gives high yields and selectivity in the useful reaction product.Type: GrantFiled: June 27, 1996Date of Patent: December 16, 1997Assignee: Ministero dell `Universita` e della Ricerca Scientifica e TecnologicaInventors: Aldo Bosetti, Pietro Cesti, Fausto Calderazzo
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Patent number: 5696221Abstract: Elastomers with improved physical properties, particularly hardness and rebound, may be prepared by the diamine chain extension or moisture cure of low isocyanate group content, toluene diisocyanate-based prepolymers prepared from a polyol component comprising a high molecular weight, low unsaturation polyoxypropylene diol and a low molecular weight diol. The elastomers are useful for applications such as rollers and other applications where hardness and rebound are important.Type: GrantFiled: July 15, 1996Date of Patent: December 9, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Nigel Barksby, Bruce D. Lawrey, Susan M. Clift
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Patent number: 5693849Abstract: This invention is directed to a method for making an iodopropargyl carbamate in an aqueous reaction medium so as to yield a more pure and stable, e.g., U.V. resistant, product in a high yield, free from environmental hazards posed by using non-aqueous solvents as the reaction medium.Type: GrantFiled: October 30, 1996Date of Patent: December 2, 1997Assignee: Troy CorporationInventor: Milton Nowak
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Patent number: 5688988Abstract: A process is described for the preparation of aromatic urethanes in which organic carbonate in a stoichiometric quantity or in a quantity higher than the stoichiometric value is reacted with an aromatic amine operating in the presence of a carbamation catalyst, wherein this catalyst is selected from zinc and/or copper carbonate hydroxide.The process gives high yields and selectivity in the useful reaction product.Type: GrantFiled: June 27, 1996Date of Patent: November 18, 1997Assignee: Ministero dell'Universita' e della Ricerca Scientifica e TechnologicaInventors: Aldo Bosetti, Pietro Cesti, Emanuele Cauchi, Ignazio Prestifilippo
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Patent number: 5688875Abstract: A hydrophilic tetramethylxylylenecarbodiimide represented by the following formula (1): ##STR1## wherein n is an average polymerization degree and is an integer of 1 to 30; R.sub.1 is a residue of an organic compound having a hydrophilic segment and at least one functional group reactive with an isocyanate group; and X is a group formed by the reaction of the functional group with the isocyanate group. The carbodiimide is free from the problems of the prior art, has good storage stability and accordingly is usable as an easy-to-handle crosslinking agent for hydrophilic resin.Type: GrantFiled: May 31, 1995Date of Patent: November 18, 1997Assignee: Nisshinbo Industries, Inc.Inventors: Eiji Sasaki, Yasuo Imashiro, Ikuo Takahashi, Naofumi Horie
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Patent number: 5663435Abstract: Reaction products of amino-alkylenecarboxylic acids with polyoxyalkylene compounds are used as paraffin dispersants for mineral oil middle distillates.Type: GrantFiled: November 29, 1995Date of Patent: September 2, 1997Assignee: BASF AktiengesellschaftInventors: Gabriele Dralle-Voss, Knut Oppenlander, Klaus Barthold, Bernd Wenderoth, Wolfgang Kasel
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Patent number: 5648445Abstract: Allophanate-modified 1,3-phenylene diisocyanates or 1,1-biphenyl diisocyanates or 1,1'-oxy-bis-(isocyanato benzenes) which are storage stable liquid at 25.degree. C. are made by reacting the diisocyanate and a mono-alcohol to form an isocyanate containing urethane groups. The urethane groups in the diisocyanate are then converted to allophanate groups. The resultant product which has an isocyanate group content of from about 10 to about 40% may be further reacted with isocyanate-reactive compounds to produce an allophanate-modified diisocyanate prepolymer containing urethane or urea groups having an isocyanate group content of from about 5 to about 40.0%. The liquid, storage-stable, allophanate-modified diisocyanates produced by these processes are particularly useful in the production of elastomers and flexible foams.Type: GrantFiled: December 22, 1995Date of Patent: July 15, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins
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Patent number: 5648349Abstract: PLA.sub.2 inhibitors selected from the group consisting of ##STR1## wherein A is selected from the group consisting of ##STR2## and Z, W, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, X, X' and Y are as defined herein.Type: GrantFiled: April 27, 1995Date of Patent: July 15, 1997Assignee: Monsanto CompanyInventor: Patrick James Lennon
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Patent number: 5646328Abstract: Low-boiling by-products are removed from diurethanes prepared by a phosgene-free process by carrier vapor distillation using alcohol vapor, preferably the vapor of the basic alcohol found in the diurethane, as the carrier vapor. The diurethanes freed of low-boiling by-products in this manner may be thermally decomposed to produce diisocyanates.Type: GrantFiled: June 20, 1996Date of Patent: July 8, 1997Assignee: Bayer AktiengesellschaftInventors: Ludwig Deibele, Oswald Wilmes, Jurgen Dahmer
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Patent number: 5635542Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.Type: GrantFiled: June 16, 1995Date of Patent: June 3, 1997Assignee: Bayer AktiengesellschaftInventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel
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Patent number: 5623085Abstract: A method for reducing the amount of microfoam in a spray-applied clear waterborne composition is provided, the clear waterborne composition including an emulsion-polymerized addition polymer bearing at least one first reactive group and a reactive modifier bearing one second reactive group and a water-soluble group, the second reactive group being reactive with the first reactive group; applying the composition to a substrate using a spray method; and drying the composition. A reduced amount of microfoam improves the clarity of a film of the composition. Also provided are monofunctional carbodiimide reactive modifiers and substrates bearing the spray-applied clear compositions.Type: GrantFiled: June 6, 1995Date of Patent: April 22, 1997Assignee: Rohm and Haas CompanyInventors: Matthew S. Gebhard, Linda S. Smith, James C. Day
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Patent number: 5610260Abstract: The present invention relates to polyisocyanate mixtures which are reaction products of 4,4'-diphenylmethane diisocyanate as the isocyanate component, are liquid at greater than 5.degree. C. and have an NCO content of 14.5 to 24% by weight and an allophanate group content (calculated as C.sub.2 HN.sub.2 O.sub.3, molecular weight = 101) of 7.7 to 14.5% by weight; a process for the production of these polyisocyanate mixtures by reacting 4,4'-diphenylmethane diisocyanate as the exclusive isocyanate component with one or more monohydric alcohols having 4 to 16 carbon atoms at an NCO/OH equivalent ratio of 5:1 to 8.5:1 and at a temperature of up to 160.degree. C. to form urethane groups and during or subsequent to urethane formation, converting the urethane groups to allophanate groups in the presence of a catalyst which promotes allophanate formation; and the use of these polyisocyanate mixtures as the polyisocyanate component in two-component polyurethane coating compositions.Type: GrantFiled: February 9, 1996Date of Patent: March 11, 1997Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Josef Pedain, Harald Mertes
