Nitrogen Containing Substituent Patents (Class 544/222)
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Patent number: 5604180Abstract: There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.Type: GrantFiled: June 2, 1995Date of Patent: February 18, 1997Inventors: Alvin D. Crews, Jr., Philip M. Harrington, Gary M. Karp, Simon D. Gill, Petra Dieterich
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Patent number: 5576411Abstract: 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 at least 1% 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.Type: GrantFiled: September 14, 1994Date of Patent: November 19, 1996Assignee: Bayer CorporationInventors: Philip E. Yeske, Edward P. Squiller, William E. Slack
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Patent number: 5565564Abstract: Polyfluoro organic compound having at least one urea linkage derived from: (1) at least one polyisocyanate containing at least three isocyanate groups, (2) at least one fluorochemical compound which contains per molecule (a) a single functional group having one or more Zerewitinoff hydrogen atoms and (b) at least two carbon atoms each of which contains least two fluorine atoms, and (3) water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups.Type: GrantFiled: March 3, 1995Date of Patent: October 15, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5552507Abstract: 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: GrantFiled: May 3, 1995Date of Patent: September 3, 1996Assignee: Bayer AktiengesellschaftInventors: Christian Wamprecht, Klaus Jost, Stefan Penninger
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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: 5519133Abstract: There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.Type: GrantFiled: June 2, 1995Date of Patent: May 21, 1996Assignee: American Cyanamid Co.Inventors: Alvin D. Crews, Jr., Philip M. Harrington, Gary M. Karp, Simon D. Gill, Petra Dieterich
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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: 5508372Abstract: The present invention relates to a process for the production of storage stable prepolymers containing free isocyanate groups by reactinga) an organic polyisocyanate component having (cyclo)aliphatically bound isocyanate groups and a maximum functionality of 4.5 withb) one or more hydroxy-functional polyacrylate resins having a content of alcoholic hydroxy groups of 0.05 to 7% by weight at an equivalent ratio of isocyanate groups of component a) to hydroxyl groups of component b) of 3:1 to 40:1, wherein components a) and b) are selected to provide a value B of at most 4 when calculated in accordance with the formula: ##EQU1## wherein F.sub.1 and F.sub.2 represent the NCO and OH functionalities of components a) and b), F.sub.1 representing the component with the lower functionality when the components differ in functionality andval.sub.A /val.sub.I represents the OH/NCO equivalent ratio of components a) and b).Type: GrantFiled: April 19, 1993Date of Patent: April 16, 1996Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Lutz Schmalstieg, Werner Kubitza, Wieland Hovestadt, Josef Pedain
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Patent number: 5473011Abstract: The present invention relates to polyisocyanate mixtures havinga) an average isocyanate functionality of at least 4.1,b) a (cyclo)aliphatically bound isocyanate group content (calculated as NCO, molecular weight =42) of 12.0 to 20.5% by weight,c) a chemically incorporated carboxyl group content (calculated as COOH, molecular weight =45) of 0.01 to 5.0% by weight andd) an ethylene oxide unit content arranged within terminal or lateral polyether chains of 0 to 10% by weight (calculated as C.sub.2 H.sub.4 O, molecular weight =44).The present invention also relates to a process for the preparation of these polyisocyanate mixtures and to their use as cross-linking agents in aqueous coating compositions containing water soluble or dispersible binders or binder components.Type: GrantFiled: April 15, 1992Date of Patent: December 5, 1995Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Laas, Rainer Rettig, Reinhard Halpaap, Klaus Nachtkamp
