Nitrogen Containing Substituent Patents (Class 544/222)
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Patent number: 4748242Abstract: The present invention is directed to a process for the production of polyisocyanates containing isocyanurate groups by trimerizing a mixture of aliphatic-cycloaliphatic diisocyanates having a sterically unhindered isocyanate group bound to a primary aliphatic carbon atom and a sterically hindered isocyanate group bound to a tertiary carbon atom which forms a part of a cycloaliphatic ring system and 1,6-diisocyanatohexane. The present invention is also directed to the polyisocyanates containing isocyanurate groups produced according to this process and to their use, optionally in blocked form, as an isocyanate component in the production of polyisocyanate polyaddition products, preferably polyurethane lacquers.Type: GrantFiled: November 12, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Halpaap, Josef Pedain, Hans-Joachim Kreuder, Gerhard Klein, Dieter Arlt
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Patent number: 4746739Abstract: A pigment dispersant is derived from a compound of molecular weight less than 600 which contains at least three functional groups, at least one of which is an epoxy group. Preferably the compound contains at least three epoxy groups, for example triglycidyl isocyanurate. The core radical derived from the said compound is bonded to more than one solvent-compatible organic radical of molecular weight at least 200, the average molecular weight of the solvent-compatible radicals being at least 500, and to a pigment-compatible radical containing a polar group.Type: GrantFiled: July 11, 1986Date of Patent: May 24, 1988Assignee: International Paint public limited companyInventors: Keith Yeats, Ian D. Eeles, Graham C. Battersby
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Patent number: 4698424Abstract: The present invention relates to isocyanato-isocyanurates corresponding to the formula ##STR1## in which X.sub.1, X.sub.2 and X.sub.3 may be the same or different and represent radicals corresponding to the formula ##STR2## wherein R.sup.1 and R.sup.2 may be the same or different and represent hydrogen or C.sub.1 -C.sub.12 alkyl groups, and p is a whole or (on a statistical average) fractional number of from 1 to 5.The present invention also relates to a process for producing these isocyanato-isocyanurates and additionally relates to the use of the new isocyanato-isocyanurates, optionally blocked by blocking agents for isocyanate groups, as the isocyanate component in the produciton of isocyanate polyaddition products, preferably polyurethane lacquers.Type: GrantFiled: October 31, 1984Date of Patent: October 6, 1987Assignee: Bayer AktiengesellschaftInventors: Theodor Engbert, Hartmut Knofel, Gerhard Wegener
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Patent number: 4697014Abstract: Storage-stable polyisocyanurate-polyisocyanates, essentially devoid of polyisocyanate monomer and dimer over time, are conveniently prepared by catalytically cyclotrimerizing an aliphatic, cycloaliphatic or aromatic polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst, and terminating the cyclotrimerization reaction when predetermined desired amount of isocyanurate group has been reached, by adding to the reaction mixture a reaction terminating amount of water.Type: GrantFiled: March 25, 1986Date of Patent: September 29, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
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Patent number: 4680325Abstract: Isocyanurate esters of thioalkanoamidophenols useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by reacting an appropriate isocyanurate trithiol, which is a selected tris-mercapto alkanoic acid ester of tris-(2-hydroxyethyl) isocyanurate with an appropriate alkenyl compound, which is a selected N-alkenyl[4-amino-(mono- or dialkyl)phenol] or, where the alkano moiety is a sole methylene group, by reaction of tris-(2-hydroxyethyl) isocyanurate with an appropriate [mercapto-N-(mono- or di-alkyl]-4-hydroxyphenylalkanamide alkenoic] acid. In a preferred embodiment, the ester is 1,3,5-tris{2-hydroxy ethyl-[3-mercapto-(3',5'-di-tert-butyl-4'-hydroxypropionanilide)]propionat e}isocyanurate.Type: GrantFiled: February 10, 1986Date of Patent: July 14, 1987Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi, Henry J. Buehler
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Patent number: 4675401Abstract: Polyisocyanurate/polyisocyanates of enhanced stability are prepared by partial catalytic cyclotrimerization of a polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst and wherein the cyclotrimerization reaction is terminated when a predetermined desired amount of isocyanurate groups has been attained, by adding to the reaction mixture, after the cooling thereof to a temperature of below 50.degree. C., a reaction terminating amount of an organic catalyst deactivating compound comprising at least one free hydroxyl moiety, or the reaction product of such hydroxylated organic catalyst deactivating compound with an isocyanate.Type: GrantFiled: October 30, 1985Date of Patent: June 23, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