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Patent number: 5606004Abstract: A process for preparing liquid lacquer polyisocyanates with aliphatically and aromatically bound isocyanate groups and an NCO content of 5 to 25 wt. % by trimerizing an isocyanate component A), containing A1) 70 to 100 wt. % of diisocyanatotoluene and A2) 0 to 30 wt. % of other aromatic isocyanates and B) aliphatic lacquer polyisocyanates, optionally with prior, simultaneous and/or subsequent reaction of a portion of the isocyanate groups with an alcohol component C) having a molecular weight of 32 to 900, and optionally in the presence of D) inert solvents; the resulting lacquer polyisocyanates; and their use in coating compositions, in particular as a cross-linking agent for polyhydroxyl compounds in two-component polyurethane coating compositions.Type: GrantFiled: July 31, 1995Date of Patent: February 25, 1997Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Josef Pedain, Lutz Schmalstieg
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Patent number: 5599926Abstract: The subject invention provides chiral receptor molecules having the structure: ##STR1## wherein A has the structure: ##STR2## and R.sub.1 and R.sub.2 are independently the same or different and are H, F, alkyl, aryl, etc.; X is CH.sub.2 or NH; Y is C.dbd.O or SO.sub.2 ; and n is 0 to about 3; which are useful for the purification of enantiomers of amino acid derivatives and other compounds. The subject invention also provides methods of preparing said receptor molecules.Type: GrantFiled: January 27, 1994Date of Patent: February 4, 1997Assignee: The Trustees of Columbia University in the City of New YorkInventors: W. Clark Still, Julian A. Simon, Shawn D. Erickson, Seung S. Yoon, Jong-In Hong
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Patent number: 5597942Abstract: Novel carbodiimides and/or oligomeric polycarbodiimides containing terminal isocyanate, urethane and/or urea groups are obtainable, for example, by condensation of 1,3-bis(1-methyl-1-isocyanatoethyl)benzene with elimination of carbon dioxide followed, if desired, by reaction of all or some of the free isocyanate groups of the resultant (poly)carbodiimides with aliphatic, cycloaliphatic or araliphatic amines, alcohols and/or alkoxypolyoxyalkylene alcohols, and are used as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups.Type: GrantFiled: January 30, 1996Date of Patent: January 28, 1997Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5587413Abstract: A fluorine rubber composition comprising a fluorine rubber and a polyfluoroalkyl group-containing block isocyanate compound represented by the following general formula:Rf(CH.sub.2)nXCONHRNHCOO(N.dbd.C--R.sup.2)mR.sup.1where Rf is a polyfluoroalkyl group having 4 to 20 carbon atoms; R is a divalent organic group; R.sup.1 is a lower alkyl group or phenyl group; R.sup.2 is a lower alkyl group; X is NH or O; n is an integer of 1 to 4 and m is 0 or 1, has a good vulcanization bond to metals without any substantial decrease in the rubber stretchability properly owned by the fluorine rubber.Type: GrantFiled: January 5, 1996Date of Patent: December 24, 1996Assignee: Nippon Mektron, LimitedInventors: Takashi Enokida, Akihiro Naraki, Eiichi Yamashita, Haruyoshi Tatsu
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Patent number: 5574122Abstract: The present invention is directed to a polyisocyanate mixturei) having an NCO content of 5 to 35% by weight and prepared from an organic diisocyanate,ii) containing up to 25% by weight of isocyanurate groups (calculated as N.sub.3, C.sub.3, O.sub.3, MW 126),iii) containing allophanate groups in an amount such that there are more equivalents of allophanate groups than urethane or urea groups and such that the polyisocyanate mixture remains stable and homogeneous in storage for 3 months at 25.degree. C. andiv) containing siloxane groups (calculated as SiO, MW 44) in an amount of 0.002 to 50% by weight,wherein the preceding percentages are based on the solids content of the polyisocyanate mixture, excluding any unreacted organic diisocyanate, and wherein the siloxane groups are incorporated by reacting an isocyanate group with a compound containing one isocyanate-reactive group directly attached to a carbon atom and one or more siloxane groups.Type: GrantFiled: September 29, 1995Date of Patent: November 12, 1996Assignee: Bayer CorporationInventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
