Trimerization Process To Form The Triazine Ring Patents (Class 544/193)
  • Patent number: 4487928
    Abstract: The present invention thus relates to a process for the preparation of polyisocyanates having isocyanurate groups by the trimerization of part of the isocyanate groups of organic polyisocyanates or of mixtures of di- and mono-isocyanates in the presence of basic compounds as trimerization catalysts, with termination of the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts used are 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacylopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane.This invention also relates to solutions suitable as catalyst components for this process, comprising 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacyclopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane dissolved in polar lacquer solvents and/or at least one compound within the molecular weight range of about 32 to 250 which has alcoholic hydroxyl groups and is liquid at room temperature.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Richter, Hanns P. M/u/ ller, Kuno Wagner
  • Patent number: 4454317
    Abstract: In a process for the trimerization of diisocyanates in the presence of a catalyst comprising quaternary ammonium salts of organic acids having the formula: ##STR1## wherein X represents the same or different radicals selected from the group consisting of C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.8 cycloalkyl, and C.sub.2 -C.sub.20 aralkyl; two X radicals taken together with at least one other heteroatom forming a hetero-ring and three X radicals taken together with the quaternary nitrogen atoms forming a hetero-ring through a common hetero-atom such that said heterocyclic ring structure is selected from the group consisting of triethylene diamine, methyl triethylene diamine, quinuclidine, N-methylmorpholine, N-ethylmorpholine, and N,N'-dimethylpiperazine; R is alkyl, cycloalkyl or aralkyl, R" is R or hydrogen; R+R" together form a C.sub.1 -C.sub.12 alkyl radical; R' is hydrogen, hydroxyl or a C.sub.1 -C.sub.12 alkyl radical, optionally containing a CH.sub.(3-b) Z.sub.
    Type: Grant
    Filed: July 23, 1982
    Date of Patent: June 12, 1984
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
  • Patent number: 4454296
    Abstract: The present invention provides novel triisocyanate compounds of the formula: ##STR1## wherein ##STR2## stands for ##STR3## the production thereof and the use thereof for polyurethane resins, especially, for solvent-free or high solids polyurethane coatings.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: June 12, 1984
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kimiya Fujinami, Ichiro Minato, Koichi Shibata
  • Patent number: 4426460
    Abstract: Improved rigid urethane and isocyanurate foam compositions having improved fire resistance are described. The urethane foams are based on furan compositions having the formula: ##STR1## and from about 100% to about 500% of a stoichiometric amount of a reactive polyisocyanate to produce a foamable composition, and sufficient blowing agent to create a foam having a density from about 1.5 to about 5 pounds per cubic foot. The product has improved fire resistence. The disclosure also described the method of decreasing the flame hazard potential of a rigid foam by adding two urethane or isocyanurate foaming ingredients the appropriate amount of one or more of the compositions listed above. The polymers described are chiefly made from adding propelyne oxide to bis (hydroxymethyl) furan.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: January 17, 1984
    Assignee: Quaker Oats Company
    Inventor: William J. Pentz
  • Patent number: 4413123
    Abstract: 1,3,5-triacrylylhexahydro-s-triazine is prepared as a solution in excess of about 10 weight percent and in yields of up to about 99 percent of theoretical by reacting acrylonitrile and trioxane with a catalytic amount of an acid having a Hammet activity function (H.sub.o) in excess of about 7.3 utilizing methylene chloride as the reaction medium.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: November 1, 1983
    Assignee: Union Carbide Corporation
    Inventors: Louis B. Conte, Jr., Walter T. Reichle
  • Patent number: 4412073
    Abstract: Monomeric or polymeric isocyanurates, e.g., polyisocyanate/polyisocyanurates, are prepared by catalytically cyclotrimerizing an isocyanate, e.g., an aliphatic or cycloaliphatic isocyanate, in the presence of an aminosilyl catalysis initiator, e.g., a mono- or diaminosilane, a silylurea or a silazane, having the structural formula:R.sub.(4-n) Si--NR'R"].sub.n (I)wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR.sub.3 or an amido radical having the structural formula: ##STR1## wherein R'" is R or SiR.sub.3, with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR.sub.
