Trimerization Process To Form The Triazine Ring Patents (Class 544/193)
-
Patent number: 5240970Abstract: 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 which comprises a quaternary ammonium carboxylate inner salt having the following formula I ##STR1## where R.sub.1 -R.sub.3 are independently C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.8 cycloalkyl or a heterocycle, C.sub.6 -C.sub.10 aryl or heteroaromatic. R.sub.1 and R.sub.2 or R.sub.1 -R.sub.3 together with the nitrogen atom can also be part of nitrogen containing ring system such as piperdine, morpholine, triethylenediamine, imidazole, or 1,8-diazabicyclo-[5.4.0]-undec-7-ene. R.sub.4 is a divalent R.sub.1.Type: GrantFiled: January 8, 1993Date of Patent: August 31, 1993Assignee: Air Products and Chemicals, Inc.Inventors: James D. Nichols, Ann C. L. Savoca, Mark L. Listemann
-
Patent number: 5235018Abstract: 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: GrantFiled: May 6, 1992Date of Patent: August 10, 1993Assignee: Miles Inc.Inventors: Terry A. Potter, William E. Slack, Patricia B. Jacobs
-
Patent number: 5233039Abstract: 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: GrantFiled: January 30, 1992Date of Patent: August 3, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Mark L. Listemann, Ann C. L. Savoca, Kristen E. Minnich, Kevin R. Lassila
-
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
-
Patent number: 5218133Abstract: 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: GrantFiled: August 20, 1992Date of Patent: June 8, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Enrico J. Pepe, Shiu-Chin H. Su, Scot M. Turner
-
Patent number: 5215860Abstract: 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: GrantFiled: August 19, 1988Date of Patent: June 1, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Fred B. McCormick, Katherine A. Brown-Wensley, Robert J. DeVoe
-
Patent number: 5212306Abstract: 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: GrantFiled: September 18, 1992Date of Patent: May 18, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Ann C. L. Savoca, Mark L. Listemann
-
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
-
Patent number: 5194609Abstract: 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: GrantFiled: July 21, 1992Date of Patent: March 16, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Ann C. L. Savoca, Mark L. Listemann
-
Patent number: 5182360Abstract: 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: GrantFiled: October 17, 1991Date of Patent: January 26, 1993Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Steven T. Nakos
-
Patent number: 5143944Abstract: 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: GrantFiled: January 30, 1992Date of Patent: September 1, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Ann C. L. Savoca, Mark L. Listemann
-
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
-
Patent number: 5124427Abstract: 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: GrantFiled: January 22, 1991Date of Patent: June 23, 1992Assignee: Miles Inc.Inventors: Terry A. Potter, William E. Slack
-
Patent number: 5102918Abstract: 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: GrantFiled: January 9, 1991Date of Patent: April 7, 1992Assignee: Nippon Polyurethane Industry Co., Ltd.Inventor: Kiyoshi Moriya
-
Patent number: 5095087Abstract: 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: GrantFiled: February 25, 1991Date of Patent: March 10, 1992Assignee: Eastman Kodak CompanyInventors: J. Stewart Witzeman, Glenn C. Jones
-
Patent number: 5036151Abstract: 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: GrantFiled: March 14, 1990Date of Patent: July 30, 1991Assignee: Bayer AktiengesellschaftInventors: Holger Ohst, Helmut-Martin Meier, Klaus Kircher
-
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
-
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
-
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
-
Patent number: 4957921Abstract: 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: GrantFiled: December 6, 1989Date of Patent: September 18, 1990Assignee: Warner-Lambert CompanyInventors: Bradley W. Caprathe, Juan C. Jaen, Sarah J. Smith, Lawrence D. Wise
-
Patent number: 4937339Abstract: 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: GrantFiled: December 16, 1988Date of Patent: June 26, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tetsunosuke Shiomura, Yoshiho Sonobe, Akihiro Yamaguchi, Ryuzi Haseyama
-
Patent number: 4880927Abstract: 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: GrantFiled: December 3, 1987Date of Patent: November 14, 1989Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Takago, Yasushi Yamamoto
-
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
-
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
-
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
-
Patent number: 4748242Abstract: The present invention is directed to a process for the production of polyisocyanates containing isocyanurate groups by trimerizing a mixture of aliphatic-cycloaliphatic diisocyanates having a sterically unhindered isocyanate group bound to a primary aliphatic carbon atom and a sterically hindered isocyanate group bound to a tertiary carbon atom which forms a part of a cycloaliphatic ring system and 1,6-diisocyanatohexane. The present invention is also directed to the polyisocyanates containing isocyanurate groups produced according to this process and to their use, optionally in blocked form, as an isocyanate component in the production of polyisocyanate polyaddition products, preferably polyurethane lacquers.Type: GrantFiled: November 12, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Halpaap, Josef Pedain, Hans-Joachim Kreuder, Gerhard Klein, Dieter Arlt