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Patent number: 5571911Abstract: The present invention relates to a composition having the general formula: ##STR1## wherein each of A, B, C, X, Y, and Z is independently O, NH, N(CH.sub.2).sub.m CH.sub.3, N(C.dbd.O) (CH.sub.2).sub.m CH.sub.3, CH.sub.2, S, or Se; each of R.sub.1, R.sub.2, and R.sub.3 is independently phenyl, 4-hydroxyphenyl, pyridyl, pyrrolyl, indolyl, naphthyl, thiophenyl, (C.dbd.O) (CH.sub.2).sub.p CH.sub.3, NH(C.dbd.O) (CH.sub.2).sub.p CH.sub.3, OH, COOH, NH.sub.2, or SH; and m, n, and p are integers between 0 and 5. The composition is a chiral receptor molecule useful for the purification of enantiomers of derivatives of amino acids and of compounds able to form hydrogen bonds. The preparation of the composition involves coupling a trifunctional aromatic molecule with three protected chiral molecules at the three aromatic groups, cleaving protecting groups, and joining adjacent chiral groups by multiple lactamizations.Type: GrantFiled: August 26, 1994Date of Patent: November 5, 1996Assignee: The Trustees of Columbia University in the City of New YorkInventors: W. Clark Still, Julian A. Simon, Jong-In Hong
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Patent number: 5559256Abstract: Novel aminediol compounds, pharmaceutical compositions containing these compounds, and methods of using these compounds in inhibiting retroviral protease, particularly useful in the treatment and/or prevention of HIV infection (AIDS).Type: GrantFiled: June 25, 1993Date of Patent: September 24, 1996Assignee: E. R. Squibb & Sons, Inc.Inventors: Eric M. Gordon, Joel C. Barrish, Gregory S. Bisacchi, Chong-Qing Sun, Joseph A. Tino, Gregory D. Vite, Robert Zahler
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Patent number: 5554711Abstract: The invention relates to reaction products prepared from(a) organic polyisocyanates,(b) 0.005 to 0.9 equivalents of a C.sub.6-24 alcohol per equivalent of NCO or latent NCO present in component (a),(c) 0.1 to 0.995 mol of cyanamide per equivalent of NCO or latent NCO present in component (a), and(d) ammonia or a volatile amine as neutralizing agent for the cyanamide groups of component (c),with the proviso that the reaction products are free from polyester and polyether groups and from halogen atoms.Type: GrantFiled: September 6, 1994Date of Patent: September 10, 1996Assignee: Bayer AktiengesellschaftInventors: Harro Tr aubel, Thomas M unzmay, Tillmann Hassel, Wilhelm Kr ummel, Hans-Albert Ehlert, Joachim Kochta
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Patent number: 5554783Abstract: A retroviral protease inhibiting compound of the formula A--X--B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.Type: GrantFiled: April 7, 1995Date of Patent: September 10, 1996Assignee: Abbott LaboratoriesInventors: Dale J. Kempf, Daniel W. Norbeck, Lynn M. Codacovi
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Patent number: 5541281Abstract: The present invention is directed to a polyisocyanate mixturei) having an NCO content of 5 to 35% by weight and prepared from an organic diisocyanate,ii) containing less than 5% by weight of isocyanurate groups (calculated as N.sub.3, C.sub.3, O.sub.3, MW 126),iii) containing allophanate groups in an amount such that there are more equivalents of allophanate groups than urethane groups andiv) containing fluorine (calculated as F, AW 19) in an amount of 0.001 to 50% by weight, based on solids.,wherein fluorine is incorporated with compounds containing two or more carbon atoms, one or more hydroxyl groups and one or more fluorine atoms. The present invention is also directed to a process for the production of this polyisocyanate mixture and to its use, optionally in blocked form, as an isocyanate component in one- or two-component coating compositions.Type: GrantFiled: December 20, 1994Date of Patent: July 30, 1996Assignee: Bayer CorporationInventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