    Type: Grant
    Filed: February 1, 1982
    Date of Patent: October 25, 1983
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Jean Robin
  • Patent number: 4382125
    Abstract: A stable isocyanurate-modified polyisocyanate prepared by trimerizing an organic polyisocyanate mixture of 45 to 70 percent by weight of diphenylmethane diisocyanate having an isomer mixture of 40 to 100 weight percent, 4,4'-, 0 to 50 weight percent 2,4-, and 0 to 10 weight percent 2,2'-diphenylmethane diisocyanate and from 30 to 55 percent by weight polymethylene polyphenylene polyisocyanate with an isocyanurate content of 20 to 33 percent by weight. Polyurethane isocyanurate foams prepared from the reaction of these isocyanates with active hydrogen compounds selected from the group consisting of diethylene glycol and ethylene oxide adducts of trimethylolpropane, trimethylolethane, and glycerine exhibit good K- factors, low friability and low smoke density.
    Type: Grant
    Filed: November 30, 1981
    Date of Patent: May 3, 1983
    Assignee: BASF Wyandotte Corporation
    Inventors: Thirumurti Narayan, Peter T. Kan, John T. Patton, Jr.
  • Patent number: 4379905
    Abstract: The subject of the invention is a process for the preparation of polyisocyanates containing isocyanurate groups which comprises trimerizing a proportion of the isocyanate groups of organic polyisocyanates or mixtures of di- and monoisocyanates in the presence of basic alkali metal compounds as catalysts and terminating the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts are complexes of(i) basic alkalimetal compounds and(ii) acyclic organic compounds which(a) have at least 6 alkylene oxide units of the formula --R--O--, wherein R represents C.sub.1 -C.sub.
    Type: Grant
    Filed: January 6, 1982
    Date of Patent: April 12, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ingo Stemmler, Hanns P. Muller, Kuno Wagner
  • Patent number: 4359550
    Abstract: Polyisocyanurate polymers are prepared by the polymerization of organic polyisocyanates in organic solvents employing trimerization catalysts. After deactivation of the catalysts and removal of the solvents, these polymers may be dispersed in polyols which are employed for the preparation of cellular and non-cellular polyurethane products displaying improved load bearing properties.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: November 16, 1982
    Assignee: BASF Wyandotte Corporation
    Inventors: Thirumurti Narayan, Gerhard G. Ramlow, Peter T. Kan
  • Patent number: 4359541
    Abstract: Polyisocyanurate polymers are prepared by polymerization of polyisocyanates in organic solvents employing trimerization catalysts. The polyisocyanates are reacted with monofunctional active hydrogen compounds prior to polymerization or subsequent to the polymerization. These polymers may be dispersed in polyols for the preparation of cellular and non-cellular polyurethane products having improved physical properties.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: November 16, 1982
    Assignee: BASF Wyandotte Corporation
    Inventors: John T. Patton, Jr., Thirumurti Narayan, Gerhard G. Ramlow
  • Patent number: 4335219
    Abstract: The reaction of an isocyanate such as toluene diisocyanate with itself to form an isocyanurate or with an active hydrogen compound such as diethylene glycol to form a urethane is catalyzed by the presence of an ar-ammonium areneoxide such as 4-dodecyl-2-trimethylammonium phenoxide.
    Type: Grant
    Filed: April 6, 1981
    Date of Patent: June 15, 1982
    Assignee: The Dow Chemical Company
    Inventors: Donald H. Clarke, George J. Pomranky, Donald L. Schmidt
  • Patent number: 4326043
    Abstract: Polyisocyanurate polymers are prepared by polymerization of polyisocyanates in organic solvents employing trimerization catalysts. The polyisocyanates are reacted with halogenated alcohols subsequent to polymerization. These polymers may be dispersed in polyols for the preparation of cellular and non-cellular polyurethane products having improved flame retardant physical properties.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: April 20, 1982
    Assignee: BASF Wyandotte Corporation
    Inventors: Thirumurti Narayan, John T. Patton, Jr.
  • Patent number: 4324879
    Abstract: The present invention is concerned with an improved process for the production of partially trimerized hexamethylene diisocyanate which yields isocyanurate isocyanates which have low viscosity and low monomer contents by the use of a quaternary ammonium hydroxide catalyst which is hydroxyalkyl substituted at its N atom.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: April 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Bock, Josef Pedain, Walter Uerdingen
  • Patent number: 4306051
    Abstract: A method for the production of blocked isocyanate- and isocyanurate group-containing compounds which comprises reacting a monomeric cycloaliphatic polyisocyanate to form an intermediate mixture comprising an isocyanurate containing at least two free isocyanate groups; and blocking the intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C., wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of the dimethylketoxime. A mixture containing isocyanurate and blocked isocyanate groups which comprises at least 10% by weight of a cycloaliphatic isocyanurate containing at least two isocyanate groups blocked with dimethylketoxime and a monomeric polyisocyanate blocked with dimethylketoxime in such amounts as necessary to complete 100% by weight of the mixture, and wherein the unblocked NCO-group content of the monomeric polyisocyanate is less than 0.5% by weight.