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Patent number: 4666902Abstract: Tetrahydropyridazinones of the formula I ##STR1## wherein R denotes an optionally substituted carbocyclic or heterocyclic radical, R.sup.1 denotes hydrogen; alkyl; aralkyl, which is optionally substituted in the aryl part; or acyl, and R.sup.2 denotes hydrogen; alkyl, which can optionally be substituted; or optionally substituted phenyl; and their acid addition compounds, if these can be prepared.The tetrahydropyridazinone derivatives of the formula I according to the invention and their physiologically acceptable salts exhibit useful pharmacological actions.Type: GrantFiled: June 8, 1984Date of Patent: May 19, 1987Assignee: Cassella AktiengesellschaftInventors: Gerhard Zoller, Rudi Beyerle, Melitta Just, Piero Martorana, Helmut Bohn, Rolf-Eberhard Nitz
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Patent number: 4657939Abstract: Novel triols which are useful for the formation of polyurethanes are produced by the reaction of a bicyclic amide acetal with cyanuric acid.Type: GrantFiled: June 13, 1986Date of Patent: April 14, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4632989Abstract: Disclosed are novel compositions capable of catalytically trimerizing organic isocyanates said compositions comprising solutions of the reaction products obtained by reacting in an inert solvent in substantially equimolar proportions electron-rich ketene-aminals with electron-poor olefins having the respective formulae (I) and (II) ##STR1## The variously substituted electron-rich ketene-aminals (I), as the name implies, have high electron density associated with the double bond because of the two tertiary amine groups while the electron-poor olefins (II) have the opposite situation due to the presence of electron withdrawing substituents R.sub.9 and R.sub.10.Also disclosed is an improved process for trimerizing organic isocyanates using the above catalyst compositions including the preparation of polyisocyanurate polymers and isocyanurate-modified polyisocyanates.Type: GrantFiled: May 28, 1985Date of Patent: December 30, 1986Assignee: The Dow Chemical CompanyInventor: Dale F. Regelman
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Patent number: 4623731Abstract: Carbamic acid derivatives having the following general formula: ##STR1## wherein R is an aromatic radical containing at least one benzene ring with at least one hydrogen atom substituted with a methyl, methylene or methine group; n=2 to 7.A method for preparing carbamic acid derivatives which comprises reacting 3(5)-methylpyrazole with an isocyanate of the general formula: R(NCO).sub.n, wherein:R is an aromatic radical containing at least one benzene ring having at least one hydrogen atom substituted with a methyl, methylene or methine group; n=2 to 7;the reaction being conducted in a melt or a solution of an inert organic solvent.Type: GrantFiled: January 25, 1984Date of Patent: November 18, 1986Inventors: Mikhail G. Ivanov, Veniamin G. Golov, Vladimir N. Kuzmin, Aida I. Alyakrinskaya, Roman Y. Mushy, Alexei D. Kovalev, Nadezhda V. Shutova, Jury A. Rodionov, Igor I. Molev, Ljudmila S. Yakovleva, Vitaly B. Berezin, Alexei I. Petrashko, Gennady M. Shuev, Boris A. Bukin, Tamara M. Belkina, deceased, by Naum S. Belkin, administrator
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Patent number: 4617391Abstract: Novel triols which are useful for the formation of polyurethanes are produced by the reaction of a bicyclic amide acetal with cyanuric acid.Type: GrantFiled: September 5, 1985Date of Patent: October 14, 1986Assignee: Ashland Oil, Inc.Inventor: Anil Goel
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Patent number: 4612374Abstract: Novel isocyanato-azetidinedione compounds are provided which have the formula ##STR1## wherein R and R.sub.1 can independently selected from hydrogen and hydrocarbyl or can be joined together and along with the carbon to which they are attached represent a cycloalkane residue having 4 to 6 ring carbon atoms, y is an integer from 1 to 7 and X is a hydrocarbon radical having a valency of y plus one.The monoisocyanate compounds are used as intermediates to provide further novel azetidinedione containing derivatives in the form of azetidinedione-isocyanurates (II) and azetidinedione-urethanes (III).All three classes of compounds can be employed as acid scavenging agents for stablizing various kinds of halogenated polymer systems. Notably, (I) and (III) form highly useful polyamide-polyureas and polyamide-polyurethanes respectively by reaction with organic polyamines.Type: GrantFiled: December 20, 1985Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventor: Shenghong A. Dai