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Patent number: 5536868Abstract: Compounds of Formula 1 bind to the opioid receptors: ##STR1## wherein R.sub.1 is a group of the formula ##STR2## where W is --(CH.sub.2).sub.a -- (where a is 0, 1, or 2), --O--, --NH--, --S--, --SO--, or --SO.sub.2 --, and Ar is phenyl, phenyl-alkyl, phenyl substituted with 1-3 halo, nitro, lower alkyl, hydroxy, amino, alkylamino, dialkylamino, and/or hydroxy-lower alkyl groups, and n is 0, 1, 2, 3, or 4;R.sub.2 and R.sub.3 are each independently H, lower alkyl, or ##STR3## where X is H, OH, lower alkyl, or lower alkoxy, and p is 0, 1, 2, or 3; R.sub.4 is ##STR4## where m is 0, 1, 2, or 3, and R is 1-3 halo, nitro, lower alkyl, hydroxy, amino, alkylamino, dialkylamino, and/or hydroxy-lower alkyl groups;R.sub.5 is cycloalkyl, bicycloalkyl, or tricycloalkyl; andR.sub.6, R.sub.7, R.sub.8, and R.sub.9 are each independently H or lower alkyl.Type: GrantFiled: February 21, 1995Date of Patent: July 16, 1996Assignee: Chiron CorporationInventors: Simon Ng, Robert L. Warne, Ronald N. Zuckermann, Eric J. Martin, Reyna J. Simon
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Patent number: 5514683Abstract: The compounds of the formula I ##STR1## and their pharmaceutical acceptable salts, which are defined herein, are ligands for cholecystokinin and/or gastrin receptors.Type: GrantFiled: August 9, 1994Date of Patent: May 7, 1996Assignee: James Black Foundation LimitedInventors: Sarkis B. Kalindjian, Caroline M. R. Low, Iain M. McDonald, Robert A. D. Hull, Nigel P. Shankley, Ildiko M. Buck, Katherine I. M. Steel, Jonathan M. R. Davies, David J. Dunstone, Elaine A. Harper, Michael J. Pether, Michael J. Bodkin, Matthew J. Tozer, Martin L. Hudson
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Hydroxy and amino functional pyrrolizidine catalyst compositions for the production of polyurethanes
Patent number: 5512603Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, cell stabilizer and a catalyst composition consisting essentially of a pyrrolizidine of the formula: ##STR1## where R.sub.1 and R.sub.2 independently are --H, --OH, ##STR2## or --NR.sub.4 R.sub.5, R.sub.3 is hydrogen, a C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl, or C.sub.7 -C.sub.11 arylalkyl group, andR.sub.4 and R.sub.5 independently represent H, a C.sub.1 -C.sub.12 alkyl group, C.sub.5 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl, or C.sub.7 -C.sub.11 arylalkyl group, provided that at least R.sub.1 or R.sub.2 is not hydrogen.Type: GrantFiled: February 22, 1994Date of Patent: April 30, 1996Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Kevin R. Lassila, Mark L. Listemann, Lisa A. Mercando, Kristen E. Minnich, Ann C. L. Savoca, Amy L. Wressell -
Patent number: 5510487Abstract: Hydroxyethylamine compounds are effective as retrovital protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: May 25, 1995Date of Patent: April 23, 1996Assignee: G.D. Searle & Co.Inventors: John J. Talley, Kathryn L. Reed
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Patent number: 5510432Abstract: Isocyanate prepolymers based on an aromatic diisocyanate and a polyether polyol in which at least 95% of the isocyanate groups are blocked by blocking agents selected fromA) about 50 to about 97 equivalent % of a phenol or substituted phenol,B) about 30 to about 50 equivalent % of a pyrazole or a substituted pyrazole andC) 0 to about 10 equivalent % of a blocking agent different from A) and B).These blocked isocyanate prepolymers are particularly useful for the production of flexible epoxy resin systems.Type: GrantFiled: May 31, 1995Date of Patent: April 23, 1996Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Rainer Rettig, Eberhard Konig