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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: 5457204Abstract: Esters or phenol ethers of the formula I or II ##STR1## in which m and n are each an integer from the range from 1 to 6; A.sup.1 is an m-valent hydrocarbon radical having 1 to 30 carbon atoms; or an m-valent hydrocarbon radical having 2 to 30 carbon atoms, which contains the heteroatoms oxygen, nitrogen and/or sulfur and the free valencies of which are located on carbon atoms; and in which A.sup.1, in the case where m=2, additionally is a direct bond;A.sup.2 is an n-valent aromatic or araliphatic hydrocarbon radical having 6 to 30 carbon atoms; or an n-valent aromatic or araliphatic hydrocarbon radical having 5 to 30 carbon atoms, which contains the heteroatoms oxygen, nitrogen and/or sulfur and n free valencies of which are located on those carbon atoms which are a constituent of aromatic rings;R.sup.1 is hydrogen; a hydrocarbon or hydrocarbonoxy radical having 1 to 36 carbon atoms, which is unsubstituted or substituted by --CO--N(R.sup.3).sub.2 or interrupted by --CO--N(R.sup.3)-- or --N(R.sup.Type: GrantFiled: July 7, 1994Date of Patent: October 10, 1995Assignee: Ciba-Geigy CorporationInventor: Alfred Steinmann
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Patent number: 5447904Abstract: The invention relates to new 3-aryl-triazine-2,4-diones of the general formula (I) ##STR1## in which Het represents a radical of the formula ##STR2## R.sup.1 represents hydrogen or halogen, R.sup.2 represents halogen, cyano or nitro andR.sup.3 represents a radical of the formula --X--R.sup.6 or --CO--X--R.sup.7, in whichR.sup.4 represents hydrogen, cyano, alkyl, alkenyl, alkinyl or halogenoalkyl,R.sup.5 represents alkyl, alkenyl or alkinyl,R.sup.6 represents hydrogen or optionally substituted alkyl,R.sup.7 represents hydrogen or optionally substituted alkyl,X represents oxygen or sulphur andZ represents oxygen or sulphur, to a process for their preparation, to new intermediates, and to their use as herbicides.Type: GrantFiled: August 17, 1993Date of Patent: September 5, 1995Assignee: Bayer AktiengesellschaftInventors: Otto Schallner, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt, Renate Vosswinkel
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Patent number: 5444146Abstract: The present invention is directed to a polyisocyanate mixture having an NCO content of 10 to 47% by weight and a viscosity of less than 10,000 mPa.s and containing isocyanurate and allophanate groups in a molar ratio of monoisocyanurates to monoallophanates of 10:1 to 1:5, wherein the allophanate groups are formed from urethane groups which are based on the reaction product of an organic diisocyanate having (cyclo)aliphatic bound isocyanate groups and an aromatic monoalcohol containing 6 to 9 carbon atoms.The present invention is also directed to a process for the production of a polyisocyanate mixture having an NCO content of 10 to 47% by weight, having a viscosity of less than 10,000 mPa.s and containing isocyanurate and allophanate groups in a molar ratio of monoisocyanurates to monoallophanates of 0:1 to 1:5 bya) catalytically trimerizing a portion of the isocyanate groups of an organic diisocyanate having (cyclo)aliphatically bound isocyanate groupsb) adding 0.01 to 0.Type: GrantFiled: January 13, 1993Date of Patent: August 22, 1995Assignee: Bayer CorporationInventors: Terry A. Potter, William E. Slack
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Patent number: 5414111Abstract: Polyfluoro organic compound having at least one urea linkage derived from: (1) at least one polyisocyanate containing at least three isocyanate groups, (2) at least one fluorochemical compound which contains per molecule (a) a single functional group having one or more Zerewitinoff hydrogen atoms and (b) at least two carbon atoms each of which contains at least two fluorine atoms, and (3) water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups.Type: GrantFiled: February 2, 1994Date of Patent: May 9, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5410073Abstract: Process comprising (I) reacting (a) at least one polyisocyanate or mixture of polyisocyanates which contains at least three isocyanate groups per molecule with (b) a stoichiometric deficiency of at least one fluorochemical compound which contains per molecule (i) a single functional group having one or more Zerewitinoff hydrogen atoms and (ii) at least two carbon atoms each of which contains at least two fluorine atoms, and (II) thereafter forming one or more urea linkages per mol of said polyisocyanate by reacting the remaining isocyanate groups with water in an amount sufficient to to react with from about 5% to about 60% of the isocyanate groups in said polyisocyanate.Type: GrantFiled: February 4, 1994Date of Patent: April 25, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jack R. Kirchner
