Biurets (i.e., Hnh-co-nh-co-hnh, Wherein Substitution May Be Made For Hydrogen Only) Patents (Class 564/38)
  • Patent number: 4731415
    Abstract: A polyisocyanate having a biuret structure obtained by allowing .alpha.,.alpha.,.alpha.',.alpha.'-tetramethyl-xylylene diisocyanate, a diisocyanate represented by the general formula:OCN--CH.sub.2 --R--CH.sub.2 --NCOwherein R is a divalent hydrocarbon residue and water to react.The polyisocyanate is used in the form of the two-part type of polyurethane composition in combination with a polyol.The composition can provide coating films which excel in every physical properties required for the coating film, such as drying property, impact resistance, weathering resistance and chemical resistance, and therefore are advantageously used, for example, as a paint for automobile repairing uses, etc.
    Type: Grant
    Filed: April 2, 1986
    Date of Patent: March 15, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shoichi Fujita, Kohji Nasu
  • Patent number: 4701555
    Abstract: The biuret content of biuret-containing urea is reduced by contacting a solution or melt of biuret-containing urea with a polar adsorbent under conditions sufficient to remove at least a portion of biuret from the urea. The resulting biuret-containing adsorbent can be regenerated for further use by contact with a polar desorbent under conditions sufficient to desorb at least a portion of the biuret contained on the adsorbent. Optionally, biuret can be recovered by recovering the biuret-containing desorbent, and biuret concentration in the desorbent can be increased by recycling the biuret-containing desorbent into contact with biuret-containing adsorbents, and biuret can be recovered from the desorbent by low temperature crystallization.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: October 20, 1987
    Assignee: Union Oil Company of California
    Inventors: Donald C. Young, James A. Green, II
  • Patent number: 4698443
    Abstract: Purified biuret is recovered from mixtures containing biuret and higher molecular weight urea condensation products by contacting melts or solutions of such mixtures with a polar adsorbent and extracting biuret from the adsorbent with a polar desorbent. The useful biuret-containing mixtures also may contain urea. These methods are capable of recovering biuret of 99.9 percent plus purity from mixture containing higher molecular weight urea condensations products such as triuret, melamine, ammelide, and others. The biuret-containing desorbent can be recycled into contact with biuret-containing adsorbents to increase its biuret concentration, concentrated by evaporation of otherwise, and/or treated to crystallize biuret. An integrated process is provided which involves pyrolyzing urea to form biuret and higher molecular weight condensation products and selectively recovering biuret from the resulting pyrolyzed urea as described.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: October 6, 1987
    Assignee: Union Oil Company of California
    Inventors: Donald C. Young, James A. Green, II
  • Patent number: 4684746
    Abstract: Improved activators for anionic polymerization of lactams are biuret-containing polyisocyanates based on non-aromatic diisocyanates.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: August 4, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf-Volker Meyer, Friedrich Fahnler, Rolf Dhein, Dietrich Michael
  • Patent number: 4654441
    Abstract: Process for the production of technical grade biuret, readily in a form suitable for use as animal feed, by the controlled pyrolysis of urea in two stages, the first stage involving the partial pyrolysis of urea at a temperature above the melting point of urea to produce a first stage intermediate reaction product containing from about 20% to about 60% urea, and not more than about 25% cyanuric acid by weight, such reaction product being then cooled and comminuted, the comminuted product then being subjected, in solid form and in the absence of a liquid carrier, to a temperature at or slightly below the softening point of the solid particulate (suitable at a temperature of from about 100.degree. C. to about 140.degree. C.) with forced air circulation through the comminuted product for a sufficient time to lower its urea content by partial sublimation of the urea and partial further reaction thereof to biuret with only minimal further conversion of urea to cyanuric acid.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: March 31, 1987
    Assignee: Moorman Manufacturing Company
    Inventors: Kurt F. Stephan, John T. Stephan, Steven R. Klein
  • Patent number: 4645859