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Patent number: 4602080Abstract: This invention relates to new salts of organic polyisocyanates containing at least one isocyanurate ring carrying a negative charge and at least one non-metal ion having a positive charge, these new salts being organic salts of mono- or polyisocyanurates containing at least two free isocyanate functions.The new organic salts according to this invention may be represented by the following general formula (I) ##STR1## in which R is a bivalent aliphatic, cycloaliphatic, aromatic or heterocyclic radical which may be substituted, Q is an onium cation substituted by four identical or different radicals which may be aliphatic, cycloaliphatic, aromatic or heterocyclic possibly substituted radicals, a is the average number of molecular isocyanurate rings which may be equal to zero or to more than zero, b is the number of tetrasubstituted heteroatoms of Q which is of at least 1 and n is the average number of ionic isocyanurate rings which is of at least 1.Type: GrantFiled: June 27, 1983Date of Patent: July 22, 1986Assignee: Societe Carbochimique en abrege "CARBOCHIM"Inventors: Pierre M. Lambert, Ignacio De Aguirre-Otegui
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Patent number: 4576747Abstract: Novel isocyanato-azetidinedione compounds are provided which have the formula ##STR1## wherein R and R.sub.1 can be independently selected from hydrogen and hydrocarbyl or can be joined together and along with the carbon to which they are attached represent a cycloalkane residue having 4 to 6 ring carbon atoms, y is an integer from 1 to 7 and X is a hydrocarbon radical having a valency of y plus one.The monoisocyanate compounds are used as intermediates to provide further novel azetidinedione containing derivatives in the form of azetidinedione-isocyanurates (II) and azetidinedione-urethanes (III).All three classes of compounds can be employed as acid scavenging agents for stabilizing various kinds of halogenated polymer systems. Notably, (I) and (III) form highly useful polyamide-polyureas and polyamide-polyurethanes respectively by reaction with organic polyamines.Type: GrantFiled: May 7, 1984Date of Patent: March 18, 1986Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
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Patent number: 4577017Abstract: Process for the preparation of an isocyanurate-compound containing isocyanate groups by trimerisation of a diisocyanate in the presence ofa compound having the formula ##STR1## in combination with an organic base, or a compound having the formula ##STR2## where R and R' are chosen from a hydrocarbon radical with 1-10 carbon atoms,--O--R.sub.1, with R.sub.1 being a hydrocarbon radical with 1-10 carbon atoms, andH.Type: GrantFiled: September 12, 1984Date of Patent: March 18, 1986Assignee: DSM Resins B.V.Inventors: Willem J. H. Hupperetz, Johannes A. H. M. Ramakers
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Patent number: 4569959Abstract: Isocyanurate esters of thioalkanoamidophenols useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by reacting an appropriate isocyanurate trithiol, which is a selected tris-mercapto alkanoic acid ester of tris-(2-hydroxyethyl) isocyanurate with an appropriate alkenyl compound, which is a selected N-alkenoyl[4-amino-(mono- or dialkyl)phenol] or, where the alkano moiety is a sole methylene group, by reaction of tris-(2-hydroxyethyl) isocyanurate with an appropriate [mercapto-N-(mono- or di-alkyl-4-hydroxyphenylalkanamide alkenoic] acid. In a preferred embodiment, the ester is 1,3,5-tris{2-hydroxy ethyl-[3-mercapto-(3',5'-di tert-butyl-4'-hydroxypropionanilide)]propionate}isocyanurate.Type: GrantFiled: January 17, 1985Date of Patent: February 11, 1986Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi, Henry J. Buehler
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Patent number: 4568674Abstract: 1-[4-(Benzothia- or -oxazol-2-ylthio- or -2-yloxy)phenyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-triones of the formula ##STR1## in which R is lower alkyl,R.sup.1 and R.sup.2 each independently is hydrogen, halogen, alkyl or alkoxy,R.sup.3 and R.sup.4 each independently is hydrogen, halogen, alkyl, alkoxy, alkylthio, fluoroalkyl, fluoroalkoxy or fluoroalkylthio, andX and Y each independently is sulphur or oxygen,or salts thereof, combat coccidioses, especially in poultry.Type: GrantFiled: February 11, 1985Date of Patent: February 4, 1986Assignee: Bayer AktiengesellschaftInventors: Axel Haberkorn, Heinrich Kolling, Toyohiko Kume, Shinpei Kuyama
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Patent number: 4562220Abstract: New polyalkyldiazaspirodecanylacetic acid derivatives are prepared by reacting diazaspirodecanes of the formula ##STR1## in which X is ##STR2## with halogenoacetic acid derivatives, and, if desired, reacting products thus obtained further with alcohols or amines. The compounds can be used as light stabilizers for plastics and lacquers.Type: GrantFiled: April 17, 1983Date of Patent: December 31, 1985Assignee: Hoechst AktiengesellschaftInventor: Hartmut Wiezer