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Patent number: 5371167Abstract: A coating composition is described comprising two components that are reactable with each other to cure the coating. The two components are:(a) a carboxyl-functional polyurethane component that is the reaction product of:(i) a polyisocyanate compound, and(ii) a compound comprising at least one acid group and at least one isocyanate-reactive group,(b) a component comprising at least two groups that are reactive with the epoxy groups on the polyurethane compound.Type: GrantFiled: October 29, 1992Date of Patent: December 6, 1994Assignee: BASF CorporationInventors: John W. Rehfuss, Walter H. Ohrbom
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Patent number: 5336749Abstract: Herein disclosed are an .alpha.-(aminocyclohexyl)alkylamine represented by the following general formula (II): ##STR1## wherein R represents hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, provided that the amino group bonded to the cyclohexyl group may be in either of the 2-, 3- and 4-positions and a method for preparing it; an .alpha.-(isocyanatocyclohexyl)alkylisocyanate of Formula (II) wherein the amino groups are replaced with isocyanato groups and a method for preparing it; polyisocyanato-isocyanurate represented by the following general formula (IV): ##STR2## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: February 17, 1993Date of Patent: August 9, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
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Patent number: 5260439Abstract: The present invention relates to a high surface hardness transparent resin having excellent scratch resistance, heat resistance and chemical resistance, a glazing material, a protective cover for display devices, an optical lens and a hard coat material comprising the aforesaid resin, and a novel polymerizable monomer which is useful as a raw material of the above-mentioned resin.The monomer is represented by the formula (I) ##STR1## (wherein R is an aliphatic residue having or not having an halogen atom, an oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or all sulfur, one X is oxygen while the other X or X's are sulfur, one X is sulfur while the other X or X's are oxygen, or two X's are oxygen while the other X's are sulfur).Type: GrantFiled: December 16, 1991Date of Patent: November 9, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Toshiyuki Suzuki, Katsuyoshi Sasagawa, Masao Imai, Yoshinobu Kanemura
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Patent number: 5258482Abstract: The present invention is directed to a polyisocyanate mixture whichi) has an NCO content of 10 to 47% by weight,ii) is prepared from a mixture of 1,6-hexamethylene diisocyanate and a cyclic organic diisocyanate having (cyclo)aliphatically-bound isocyanate groups in a molar ratio of 10:90 to 90:10 andiii) contains isocyanurate and allophanate groups in a molar ratio of monoisocyanurates to monoallophanates of 10:1 to 1:5, wherein the allophanate groups are formed from urethane groups which are based on the reaction product of an organic diisocyanate having (cyclo)aliphatically bound isocyanate groups and a monoalcohol containing at least 1 carbon atom and having a molecular weight of up to 2500.The present invention is also directed to a process for the production of these polyisocyanate mixtures and to their use, optionally in blocked form, as an isocyanate component in two-component coating compositions.Type: GrantFiled: June 12, 1992Date of Patent: November 2, 1993Assignee: Miles Inc.Inventors: Patricia B. Jacobs, Terry A. Potter, Richard R. Roesler, Roger W. Rumer
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Patent number: 5239073Abstract: The invention relates to isocyanurate-containing, organosilicon compounds of the general formula ##STR1## in which Q=--(CH.sub.2).sub.3 SiR.sub.2 O(SiR.sub.2 O).sub.n SiR.sub.2 R', n is an integer from 0 to 25 and x is an integer from 0 to 10, and the following holds for the residues R and R', which can be the same or different:R=alkyl, cycloalkyl, aryl, arylalkyl or alkylaryl, andR'=an epoxy-functional residue with 4 to 10 C-atoms or a (meth)acrylate-functional residue with at least 6 C-atoms.Type: GrantFiled: November 8, 1991Date of Patent: August 24, 1993Assignee: Siemens AktiengesellschaftInventors: Bernhard Stapp, Helmut Markert, Lothar Schoen