    Type: Grant
    Filed: March 28, 1980
    Date of Patent: December 15, 1981
    Assignee: Chemische Werke Huls AG
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 4293680
    Abstract: The instant invention is directed to a process for the production of diisocyanate mixtures of 2,4-diisocyanato toluene and 2,6-diisocyanato toluene, having from 36 to 90% by weight, based on the total mixture, of 2,6-diisocyanato toluene, comprising: trimerizing some of the isocyanate groups of a diisocyanate mixture of 2,4-diisocyanato toluene and 2,6-diisocyanato toluene, having a maximum content of 2,6-diisocyanato toluene of 35% by weight based on the total mixture and isolating from the reaction mixture which is thus obtained, a diisocyanate mixture having an increased content of 2,6-diisocyanato toluene.The invention is also directed to the use of these mixtures as synthesis components in the production of polyurethane elastomers.
    Type: Grant
    Filed: August 6, 1980
    Date of Patent: October 6, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jan Mazanek, Hanns P. Nuller
  • Patent number: 4291161
    Abstract: The compound of N,N',N"-trimethyl trithioisocyanurate and the novel compound N,N',N"-trimethyl 2-iminodithioisocyanurate have been found to be effective in protecting rice against Pyricylaria oryzae.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: September 22, 1981
    Assignee: Dupaar International Research B.V.
    Inventors: Hendrik Dolman, Johannes Kuipers
  • Patent number: 4283535
    Abstract: A method of preparing 2,4,6-triketohexahydrotriazines which comprises catalytically trimerizing an organic isocyanate at 60.degree.-150.degree. C. in an inert, polar solvent present in an amount of 5-40 weight % with respect to the quantity of said isocyanate, in the presence of 0.1-5 weight % of a catalyst of the formula ##STR1## or hydrated derivatives of said catalyst, wherein R is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Me.sup.+2 is a bivalent metal cation; interrupting the trimerization at a conversion of about 50% by cooling; and then isolating the 2,4,6-triketohexahydrotriazine.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: August 11, 1981
    Assignee: Chemische Werke Huls AG
    Inventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
  • Patent number: 4282356
    Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable quaternary ammonium or acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;n represents zero or 1;R.sup.7 represents hydrogen or C.sub.1-6 alkyl;R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, phenyl, benzyl, or C.sub.3-6 cycloalkyl;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; andR.sup.
    Type: Grant
    Filed: June 10, 1980
    Date of Patent: August 4, 1981
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4265798
    Abstract: Potassium salt of 2-pyrrolidinone is used as a catalyst to cyclotrimerize an organic diisocyanate, yielding a mixture of monomeric cyclotrimerized product (isocyanurate) and oligomers thereof, soluble in common organic solvents and vinyl monomers. The catalyst can be used to make one-shot isocyanurate-crosslinked polyurethanes. Prepolymers and moisture-curing coating compositions can also be prepared.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: May 5, 1981
    Assignee: Uniroyal Ltd.
    Inventor: Anupama Mishra
  • Patent number: 4264498
    Abstract: A process for preparing an azetidinone of the formula: ##STR1## which comprises reacting a C-unsubstituted methyleneamine of the formula: ##STR2## with R.sup.2 --CH.sub.2 COOH, its acid halide or anhydride, in the presence of boron trihalide and an organic base, wherein R.sup.1 is an organic residue bearing a carboxy group or its derivative and R.sup.2 is azido, substituted amino, halogen, acyloxy, alkoxy, aryloxy or aralkoxy.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: April 28, 1981
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takashi Kamiya, Masashi Hashimoto, Osamu Nakaguti, Teruo Oku, Yoshiharu Nakai, Hidekazu Takeno
  • Patent number: 4255569
    Abstract: The instant invention is directed to a process for the production of isocyanate polyisocyanates containing at least 50%, by weight, of tris-isocyanatomonoisocyanurates and at most 3%, by weight, of isocyanurate-free diisocyanate. The process comprises catalytically trimerizing the organic diisocyanates free from isocyanurate groups and terminating the trimerization reaction by deactivation of the catalyst after 5 to 40% of the isocyanate groups of the isocyanurate-free diisocyanate have been trimerized. The unreacted isocyanurate-free diisocyanate is then distilled off in the presence of from 1 to 30%, by weight, based on the end product obtained as distillation residue, of an inert liquid distillation aid which boils at a temperature at least 50.degree. C. above the boiling point of the isocyanurate-free diisocyanate.The invention is also directed to the products produced by this process.