-
Patent number: 4743627Abstract: 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: GrantFiled: September 14, 1987Date of Patent: May 10, 1988Assignee: BASF CorporationInventors: Thirumurti Narayan, Peter T. Kan
-
Patent number: 4713442Abstract: 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: GrantFiled: February 27, 1986Date of Patent: December 15, 1987Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Daniel J. Murray
-
Patent number: 4699933Abstract: 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: GrantFiled: October 14, 1986Date of Patent: October 13, 1987Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Mary N. White
-
Patent number: 4696991Abstract: 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: GrantFiled: August 6, 1986Date of Patent: September 29, 1987Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshimichi Kobayashi, Hisaharu Hotta
-
Patent number: 4697014Abstract: Storage-stable polyisocyanurate-polyisocyanates, essentially devoid of polyisocyanate monomer and dimer over time, are conveniently prepared by catalytically cyclotrimerizing an aliphatic, cycloaliphatic or aromatic polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst, and terminating the cyclotrimerization reaction when predetermined desired amount of isocyanurate group has been reached, by adding to the reaction mixture a reaction terminating amount of water.Type: GrantFiled: March 25, 1986Date of Patent: September 29, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
-
Patent number: 4680394Abstract: 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: GrantFiled: September 23, 1985Date of Patent: July 14, 1987Assignee: Allied CorporationInventor: John H. Bonfield
-
Patent number: 4675401Abstract: Polyisocyanurate/polyisocyanates of enhanced stability are prepared by partial catalytic cyclotrimerization of a polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst and wherein the cyclotrimerization reaction is terminated when a predetermined desired amount of isocyanurate groups has been attained, by adding to the reaction mixture, after the cooling thereof to a temperature of below 50.degree. C., a reaction terminating amount of an organic catalyst deactivating compound comprising at least one free hydroxyl moiety, or the reaction product of such hydroxylated organic catalyst deactivating compound with an isocyanate.Type: GrantFiled: October 30, 1985Date of Patent: June 23, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
-
Patent number: 4647623Abstract: 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: GrantFiled: September 17, 1985Date of Patent: March 3, 1987Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Mitsuo Kase, Noboru Okoshi, Kazue Tsuyuzaki
-
Patent number: 4632989Abstract: Disclosed are novel compositions capable of catalytically trimerizing organic isocyanates said compositions comprising solutions of the reaction products obtained by reacting in an inert solvent in substantially equimolar proportions electron-rich ketene-aminals with electron-poor olefins having the respective formulae (I) and (II) ##STR1## The variously substituted electron-rich ketene-aminals (I), as the name implies, have high electron density associated with the double bond because of the two tertiary amine groups while the electron-poor olefins (II) have the opposite situation due to the presence of electron withdrawing substituents R.sub.9 and R.sub.10.Also disclosed is an improved process for trimerizing organic isocyanates using the above catalyst compositions including the preparation of polyisocyanurate polymers and isocyanurate-modified polyisocyanates.Type: GrantFiled: May 28, 1985Date of Patent: December 30, 1986Assignee: The Dow Chemical CompanyInventor: Dale F. Regelman
-
Patent number: 4623731Abstract: Carbamic acid derivatives having the following general formula: ##STR1## wherein R is an aromatic radical containing at least one benzene ring with at least one hydrogen atom substituted with a methyl, methylene or methine group; n=2 to 7.A method for preparing carbamic acid derivatives which comprises reacting 3(5)-methylpyrazole with an isocyanate of the general formula: R(NCO).sub.n, wherein:R is an aromatic radical containing at least one benzene ring having at least one hydrogen atom substituted with a methyl, methylene or methine group; n=2 to 7;the reaction being conducted in a melt or a solution of an inert organic solvent.Type: GrantFiled: January 25, 1984Date of Patent: November 18, 1986Inventors: Mikhail G. Ivanov, Veniamin G. Golov, Vladimir N. Kuzmin, Aida I. Alyakrinskaya, Roman Y. Mushy, Alexei D. Kovalev, Nadezhda V. Shutova, Jury A. Rodionov, Igor I. Molev, Ljudmila S. Yakovleva, Vitaly B. Berezin, Alexei I. Petrashko, Gennady M. Shuev, Boris A. Bukin, Tamara M. Belkina, deceased, by Naum S. Belkin, administrator
-
Patent number: 4614785Abstract: 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: GrantFiled: August 14, 1985Date of Patent: September 30, 1986Assignee: Bayer AktiengesellschaftInventors: Roland Richter, Hanns P. Muller, Werner Kubitza, Theodor Engbert, Gerhard Mennicken
-
Patent number: 4607103Abstract: 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: GrantFiled: August 13, 1985Date of Patent: August 19, 1986Assignee: General Electric Company, Silicone Products DivisionInventors: Otto S. Zamek, Richard J. Stein
-
Patent number: 4602049Abstract: 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: GrantFiled: September 23, 1985Date of Patent: July 22, 1986Assignee: The Dow Chemical CompanyInventor: Dale F. Regelman
-
Patent number: 4582888Abstract: 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: GrantFiled: February 28, 1985Date of Patent: April 15, 1986Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Mitsuo Kase, Noboru Okoshi, Kazue Tsuyuzaki