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Patent number: 5221743Abstract: This invention relates to a process for preparing a trimer by the steps of: (a) cyclotrimerizing a polyisocyanate in the presence a polymer-bound trimerization catalyst by contacting said polyisocyanate with said catalyst at a temperature of between about 20.degree. and about 135.degree. C. in a reaction to form an isocyanurate-containing cyclotrimerized isocyanate wherein a portion of the isocyanate moieties comprising said polyisocyanate are converted to isocyanurate groups, and (b) separating said catalyst from said cyclotrimerized isocyanate in order to stop said reaction after a desired amount of isocyanate moieties in said polyisocyanate have been converted to isocyanurate moieties.Type: GrantFiled: March 2, 1992Date of Patent: June 22, 1993Assignee: Olin CorporationInventors: Stephen L. Goldstein, Curtis P. Smith
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Patent number: 5208334Abstract: The present invention is directed to a process for the production of a polyisocyanate composition having an NCO content of 10 to 47% by weight and a viscosity of less than 2,500 mPa.s, wherein the viscosity is determined from a mixture containing less than 1% by weight of the starting organic diisocyanate, and containing isocyanurate and allophanate groups in a molar ratio of monoisocyanurates to monoallophanates of 10:1 to 1:5 bya) catalytically trimerizing a portion of the isocyanate groups of an organic diisocyanate having (cyclo)aliphatically bound isocyanate groupsb) adding 0.01 to 0.Type: GrantFiled: June 9, 1992Date of Patent: May 4, 1993Assignee: Miles Inc.Inventors: Terry A. Potter, William E. Slack
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Patent number: 5206332Abstract: A curing agent for the production of low gloss powder coatings based on epoxy resins consists essentially of a mixture of the components a) 2-imidazoline derivative having a melting point of >60.degree. C. and b) cyanuric acid as well as, if desired, anticaking agents or/and stabilizers. The low gloss powder coatings produced with these curing agents have the desired low degrees of gloss and good adhesive strengths, they form smooth and uniform surfaces and show no signs of yellowing even after long stoving times.Type: GrantFiled: December 27, 1991Date of Patent: April 27, 1993Assignee: SKW Trostberg AktiengesellschaftInventors: Benedikt Hammer, Thomas Guthner, Helmut Hintermaier
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Patent number: 5182390Abstract: Tris[2-hydroxy-3-(2,2,6,6-tetramethyl-4-piperidylamino)propyl] isocyanurate is useful as a light stabilizer for organic materials. A composition comprising an organic material and the isocyanurate is stable against light and also excellent in heat resistance. The isocyanurate can be produced by the reaction between tris(2,3-epoxypropyl) isocyanurate and 4-amino-2,2,6,6-tetramethylpiperidine.Type: GrantFiled: October 28, 1991Date of Patent: January 26, 1993Assignees: Kyodo Chemical Company Limited, Sumitomo Chemical Company, LimitedInventors: Seiji Sagawa, Toshio Kano, Shinichi Yachigo, Kanako Ida
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Patent number: 5144031Abstract: The present invention relates to a process for the production of isocyanurate group-containing polyisocyanates by partially trimerizing the isocyanate groups of (cyclo)aliphatic diisocyanates in the presence of catalysts which accelerate the trimerization of isocyanate groups and optionally in the presence of an inert solvent, terminating the trimerization reaction at the desired degree of trimerization and removing unreacted starting diisocyanate and any other volatile constituents, characterized in that at least one monohydric alcohol containing ester groups corresponding to the formula ##STR1## is added to the reaction mixture prior to removing the excess starting diisocyanate in a quantity of 1 to 30% by weight, based on the weight of the diisocyanate starting material, and reacted with a portion of the isocyanate groups to form urethane groups, provided that after the trimerization and urethanization reactions, the reaction mixture contains at least 10% by weigth of unreacted starting diisocyanate, basedType: GrantFiled: May 6, 1991Date of Patent: September 1, 1992Assignee: Bayer AktiengesellschaftInventor: Josef Pedain