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Patent number: 5504241Abstract: There is now provided a carbodiimide or polycarbodiimide of the formula: ##STR1## where the R radicals are identical or different and are selected from the group consisting of --NHCONHR.sup.1 --, --NHCONR.sup.1 R.sup.2 --, and --NHCOOR.sup.3 --, where R.sup.1 and R.sup.2 may be identical or different and are alkyl, cycloalkyl, or aralkyl, and R.sup.3 is identical to R.sup.1 or is alkoxypolyoxyalkylene, and n is an integer from 0 to 10.There is also provided an ester containing plastic which contains this carbodiimide as an anti-hydrolysis agent. The plastics may be a polyurethane cellular or non-cellular elastomer or thermoplastic.Type: GrantFiled: March 7, 1995Date of Patent: April 2, 1996Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5498747Abstract: The present invention relates to novel carbodiimides or oligomeric polycarbodiimides containing terminal isocyanate, urea and/or urethane groups, methods for their preparation, and their use as hydrolysis stabilizers.Type: GrantFiled: March 7, 1995Date of Patent: March 12, 1996Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5492917Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.Type: GrantFiled: September 29, 1993Date of Patent: February 20, 1996Assignee: Merck & Co., Inc.Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
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Patent number: 5488131Abstract: A method for synthesizing enantiomerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the alpha carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98%, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.Type: GrantFiled: March 23, 1994Date of Patent: January 30, 1996Assignee: California Institute of TechnologyInventor: Andrew G. Myers
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Patent number: 5478835Abstract: Disclosed is a tricyclic compound represented by the formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represents hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, amino, C1-6 alkylamino, halogenated C1-6 alkyl, halogenated C1-6 alkoxy, halogen, nitro, cyano, carboxy, C1-6 alkoxycarbonyl, hydroxymethyl, CR.sup.9 R.sup.10 CO.sub.2 R.sup.11 (wherein each of R.sup.9, R.sup.10 and R.sup.11 independently represents hydrogen or C1-6 alkyl) or CONR.sup.12 R.sup.13 (wherein each of R.sup.12 and R.sup.13 independently represents hydrogen or C1-6-alkyl); R.sup.5 represents hydrogen or C1-6 alkyl; each of R.sup.6, R.sup.7 and R.sup.8 independently represents hydrogen, C1-6 alkyl, hydroxy, C1-6 alkoxy, C1-6 alkanoyloxy, C1-6 alkylthio, thiocyanato or halogen; X represents CH or N; Y.sup.1 -Y.sup.2 represents CH.sub.2 -O, CH.sub.2 -S(O).sub.n, (wherein n represents 0, 1, or 2), CH.sub.2 CH.sub.2, CH.dbd.CH or CON(R.sup.14) (wherein R.sup.Type: GrantFiled: May 2, 1994Date of Patent: December 26, 1995Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Toshiaki Kumazawa, Masashi Yanase, Hiroyuki Harakawa, Hiroyuki Obase, Shoji Oda, Shiro Shirakura, Koji Yamada, Kazuhiro Kubo
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Patent number: 5459222Abstract: Polyurethanes and polyesters are described which are the reaction products of an aromatic, aliphatic or cycloaliphatic diisocyanate, or of a diacid or diacid derivative respectively, with a diol containing a pendent UV-absorbing moiety, optionally also with one or more other diols or diamines. These UV-absorbing polycondensates can be applied to the surfaces of substrates by exhaustion methods or by spraying and act to protect polymers and dyes from degradation by UV radiation. They are therefore useful, either alone or in combination with other coating materials, for the treatment of wood, paper, textiles, leather or other surfaces which are exposed to degrading radiation.Type: GrantFiled: June 4, 1993Date of Patent: October 17, 1995Assignee: Ciba-Geigy CorporationInventors: Juliana Rodgers, Istvan Borsody, Athanasios Karydas, Robert A. Falk, Karl F. Mueller, Michele Kovaleski
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Patent number: 5459204Abstract: The invention relates to a new polyamine of the following composition: ##STR1## wherein 1.gtoreq.n.gtoreq.6, R represents the hydrocarbon radical of a (cyclo)aliphatic, araliphatic or aromatic diisocyanate having 6-20 C atoms or a trimer thereof andwherein when 2.gtoreq.n.gtoreq.6,R.sup.1 represents an n-valent organic radical such as is formed by removal of n OH groups from a polyhydroxy compound which optionally contains ether oxygen atoms and has an average molecular weight Mn of between 60 and 5,000; andwhen n=1,R.sup.1 represents ##STR2## It furthermore relates to a process for the preparation of a polyamine, in which certain diisocyanates, adducts of diisocyanates with polyols or trimers thereof are reacted with the Schiff base of the following composition: ##STR3## wherein R.sup.2 =H or a branched or unbranched C.sub.1-14 -alkyl radical and R.sup.3 =a branched or unbranched C.sub.1-14 -alkyl radical, an C.sub.1-14 alkyl-substituted phenyl radical or a C.sub.1 -C.sub.Type: GrantFiled: March 7, 1994Date of Patent: October 17, 1995Assignee: Huels AktiengesellschaftInventors: Rainer Lomoelder, Wilfried Paulen, Felix Schmitt, Elmar Wolf