-
Patent number: 4576747Abstract: Novel isocyanato-azetidinedione compounds are provided which have the formula ##STR1## wherein R and R.sub.1 can be independently selected from hydrogen and hydrocarbyl or can be joined together and along with the carbon to which they are attached represent a cycloalkane residue having 4 to 6 ring carbon atoms, y is an integer from 1 to 7 and X is a hydrocarbon radical having a valency of y plus one.The monoisocyanate compounds are used as intermediates to provide further novel azetidinedione containing derivatives in the form of azetidinedione-isocyanurates (II) and azetidinedione-urethanes (III).All three classes of compounds can be employed as acid scavenging agents for stabilizing various kinds of halogenated polymer systems. Notably, (I) and (III) form highly useful polyamide-polyureas and polyamide-polyurethanes respectively by reaction with organic polyamines.Type: GrantFiled: May 7, 1984Date of Patent: March 18, 1986Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
-
Patent number: 4577017Abstract: Process for the preparation of an isocyanurate-compound containing isocyanate groups by trimerisation of a diisocyanate in the presence ofa compound having the formula ##STR1## in combination with an organic base, or a compound having the formula ##STR2## where R and R' are chosen from a hydrocarbon radical with 1-10 carbon atoms,--O--R.sub.1, with R.sub.1 being a hydrocarbon radical with 1-10 carbon atoms, andH.Type: GrantFiled: September 12, 1984Date of Patent: March 18, 1986Assignee: DSM Resins B.V.Inventors: Willem J. H. Hupperetz, Johannes A. H. M. Ramakers
-
Patent number: 4552946Abstract: This invention relates to a new process for the production of polyisocyanates containing isocyanurate groups by partial trimerization of the isocyanate groups of organic polyisocyanates comprising(a) compounds or mixtures of compounds corresponding to the formula ##STR1## wherein R represents a saturated, aliphatic hydrocarbon radical having from 8 to 15 carbon atoms, and optionally(b) up to about 95 NCO equivalent %, based on the total of (a)+(b), of other organic polyisocyantes.This invention also relates to the compounds which may be obtained according to this process and to the use thereof for the production of isocyanate-polyaddition products such as polyurethanes.Type: GrantFiled: January 19, 1984Date of Patent: November 12, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Josef Pedain, Bernd Riberi, Gerhard Mennicken
-
Patent number: 4540781Abstract: Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids or half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids.Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20.degree. C.) which makes the present method particularly suitable to systems for molding polyiso-cyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.Type: GrantFiled: August 11, 1983Date of Patent: September 10, 1985Assignee: The Upjohn CompanyInventor: Edward A. Barsa
-
Patent number: 4537961Abstract: Polyisocyanato-polyisocyanurates are prepared by catalytically cyclotrimerizing a polyisocyanate in the presence of a catalytically effective amount of an aminosilyl catalyst, and which is characterizing by terminating the cyclotrimerization reaction when a predetermined desired amount of isocyanurate groups has been obtained, by adding to the reaction mixture a reaction terminating amount of an organic catalyst deactivating compound comprising at least one free hydroxyl moiety, or the reaction product of such hydroxylated organic catalyst deactivating compound with an isocyanate.Type: GrantFiled: March 1, 1983Date of Patent: August 27, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
-
Patent number: 4536490Abstract: Disclosed are novel compositions capable of catalytically trimerizing organic isocyanates said compositions comprising solutions of the reaction products obtained by reacting in an inert solvent in substantially equimolar proportions electron-rich ketene-aminals with electron-poor olefins having the respective formulae (I) and (II) ##STR1## The variously substituted electron-rich ketene-aminals (I), as the name implies, have high electron density associated with the double bond because of the two tertiary amine groups while the electron-poor olefins (II) have the opposite situation due to the presence of electron withdrawing substituents R.sub.9 and R.sub.10.Also disclosed is an improved process for trimerizing organic isocyanates using the above catalyst compositions including the preparation of polyisocyanurate polymers and isocyanurate-modified polyisocyanates.Type: GrantFiled: March 8, 1984Date of Patent: August 20, 1985Assignee: The Upjohn CompanyInventor: Dale F. Regelman
-
Patent number: 4528366Abstract: 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: GrantFiled: February 15, 1984Date of Patent: July 9, 1985Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, David V. Dellar
-
Patent number: 4518761Abstract: 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: GrantFiled: November 4, 1982Date of Patent: May 21, 1985Assignee: Bayer AktiengesellschaftInventors: Roland Richter, Hanns P. Muller, Kuno Wagner, Bernd Riberi, Jurg Frohlich
-
Patent number: 4503226Abstract: 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: GrantFiled: April 30, 1984Date of Patent: March 5, 1985Assignee: Olin CorporationInventors: Kuo-Chang Tang, Phillip T. Berkowitz
-
Patent number: 4499253Abstract: 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: GrantFiled: July 18, 1983Date of Patent: February 12, 1985Assignee: Bayer AktiengesellschaftInventors: Dimitrios Kerimis, Hanns P. Muller, Kuno Wagner