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Patent number: 5128423Abstract: Compounds of the general formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or benzyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, orR.sub.1 and R.sub.2, together with the linking carbon atom, form a 5- or 6-membered ring, andR.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and are hydrogen, C.sub.1 -C.sub.12 alkyl, phenyl or phenyl substituted by 1 to 3 members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen or C.sub.1 -C.sub.4 alkoxy or are a group of formula --CH.sub.2 OR.sub.11, where R.sub.11, where R.sub.11 is C.sub.1 -C.sub.12 alkyl, phenyl or phenyl substituted by 1 to 3 members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen or C.sub.1 -C.sub.4 alkoxy, or are --C(O)--R.sub.12, and R.sub.12, and R.sub.12 is C.sub.1 -C.sub.12 alkyl,R.sub.7 is C.sub.1 -C.sub.4 alkylene, R.sub.8 is C.sub.1 -C.sub.8 alkylene, R.sub.9 is C.sub.1 -C.sub.4 alkyl, or two radicals R.sub.9 together are C.sub.Type: GrantFiled: June 17, 1991Date of Patent: July 7, 1992Assignee: Ciba-Geigy CorporationInventors: Giovanni Parrinello, Rolf Mulhaupt, Hubert Simon
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Patent number: 5128471Abstract: The present invention relates to a process for the production of primary amines containing aliphatically or cycloaliphatically bound amino groups, characterized in that the isocyanate groups of organic isocyanates containing aliphatically and/or cycloaliphatically bound isocyanate groups are formylated with formic acid in a first reaction step and the N-formyl groups are subsequently converted into amino groups.The present invention also relates to polyamine mixtures obtained by this process and containinga) about 40 to 90% by weight, based on the total weight of components a) and b), of N,N',N"-tris-(6-aminohexyl)-isocyanurate andb) about 10 to 60% by weight, based on the total weight of components a) and b), of higher homologs of this triamine containing more than one isocyanurate ring.Finally, the present invention relates to the use of these polyamine mixtures as hardeners for polymer precursors containing epoxide or isocyanate groups.Type: GrantFiled: April 10, 1990Date of Patent: July 7, 1992Assignee: Bayer AktiengesellschaftInventor: Hans J. Scholl
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Patent number: 5106988Abstract: New silanes containing at least two oxazolidinic moieties can be defined by means of the general formula: ##STR1## wherein X.sub.1, X.sub.2, X.sub.3 and X.sub.4 have the meaning as reported in the specification, and each one of A.sub.1, A.sub.2 and A.sub.3 represents from 0 to a plurality of siloxane radicals--SiO--and are better defined in the text of the specification.These compounds are useful as crosslinking agents for moisture-hardening systems based on polyisocyanates, of acrylate polymers and of polyepoxides in compositions for coatings, sealants and adhesive agents.Type: GrantFiled: April 18, 1990Date of Patent: April 21, 1992Assignee: Enichem Synthesis S.p.A.Inventor: Alberto Greco
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Patent number: 5084459Abstract: There is provided a pest control composition containing a compound represented by the formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and independently mean a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted and X means an electron attracting group or a salt thereof.The compounds are of minimal toxicity to man, domestic animals and fish and selectively display remarkable control effect on pests.Type: GrantFiled: October 25, 1989Date of Patent: January 28, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi, Noriko Higuchi
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Patent number: 5077291Abstract: Fungicidal trisubstituted 1,3,5-triazine-2,4,6-triones of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are different radicals andR.sup.1 represents an optionally substituted aliphatic or cycloaliphatic radical,R.sup.2 represents an optionally substituted aliphatic radical andR.sup.3 represents an optionally substituted aralkyl radical.Type: GrantFiled: September 20, 1990Date of Patent: December 31, 1991Assignee: Bayer AktiengesellschaftInventors: Hermann Uhr, Alfons Adler, Arno Widdig, Hermann Hagemann, Gerd Hanssler
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Patent number: 5070137Abstract: Disclosed is a process for preparing isocyanurate-type polyisocyanates characterized by reacting an aliphatic or alicyclic diisocyanate compound comprising hexamethylene diisocyanate as a major component in the presence of an isocyanuration catalyst represented by general formula [I], ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrocarbon group containing 1 to 20 carbon atoms, or a hydrocarbon group containing one or more hetero atoms; at least two of R.sup.1, R.sup.2 and R.sup.3 may be linked to each other; R.sup.4 indicates a hydrogen atom or a hydrocarbon group containing 1 to 20 carbon atoms; and R.sup.5, R.sup.6 and R.sup.7 independently represent a hydrocarbon group containing 1 to 20 carbon atoms. Diol-modified isocyanurate-type polyisocyanates can be prepared additionally using a hydrocarbon diol in the process.Type: GrantFiled: July 21, 1989Date of Patent: December 3, 1991Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Mitsuo Kase, Yoichi Kawasaki, Noboru Okoshi