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Patent number: 5457108Abstract: The invention relates to substituted 5-oxo-di-benzo[a,d]cyclohepta-1,4-dienes of the formula (I) ##STR1## processes for their preparation and their use as retroviral agents.Type: GrantFiled: September 17, 1993Date of Patent: October 10, 1995Assignee: Bayer AktiengesellschaftInventors: Hanno Wild, Jutta Hansen, Jorg Lautz, Arnold Paessens
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Patent number: 5453536Abstract: Polycarbamates of a polyisocyanate and secondary alcohols are disclosed. These carbamates are characterized in being readily pyrolyzed to form the corresponding polyisocyanate and alcohol with low formation of tars and other by-products. Thus, these polycarbamates can be pyrolyzed under relatively mild conditions, and in the absence of solvent and catalyst.Type: GrantFiled: March 10, 1994Date of Patent: September 26, 1995Assignee: The Dow Chemical CompanyInventors: Shenghong A. Dai, Chester R. Norman, Hong-Anh Nguyen
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Patent number: 5442090Abstract: Radiation-curable urethane acrylate compounds containing amine and urea groups and based on di- or polyisocyanates, hydroxy compounds and amines contain secondary or tertiary amino groups which are bonded to isocyanate via hydroxyl groups and are obtainable by an addition reaction of primary or secondary amines with hydroxyacrylates.Type: GrantFiled: March 4, 1991Date of Patent: August 15, 1995Assignee: BASF AktiengesellschaftInventors: Erich Beck, Wolfram Weiss, Hans Renz, Alfred Lindner
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Patent number: 5424474Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphono- and phosphinocarboxylic acids containing hydroxyl and/or mercapto groups, their use as waterproofing and/or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 23, 1993Date of Patent: June 13, 1995Assignee: Bayer AGInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5414120Abstract: The present invention relates to novel polyether-substituted compounds of imides and their use as surface-active agents.Type: GrantFiled: November 12, 1993Date of Patent: May 9, 1995Assignee: Bayer AGInventors: Klaus Pohmer, Rainer Weber, Cornelia Dorzbach-Lange, Reinhard Haida, Hans-Heinrich Moretto
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Patent number: 5414102Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphonocarboxylic acids containing acrylate and/or methacrylate groups, their use as waterproofing or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 27, 1993Date of Patent: May 9, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5405987Abstract: The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.Type: GrantFiled: March 28, 1991Date of Patent: April 11, 1995Assignee: Hoechst Celanese CorporationInventors: Varadaraj Elango, Donald R. Larkin, John R. Fritch, Michael P. Bodman, Werner H. Mueller, Bernard F. Gupton, John C. Saukaitis
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Patent number: 5403952Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.Type: GrantFiled: October 8, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
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Patent number: 5401878Abstract: A fluorine-containing polyimide having a low dielectric constant, low water absorption and excellent heat resistance and moisture resistance and a precursor thereof such as a fluorine-containing polyamide-acid, can be prepared by reacting an acid anhydride with an aromatic diamine having perfluoroalkyl group.Type: GrantFiled: September 1, 1993Date of Patent: March 28, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Masami Yusa, Shinji Takeda, Yasuo Miyadera