    Abstract: Methods are provided for recovering purified biuret from aqueous solutions containing biuret and higher molecular weight urea condensation products by contacting such solutions with the hydroxide ion form of an anion exchanger and extracting biuret from the ion exchanger with an aqueous extractant. The useful biuret-containing solutions also may contain urea. These methods are capable of recovering biuret of 99.9 percent plus purity from solutions containing higher molecular weight urea condensations products such as triuret, melamine, ammelide, and others. Elevated temperatures increase biuret recovery rate and concentration, and the extractant can be recycled into contact with additional biuret-containing anion exchangers to increase biuret concentration even further. The biuret-containing extract can be employed as is, concentrated by evaporation or otherwise, or treated to crystallize biuret.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: February 24, 1987
    Assignee: Union Oil Company of California
    Inventors: James A. Green, II, Donald C. Young
  • Patent number: 4625052
    Abstract: The present invention is directed to a process for the production of polyisocyanates which have a biuret structure by reacting aliphatic diisocyanates with water at elevated temperature, characterized in that the reaction is carried out in the presence of:(a) .alpha., .alpha., .alpha.-tri-substituted acetic acids, which do not have any further isocyanate-reactive group other than the carboxyl group,and/or(b) anhydrides of acids of the type mentioned in (a)wherein up to 0.39 mols of component (a) are used per mol of water, up to about 2 mols of component (b) are used per mol of water, and the total quantity of components (a) and (b) is at least 0.02 to about 2 mols per mol of water.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: November 25, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Konig, Josef Pedain, Helmut Woynar
  • Patent number: 4613686
    Abstract: The present invention relates to a process for the preparation of polyisocyanates which have a biuret structure of reacting excess quantities of aliphatic diisocyanates with biuretizing agents at elevated temperature, characterized in that the biuretizing agent contains(a) .alpha.,.alpha.,.alpha.-trisubstituted acetic acids which do not contain isocyanate-reactive groups apart from the carboxyl group, and optionally(b) water,wherein the molar ratio of biuretizing components (a) to (b) is within the range of from 1:0 to 1:2.5.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: September 23, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Konig, Josef Pedain, Helmut Woynar
  • Patent number: 4560738
    Abstract: A novel pest-combating agent of increased duration of action is produced by reacting a pest-combating agent having at least one hydrogen atom active in a Zerewitinoff reaction other than a hydrogen atom which is part of a carbamic acid ester group ##STR1## with a polyether isocyanate, the reaction with the polyether isocyanate taking place on said other hydrogen atom.
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: December 24, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Richter, Paul Reinecke, Hanns P. Muller, Gerhard Bonse, Wilhelm Brandes
  • Patent number: 4540820
    Abstract: Preparation of a composition particularly suitable for use as feedstock in the production of animal feed grade biuret by solid state pyrolyzation thereof in a recirculating oven, which composition comprises from about 37% to about 25% urea, from about 45% to about 60% biuret, and from about 3% to about 20% cyanuric acid, by weight, such preparation involving sparging air or other non-reactive gas through a urea charge at a temperature of from about 145.degree. C. to about 165.degree. C. and at a rate of between about two to about ten cu. ft. of gas/hr/lb of urea for a period of at least four hours, then cooling and comminuting the product.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: September 10, 1985
    Assignee: Moorman Manufacturing Company
    Inventors: Kurt F. Stephan, John T. Stephan
  • Patent number: 4532317
    Abstract: Aromatic polyamines containing aromatic primary amino groups as well as urethane and polyester groups are made by hydrolyzing an isocyanate in the presence of a basic material and water to form a carbamate and then converting the carbamate groups to amino groups. The isocyanate starting material contains aromatic isocyanate groups (as well as urethane and polyester groups) and has an NCO content of from 0.5 to 11.5 wt %. The basic compound is selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal silicates, alkali metal sulfides, alkali metal cyanides, tetraalkylammonium hydroxides and mixtures thereof. Water is used in a quantity such that at least one mole of water is present for each equivalent of NCO groups. The carbamate groups may be converted to amino groups by treating the carbamate-containing mixture with a proton donor or with heat or with a solvent. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4532266
    Abstract: Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: July 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Balle, Dieter Dieterich, Holger Meyborg
  • Patent number: 4525590
    Abstract: The invention relates to an improved process for the production of polyamines containing urethane and/or urea and/or biuret and/or isocyanurate groups and, preferably, also alkylene ether, carbonate and/or acetal groups by the alkaline hydrolysis of corresponding compounds containing terminal aliphatic and/or aromatic isocyanate groups.To this end, the compounds containing terminal NCO-groups, preferably NCO-preadducts, are converted by means of selected bases into the carbamates and neutralized by introduction into equivalent quantities of acid or by the simultaneous introduction of the components in equivalent quantities into a reaction vessel, after which the polyamines are directly isolated by methods known per se.The invention also relates to the use of the polyamines obtained by the process for the production of polyurethanes.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: June 25, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Klaus Konig, Holger Meyborg, Walter Meckel, Armin Zenner
  • Patent number: 4472568
    Abstract: This invention relates to an improved process for the preparation of aromatic polyamines containing urethane and/or biuret and/or urea and/or isocyanurate groups and preferably also ether groups by the hydrolysis of poly-N-monoaryl-N',N'-dialkyl urea compounds (1-aryl-3,3-dialkyl ureas). The ureas are obtained by the reaction of secondary aliphatic, cycloaliphatic or saturated heterocyclic amines with divalent to tetravalent isocyanate compounds containing isocyanate end groups attached to aromatic residues. The ureas correspond to the general formula: ##STR1## wherein R.sup.1, R.sup.2 denote alkyl or cycloalkyl groups, or together form a ring andA denotes a divalent to tetravalent residue attached to the ureas by aromatic groups.Hydrolysis is carried out in the presence of water and up to two equivalents of a base containing hydroxide ions and/or up to two equivalents of a compound containing tertiary amino groups, optionally in the presence of solvents.
    Type: Grant
    Filed: October 28, 1982
    Date of Patent: September 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Grogler
  • Patent number: 4386218
    Abstract: A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0.3:1 to .gtoreq.1.01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched-chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: May 31, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Dieter Dieterich, Holger Meyborg
  • Patent number: 4382956
    Abstract: N-Sulphenylated biurets of the formula ##STR1## in which R.sup.1 represents a trihalogenomethyl radical,R.sup.2 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical andR.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom, an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or the amino or hydroxyl group, or together with the connecting nitrogen atom represent a five-membered or six-membered heterocyclic ring, the ring carbon atoms of which are optionally interrupted by one or more further hetero-atoms,which possess fungicidal activity.
    Type: Grant
    Filed: December 15, 1981
    Date of Patent: May 10, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Engelbert Kuhle, Volker Paul, Wilhelm Brandes
  • Patent number: 4344893
    Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: August 17, 1982
    Assignee: The Boots Company Limited
    Inventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
  • Patent number: 4331680
    Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: May 25, 1982
    Assignee: The Boots Company
    Inventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
  • Patent number: 4293713
    Abstract: A novel 1,1,3,5-substituted biuret compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are respectively the same or different, and each are alkyl groups having 1 to 4 carbon atoms; R.sup.3 is a cyclohexyl group or a phenyl group which may be unsubstituted or may have at least one substituent selected from the group consisting of chlorine, bromine, fluorine, methyl, trifluoromethyl, dimethylamino, methoxy, methylthio, nitro and acetyl. The novel 1,1,3,5-substituted biuret compounds are useful as an analgesic, anti-inflammatory and/or anti-pyretic agent.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: October 6, 1981
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Hajime Fujimura, Yasuzo Hiramatsu, Takahiro Yabuuchi, Masakatu Hisaki, Katsuo Takikawa, Takaji Honna, Hidekazu Miyake, Makoto Kajitani