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Patent number: 5064960Abstract: The present invention relates to a process for the preparation of a composition containing an isocyanurate polyisocyanate dissolved in a solvent inert to isocyanate groups bya) reacting 2.5 to 7% of the isocyanate groups of a starting diisocyanate based on 2,4-diisocyanatotoluene or a mixture of 2,4-diisocyanatotoluene and 2,6-diisocyanatotoluene with a monohydric alcohol corresponding to the formula ##STR1## wherein R.sub.1 is an aliphatic or cycloaliphatic C.sub.6-18 hydrocarbon radical which may be olefinically unsaturated,R.sub.Type: GrantFiled: August 22, 1990Date of Patent: November 12, 1991Assignee: Bayer AktiengesellschaftInventors: Josef Pedain, Dieter Margotte
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Patent number: 5047546Abstract: Compounds of the general formula I ##STR1## wherein R.sub.1 is a hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or benzy.,R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, orR.sub.1 and R.sub.2, together with the linking carbon atom, form a 5- or 6-membered ring, andR.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and are hydrogen, C.sub.1 -C.sub.12 alkyl, phenyl or phenyl substituted by 1 to 3 members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen or C.sub.1 -C.sub.4 alkoxy or are a group of formula --CH.sub.2 OR.sub.11, where R.sub.11 is C.sub.1 -C.sub.12 alkyl, phenyl or phenyl substituted by 1 to 3 members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen or C.sub.1 -C.sub.4 alkoxy, or are --C(O)-R.sub.12, and R.sub.12 is C.sub.1 -C.sub.12 alkyl,R.sub.7 is C.sub.1 -C.sub.4 alkylene, R.sub.8 is C.sub.1 -C.sub.8 alkylene, R.sub.9 is C.sub.1 -C.sub.4 alkyl, or two radicals R.sub.9 together are C.sub.1 -C.sub.4 alkylene, and R.Type: GrantFiled: November 9, 1990Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Giovanni Parrinello, Rolf Mulhaupt, Hubert Simon
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Patent number: 5030671Abstract: A composition containing a) a chlorine-containing polymer, b) at least one Me(II) carboxylate and/or Me(II) phenolate, wherein Me(II) represents Ba, Ca, Mg, Sr or Zn, and c) at least one compound of formula I ##STR1## wherein n is 1, 2, 3, 4 or 6 and, when n is 1, X is C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 -alkenyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl, phenyl substituted by from 1 to 3 radicals or C.sub.7 -C.sub.9 phenylalkyl substituted on the phenyl ring by from 1 to 3 radicals, the radicals being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, chlorine, hydroxy, methoxy and ethoxy; when n is 2, X is C.sub.2 -C.sub.12 alkylene, C.sub.2 -C.sub.12 alkylene substituted by phenyl, or C.sub.2 -C.sub.12 alkylene interrupted by oxygen or sulfur atoms; when n is 3, X is, for example, C.sub.3 -C.sub.7 alkanetriyl; when n is 4, X is, for example, C.sub.4 .varies.C.sub.Type: GrantFiled: October 16, 1989Date of Patent: July 9, 1991Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Gerd Abeler
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Patent number: 5013838Abstract: The present invention relates to a process for the production of an isocyanurate group-containing polyisocyanate by(a) partially reacting the isocyanate groups of an organic diisocyanate containing aliphatically and/or cycloaliphatically bound isocyanate groups in the presence of an ammonium or phosphonium fluoride trimerization catalyst,(b) introducing carbon dioxide into the reaction mixture at least periodically during the reaction and(c) terminating the reaction at the desired degree of conversion.The present invention also relates to the isocyanurate group-containing polyisocyanates obtained in accordance with this process.Type: GrantFiled: January 19, 1990Date of Patent: May 7, 1991Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Scholl