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Patent number: 5399736Abstract: This invention relates to a process for the preparation of highly pure aromatic diurethanes and/or polyurethanes by reaction of the corresponding aromatic diamines and/or polyamines with unsubstituted carbamates with the release of ammonia. The reaction is carried out in the presence of excess carbamates. The resultant reaction mixture is freed from any solvents used, and the formed aromatic diurethanes and/or polyurethanes are purified by extraction with water.Type: GrantFiled: December 10, 1992Date of Patent: March 21, 1995Assignee: Bayer AktiengesellschaftInventors: Wolfgang Friederichs, Stefan Penninger, Stefan Wershofen
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Patent number: 5393904Abstract: Copolymerizable oxime ethers of the general formula ##STR1## where A is a divalent linking member, R.sup.1 and R.sup.2 independently of one another are each C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy, C.sub.5 -C.sub.10 -cycloalkyl or C.sub.5 -C.sub.10 -aryl, each of which may furthermore contain 1-3 nonadjacent nitrogen, oxygen or sulfur atoms as heteroatoms in the carbon chain or in the carbon ring and may be substituted by from one to three C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy groups, R.sup.1 or R.sup.2 may be hydrogen or R.sup.1 and R.sup.2 together form a bridge of 3 to 14 carbon atoms, where some of the carbon atoms may furthermore be part of an aromatic ring, Z is an n-valent organic radical which contains a copolymerizable ethylenically unsaturated group and n is an integer of from 1 to 3.Type: GrantFiled: February 25, 1994Date of Patent: February 28, 1995Assignee: BASF AktiengesellschaftInventors: Kaspar Bott, Gerhard Bauer, Karl Haeberle
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Patent number: 5391805Abstract: An urethane compound is produced in high yield under mild conditions by reacting a formamide compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst or by reacting an amine compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst and methyl formate. Separation and recovery of the catalyst and purification of the urethane compound can be carried out very readily, and since control of water content is not particularly required in this invention, an amine compound and dimethyl carbonate of poor quality can be used.Type: GrantFiled: January 28, 1994Date of Patent: February 21, 1995Assignee: Mitsubishi Gas Chemical Company Inc.Inventors: Tomoo Tsujimoto, Takashi Okawa
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Patent number: 5384424Abstract: The present invention relates to a process for the selective preparation of 4,4-methylene-bis-(N-phenylalkylcarbamate) which comprises condensing N-phenylalkylcarbamate with a methylating agent in the presence of an acidic ion-exchange resin or an aqueous acid as a catalyst and a non polar aprotic solvent and filtrating a condensation product at a temperature greater than the melting point of N-phenylalkylcarbamate to separate 4,4-methylene-bis-(N-phenylalkylcarbamate).Type: GrantFiled: June 25, 1992Date of Patent: January 24, 1995Assignee: Lucky LimitedInventors: Jae S. Oh, Eung J. Kim
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Patent number: 5364850Abstract: The present invention provides substituted tyrosyl diamide compounds of general Formula I: ##STR1## and the pharmaceutically-acceptable salts thereof, which are useful for inducing analgesia in animals, pharmaceutical compositions comprising a pharmaceutically-acceptable carrier and a compound of Formula I, and a method for inducing analgesia in an animal in need thereof comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.Type: GrantFiled: September 24, 1993Date of Patent: November 15, 1994Assignee: G. D. Searle & Co.Inventors: Donald W. Hansen, Jr., Nizal S. Chandrakumar, Karen B. Peterson, Sofya Tsymbalov, Robert K. Husa