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Patent number: 4552946Abstract: This invention relates to a new process for the production of polyisocyanates containing isocyanurate groups by partial trimerization of the isocyanate groups of organic polyisocyanates comprising(a) compounds or mixtures of compounds corresponding to the formula ##STR1## wherein R represents a saturated, aliphatic hydrocarbon radical having from 8 to 15 carbon atoms, and optionally(b) up to about 95 NCO equivalent %, based on the total of (a)+(b), of other organic polyisocyantes.This invention also relates to the compounds which may be obtained according to this process and to the use thereof for the production of isocyanate-polyaddition products such as polyurethanes.Type: GrantFiled: January 19, 1984Date of Patent: November 12, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Josef Pedain, Bernd Riberi, Gerhard Mennicken
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Patent number: 4540781Abstract: Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids or half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids.Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20.degree. C.) which makes the present method particularly suitable to systems for molding polyiso-cyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.Type: GrantFiled: August 11, 1983Date of Patent: September 10, 1985Assignee: The Upjohn CompanyInventor: Edward A. Barsa
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Patent number: 4537961Abstract: Polyisocyanato-polyisocyanurates are prepared by catalytically cyclotrimerizing a polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst, and which is characterizing by terminating the cyclotrimerization reaction when a predetermined desired amount of isocyanurate groups has been obtained, by adding to the reaction mixture a reaction terminating amount of an organic catalyst deactivating compound comprising at least one free hydroxyl moiety, or the reaction product of such hydroxylated organic catalyst deactivating compound with an isocyanate.Type: GrantFiled: March 1, 1983Date of Patent: August 27, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
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Patent number: 4525590Abstract: The invention relates to an improved process for the production of polyamines containing urethane and/or urea and/or biuret and/or isocyanurate groups and, preferably, also alkylene ether, carbonate and/or acetal groups by the alkaline hydrolysis of corresponding compounds containing terminal aliphatic and/or aromatic isocyanate groups.To this end, the compounds containing terminal NCO-groups, preferably NCO-preadducts, are converted by means of selected bases into the carbamates and neutralized by introduction into equivalent quantities of acid or by the simultaneous introduction of the components in equivalent quantities into a reaction vessel, after which the polyamines are directly isolated by methods known per se.The invention also relates to the use of the polyamines obtained by the process for the production of polyurethanes.Type: GrantFiled: July 15, 1982Date of Patent: June 25, 1985Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Klaus Konig, Holger Meyborg, Walter Meckel, Armin Zenner
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Patent number: 4512797Abstract: 1,3,5-Triazinones of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: January 28, 1983Date of Patent: April 23, 1985Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Gerhard Hamprecht, Bruno Wuerzer
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Patent number: 4500663Abstract: N,N,N-tris(2,2,6,6-tetramethyl-4-piperidone ketal)-1,3,5-triazines are provided, having the formula: ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen and alkyl having from one to about four carbon atoms; andR.sub.2 is selected from the group consisting of hydrogen; oxyl O; alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms; alkanoyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms; as well as synthetic resin compositions having an improved resistance to deterioration and containing such compounds.Type: GrantFiled: March 25, 1983Date of Patent: February 19, 1985Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
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Patent number: 4496757Abstract: Ultraviolet-absorbing stabilizers of the formula E-(G-R).sub.n, L-(G-E).sub.m, or [G-E.sub.1 -G-Q].sub.p where E is a radical derived from an oxanilide, benzalmalonate, .alpha.-cyanocinnamate or o-hydroxphenylbenzotriazole, E.sub.1 is a radical derived from an oxanilide, G is --OCH.sub.2 CHOH--, R is alkyl, phenyl or --CH.sub.2 OT where T is alkyl or alkenyl, n is 1 or 2, m is 2 or 3, L is a direct bond, alkylene or other bis or tris radical, Q has the same meaning as L when m is 2, and p is 1 to 4, are particularly resistant to loss during weathering of outdoor thermoset or thermoplastic coating systems while exhibiting good stabilization efficacy and compatibility in said systems.Type: GrantFiled: September 30, 1982Date of Patent: January 29, 1985Assignee: Ciba-Geigy CorporationInventors: Martin Dexter, Roland A. E. Winter
