Trimerization Process To Form The Triazine Ring Patents (Class 544/193)
  • Patent number: 5235018
    Abstract: 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 a monoalcohol containing at least 10 carbon atoms and having a molecular weight of 158 to 2500.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 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.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: August 10, 1993
    Assignee: Miles Inc.
    Inventors: Terry A. Potter, William E. Slack, Patricia B. Jacobs
  • Patent number: 5233039
    Abstract: 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 consisting essentially of at least one compound of the following formula; ##STR1## where R is hydrogen, c.sub.1 -c.sub.8 alkyl, c.sub.6 -c.sub.10 aryl or c.sub.7 -c.sub.10 aralkyl, and n is 0-3. The preferred catalyst consists essentially of of the compound when n is 0, namely 3-quinuclidinol.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: August 3, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Mark L. Listemann, Ann C. L. Savoca, Kristen E. Minnich, Kevin R. Lassila
  • Patent number: 5221743
    Abstract: 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: Grant
    Filed: March 2, 1992
    Date of Patent: June 22, 1993
    Assignee: Olin Corporation
    Inventors: Stephen L. Goldstein, Curtis P. Smith
  • Patent number: 5218133
    Abstract: This invention provides a process for making a silylorganocarbamate or a silylisocyanurate which process comprises reacting an aminosilane with a dialkyl carbonate, diaryl carbonate or a mixture thereof in the presence of a basic catalyst to obtain the silylorganocarbamate; optionally, neutralizing the basic catalyst and residual aminosilane with a neutralizing agent; and adding a cracking catalyst and heating at subatmospheric pressure to obtain the silylisocyanurate; or heating a silylorganocarbamate at a temperature sufficient for dissociation of the carbamate at subatmospheric pressure in the presence of a cracking catalyst and a timerization catalyst to obtain a silylisocyanurate.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: June 8, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Enrico J. Pepe, Shiu-Chin H. Su, Scot M. Turner
  • Patent number: 5215860
    Abstract: Energy polymerizable compositions comprising at least one cyanate monomer and as curing agent an organometallic compound are disclosed. The compositions are useful in applications requiring high performance, such as high temperature performance; in composites, particularly structural composities; structural adhesives; tooling for structural composities; electronic applications such as printed wiring boards and semiconductor encapsulants; graphic arts; injection molding and prepregs; and high performance binders.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: June 1, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
  • Patent number: 5212306
    Abstract: A method for catalyzing the trimerization of an isocyanate and/or the reaction between an isocyanate and an active hydrogen-containing compound, the improvement which comprises employing a catalyst composition consisting essentially of the addition product of a tertiary amine urethane catalyst and a boron compound of the formulaR.sub.n BX.sub.3-nwheren represents 0, 1, 2 or 3,X represents F, Cl, Br, OCOR', OR" or mixtures thereof, andR, R' and R" independently represent C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.8cycloalkyl, C.sub.6 -C.sub.10 aryl or mixtures thereof.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: May 18, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ann C. L. Savoca, Mark L. Listemann
  • Patent number: 5208334
    Abstract: 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: Grant
    Filed: June 9, 1992
    Date of Patent: May 4, 1993
    Assignee: Miles Inc.
    Inventors: Terry A. Potter, William E. Slack
  • Patent number: 5194609
    Abstract: 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 consisting essentially of at least one compound of the following formula: ##STR1## where R is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.10 aralkyl, and n is 0-3. The preferred catalyst consists essentially of the compound when n is 0, namely 3-quinuclidinol.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: March 16, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ann C. L. Savoca, Mark L. Listemann
  • Patent number: 5182360
    Abstract: Tris(norbornenyl) isocyanurate compounds of the formula: ##STR1## wherein R.sup.1 is either H or methyl group, are prepared from the base-catalyzed trimerization of norbornenyl isocyanate. Tris(norbornenyl) isocyanurate is suitable for use as a crosslinker in thiol-ene formulations containing a difunctional thiol oligomer or in systems containing norbornene-difunctional oligomers and polyfunctional thiols, producing improved high temperature properties for the cured compositions.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: January 26, 1993
    Assignee: Loctite Corporation
    Inventors: Anthony F. Jacobine, Steven T. Nakos
  • Patent number: 5144031
    Abstract: 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, based
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: September 1, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Josef Pedain
  • Patent number: 5143944
    Abstract: 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 consisting essentially of at least one compound of the following formula: ##STR1## where R is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.10 aralkyl, and n is 0-3. The preferred catalyst consists essentially of of the compound when n is 0, namely 3-quinuclidinol.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: September 1, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Ann C. L. Savoca, Mark L. Listemann
  • Patent number: 5124427
    Abstract: 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 a monoalcohol containing 1 to 5 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 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: Grant
    Filed: January 22, 1991
    Date of Patent: June 23, 1992
    Assignee: Miles Inc.
    Inventors: Terry A. Potter, William E. Slack
  • Patent number: 5102918
    Abstract: A modified organic polyisocyanate is prepared in such a manner that a trimerization catalyst, an organic phosphite estr, and a surfactant, and optionally a ferrocene compound are added to an organic isocyanate and/or a partially urethanized organic polyisocyanate to cause isocyanuration in an extent that not more than 20% by weight of entire isocyanate groups are isocyanurated; and a stopper is added, if necessary.
    Type: Grant
    Filed: January 9, 1991
    Date of Patent: April 7, 1992
    Assignee: Nippon Polyurethane Industry Co., Ltd.
    Inventor: Kiyoshi Moriya
  • Patent number: 5095087
    Abstract: Disclosed are certain ketoxime-blocked polyisocyanates and polyester compositions containing the ketoxime-blocked polyisocyanates. Also disclosed are thermosetting powder coating compositions comprising one or more polyesters and at least one of the ketoxime-blocked polyisocyanates and articles coated with the powder coating compositions.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: March 10, 1992
    Assignee: Eastman Kodak Company
    Inventors: J. Stewart Witzeman, Glenn C. Jones
  • Patent number: 5036151
    Abstract: The invention relates to trimerized aliphatic isocyanates produced by special processes, to their use as mold release agents in thermoplastic aromatic polycarbonates and/or thermoplastic aromatic polyestercarbonates and/or thermoplastic aromatic polyesters, optionally using standard additives, to the readily demoldable molding compounds thus obtained on the basis of the thermoplastic polycarbonates, polyestercarbonates and/or polyesters and to processes for the production of these readily demoldable molding compounds.
    Type: Grant
    Filed: March 14, 1990
    Date of Patent: July 30, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Holger Ohst, Helmut-Martin Meier, Klaus Kircher
  • Patent number: 5013838
    Abstract: 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: Grant
    Filed: January 19, 1990
    Date of Patent: May 7, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Scholl
  • Patent number: 4992548
    Abstract: 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: Grant
    Filed: August 8, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Josef Pedain
  • Patent number: 4963675
    Abstract: 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: Grant
    Filed: March 29, 1989
    Date of Patent: October 16, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean Robin, Andre Blind
  • Patent number: 4957921
    Abstract: Substituted cyclohexanols are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.
    Type: Grant
    Filed: December 6, 1989
    Date of Patent: September 18, 1990
    Assignee: Warner-Lambert Company
    Inventors: Bradley W. Caprathe, Juan C. Jaen, Sarah J. Smith, Lawrence D. Wise
  • Patent number: 4937339
    Abstract: In a process for preparing isocyanurate ring-containing materials useful in the production of lacquers and foams which comprises trimerizing an organic isocyanate compound in the presence of a catalyst, the use of potassium fluoride as the catalyst makes it possible to yield the desired product rapidly without formation of by-products. More preferably, the reaction efficiency can further be enhanced by using a polyethylene oxide compound, a quaternary ammonium salt and/or a phosphonium compound in combination with potassium fluoride.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: June 26, 1990
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tetsunosuke Shiomura, Yoshiho Sonobe, Akihiro Yamaguchi, Ryuzi Haseyama
  • Patent number: 4880927
    Abstract: A method for preparing a cyclic isocyanuric ester having organosilicon groups which comprises thermally treating an isocyanic ester for addition reaction in the presence of an alkali metal hydroxide or alkoxide. By the above reaction, a cyclic trimer of the starting isocyanic ester can be selectively obtained. The catalyst can be readily removed from the reaction system.
    Type: Grant
    Filed: December 3, 1987
    Date of Patent: November 14, 1989
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Takago, Yasushi Yamamoto
  • Patent number: 4868298
    Abstract: A continuous method for the high-yield, one-step, solvent-free manufacture of blocked polyisocyanurate compounds useful as curing agents in powder coating compositions. The preferred method of manufacture is to pre-mix a blocking agent and a polymerization catalyst (BAC mix) prior to injection with an organic isocyanate monomer having two or more isocyanate groups (herein termed a polyisocyanate) into a preheated reaction zone wherein the BAC mix and the polyisocyanate react to form the blocked polyisocyanurate compound that is obtained after discharge from the reaction zone and cooling.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: September 19, 1989
    Assignee: Cargill, Incorporated
    Inventor: Larry F. Brinkman
  • Patent number: 4864025
    Abstract: 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: Grant
    Filed: December 2, 1987
    Date of Patent: September 5, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean Robin, Andre Blind
  • Patent number: 4837321
    Abstract: 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: Grant
    Filed: December 4, 1986
    Date of Patent: June 6, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dimitrios Kerimis, Hanns P. Muller
  • Patent number: 4748242
    Abstract: 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: Grant
    Filed: November 12, 1986
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Halpaap, Josef Pedain, Hans-Joachim Kreuder, Gerhard Klein, Dieter Arlt
  • Patent number: 4743627
    Abstract: A method for producing liquid isocyanurate modified Polymeric MDI composition containing a high two-ring MDI content, and foams made therefrom is described. The method comprises trimerizing a polymeric MDI in the presence of catalytically effective amount of a trimerization catalyst to form an isocyanurate containing polyisocyanate having a viscosity of about 100,000 mPas. The trimerization catalyst is thereafter deactivated and the isocyanurate-modified polyisocyanate is blended with a methylene bis(phenylisocyanate) (MDI) to form a final product having a two-ring content of about 60 percent of the total ring content and a viscosity comparable to polymeric MDI. Foams produced using this liquid isocyanurate modified polymeric MDI are of a substantially lighter color than those produced from standard polymeric MDI.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: May 10, 1988
    Assignee: BASF Corporation
    Inventors: Thirumurti Narayan, Peter T. Kan
  • Patent number: 4713442
    Abstract: This invention relates to a polyaromatic cyanate which corresponds to the formula ##STR1## wherein: Ar is an aromatic radical;B is a C.sub.7-20 polycyclic aliphatic radical;D is independently in each occurrence any nonactive hydrogen-containing substituent;q, r and s are independently in each occurrence the integers 0, 1, 2, or 3; with the proviso that the sum of q, 4 and s is greater than or equal to 2;t is independently in each occurrence an integer of between about 0 and 4 inclusive; andx is a number between about 0 and 5 inclusive.Another aspect of this invention is a novel polytriazine which comprises the reaction product of the polyaromatic cyanate esters of this invention. The novel polytriazines may further comprise the reaction product of the novel polyaromatic cyanates of this invention in admixture with other cyanates known in the art as useful for the preparation of polytriazines.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Daniel J. Murray
  • Patent number: 4699933
    Abstract: The present invention is directed to polyurethane compositions containing triazine or both triazine and oxazoline or imino carbamate groups which are prepared by reacting:1.(a) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group, or(b) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one oxazoline group, or(c) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one imino carbamate group, or(d) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one other N-heterocyclic group, or(e) a mixture of the above and2. at least one material having more than one isocyanate group per moleculewherein the components are employed in proportions which provide a ratio of isocyanate groups to hydroxy groups of from about 0.05:1.0 to about 10.0:1.0, preferably from about 0.95:1.0 to about 1.5:1.0.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: October 13, 1987
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Mary N. White
  • Patent number: 4696991
    Abstract: A blocked polyisocyanurate having the formula: ##STR1## wherein each of X, Y and Z which may be the same or different, is a residue of a diisocyanate compound devoid of the isocyanate groups, each of R.sup.1, R.sup.2 and R.sup.3 which may be the same or different, is a group selected from the group consisting of C.sub.1 -C.sub.20 alkyl, alkoxyalkyl, aryl, alkaryl and aralkyl, and n is an integer of from 1 to 10.
    Type: Grant
    Filed: August 6, 1986
    Date of Patent: September 29, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yoshimichi Kobayashi, Hisaharu Hotta
  • Patent number: 4697014
    Abstract: 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: Grant
    Filed: March 25, 1986
    Date of Patent: September 29, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Jean Robin
  • Patent number: 4680394
    Abstract: An improved process for preparing formaldoxime trimer is provided in which loss of the product is minimized and the prior art problems of long retention times to afford precipitation of the trimer which is difficult to filter and which occludes the undesirable salt of the acid that is difficult to remove. The method disclosed involved oximation of paraformaldehyde using dehydroxylamine sulfate and ammonia gas followed by steam stripping to recover formaldoxime and separate trimerization thereof followed by filtration recovery and drying.The formaldoxime trimer is produced in essentially quantitative yield and proceeds specifically by a procedure of steam stripping out the formaldoxime monomer from the synthesis liquor and allowing separate trimer formation and recovery. The product is free from inorganic salts and the mother liquor with formaldoxime monomer content, resulting from its recovery by filtration, does not represent a yield loss in that it is recyclable to the next synthesis reaction.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: July 14, 1987
    Assignee: Allied Corporation
    Inventor: John H. Bonfield
  • Patent number: 4675401
    Abstract: 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: Grant
    Filed: October 30, 1985
    Date of Patent: June 23, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Jean Robin
  • Patent number: 4647623
    Abstract: A process for producing a polyisocyanate containing an isocyanurate ring which comprises reacting at least one diisocyanate compound selected from the group consisting of alkylene diisocyanates, cycloalkylene diisocyanates and aralkylene diisocyanates with a cycloalkylene diol in the presence of an isocyanurating catalyst; and a resin composition for use in non-yellowing fast-drying urethane paints, comprising (A) the aforesaid polyisocyanate and (B) an acrylic polyol having a number average molecular weight of 2,000 to 30,000 and a hydroxyl value of 20 to 200.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: March 3, 1987
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Mitsuo Kase, Noboru Okoshi, Kazue Tsuyuzaki
  • Patent number: 4632989
    Abstract: 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: Grant
    Filed: May 28, 1985
    Date of Patent: December 30, 1986
    Assignee: The Dow Chemical Company
    Inventor: Dale F. Regelman
  • Patent number: 4623731
    Abstract: 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: Grant
    Filed: January 25, 1984
    Date of Patent: November 18, 1986
    Inventors: 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
  • Patent number: 4614785
    Abstract: The present invention relates to a process for the production of oligomeric polyisocyanates by the dimerization or trimerization of a portion of the isocyanate groups in organic polyisocyanates in the presence of tertiary phosphines or in the presence of a peralkylated phosphorus acid triamides as catalyst, followed by termination of the dimerization and/or trimerization reaction at the required degree of oligomerization by the addition of a catalyst poison, characterized in that a sulfonyl isocyanate is used as the catalyst poison.The present invention also relates to the use of the oligomeric polyisocyanates obtained by this process, optionally in admixture with unreacted starting polyisocyanate or optionally blocked by blocking agents for isocyanate groups, as the polyisocyanate component in the production of polyurethane plastics.
    Type: Grant
    Filed: August 14, 1985
    Date of Patent: September 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Richter, Hanns P. Muller, Werner Kubitza, Theodor Engbert, Gerhard Mennicken
  • Patent number: 4607103
    Abstract: There is provided a method for making blocked isocyanate trimers comprising (A) blocking at least one organic diisocyanate with at least one blocking compound, such as a monohydroxy compound and thereafter (B) heating the reaction product of step (A) in the presence of a catalyst having the general formula ##STR1## where each R is independently selected from hydrogen and lower alkyl radicals and R.sup.1 is an alkylene radical having up to about six carbon atoms; for an amount of time effective for forming blocked isocyanate trimers.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: August 19, 1986
    Assignee: General Electric Company, Silicone Products Division
    Inventors: Otto S. Zamek, Richard J. Stein
  • Patent number: 4602049
    Abstract: Disclosed is a novel class of amidinium salts having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 when taken individually are independently selected from lower-alkyl, aralkyl and cycloalkyl, and, when taken together with the respective nitrogen atoms to which they are attached, R.sub.1 together with R.sub.2, and R.sub.3 together with R.sub.4 independently represent heterocyclic groups having 5 to 7 ring atoms, R.sub.5, R.sub.6, R.sub.7, and R.sub.8 are independently selected from hydrogen, lower-alkyl, aryl, aralkyl, and cycloalkyl.The amidinium salts are very active catalysts for converting organic isocyanates to products containing isocyanurate and carbodiimide linkages.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: July 22, 1986
    Assignee: The Dow Chemical Company
    Inventor: Dale F. Regelman
  • Patent number: 4582888
    Abstract: A process for producing a polyisocyanate containing an isocyanurate ring, which comprises reacting at least one diisocyanate compound selected from the group consisting of alkylene diisocyanates, cycloalkylene diisocyanates and aralkylene diisocyanates with a diol having a molecular weight of 100 to 1,000 and containing at least 3 hydrocarbon substituents per molecule in the presence of an isocyanurating catalyst. A resin composition for urethane paints comprising the polyisocyanate as an essential ingredient.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: April 15, 1986
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Mitsuo Kase, Noboru Okoshi, Kazue Tsuyuzaki
  • Patent number: 4576747
    Abstract: 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: Grant
    Filed: May 7, 1984
    Date of Patent: March 18, 1986
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4577017
    Abstract: 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: Grant
    Filed: September 12, 1984
    Date of Patent: March 18, 1986
    Assignee: DSM Resins B.V.
    Inventors: Willem J. H. Hupperetz, Johannes A. H. M. Ramakers
  • Patent number: 4552946
    Abstract: 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: Grant
    Filed: January 19, 1984
    Date of Patent: November 12, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Josef Pedain, Bernd Riberi, Gerhard Mennicken
  • Patent number: 4540781
    Abstract: 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: Grant
    Filed: August 11, 1983
    Date of Patent: September 10, 1985
    Assignee: The Upjohn Company
    Inventor: Edward A. Barsa
  • Patent number: 4537961
    Abstract: 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: Grant
    Filed: March 1, 1983
    Date of Patent: August 27, 1985
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Jean Robin
  • Patent number: 4536490
    Abstract: 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: Grant
    Filed: March 8, 1984
    Date of Patent: August 20, 1985
    Assignee: The Upjohn Company
    Inventor: Dale F. Regelman
  • Patent number: 4528366
    Abstract: This invention is a process for the preparation of polytriazines comprising contacting aromatic polycyanates in the presence of a catalytic amount of a cobalt salt of a C.sub.6-20 carboxylic acid at a temperature between about 20.degree. C. and about 200.degree. C.
    Type: Grant
    Filed: February 15, 1984
    Date of Patent: July 9, 1985
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, David V. Dellar
  • Patent number: 4518761
    Abstract: The present invention is directed to a new process for the preparation of mixed trimers by at least partly trimerizing the isocyanate groups of at least two organic isocyanates of a reactivity which differs in the sense of the trimerization reaction, in the presence of trimerization catalysts and optionally interrupting the trimerization reaction at the respectively desired degree of trimerization, in which process the less reactive isocyanate component is introduced, polymerization is then commenced in the presence of the catalyst with the trimerization of at least 0.1% of the isocyanate groups and the more reactive isocyanate component is finally metered into the reaction mixture thus obtained; the mixed trimers obtained according to this process; and the use of the mixed trimers having free isocyanate groups obtained by this process, optionally in a form blocked by blocking agents for organic polyisocyanates, as a starting material for the production of polyurethane plastics materials.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: May 21, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Richter, Hanns P. Muller, Kuno Wagner, Bernd Riberi, Jurg Frohlich
  • Patent number: 4503226
    Abstract: A process for trimerizing organic polyisocyanates using a select catalyst comprising a quaternary ammonium carboxylic acid salt and a carboxylic acid halide or anhydride. The trimerization products are especially suitable for use in the preparation of polyurethane molding compositions.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: March 5, 1985
    Assignee: Olin Corporation
    Inventors: Kuo-Chang Tang, Phillip T. Berkowitz
  • Patent number: 4499253
    Abstract: The present invention relates to a process for the preparation of polyisocyanates containing isocyanurate groups by the trimerization of a proportion of the isocyanate groups of organic polyisocyanates and termination of the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts employed are quaternary ammonium salts based on the reaction product of tertiary amines and esters of acids of phosphorus which have an alkylating action. The invention also relates to the use of the polyisocyanates with isocyanurate groups obtainable by this process, optionally in a form freed from excess starting polyisocyanates and/or optionally in a form in which the isocyanate groups are blocked with blocking agents, as isocyanate components for the preparation of isocyanate-polyaddition products, especially polyurethanes.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: February 12, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dimitrios Kerimis, Hanns P. Muller, Kuno Wagner
  • Patent number: 4491663
    Abstract: Novel trifunctinal blocked isocyanates containing an isocyanurate ring and method of preparing are disclosed. Use of blocked isocyanates of invention as crosslinker for aqueous and nonaqueous compositions is also taught.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: January 1, 1985
    Assignee: Ford Motor Company
    Inventors: Panagiotis I. Kordomenos, Andrew H. Dervan