Acyclic Carbon Bonded Directly To The Isocyanate Group Patents (Class 560/355)
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Patent number: 6489429Abstract: There is disclosed a resin composition for electrodeposition paint comprising (A) a resin containing hydroxyl group, and (B) a polyisocyanate compound blocked with an amidoalcohol having at least one amide bond and at least one alcoholic hydroxyl group in the molecule, excellent in storage stability and capable of forming a coating film excellent in low temperature curability.Type: GrantFiled: June 12, 2001Date of Patent: December 3, 2002Assignee: Kansai Paint Co., Ltd.Inventors: Shigeo Nishiguchi, Sinzi Hirato, Reijiro Nishida
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Patent number: 6455729Abstract: The invention provides a novel polyisocyanate compound which is useful as a starting material for an optical material having a high refractive index, a low dispersion and excellent optical characteristics, and a process for producing this compound at good efficiency. The invention also provides an optical material having a high refractive index, a low dispersion, an excellent transparency without optical distortion and having good solvent resistance and weatherability.Type: GrantFiled: January 28, 2002Date of Patent: September 24, 2002Assignee: Hoya CorporationInventors: Yoshitaka Kitahara, Jian Jiang
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Patent number: 6452003Abstract: The present invention provides a process, which includes: partially trimerizing isophorone diisocyanate in the presence of a catalyst having the formula: [R—NX3]⊕Y⊖ wherein R and X are butyl groups and Y− is CH3COO−; or wherein R is a benzyl group, Y− is a carboxylate anion having from 4 to 8 carbon atoms and each X is an alkylene group having from 2 to 3 carbon atoms, wherein the three alkylene groups share a common carbon atom and, together with the N atom in the formula, form a tricyclic structure, and wherein at least one alkyene group has at least one OH group in an &agr; or &bgr; &ggr; position relative to the N atom, to obtain a monomer-containing polyisocyanurate mixture. The present invention also provides a monomer-containing polyisocyanurate mixture made from the above process.Type: GrantFiled: July 6, 2001Date of Patent: September 17, 2002Assignee: Degussa AGInventors: Michael Ewald, Rainer Lomoelder, Stephan Kohlstruk
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Patent number: 6426414Abstract: The present invention relates to water dispersible polyisocyanate mixtures prepared from aliphatic, cycloaliphatic, araliphatic and/or aromatic diisocyanates and having a) an average isocyanate functionality of at least 2.0, b) a content of 5.0 to 25.0 wt. %, based on resin solids, of isocyanate groups (calculated as NCO; molecular weight=42) and c) a content of 2 to 50 wt. %, based on resin solids, of ethylene oxide units calculated as C2H2O; molecular weight 44) incorporated within polyether chains containing an average of 5 to 35 ethylene oxide units, wherein at least 60 mole % of the polyether chains are connected via allophanate groups to two polyisocyanate molecules which are each prepared from at least two diisocyanate molecules. The present invention also relates to a process for the preparation of these water dispersible polyisocyanate.Type: GrantFiled: May 14, 1999Date of Patent: July 30, 2002Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Laas, Reinhard Halpaap, Christian Wamprecht
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Patent number: 6420508Abstract: The present invention relates to polyisocyanate mixtures prepared from aliphatic and/or cycloaliphatic diisocyanates and having a) an average isocyanate functionality of at least 2.0, b) a content of isocyanate groups (calculated as NCO; molecular weight=42) of 4.0 to 28.0 wt. % and c) a content of alkoxy groups having up to 36 carbon atoms of 2.0 to 37.5 wt. %, wherein the alkoxy groups are constituents of allophanate groups or optionally urethane groups, provided that >50 mol % of the alkoxy groups are a constituent of allophanate groups that are connected to at least two polyisocyanate molecules which are each prepared from at least two diisocyanates. The present invention also relates to a process for preparing these polyisocyanate mixtures and to coating compositions, which are highly diluted or dilutable with non-polar solvents and contain these polyisocyanate mixtures and lacquer binders or binder components optionally containing isocyanate-reactive groups.Type: GrantFiled: June 8, 2000Date of Patent: July 16, 2002Assignee: Bayer AktiengesellschaftInventors: Karsten Danielmeier, Lutz Schmalstieg, Hans-Josef Laas, Harald Mertes, Reinhard Jahn