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Patent number: 4992548Abstract: The present invention is directed to catalysts obtained by mixing alkali fluorides with quaternary ammonium or phosphonium salts.The present invention is also directed to a process for the production of these catalysts by stirring alkali fluorides and quaternary ammonium or phosphonium salts in alcohol, separating any deposits formed, removing the alcohol and converting the catalyst into useful form by dilution in solvents or absorption onto support materials.Finally, the present invention is directed to the use of the new catalysts as trimerization catalysts for the production of polyisocyanates containing isocyanurate groups.Type: GrantFiled: August 8, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Josef Pedain
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Patent number: 4983655Abstract: A plastisol composition comprising polyvinyl chloride as a main component, a plasticizer and a blocked compound of diisocyanate polymer with styrenated phenol as an adhesion-improver, and optionally a powdery curing agent having a melting point of 50.degree. to 150.degree. C. which is surface-treated, said composition having improved adhesion properties when gelated under low temperature conditions such as at 110.degree. to 130.degree. C. for 15 to 30 minutes and being useful as an adhesive, a sealant, or a coating agent, particularly as a sealant for the body of automobiles, and a novel blocked polyisocyanurate compound useful as an adhesion-improver for the above plastisol composition and also as an adhesive, a coating agent, a sealant, and an crosslinking agent for an active hydrogen-containing high molecular weight compound.Type: GrantFiled: June 23, 1989Date of Patent: January 8, 1991Assignee: Sunstar Giken Kabushiki KaishaInventors: Yoshihiro Nakata, Tadao Kunishige
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Patent number: 4963675Abstract: Substantially pure isocyanurate/polyisocyanates, i.e., containing no more than about 0.03% by weight of residual diisocyanate monomer and no more than about 1% by weight of diisocyanate dimer, are produced by extracting impure cyclotrimerized diisocyanates with an inert gas in either the liquid or supercritical state.Type: GrantFiled: March 29, 1989Date of Patent: October 16, 1990Assignee: Rhone-Poulenc ChimieInventors: Jean Robin, Andre Blind
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Patent number: 4933341Abstract: Protecting against parasitic protozoa with substituted 1,3,5-triazinetriones of the formula ##STR1## in which R.sup.1 represents aromatic or heteroaromatic radicals, each of which is optionally substituted,R.sup.2 represents H, alkyl, alkenyl, alkinyl or aralkyl, each of which is optionally substituted,R.sup.3 represents one or more identical or different radicals from the group consisting of hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy, halogenoalkylthio, cyano, alkoxycarbonyl, alkylsulphonyl and halogenoalkylsulphonyl,R.sup.4 represents hydrogen, a straight-chain, branched or cyclic alkyl radical, alkenyl, alkinyl, aralkyl or aryl, each of which is optionally substituted, andR.sup.5 represents hydrogen, optionally substituted alkyl, alkenyl, alkinyl or aralkyl.Also novel intermediates therefor.Type: GrantFiled: September 28, 1989Date of Patent: June 12, 1990Assignee: Bayer AktiengesellschaftInventors: Werner Lindner, Axel Haberkorn
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Patent number: 4927824Abstract: Fungicidal trisubstituted 1,3,5-triazine-2,4,6-triones of the formula ##STR1## in which R.sup.1 stands for an optionally substituted aliphatic, aromatic or cycloaliphatic radical,R.sup.2 stands for an optionally substituted aliphatic radical andR.sup.3 stands for optionally substituted, heterocyclically fused phenyl.Type: GrantFiled: March 17, 1989Date of Patent: May 22, 1990Assignee: Bayer AktiengesellschaftInventors: Alfons Adler, Arno Widdig, Engelbert Kuhle, Wolfgang Fuhrer, Hermann Hagemann, Gerd Hanssler
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Patent number: 4904781Abstract: 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 12, 1988Date of Patent: February 27, 1990Inventors: Mikhall 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: 4898979Abstract: The novel process ##STR1## gives the end products, known as animal growth-promoters and coccidiostatics. Intermediates II are new.Type: GrantFiled: September 8, 1987Date of Patent: February 6, 1990Assignee: Bayer AktiengesellschaftInventors: Bernd Gallenkamp, Andreas Gunther, Karl-Heinrich Mohrmann, Thomas Schmidt
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Patent number: 4874860Abstract: The novel process ##STR1## gives the end products, known as animal growth-promoters and cooccidiostatics. Intermediates II are new.Type: GrantFiled: December 18, 1987Date of Patent: October 17, 1989Assignee: Bayer AktiengesellschaftInventors: Bernd Gallenkamp, Andreas Gunther, Karl-Heinrich Mohrmann, Thomas Schmidt
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Patent number: 4868298Abstract: 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: GrantFiled: June 22, 1988Date of Patent: September 19, 1989Assignee: Cargill, IncorporatedInventor: Larry F. Brinkman
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Patent number: 4864025Abstract: Substantially pure isocyanurate/polyisocyanates, i.e., containing no more than about 0.03% by weight of residual diisocyanate monomer and no more than about 1% by weight of diisocyanate dimer, are produced by extracting impure cyclotrimerized diisocyanates with an inert gas in either the liquid or supercritical state.Type: GrantFiled: December 2, 1987Date of Patent: September 5, 1989Assignee: Rhone-Poulenc ChimieInventors: Jean Robin, Andre Blind
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Patent number: 4855334Abstract: A curable resin composition comprising an isocyanuric ring-containing urethane-modified radical-polymerizable compound. The composition can give a protective coating having excellent surface mar resistance and improved secondary adhesion.Type: GrantFiled: June 3, 1985Date of Patent: August 8, 1989Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Osamu Maruyama, Hidenobu Ishikawa, Nobuo Takahashi
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Patent number: 4851531Abstract: The present invention is directed to isocyanato isocyanurates prepared from diisocyanates which contain a sterically unhindered isocyanate group bound to a primary aliphatic carbon atom and a sterically hindered isocyanate group which is bound to a tertiary carbon atom forming part of a cycloaliphatic ring system, said diisocyanate having an NCO content of about 20 to 50% by weight. The present invention is further directed to a process for preparing these isocyanato isocyanurates by catalytic trimerization and the use of the isocyanato isocyanurates in a process for the production of polyisocyanate polyaddition products, preferably two-component polyurethane stoving lacquers.Type: GrantFiled: July 16, 1987Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Reinhard Halpaap, Gerhard Klein, Roland Richter, Hanns P. Muller, Josef Pedain, Hans-Joachim Kreuder
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Patent number: 4839359Abstract: Fungicidally active trisubstituted 1,3,5-triazine-2,4,6-trione of the formula ##STR1## in which Ar represents optionally substituted aryl,R.sup.1 represents an optionally substituted aliphatic or cycloaliphatic radical andR.sup.2 represents an optionally substituted aliphatic radical.Type: GrantFiled: November 5, 1987Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventors: Wolfgang Fuhrer, Engelbert Kuhle, Alfons Adler, Gerd Hanssler
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Patent number: 4837321Abstract: The present invention is directed to a process for the preparation of isocyanurate group-containing polyisocyanates by trimerizing a portion of the isocyanate groups of an organic polyisocyanate and terminating the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalyst used is a quaternary phosphonium salt of a tertiary phosphine and an alkylating ester of an acid of phosphorus. The present invention also relates to the use of the polyisocyanates obtained according to this process, optionally, in a form that has been freed from excess starting polyisoyanate and/or optionally blocked with blocking agents for isocyanate groups as the isocyanate component for the preparation of polyisocyanate polyaddition products, preferably polyurethanes.Type: GrantFiled: December 4, 1986Date of Patent: June 6, 1989Assignee: Bayer AktiengesellschaftInventors: Dimitrios Kerimis, Hanns P. Muller
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Patent number: 4788287Abstract: A high performance water and oil repellant composed of a compound comprising at least two terminal segments and an intermediate segment connecting the terminal segments and having a molecular weight of from 800 to 20,000, each terminal segment containing at least one polyfluoroalkyl group connected by a --CONH-- linking group, said intermediate segment being a urethane oligomer containing at least two --CONH-- linking groups in one molecule, and said terminal segments and intermediate segment being connected by a --CONH-- linking group.Type: GrantFiled: September 3, 1986Date of Patent: November 29, 1988Assignee: Asahi Glass Company Ltd.Inventors: Masashi Matsuo, Masayuki Tamura, Katsuji Ito