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Patent number: 4487928Abstract: The present invention thus relates to a process for the preparation of polyisocyanates having isocyanurate groups by the trimerization of part of the isocyanate groups of organic polyisocyanates or of mixtures of di- and mono-isocyanates in the presence of basic compounds as trimerization catalysts, with termination of the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts used are 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacylopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane.This invention also relates to solutions suitable as catalyst components for this process, comprising 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacyclopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane dissolved in polar lacquer solvents and/or at least one compound within the molecular weight range of about 32 to 250 which has alcoholic hydroxyl groups and is liquid at room temperature.Type: GrantFiled: December 23, 1981Date of Patent: December 11, 1984Assignee: Bayer AktiengesellschaftInventors: Roland Richter, Hanns P. M/u/ ller, Kuno Wagner
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Patent number: 4480094Abstract: Benzil-di[.beta.-(di-.beta.-methallylisocyanuryl)ethyl]ketal of the following structural formula: ##STR1## and other novel benzil ketal derivatives. The novel benzil ketal derivatives are characterized by having a structure in which an isocyanuryl-containing group is bonded to each of the two oxygen atoms of ketal. Because these compounds have a high decomposition or sublimation temperature and ability to initiate photopolymerization, they are useful as photopolymerization initiators in the production of photopolymerizable shaped articles from a molten blend of a photopolymerizable thermoplastic polymer composition.Type: GrantFiled: May 11, 1982Date of Patent: October 30, 1984Assignee: Teijin LimitedInventors: Tsuneo Hagiwara, Akihiro Horike
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Patent number: 4476054Abstract: A process for producing a substantially isocyanurate-free uretidione dimer of isophorone diisocyanate, which is more than 98% decomposable by heat to isophorone diisocyanate, which comprises dimerizing isophorone diisocyanate, optionally in an inert organic solvent, in the presence of a catalyst of the formula X.sub.m P(NR.sub.2).sub.3-m wherein m=0, 1, 2; X=Cl OR of R wherein R is selected from the group consisting of the same or different aklyl radical, aralkyl radical, cycloalkyl radical, substituted cycloalkyl radical and radicals wherein two or more of the aforementioned radicals form a hererocyclic ring together with the nitrogen atom; at temperatures of 0.degree.-80.degree. C., isolating the resulting 1,3-diazacyclobutane-2,4-dione, after 5-70% conversion, without previous inactivation of the catalyst, from the reaction mixture as the residue of a thin film distillation and isolating the catalyst and monomer as the distillate.Type: GrantFiled: August 13, 1981Date of Patent: October 9, 1984Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
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Patent number: 4476302Abstract: New esters and urethanes containing polyalkylpiperidylaminotriazine groups of the formula ##STR1## are prepared from carboxylic acid exters or isocyanates and triazinyl alcohols. The compounds are valuable stabilizers for polymeric materials.Type: GrantFiled: March 15, 1982Date of Patent: October 9, 1984Assignee: Hoechst AktiengesellschaftInventors: Hartmut Wiezer, Gerhard Pfahler
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Patent number: 4469867Abstract: Polyisocyanatoisocyanurates of the formula ##STR1## wherein the R groups may be the same or different and are aliphatic divalent radicals selected from the group consisting of divalent aliphatic radicals having the formulas ##STR2## and n is a whole or fractional number from 1 to 5, are useful as isocyanate hardeners in polyurethane resin coatings.Type: GrantFiled: December 30, 1982Date of Patent: September 4, 1984Assignee: Chemische Werke Huls AktiengesellschaftInventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
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Patent number: 4419513Abstract: The present invention relates to a process for the preparation of novel isocyanato-isocyanurates by the catalytic and 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane in a mole ratio of about 1:4 to 4:1, and to the products produced therefrom.The present invention also relates to the use of these products, optionally in blocked form, as the isocyanate component in polyurethane lacquers.Type: GrantFiled: August 27, 1981Date of Patent: December 6, 1983Assignee: Bayer AktiengesellschaftInventors: Peter Breidenbach, Manfred Bock, Josef Pedain, Gerhard Mennicken