    Type: Grant
    Filed: May 4, 1979
    Date of Patent: March 10, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jurgen Muller, Rudolf Hombach, Manfred Dollhausen, Joachim Zirner
  • Patent number: 4255453
    Abstract: A process for the production of isocyanates by the addition of carbon monoxide to a metal or aryl carbamate.
    Type: Grant
    Filed: August 16, 1977
    Date of Patent: March 10, 1981
    Inventor: Robert K. Jordan
  • Patent number: 4246132
    Abstract: A method for the production of blocked isocyanate-and isocyanurate group-containing compounds which comprises:transforming a monomeric aliphatic or cycloaliphatic polyisocyanate or a mixture thereof into an intermediate mixture comprising an isocyanurate containing at least 2 free isocyanate groups; andblocking said intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C.;wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of said dimethylketoxime.The mixtures of the present invention are particularly suited as co-catalysts for the anionic polymerization of epsilon-caprolactam, as well as hardeners for higher functional thermoplastic compounds which contain Zerewitinoff-active hydrogen atoms.
    Type: Grant
    Filed: July 20, 1978
    Date of Patent: January 20, 1981
    Assignee: Chemische Werke Huls AG
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 4216316
    Abstract: A process is disclosed for the preparation of alkyl cyanates, alkyl isocyanurates, multifunctional alkyl cyanates, and oligomers of multifunctional alkyl isocyanates by reacting cyanogen halide with the corresponding thallium(I) salt of an alkanol at reduced temperatures, optionally in the presence of an inert solvent. Subsequently, warming the resulting product to ambient temperature causes isomerization to the corresponding aliphatic isocyanate and ultimately oligomerization to form trialkyl isocyanurate or oligomers of multifunctional alkyl isocyanates.
    Type: Grant
    Filed: February 8, 1979
    Date of Patent: August 5, 1980
    Assignee: The Dow Chemical Company
    Inventor: Edward E. Flagg
  • Patent number: 4182887
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is mono- or di-substituted amino, where the substituents are selected from the group consisting of alkyl of 1 to 6 carbon atoms, cyclohexyl, allyl and benzyl; unsubstituted, mono-substituted or di-substituted pyrrolidino, piperidino, hexamethyleneimino, morpholino, piperazino, thiomorpholino, 1-oxido-thiomorpholino or 1,1-dioxido-thiomorpholino, where the substituents are selected from the group consisting of methyl, hydroxymethyl, hydroxyl, phenyl and benzyl; 1,2,5,6-tetrahydropyridino; 1,2,3,4-tetrahydroisoquinolino; indolino; or 3,6-ethylene-hexamethyleneimino;R.sub.2 is hydrogen, methyl or benzyl; andR.sub.3 is hydrogen, halogen, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antiphlogistics and antithrombotics.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: January 8, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Josef Roch, Erich Muller, Berthold Narr, Josef Nickl, Walter Haarmann
  • Patent number: 4159262
    Abstract: Triazine compounds and cross-linked polymer compositions are made by heating aromatic nitriles to a temperature in the range of from about 100.degree. C. to about 700.degree. C., and preferably in the range of from about 200.degree. C. to about 350.degree. C. in the presence of a catalyst or mixture of catalysts selected from one or more of the following groups: (A) organic sulfonic and sulfinic acids, (B) organic phosphonic and phosphinic acids, and (C) metallic acetylacetonates, at a pressure in the range of from about atmospheric pressure to about 10,000 p.s.i., and preferably in the range of from about 200 p.s.i. to about 750 p.s.i.
    Type: Grant
    Filed: May 12, 1977
    Date of Patent: June 26, 1979
    Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space Administration
    Inventor: Li-Chen Hsu
  • Patent number: 4145544
    Abstract: Disclosed is a process for the preparation of ethylenically unsaturated isocyanurates which comprises a first step of trimerizing an aromatic polyisocyanate in the presence of an isocyanate trimerization catalyst and an ethylenically unsaturated solvent wherein at least 20% by weight of the solvent is an ethylenically unsaturated polar solvent, to form an isocyanate-containing isocyanurate and a second step of reacting the isocyanate-containing isocyanurate with a monohydric alcohol containing a vinylidene group to form an ethylenically unsaturated isocyanurate. The resulting solution of an ethylenically unsaturated isocyanurate dissolved in an ethylenically unsaturated solvent may be cured to form resins having excellent high temperature resistant properties.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: March 20, 1979
    Assignee: ICI Americas Inc.