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Publication number: 20020035232Abstract: The invention concerns an isocyanate composition at least partially masked, characterized in that it is masked by at least two agents, one of which at least has a non-carbon carboxylic function. The invention is applicable to organic synthesis.Type: ApplicationFiled: October 9, 2001Publication date: March 21, 2002Inventor: Jean-Marie Bernard
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Publication number: 20020007036Abstract: High-functionality polyisocyanates are prepared by a process which comprisesType: ApplicationFiled: March 19, 2001Publication date: January 17, 2002Inventors: Bernd Bruchmann, Hans Renz, Rainer Koniger, Ulrike Ehe, Ulrich Treuling, Rudolf Muller-Mall
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Publication number: 20010039325Abstract: Unique masked isocyanates well suited for formulation into a variety of coating compositions, for example paint powders, are prepared by condensing an isocyanate with a ring-hydroxylated aromatic compound bearing at least one substituent which comprises a carbonyl or nitrile functional group and the apparent melting point of which being at least 30° C.Type: ApplicationFiled: October 29, 1997Publication date: November 8, 2001Inventors: PIERRE ARDAUD, JEAN-MARIE BERNARD
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Publication number: 20010034429Abstract: Polyisocyanates of the formula (I) (polyisocyanate I),Type: ApplicationFiled: January 26, 2001Publication date: October 25, 2001Applicant: BASF AktiengesellschaftInventors: Bernd Bruchmann, Hans Renz, Gunter Mohrhardt, Hubert Baumgart, Simone Bitter
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Patent number: 6262296Abstract: A polyisocyanate prepolymer with isocyanate group on terminal obtainable by reaction of (A) polyoxyalkylenepolyol, (B) polyhydric alcohol having a molecular weight of 90 to 250 and the number of hydroxyl group of 2 to 3 with branched alkyl group and/or cyclohexane ring and (C) organic polyisocyanate composed of bis(isocyanatemethyl)cyclohexane, wherein NCO group content in the polyisocyanate prepolymer is 8% by weight or above and urethane group content in the polyisocyanate prepolymer is 8% by weight or above and sum total of NCO group content and urethane group content is 16 to 30% by weight and a concentration of unreacted (C) organic polyisocyanate remained in the polyisocyanate prepolymer is 1% by weight or below.Type: GrantFiled: April 14, 2000Date of Patent: July 17, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takeshi Nomura, Takeshi Koyama, Yutaka Kono
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Patent number: 6242530Abstract: The present invention relates to (cyclo)aliphatic polyisocyanates which have a content of blocked and unblocked isocyanate groups (calculated a NCO) of 5 to 25 wt. %, in which at least 95% of the isocyanate groups are present in a form blocked with blocking agents, and which also contain 0.1 to 5.0 wt. % of amines having a structural unit corresponding to formula (I) The present invention also relates to the use of the blocked polyisocyanates according to the invention as crosslinking agents for organic polyhydroxyl compounds in 1C-PUR stoving lacquers, especially for automotive clearcoats and coil coating lacquers.Type: GrantFiled: September 3, 1997Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Eberhard König, Karl-Ludwig Noble, Theodor Engbert
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Patent number: 6180745Abstract: The present invention relates to moisture-curable compositions which have a) a content of (cyclo)aliphatically-bound isocyanate groups (calculated as NCO, MW 42) of 0.2 to 22% by weight and b) a content of succinyl urea groups (calculated as —NH—CO—N—, MW 57) of 0.1 to 14% by weight, and c) an equivalent ratio of (cyclo)aliphatically-bound isocyanate groups to succinyl urea groups of 4:1 to 1:1, wherein the preceding percentages are based on resin solids content of the moisture-curable compositions. The present invention also relates to coating, adhesive or sealing compositions containing these moisture-curable compounds as the binder.Type: GrantFiled: November 8, 1999Date of Patent: January 30, 2001Assignee: Bayer CorporationInventor: Richard R. Roesler
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Patent number: 6177535Abstract: A process for preparing radiation-curable, urethane-functional prepolymers by reacting an isocyanate-functional component A with an OH-containing component B, wherein either component A embraces two different isocyanate compounds A1 or one isocyanate compound A1 and at least one isocyanate compound A2 or component B embraces at least two different compounds B1. Also, the prepolymers obtainable by the process and the radiation-curable formulations comprising them. Furthermore, the use of the radiation-curable formulations for coating substrates, a method of coating substrates, and the coated substrates themselves.Type: GrantFiled: September 21, 1998Date of Patent: January 23, 2001Assignee: BASF AktiengesellchaftInventors: Reinhold Schwalm, Rainer Königer, Wolfgang Paulus, Wolfgang Reich, Erich Beck, Matthias Lokai, Klaus Menzel
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Patent number: 6111053Abstract: The invention relates to olefinically unsaturated polyisocyanates containing allophanate groups and having an NCO content of 6 to 20% by weight, an iodine value of 15 to 150, a content of hydrocarbon chains containing 12 to 30 carbon atoms of 100 to 700 mg/g and a content of allophanate groups of 10 to 300 mg/g, to a process for their production by reaction of a polyisocyanate component containing urethane groups with excess polyisocyanates, and to a one-component coating composition containing these olefinically unsaturated polyisocyanates as binders.Type: GrantFiled: May 8, 1995Date of Patent: August 29, 2000Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Eberhard Arning, Lutz Schmalstieg, Harald Mertes, Jurgen Schwindt
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Polymeric vehicles which include a phenol blocked isocyanate having aliphatic hydroxyl fucntionality
Patent number: 6051674Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenol blocked isocyanate having reactive aliphatic hydroxyl groups. The phenol blocked isocyanate may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group and one phenolic hydroxyl group.Type: GrantFiled: August 26, 1996Date of Patent: April 18, 2000Assignee: Exxon Chemical Patents, Inc.Inventors: Albert I. Yezrielev, Frank N. Jones, Ramachandran P. Subrayan, Vijay Swarup -
Patent number: 5961878Abstract: The invention relates to non-crystallising, amine-blocked polyisocyanates, to the preparation thereof and to their in one-component polyurethane stoving compositions, in particular for coil-coating applications.Type: GrantFiled: September 2, 1998Date of Patent: October 5, 1999Assignee: Bayer AktiengesellschaftInventors: Eberhard Konig, Karl-Ludwig Noble, Christian Fussel
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Patent number: 5951911Abstract: The present invention relates to ethylenically unsaturated polyurethanes which are substantially free from isocyanate groups and havea) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 10% by weight,b) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 20% by weight andc) a total content of ethylenically unsaturated groups of (calculated as C.dbd.C, MW 24) of 1 to 15% by weight.The present invention also relates to ethylenically unsaturated polyisocyanates which contain allophanate groups and havei) an NCO content of 5 to 25% by weight,ii) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 15% by weight andiii) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 30%.Type: GrantFiled: January 9, 1998Date of Patent: September 14, 1999Assignee: Bayer CorporationInventors: Lanny D. Venham, Arthur W. Mason, Michael K. Jeffries, Michael J. Dvorchak
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Patent number: 5905151Abstract: This invention relates to a process for trimerizing organic polyisocyanates in the presence of thermally active catalyst systems. The catalyst systems comprise (a) compounds selected from the group consisting of 1) lithium salts of aliphatic or aromatic carboxylic acids, 2) lithium salts of hydroxyl group containing compounds wherein the hydroxyl groups are directed attached to an aromatic ring, and 3) lithium hydroxide; used in conjunction with (b) an organic compound which contains at least one hydroxyl group.Type: GrantFiled: February 18, 1993Date of Patent: May 18, 1999Assignee: Bayer CorporationInventors: William E. Slack, Hersel T. Kemp, II
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Patent number: 5880312Abstract: Disclosed is a semicarbazide derivative represented by formula (1) or a terminal-blocked form thereof: ##STR1## wherein R.sup.1 represents a terminal isocyanate group-free polyisocyanate residue or a terminal isocyanate group-free triisocyanate residue; R.sup.2 represents an alkylene group, a cycloalkylene group, or an arylene group; each R.sup.3 independently represents a hydrogen atom or an alkyl group; n is zero or 1; and each of l and m is independently zero or a positive integer, provided that l and m satisfy the relationship 3.ltoreq.(l+m).ltoreq.20. Also disclosed is (.delta.) a composition comprising (.alpha.) at least one member selected from the group consisting of the semicarbazide derivative and a terminal-blocked form thereof and (.beta.) at least one member selected from the group consisting of a hydrophilic group-containing compound and a terminal-blocked form thereof. Also disclosed is a coating composition comprising (.gamma.) a polycarbonyl compound, and component (.alpha.) or composition (.Type: GrantFiled: December 23, 1996Date of Patent: March 9, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Akira Nakabayashi, Tetsuya Murakami
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Patent number: 5849855Abstract: Disclosed is a blocked polyisocyanate composition comprising: a blocked polyisocyanate obtained by blocking the terminal isocyanate groups of a two or more terminal isocyanate groups-containing polyisocyanate derived from at least one diisocyanate selected from an aliphatic diisocyanate and an alicyclic diisocyanate with a blocking agent comprising at least one active methylene compound selected from a malonic diester and an acetoacetic ester; and a salt of a basic compound with an acidic compound, or a mixture of the salt with the basic compound or the acidic compound, the composition having a pH value of from 1 to 8.5. The blocked polyisocyanate composition of the present invention not only exhibits high stability even under high temperature conditions, but also is capable of maintaining such high stability for a prolonged period of time.Type: GrantFiled: August 19, 1996Date of Patent: December 15, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Taketoshi Usui, Yoshiyuki Asahina
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Patent number: 5849944Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible by the use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.Type: GrantFiled: May 27, 1997Date of Patent: December 15, 1998Assignee: ARCO Chemical Technology, L.P.Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
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Patent number: 5821316Abstract: An isocyanate-terminated polyurethane prepolymer comprising the reaction product of a polyisocyanate and a polyol composition consisting essentially of a polyether polyol of 350-2000 equivalent weight and a low molecular weight polyol of 62 to<300 molecular weight, in an equivalent ratio of low molecular weight polyol to polyether polyol of 0.25-2.7:1. A polyurethane-urea elastomer having good dynamic properties can be prepared by reacting the isocyanate-terminated prepolymer with an aromatic amine chain extender at an equivalent ratio of 0.9-1.1:1.Type: GrantFiled: January 24, 1997Date of Patent: October 13, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Jeffrey Raymond Quay, Edwin Lee McInnis
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Patent number: 5798409Abstract: The present invention relates to two-part reactive polyurethane compositons and the cured coatings prepared therefrom. The invention also relates to particular compositions and cured coatings therefrom that exhibit high damping character, excellent scratch-resistance, excellent mar-resistance, and self-healing characteristics. The invention also relates to a novel polyurethane prepolymer useful in some ofthe compositions. The invention also relates to method of making certain coatings of the invention.Type: GrantFiled: April 1, 1997Date of Patent: August 25, 1998Assignee: Minnesota Mining & Manufacturing CompanyInventor: Chia-Tie Ho
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Patent number: 5739207Abstract: Urethane-filled polyisocyanates are produced by (a) reacting a hexamethylene diisocyanate-containing residue having less than 10% by weight monomeric hexamethylene diisocyanate and a total NCO content of at least 25% with an alcohol containing at least one ether linkage in an equivalent ratio of isocyanate to hydroxyl groups of from about 0.9:1 to about 1.0:0.9 and (b) dissolving the product of (a) in a polyisocyanate. These urethane-filled polyisocyanates are particularly useful in the production of polyurethanes.Type: GrantFiled: December 27, 1996Date of Patent: April 14, 1998Assignee: Bayer CorporationInventor: William E. Slack
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Patent number: 5725612Abstract: New, highly effective detergent/dispersants for use in spark ignition fuels are described. They are Mannich condensation products formed from (i) one mole part of at least one substituted hydroxyaromatic compound having on the ring both (a) an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight in the range of about 500 to about 3000, and (b) a C.sub.1-4 alkyl; (ii) from 0.8 to 1.5 mole part(s) of aliphatic polyamine having one and only one primary or secondary amino group in the molecule capable of participating in the Mannich condensation reaction; and (iii) from 0.8 to 1.3 mole part(s) of aldehyde, provided that the mole ratio of aldehyde to amine is 1.2:1 or less. Carrier fluids such as poly(oxyalkylene) compounds further enhance the effectiveness of these Mannich condensation products in minimizing or reducing intake valve deposits and/or intake valve sticking.Type: GrantFiled: April 10, 1997Date of Patent: March 10, 1998Assignee: Ethyl CorporationInventors: Dennis J. Malfer, William J. Colucci, Randall M. Franklin
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Patent number: 5714564Abstract: The present invention is directed to a polyisocyanate containinga) polyisocyanates containing isocyanurate groups and corresponding to formula 1 ##STR1## wherein R represents the residue obtained by removing one of the isocyanate groups from 4-isocyanatomethyl-1,8-octamethylene diisocyanate,optionally in admixture withb) unreacted 4-isocyanatomethyl-1,8-octamethylene diisocyanate,c) higher homologs of the polyisocyanates set forth in formula 1 containing more than one isocyanurate group andd) a polyisocyanate containing allophanate groups.The present invention also relates to the use of these polyisocyanate mixtures, optionally in blocked form, as an isocyanate component in one- or two-component coating compositions.Type: GrantFiled: August 21, 1996Date of Patent: February 3, 1998Assignee: Bayer CorporationInventor: Myron W. Shaffer
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Patent number: 5710191Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising at least one compound of either of the following formulas IA and IB: ##STR1## where R is hydrogen, methyl or hydroxymethyl. The preferred catalysts comprise 3-hydroxymethyl quinuclidine, 3-methyl-3-hydroxymethyl quinuclidine and 4-hydroxymethyl quinuclidine.Type: GrantFiled: May 21, 1996Date of Patent: January 20, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Mark Leo Listemann, Kristen Elaine Minnich, Brian Eugene Farrell, Lisa Ann Mercando, Michael John Kimock, James Dudley Nichols
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Patent number: 5710319Abstract: The invention relates to a process for the preparation of quinazoline-2,4-diones of the formula (I) ##STR1## in which R.sup.1 is (C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.8)cycloalkyl or (C.sub.7 -C.sub.10)aralkyl, it being possible for the aryl group to be substituted by one or more halogen atoms, andR.sup.2, R.sup.3, R.sup.4 and R.sup.5, independently of one another, are halogen, alkyl, alkoxy or hydrogen, which comprises reacting anthranilic acid esters of the formula (II) ##STR2## in which R is (C.sub.1 -C.sub.10)alkyl and R.sup.2 to R.sup.5 are as defined above, with isocyanates R.sup.1 -.dbd.C.dbd.O in an aprotic reaction medium to give carbamoylanthranilic acid esters of the formula (III) ##STR3## in which R, R.sup.1 to R.sup.5 are as defined above, and cyclizing these products in the presence of alkali metal alcoholates, alkali metal amides, alkali metal hydrides, alkaline earth metal alcoholates, alkaline earth metal amides, alkaline earth metal hydrides or tetraalkylammonium hydroxides.Type: GrantFiled: November 16, 1995Date of Patent: January 20, 1998Assignee: Hoechst AktiengesellschaftInventor: Robert Cosmo
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Patent number: 5703271Abstract: A method of synthesizing multitier cascade polymers and the polymers made thereby are formed by reacting at least one tier of a polymer with a functionalized isocyanate having the following formula:O.dbd.C.dbd.N--C(CH.sub.2 --R).sub.3with R being selected from the group including:--(CH.sub.2).sub.n --CH.sub.2 --COOR' a)with R' being selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl- polycycloalkyl, adamantyl, n=0-10;--O--(CH.sub.2).sub.n --CH.sub.2 --COOR'--O--(CH.sub.2).sub.n --CH.sub.2 --CN b)with R' being selected from the group consisting of alkyl (c-1 to C(20), cycloalkyl (C-3 to C-10), aryl heteroaryl, polycycloalkyl, adamantyl, n=0-10; and--CH.sub.2 --(CH.sub.2).sub.Type: GrantFiled: April 2, 1996Date of Patent: December 30, 1997Assignee: University of South FloridaInventors: George R. Newkome, Claus Weis
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Patent number: 5693686Abstract: A polyisocyanate having an acid value of at least 0.01% HCl is used to produce polyisocyanate, polyisocyanurate and polyurethane urea foams with an HCFC blowing agent. The use of such a polyisocyanate is advantageous because the polyisocyanate does not cause significant decomposition of the HCFC blowing agent.Type: GrantFiled: February 10, 1994Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: John F. Szabat, Charles E. Mortimer, Joseph M. Sutej, Jeanne L. Beaumont, Steven L. Schilling, Harold R. Parsons, Robert P. Yeater
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Patent number: 5691441Abstract: Substitution of from 5 to 50 equivalent percent of an ultra-low unsaturation polyoxypropylene diol for PTMEG in isocyanate-terminated prepolymers used in spandex production is found to lower considerably both prepolymer viscosity and hysteresis while substantially retaining other desirable physical properties. Such products may offer higher fiber production rates than are possible while employing an all PTMEG-derived polymer.Type: GrantFiled: October 11, 1996Date of Patent: November 25, 1997Assignee: Arco Chemical Technology, L.P.Inventors: Stephen D. Seneker, Bruce D. Lawrey
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Patent number: 5677412Abstract: Poly(ether-urethanes) can be made from cyclic ethers and organic isocyanates by using selected metal compounds as catalysts. Polymers useful as thermoplastic elastomers, spandex fibers or urethane rubbers can be made by reacting diisocyanates containing functional groups with a tetrahydrofuran, especially tetrahydrofuran itself. The invention also discloses an improved process for the cationic polymerization of a cyclic ether by using an organic isocyanate.Type: GrantFiled: March 19, 1996Date of Patent: October 14, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Neville Everton Drysdale
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Patent number: 5634951Abstract: New, highly effective detergent/dispersants for use in spark ignition fuels are described. They are Mannich condensation products formed from (i) one mole part of hydroxyaromatic compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight in the range of about 500 to about 3000, (ii) from 0.8 to 1.5 mole part(s) of aliphatic polyamine having one and only one primary or secondary amino group in the molecule capable of participating in the Mannich condensation reaction, and (iii) from 0.8 to 1.3 mole part(s) of aldehyde, provided that the mole ratio of aldehyde to amine is 1.2 or less. Carrier fluids such as poly(oxyalkylene) compounds further enhance the effectiveness of these Mannich condensation products in minimizing or reducing intake valve deposits and/or intake valve sticking.Type: GrantFiled: June 7, 1996Date of Patent: June 3, 1997Assignee: Ethyl CorporationInventors: William J. Colucci, F. Alexander Pettigrew, Lawrence J. Cunningham
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Patent number: 5625026Abstract: An amide group-containing epoxy resin obtained by reacting an epoxy resin with an amide group-containing diisocyanate obtained by reacting a diisocyanate with a dicarboxylic acid gives a uniform cured article showing high adhesiveness and is usable as an adhesive, a coating composition, and the like.Type: GrantFiled: May 18, 1994Date of Patent: April 29, 1997Assignee: Hitachi Chemical Company, Ltd.Inventors: Kenji Suzuki, Yoshiyuki Mukoyama, Toshihiko Ito
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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: 5606001Abstract: The present invention relates to a polyisocyanates containing allophanate groups and optionally isocyanurate groups that are prepared by reacting compounds whichi) are substantially free of hydroxyl groups and isocyanate groups,ii) have an average of at least two urethane groups per molecule andiii) are the reaction products of linear or branched, aliphatic isocyanates with organic hydroxyl compounds,with an excess quantity, based on the urethane groups, of 4,4'-bis-(isocyanatocyclohexyl)-methane to form polyisocyanates containing allophanate groups and optionally isocyanurate groups and optionally removing at least a portion of the unreacted excess 4,4'-bis-(isocyanatocyclohexyl)-methane. The present invention also relates to a process for the production of these polyisocyanates and to their use as binders or binder components in coating compositions.Type: GrantFiled: September 14, 1995Date of Patent: February 25, 1997Assignee: Bayer CorporationInventor: Myron W. Shaffer
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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: 5556891Abstract: The invention relates to prepolymers containing isocyanate groups which can be prepared by reactinga) organic isocyanates withb) polyetherols containing at least 2 hydroxyl groups per molecule and having molecular weights of greater than 400 and/or polyesterols containing at least 2 hydroxyl groups per molecule and having molecular weights of greater than 400,c) isocyanate-reactive compounds which are at least difunctional and have molecular weights of from 18 to 399, and, if desired,d) Lewis and/or Bronsted acidic compounds ande) conventional auxiliaries and additives, such as antioxidants, light stabilizers or fillers,wherein at least one aromatic aminopolyether alcohol of the formula ##STR1## where R is aryl, alkylaryl containing one or more C.sub.1 - to C.sub.4 -alkyl groups, haloaryl, nitroaryl or cyanoaryl,R' and R" are identical or different and are, independently of one another, hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl, alkoxyaryl or aroxyaryl,x and y are independent of one another andx+y.gtoreq.Type: GrantFiled: November 1, 1995Date of Patent: September 17, 1996Assignee: BASF Schwarzheide GmbHInventors: Holger Seifert, Juergen Winkler, Regina Pretzsch, Robert O'Meara
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Patent number: 5554787Abstract: Novel 2,2 -dialkylpentane-1,5-diisocyantes, 2,2-dialkylpentane-1,5-diurethanes and 2,2-dialkylpentane-1,5-dicarbamoyl chlorides of the formula ##STR1## where R.sup.1 and R.sup.2 are identical or different linear C.sub.1 -to C.sub.12 -alkyl, branched C.sub.3 - to C.sub.12 -alkyl, branched C.sub.2 - to C.sub.12 -alkenyl or branched C.sub.4 - to C.sub.12 -alkenyl,or R.sup.1 and R.sup.2 together are alkylene having from 4 to 7 carbon atoms, which is unsubstituted or substituted by from 1 to 5 C.sub.1 - to C.sub.4 -alkyl groups, and X is NCO, NH--CO.sub.2 R.sup.3, NHCO.sub.2 R.sup.4 or NHCOCl, where R.sup.3 and R.sup.4 are identical or different and are linear C.sub.1 - to C.sub.20 -alkyl, branched C.sub.3 - to C.sub.20 -alkyl or C.sub.5 - to C.sub.12 -cycloalkyl, are described.Type: GrantFiled: February 3, 1995Date of Patent: September 10, 1996Assignee: BASF AktiengesellschaftInventors: Franz Merger, Andreas Otterbach, Tom Witzel, Hans Renz
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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: 5527925Abstract: Compounds of formula I: ##STR1## are disclosed. The compounds are photoinitiators which can be functionalized by means of ethylenic groups or can be bonded to H-active substances, in order, for example, to modify surfaces by means of photopolymerizable substances. The compounds are especially useful in the manufacture of contact lenses.Type: GrantFiled: June 24, 1994Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Chabrecek, Dieter Lohmann
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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: 5347044Abstract: Novel trans-beta-isocyanatoacrylate esters, their preparation and use in forming novel polymeric compositions, including polymers useful as adhesives, are disclosed. The trans-beta-isocyanatoacrylate esters have the formula: ##STR1## wherein R is C.sub.1 -C.sub.18 linear or branched alkyls; C.sub.5 -C.sub.6 cycloalkyl; aryl; alkaryl; aralkyl; C.sub.1 -C.sub.18 halogenated alkyl; halogenated aryl; C.sub.1 -C.sub.8 alkoxyalkyl; or alkoxyaryl.Type: GrantFiled: April 6, 1992Date of Patent: September 13, 1994Assignee: Curators of the University of MissouriInventors: Thomas J. Byerley, Cecil C. Chappelow, J. David Eick
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Patent number: 5319133Abstract: The present invention relates to a process for preparation of an isocyanate comprising (a) reacting an amide with an aqueous solution of hypochlorous acid in the presence of an water-immiscible organic solvent to produce an N-chloro amide; and (b) reacting said N-chloro amide with a base in the presence of a phase transfer catalyst and a water immiscible organic solvent to produce an isocyanate.Type: GrantFiled: December 28, 1992Date of Patent: June 7, 1994Assignee: Olin CorporationInventors: Robert J. Raynor, Thomas A. Knowles
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Patent number: 5274182Abstract: Saturated, liquid, low molecular weight and low-viscosity isobutylene polymers terminally functionalized by special groups, which correspond to the following formula ##STR1## are produced by solution ozonolysis of high molecular weight isobutylene/diene copolymers containing diene monomers, stabilization of the products obtained after the ozone treatment by addition of peroxide decomposers and subsequent reduction with hydrogen in the presence of hydrogenation catalysts under pressures of 10 to 300 bar and at temperatures of 20.degree. to 300.degree. C., optionally in the presence of sulfur or amines or ammonia.Type: GrantFiled: June 26, 1992Date of Patent: December 28, 1993Assignee: Bayer AktiengesellschaftInventors: Richard Weider, Thomas Scholl
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Patent number: 5258452Abstract: The present invention relates to polyisocyanates containing tertiary nitrogen with an (average) NCO functionality of 2.3 to 4.3 which, despite the presence of tertiary nitrogen and isocyanate groups in the same molecule, would be stable in storage, could be dissolved or dispersed in water without difficulty, optionally after at least partial alkylation or protonation, and would be suitable as starting components in the production of polyurethane plastics and, above all, as crosslinking agents for water-containing binders or binder components.Type: GrantFiled: September 4, 1992Date of Patent: November 2, 1993Assignee: Bayer AktiengesellschaftInventor: Helmut Reiff
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Patent number: 5250723Abstract: A novel polymerizable monomer represented by the formula (I) useful as a raw material for the high surface hardness transparent resin. ##STR1## wherein R is an aliphatic residue having or not having an oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, or an alicyclic residue, l is 0 or 1, each of i and j is an integer of 1 or more, and when l=0, i=j=1, when l=1, (i+j) is 4 or less, when j=1, X is oxygen or sulfur, when j.gtoreq.2, all X's are oxygen or sulfur, or one X is oxygen and the other X's are sulfur, or one X is sulfur and the other X's are oxygen.The high surface hardness transparent resin comprises a crosslinked polymer prepared by copolymerizing a monomer (A) represented by the formula (I) as above and a monomer (B) containing one or more functional groups of at least one kind selected from the group consisting of CH.sub.2 .dbd.CH--C(O)--O--, CH.sub.2 .dbd.C(CH.sub.Type: GrantFiled: August 10, 1992Date of Patent: October 5, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Toshiyuki Suzuki, Katsuyoshi Sasagawa, Masao Imai, Yoshinobu Kanemura
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Patent number: 5215618Abstract: Disclosed herein is a process for bonding substrates comprising applying a hot-melt adhesive to the surface of at least one of the substrates and contacting the surface of said substrate with the surface of the other substrate, said adhesive containing an ester group-containing polyisocyanate which is a solid below 30.degree. C. and liquid above 100.degree. C., corresponding to formula (I)A(OCO-B-NCO).sub.n (I)in whichn stands for a whole number or a fraction (statistical average) of from 2 to 6,A stands for an n-valent organic group such as is obtained by removal of hydroxyl groups from an n-valent polyhydroxyl compound in the molecular weight (Mn) range of from 800 to 6000 containing ester and/or carbonate groups andB stands for an aliphatic, cycloaliphatic or aromatic hydrocarbon group having up to 18 carbon atoms.Type: GrantFiled: August 8, 1991Date of Patent: June 1, 1993Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Eduard Haensel, Klaus Nachtkamp, Heinrich Konigshofen, Otto Ganster
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Patent number: 5210284Abstract: Organic mono- or di-isocyanates are prepared by the decomposition of the corresponding urethanes, by means of a continuous process in which:(a) an urethane flow is continuously fed to a decomposition reactor containing a liquid mixture, composed of a high boiling inert organic solvent, of an unaltered urethane and isocyanate, kept at the boiling conditions of the solvent, at a temperature suitable to decompose the urethane and evaporate the alcohol which is the co-product of the reaction;(b) the liquid mixture is continuously withdrawn from the reactor in (a) and is fed to a flash equipment, at an operating temperature lower than the decomposition temperature of the urethane, where the isocyanate is partially evaporated and the residuous liquid mixture is recycled to the reactor in (a); and(c) the steam flow generated in (b) is distilled to separate the isocyanate in pure or substantially pure form.Type: GrantFiled: December 19, 1991Date of Patent: May 11, 1993Assignee: Enichem Synthesis S.p.A.Inventors: Franco Mizia, Carlo Calderoni