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Patent number: 4412073Abstract: Monomeric or polymeric isocyanurates, e.g., polyisocyanate/polyisocyanurates, are prepared by catalytically cyclotrimerizing an isocyanate, e.g., an aliphatic or cycloaliphatic isocyanate, in the presence of an aminosilyl catalysis initiator, e.g., a mono- or diaminosilane, a silylurea or a silazane, having the structural formula:R.sub.(4-n) Si--NR'R"].sub.n (I)wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR.sub.3 or an amido radical having the structural formula: ##STR1## wherein R'" is R or SiR.sub.3, with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR.sub.Type: GrantFiled: February 1, 1982Date of Patent: October 25, 1983Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
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Patent number: 4393060Abstract: N-substituted-diglycidyl-isocyanurates having the formula: ##STR1## wherein R represents a hydrocarbon-containing radical selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and cycloalkyl, optionally containing:(a) heterocycles except epoxides, and unsaturation, and(b) substituents selected from the group consisting of halogen, hydroxyl, amino, N-substituted amino, mercapto, alkylmercapto, arylmercapto, alkylsulfoxy, arylsulfoxy, alkoxy, aryloxy and acyloxy,and R.sub.1 represents a member selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms, as well as the method for preparing said N-substituted-diglycidyl-isocyanurates, therapeutic compositions with cytostatic action comprising said N-substituted-diglycidyl-isocyanurates, and a method of treatment of malignant neoplasias in warm-blooded animals by administering a therapeutically effective amount of said N-substituted-diglycidyl-isocyanurate.Type: GrantFiled: October 7, 1980Date of Patent: July 12, 1983Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Herbert Fischer, Manfred Budnowski, Ulrich Zeidler
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Patent number: 4388245Abstract: A process for preparing a modified aliphatic, alicyclic or araliphatic organic polyisocyanate composition which comprises heating an aliphatic, alicyclic or araliphatic organic polyisocyanate composition having at least two isocyanate groups in one molecule at a temperature of from about 100.degree. C. to about 200.degree. C. in the presence of an aliphatic, alicyclic or araliphatic organic diisocyanate monomer in an amount of at least about 1/2 of the weight of the organic polyisocyanate composition and removing unreacted aliphatic, alicyclic or araliphatic organic diisocyanate monomer.Type: GrantFiled: August 17, 1981Date of Patent: June 14, 1983Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kaoru Ueyanagi, Akira Ide, Masaaki Kato, Kazuro Komatsu
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Patent number: 4386167Abstract: Polyisocyanurate polymers containing pendant urea groups are prepared by polymerization of polyisocyanates in organic solvents employing appropriate trimerization catalysts and then end-capping the polyisocyanurate polymer with ammonia or ammonium hydroxide. These end-capped polyisocyanurate polymers which contain pendant urea groups are dispersed in polyols to yield fine particulate dispersions. Cellular and non-cellular urethane products prepared using these dispersions displayed improved physical properties.Type: GrantFiled: April 19, 1982Date of Patent: May 31, 1983Assignee: BASF Wyandotte CorporationInventors: John T. Patton, Jr., Thirumurti Narayan
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Patent number: 4379905Abstract: The subject of the invention is a process for the preparation of polyisocyanates containing isocyanurate groups which comprises trimerizing a proportion of the isocyanate groups of organic polyisocyanates or mixtures of di- and monoisocyanates in the presence of basic alkali metal compounds as catalysts and terminating the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts are complexes of(i) basic alkalimetal compounds and(ii) acyclic organic compounds which(a) have at least 6 alkylene oxide units of the formula --R--O--, wherein R represents C.sub.1 -C.sub.Type: GrantFiled: January 6, 1982Date of Patent: April 12, 1983Assignee: Bayer AktiengesellschaftInventors: Ingo Stemmler, Hanns P. Muller, Kuno Wagner
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Patent number: 4336183Abstract: 2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines are provided, useful as stabilizers for organic polymeric materials, and having the general formula: ##STR1##Type: GrantFiled: August 14, 1980Date of Patent: June 22, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Yutaka Nakahara, Toshihiro Shibata, Naohiro Kubota
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Patent number: 4317911Abstract: New cyanuric acid derivatives containing at least one hindered phenolic moiety and at least one hindered amine moiety are effectful light stabilizers and antioxidants for polymeric materials.Type: GrantFiled: July 1, 1977Date of Patent: March 2, 1982Assignee: Ciba-Geigy CorporationInventors: Michael Rasberger, Friedrich Karrer