    Inventor: Erich Kuehn
  • Patent number: 4124545
    Abstract: Novel compounds which upon heating are converted into the corresponding phenol which is a catalyst for the trimerization of compounds having isocyanato groups to form isocyanurates have the formula: ##STR1## in which N REPRESENTS AN INTEGER OF FROM 1 TO 4A represents an aromatic hydrocarbon group obtained by removing the NCO group from a monomeric aromatic monoisocyanate containing 6 - 14 carbon atoms,R.sub.1 and R.sub.2 may be the same or different and represent a C.sub.1 to C.sub.6 alkyl group or a polymethylene chain containing 4 to 8 carbon atoms which together with the nitrogen atom form a heterocyclic ring,R.sub.3 may be hydrogen, chlorine, bromine or a C.sub.1 - C.sub.18 -alkyl group.
    Type: Grant
    Filed: June 22, 1977
    Date of Patent: November 7, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Hocker, Hans-Joachim Diehr, Rudolf Merten
  • Patent number: 4113945
    Abstract: A novel catalyst system is described that is useful in the trimerization of organic isocyanates. The system comprises (1) N,N',N"-trisdialkylaminoalkyl-s-hexahydrotriazine and (2) a compound selected from the group consisting of 3,5-bis(N,N-dialkylaminoalkyl)-1,3,5-tetrahydrooxadiazine, 5-(N,N-dialkylaminoalkyl)-1,3,5-dihydrodioxazine and the mixtures thereof.
    Type: Grant
    Filed: July 1, 1977
    Date of Patent: September 12, 1978
    Assignee: Armstrong Cork Company
    Inventor: William J. Kauffman
  • Patent number: 4076494
    Abstract: Disclosed is a preparation, for use in the production of inks for transfer printing, which preparation comprises, in intimate admixture, a disperse dye and/or dispersion optical brightener, sublimable in the range of from 180.degree. to 220.degree. C, and a dispersing aid being a compound of formula I, ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently, are straight or branched chain C.sub.2-8 alkylene radicals, the OH groups being bound other than onto the carbon atoms adjacent the nitrogen atoms,The production and use thereof.
    Type: Grant
    Filed: November 3, 1976
    Date of Patent: February 28, 1978
    Assignee: Sandoz Ltd.
    Inventors: Johann Schuster, Karl Taubert
  • Patent number: 4061856
    Abstract: Triazine compounds and cross-linked polymer compositions are made by heating aromatic nitriles to a temperature in the range of from about 100.degree.0 C. to about 700.degree. C., and preferably in the range of from about 200.degree. C. to about 350.degree. C. in the presence of a catalyst or mixture of catalysts selected from one or more of the following groups: (A) organic sulfonic and sulfinic acids, (B) organic phosphonic and phosphinic acids, and (C) metallic acetylacetonates, at a pressure in the range of from about atmospheric pressure to about 10,000 p.s.i., and preferably in the range of from about 200 p.s.i. to about 750 p.s.i.
    Type: Grant
    Filed: October 10, 1974
    Date of Patent: December 6, 1977
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Li-Chen Hsu
  • Patent number: 4059610
    Abstract: Isocyanic acid derivatives are prepared by reacting an organic halogen compound with an alkali cyanate in N,N-disubstituted organic acid amides, N,N-disubstituted sulfonic acid amides, sulfoxides, sulfones or macrocyclic polyethers, at 70.degree. to 200.degree. C, in the presence of organic polyhalogen compounds selected from compounds having dihalogenomethyl group, dihalogenomethylene group, or trihalogenomethyl group and tetrahalogenomethane, in an amount in the range of from 1 to 20 weight percent based on the weight of said organic halogen compounds.
    Type: Grant
    Filed: May 14, 1976
    Date of Patent: November 22, 1977
    Assignee: Kao Soap Co., Ltd.
    Inventors: Susumu Handa, Yoshiaki Tanaka, Atsushi Nishibata, Sadashi Ueda, Yoshiaki Inamoto, Masahiro Saito, Fumio Tanimoto, Hisao Kitano