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Patent number: 4309546Abstract: Pyrrolidiones of the formula I ##STR1## wherein n is 1, 2, 3 or 4, R.sub.1 is free or esterified hydroxyl or hydroxyl which has been converted to a salt or is substituted or unsubstituted amino, X is a direct bond or a linking member and Pip is a substituted or unsubstituted 2,2,6,6-tetraalkylpiperidin-4-yl or a 2,2,6,6-tetraalkylpiperidin-4-ylidene, which pyrrolidones can be oligomerized or polymerized by linking R.sub.1 with X or by linking R.sub.1 with Pip. These compounds are used as light stabilizers for polymers.Type: GrantFiled: April 24, 1980Date of Patent: January 5, 1982Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4306051Abstract: A method for the production of blocked isocyanate- and isocyanurate group-containing compounds which comprises reacting a monomeric cycloaliphatic polyisocyanate to form an intermediate mixture comprising an isocyanurate containing at least two free isocyanate groups; and blocking the intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C., wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of the dimethylketoxime. A mixture containing isocyanurate and blocked isocyanate groups which comprises at least 10% by weight of a cycloaliphatic isocyanurate containing at least two isocyanate groups blocked with dimethylketoxime and a monomeric polyisocyanate blocked with dimethylketoxime in such amounts as necessary to complete 100% by weight of the mixture, and wherein the unblocked NCO-group content of the monomeric polyisocyanate is less than 0.5% by weight.Type: GrantFiled: March 28, 1980Date of Patent: December 15, 1981Assignee: Chemische Werke Huls AGInventors: Rainer Gras, Elmar Wolf
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Patent number: 4283535Abstract: A method of preparing 2,4,6-triketohexahydrotriazines which comprises catalytically trimerizing an organic isocyanate at 60.degree.-150.degree. C. in an inert, polar solvent present in an amount of 5-40 weight % with respect to the quantity of said isocyanate, in the presence of 0.1-5 weight % of a catalyst of the formula ##STR1## or hydrated derivatives of said catalyst, wherein R is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Me.sup.+2 is a bivalent metal cation; interrupting the trimerization at a conversion of about 50% by cooling; and then isolating the 2,4,6-triketohexahydrotriazine.Type: GrantFiled: May 14, 1979Date of Patent: August 11, 1981Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
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Patent number: 4255569Abstract: The instant invention is directed to a process for the production of isocyanate polyisocyanates containing at least 50%, by weight, of tris-isocyanatomonoisocyanurates and at most 3%, by weight, of isocyanurate-free diisocyanate. The process comprises catalytically trimerizing the organic diisocyanates free from isocyanurate groups and terminating the trimerization reaction by deactivation of the catalyst after 5 to 40% of the isocyanate groups of the isocyanurate-free diisocyanate have been trimerized. The unreacted isocyanurate-free diisocyanate is then distilled off in the presence of from 1 to 30%, by weight, based on the end product obtained as distillation residue, of an inert liquid distillation aid which boils at a temperature at least 50.degree. C. above the boiling point of the isocyanurate-free diisocyanate.The invention is also directed to the products produced by this process.Type: GrantFiled: May 4, 1979Date of Patent: March 10, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Jurgen Muller, Rudolf Hombach, Manfred Dollhausen, Joachim Zirner
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Patent number: 4249011Abstract: Ethylenically unsaturated crosslinking agents and polymerizable monomers are disclosed. These agents contain a heterocyclic nucleus and are capable of forming oxygen insensitive, radiation curable systems.Type: GrantFiled: June 25, 1979Date of Patent: February 3, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Larry A. Wendling
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Patent number: 4246132Abstract: A method for the production of blocked isocyanate-and isocyanurate group-containing compounds which comprises:transforming a monomeric aliphatic or cycloaliphatic polyisocyanate or a mixture thereof into an intermediate mixture comprising an isocyanurate containing at least 2 free isocyanate groups; andblocking said intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C.;wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of said dimethylketoxime.The mixtures of the present invention are particularly suited as co-catalysts for the anionic polymerization of epsilon-caprolactam, as well as hardeners for higher functional thermoplastic compounds which contain Zerewitinoff-active hydrogen atoms.Type: GrantFiled: July 20, 1978Date of Patent: January 20, 1981Assignee: Chemische Werke Huls AGInventors: Rainer Gras, Elmar Wolf
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Patent number: 4229576Abstract: Novel anthranilates of oxyalkylated cyanuric acid are obtained by reacting the oxyalkylated cyanuric acid, for example 1,3,5-tris-(2'-hydroxyethyl) isocyanurate, with isatoic anhydride. The anthranilates are valuable chain extenders and crosslinking agents in the production of polyurethanes and polyurea resins and can also be used as curing agents for epoxide resins.Type: GrantFiled: December 4, 1978Date of Patent: October 21, 1980Assignee: Ciba-Geigy CorporationInventors: Jurgen Habermeier, Roland Moser, Wolfgang Seiz
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Patent number: 4216316Abstract: A process is disclosed for the preparation of alkyl cyanates, alkyl isocyanurates, multifunctional alkyl cyanates, and oligomers of multifunctional alkyl isocyanates by reacting cyanogen halide with the corresponding thallium(I) salt of an alkanol at reduced temperatures, optionally in the presence of an inert solvent. Subsequently, warming the resulting product to ambient temperature causes isomerization to the corresponding aliphatic isocyanate and ultimately oligomerization to form trialkyl isocyanurate or oligomers of multifunctional alkyl isocyanates.Type: GrantFiled: February 8, 1979Date of Patent: August 5, 1980Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
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Patent number: 4189577Abstract: An imidazole-isocyanuric acid adduct having the following formula is disclosed: ##STR1## wherein R.sub.1 is a member selected from the group consisting of a hydrogen atom, a .beta.-cyanoethyl group and a .beta.-[3,5-diamino-s-triazinyl-(1)]-ethyl group, R.sub.2 stands for a monovalent hydrocarbon group having up to 17 carbon atoms, R.sub.3 is a member selected from the group consisting of a hydrogen atom and an alkyl group having up to 4 carbon atoms, with the proviso that when R.sub.1 is a hydrogen atom, R.sub.2 is a methyl or phenyl group and R.sub.3 is a hydrogen atom and when R.sub.1 is a .beta.-cyanoethyl group, R.sub.2 is a phenyl group and R.sub.3 is a hydrogen atom, and n is a number of from 0 to 2.This adduct has peculiar characteristics not possessed by ordinary salts. Namely, the adduct is stable in water, and it decomposes in a solvent or under heating. The adduct is valuable as a curing agent for epoxy resins, and it can be utilized for purification of imidazoles.Type: GrantFiled: March 13, 1978Date of Patent: February 19, 1980Assignee: Shikoku Chemicals CorporationInventors: Natsuo Sawa, Tadao Nomoto, Keiko Iuchi, Toshihiro Suzuki, Shunichi Kawata
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Patent number: 4183796Abstract: A radiation curable oligomer which cures to provide a combination of improved elongation and tensile strength is constituted by a selected hydroxy functional polyester having its active hydrogen atoms end-capped by reaction with ethylenically unsaturated monoisocyanate. This polyester is the reaction product of one mole of tris (2-hydroxyethyl) isocyanurate with three moles of saturated dicarboxylic acid and three moles of diol, these proportions being variable within the limits of .+-.20%, the polyester reaction product having an acid value of less than 20, preferably less than 5, and providing hydroxyl-terminated branches having an average length corresponding to a calculated molecular weight of 100-1500.Type: GrantFiled: February 9, 1978Date of Patent: January 15, 1980Assignee: DeSoto, Inc.Inventors: Robert E. Ansel, John C. Graham
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Patent number: 4179577Abstract: The esters are soluble in an aqueous solution of a base before exposure to actinic radiation but, on exposure to actinic radiation, polymerize and become insoluble in such an aqueous solution. Development of photopolymerized images does not therefore require the use of toxic or flammable organic solvents. They contain free carboxyl groups and at least one unit of the formulae I-IV ##STR1## where R.sup.1 is a carbon atom chain containing specified groupings, such as one of formula --CH.dbd.CH--CO--CH.dbd.CH--, --CH.dbd.CHCO--, --COCH.dbd.CHC.sub.6 H.sub.4 CH.dbd.CHCO--, or ##STR2## and Y is oxygen or sulfur. They are obtained by the reaction of an at least dianhydride of a polycarboxylic acid with alcoholic hydroxyl groups of an alcohol containing at least one unit of formula I-IV.Type: GrantFiled: December 27, 1977Date of Patent: December 18, 1979Assignee: Ciba-Geigy CorporationInventor: George E. Green
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Patent number: RE31261Abstract: 2,2,6,6-Tetrasubstituted-4-piperidyl carboxy heterocyclic compounds are provided which are useful as stabilizers for organic polymeric materials.Type: GrantFiled: November 27, 1981Date of Patent: May 31, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata