Polycarbamic Patents (Class 560/158)
  • Patent number: 4748226
    Abstract: This invention relates to novel 2-(alkoxymethyl) pentane-1,5-diisocyanates, 2-(alkoxymethyl)-pentane-1,5-diurethanes, and 2-(alkoxymethyl)-pentane 1,5-dicarbamic acid chlorides having the structure: ##STR1## in which R is a straight chain or branched C.sub.1 -C.sub.20 -alkyl radical, a straight chain or branched C.sub.2 -C.sub.20 -alkenyl radical, a straight chain or branched C.sub.3 -C.sub.20 -oxaalkyl radical, an optionally substituted C.sub.5 -C.sub.12 -cycloalkyl radical, or an optionally substituted C.sub.7 -C.sub.20 -aralkyl radical and X is a --NCO--, --NH--CO.sub.2 R.sup.1 --, --NHCO.sub.2 R.sup.2 -- OR - NHCOCl-group whereby R.sup.1 and R.sup.2 can be the same or different and are a straight chain or branched C.sub.1 -C.sub.20 -alkyl radical or a C.sub.5 -C.sub.12 cycloalkyl radical, as well as a process for their preparation.
    Type: Grant
    Filed: September 16, 1987
    Date of Patent: May 31, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Wolfgang Schwarz
  • Patent number: 4748267
    Abstract: Fluorochemical biurets containing one or more monovalent fluoroaliphatic radicals having at least three fully fluorinated terminal carbon atoms and one or more biuret moieties, the radicals and moieties bonded together by hetero atom-containing or organic linking groups are provided. These fluorochemical biurets are useful in the form of aqueous dispersions or emulsions or organic solutions in the treatment of fibrous substrates, such as textile fibers, to impart oil and water repellency.
    Type: Grant
    Filed: February 18, 1987
    Date of Patent: May 31, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: John C. Chang
  • Patent number: 4742169
    Abstract: The invention is a process for the preparation of halohydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products in the further presence of an acid scavenger capable of forming a salt with the hydrogen halide by-product formed, in an amount sufficient to prevent the formation of unwanted by-products, in a polar organic solvent under conditions such that a halohydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.
    Type: Grant
    Filed: April 5, 1985
    Date of Patent: May 3, 1988
    Assignee: The Dow Chemical Company
    Inventors: Marsha A. Paul, George A. Doorakian
  • Patent number: 4742125
    Abstract: The present invention is directed to a process for the production of oligourethanes having terminal mercapto groups by reacting organic polyisocyanates with sub-equivalent quantities of organic polyhydroxyl compounds and a mercapto-alkanol in the presence of at least one ester of phosphoric acid containing at least one hydroxyl group bound to phosphorus. The present invention is also directed to the mercapto group-containing oligourethanes obtainable by this process and their use as binders for oxidatively-hardenable coating and sealing compositions, additives for epoxide resins and cross-linking agents for plastics materials and plastics crude products containing olefinic double bonds.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: May 3, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Schmidt, Wolfgang Wellner, Josef Pedain, Hermann Gruber
  • Patent number: 4740610
    Abstract: The invention describes a process for the preparation of N,o-substituted mono- and/or polyurethanes of formulaR.sup.1 [--NHCOOR.sup.2 ].sub.n,in whichR.sup.1 is an aliphatic, cycloaliphatic, aromatic, araliphatic, or heterocyclic radical, which may be substituted,R.sup.2 is an aliphatic, cycloaliphatic, or araliphatic radical which may be substituted with alkoxy or polyoxyalkylene groups, andn is a whole number from 1 to 5,through the reaction of N-substituted allophanates and/or polyallophanates with alcohols R.sup.2 OH in the presence or absence of catalysts at temperatures of at least 160.degree. C., preferably from 165.degree. to 250.degree. C.
    Type: Grant
    Filed: August 21, 1986
    Date of Patent: April 26, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae
  • Patent number: 4727128
    Abstract: The present invention is directed to a process for the preparation of a diisocyanate by reacting a diisocyanate with 2,2,4-trimethyl-pentanediol-(1,3) or reaction products of this diol which contain either ether or ester groups and optionally other diols or triols. The present invention is additionally directed to the diisocyanates produced by this process and to their use in one-component and two-component coating compositions.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: February 23, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Pedain, Bernd Riberi, Michael Sonntag, Klaus Konig, Jurg Frohlich
  • Patent number: 4724252
    Abstract: Polyamines containing aromatically bound primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a compound containing an amidine and/or guanidine group and a water-miscible, aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material contains aromatically bound NCO groups and has NCO content of from 0.5 to 40 wt. %. The compound containing amidine and/or guanidine groups functions as a catalyst and is used in a quantity of at least 0.001 parts by weight for every 100 parts by weight of isocyanate. The water-miscible solvent is used in a quantity of at least 10 parts by weight for every 100 parts by weight of polyisocyanate. The polyamines thus-produced are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: August 11, 1986
    Date of Patent: February 9, 1988
    Assignee: Bayer Akitengesellschaft
    Inventor: Werner Rasshofer
  • Patent number: 4723032
    Abstract: Modified polyamines containing carbamates, urethane and/or urea and/or thiourethane groups and having a primary amine content of from 0.1 to 20.2 wt % are produced by (a) mixing an organic isocyanate with a base in the presence of at least one hydrogen-active compound and water and (b) converting the carbamate, urethane and/or urea and/or thiourethane groups to amino groups. The isocyanate starting material has an isocyanate content of from 0.5 to 40 wt. %. The hydrogen-active compound contains a hydroxy and/or amino and/or thiol group. Water is used in a quantity such that one mol of water is present for each isocyanate equivalent. Conversion to form the amino groups is accomplished by treatment with a proton donor and/or thermal decomposition and/or solvent extraction. The polyamines thus-produced are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: February 2, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Dieter Dieterich
  • Patent number: 4720569
    Abstract: A polycarbamic acid ester-type curing agent for thermosetting resin paints, said curing agent containing per molecule at least two groups represented by the following formula ##STR1## wherein Y represents ##STR2## --O--, or --S--; R.sub.1 represents a direct bond, or a divalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group, provided that when Y is ##STR3## R.sub.1 represents a direct bond; R.sub.2 and R.sub.4, independently from each other, represent a hydrogen atom, or an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by an amino group, a hydroxyl group or an alkoxy group, or a group of the formula ##STR4## and R.sub.3 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: January 19, 1988
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Akira Tominaga
  • Patent number: 4717740
    Abstract: An aqueous alkaline developable UV curable urethane acrylate compound and composition are used for making flexible solder mask coatings, characterized by rapid development in an aqueous, alkaline medium, and advantageous performance properties.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: January 5, 1988
    Assignee: M&T Chemicals Inc.
    Inventors: Paul L. K. Hung, Kenneth K. S. Tseng
  • Patent number: 4713476
    Abstract: A process for the preparation of aliphatic, cycloaliphatic, arylaliphatic and aliphatic-cycloaliphatic di- and polyurethanes wherein primary aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyamines are reacted with urea and a primary or secondary aliphatic alcohol at temperatures of above 190.degree. C. to 300.degree. C., following which ammonia and other by-products are separated from the aliphatic, cycloaliphatic, arylaliphatic or aliphatic-cycloaliphatic di- or polyurethane product.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: December 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae
  • Patent number: 4705885
    Abstract: Polymerizable carbamoyloxyalkyldicarboxylic acid esters, carrying hydroxyl groups, of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or allyl or hydroxyalkyl having in each case 1 to 30 carbon atoms in the alkyl radical, R.sup.2 represents alkyl or hydroxyalkyl having in each case 1 to 30 carbon atoms in the alkyl radical or the radical ##STR2## subject to the proviso that R.sup.1 is hydrogen and x is an integer from 2 to 20, R.sup.3 represents linear or branched alkylene having 2 to 5 carbon atoms, R.sup.4 represents hydrogen or methyl and R.sup.5 represents hydroxyalkyl or hydroxyaminoalkyl having in each case 2 to 20 carbon atoms in the alkyl radical or an alkyl radical of this type which also contains ester and/or ether groups, and a process for their preparation.The esters according to the invention can be used for the preparation of copolymers.
    Type: Grant
    Filed: February 6, 1986
    Date of Patent: November 10, 1987
    Assignee: Hoechst AG
    Inventors: Christoph Just, Dieter Plath, Gerd Walz
  • Patent number: 4704420
    Abstract: Highly functional fluorinated polyisocyanates of the formula: ##STR1## wherein Z.sub.1 represents the functional group --O--CO--NH--R--NCO;Z.sub.2 represents the difunctional group --O--CO--NH--R--NH--CO--O--;R.sub.f is a radical derived from fluoropolyethers having a molecular weight between 500 and 7000;T represents a trivalent or tetravalent radical derived from a polyol;q is zero or 1; ands is 1 or 2.Also, varnishes containing said highly functional fluorinated polyisocyanates of formula (I).
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: November 3, 1987
    Assignee: Montedison S.p.A.
    Inventors: Franco Federici, Giorgio Pin, Ennio Cozzi
  • Patent number: 4695645
    Abstract: The invention describes a process for the preparation of N,o-substituted mono- and/or polyurethanes of formulaR.sup.1 [--NHCOOR.sup.2 ].sub.n,in whichR.sup.1 is an aliphatic, cycloaliphatic, aromatic, araliphatic, or heterocyclic radical, which may be substituted,R.sup.2 is an aliphatic, cycloaliphatic, or araliphatic radical which may be substituted with alkoxy or polyoxyalkylene groups, andis a whole number from 1 to 5,through the reaction of N-substituted allophanates and/or polyallophanates with alcohols R.sup.2 OH in the presence or absence of catalysts at temperatures of at least 160.degree. C., preferably from 165.degree. to 250.degree. C.
    Type: Grant
    Filed: July 20, 1984
    Date of Patent: September 22, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae
  • Patent number: 4689353
    Abstract: Polyahls comprising(1) a backbone having a random arrangement of(a) a plurality of alkylene urethane and/or(b) alkylene urea moieties and, optionally,(c) a plurality of alkylene carbonate and/or alkyleneoxy moieties, and/or alkylene moieties of greater than 6 carbons, and(2) a plurality of active hydrogen moieties covalently bonded to the backbone or a side chain of the backbone provided that at least one of said active hydrogen moieties is hydroxyl and at least one of said active hydrogen moieties is amino are described.Isocyanate-functional prepolymers are formed by the reaction of these polyahls with polyisocyanates. Polyurethane or polyurea compositions can be formed by the reaction of these isocyanate-functional prepolymers with a polyol or polyamine.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: August 25, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert F. Harris
  • Patent number: 4687872
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: August 18, 1987
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm
  • Patent number: 4677221
    Abstract: The present invention relates to a process for the production of aliphatic and/or cycloaliphatic diisocyanates which are color stable to heat, which is characterized in that a diisocyanate with aliphatically-and/or cycloaliphatically-bound isocyanate groups is heated in the presence of about 0.1 to 3% by weight, based on the diisocyanate, of at least one compound which is soluble in the diisocyanate and contains at least 3% by weight of structural units corresponding to the formula: ##STR1## for up to about 5 hours at a temperature of about 100.degree. to 220.degree. C. and the diisocyanate which has been treated in this way is subsequently purified by distillation.The present invention also relates to the use of the products of the present process for the production of modified polyisocyanates having improved coloration.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: June 30, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hanns P. Muller, Werner Clarenz, Heinrich Grave
  • Patent number: 4672137
    Abstract: 1,3-Di(alkoxycarbonylamino)propanes of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 can be identical or different and each is hydrogen, or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, and R.sup.4 is an aliphatic, cycloaliphatic or araliphatic radical, are prepared by reacting an .alpha.,.beta.-unsaturated aldehyde with a carbamic acid ester by reacting in a first stage as the .alpha.,.beta.-unsaturated aldehyde a compound of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings, with a carbamic acid ester of the general formula III ##STR3## where R.sup.4 has the abovementioned meanings, at 0.degree.-150.degree. C. to give a 1,1,3-tri(alkoxycarbonylamino)propane of the general formua IV ##STR4## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, and in a second stage heating the compound of the general formula (IV) in the presence of a hydrogenation catalyst and hydrogen under 1-300 bar at 100.
    Type: Grant
    Filed: April 29, 1986
    Date of Patent: June 9, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Joerg Liebe
  • Patent number: 4668710
    Abstract: Included are trihalovinyl polyol ethers. The compositions have pendant 1,2,2-trihaloethenyl moieties. The compositions may be low viscosity oils or highly polymeric such as incorporated with a urethane or other polymers. One of the uses of the compositions is as flame retardants which may have high thermal stability and scorch resistance.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, William J. Kruper, Jr.
  • Patent number: 4668406
    Abstract: Fluorochemical biurets containing one or more monovalent fluoroaliphatic radicals having at least three fully fluorinated terminal carbon atoms and one or more biuret moieties, the radicals and moieties bonded together by hetero atom-containing or organic linking groups are provided. These fluorochemical biurets are useful in the form of aqueous dispersions or emulsions or organic solutions in the treatment of fibrous substrates, such as textile fibers, to impart oil and water repellency.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: May 26, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: John C. Chang
  • Patent number: 4663472
    Abstract: A process for the transesterification of urethanes comprises reacting a urethane with an alcohol at elevated temperature in the presence of a Lewis base containing catalyst.The process is particularly useful when the alcohol used is a polyol since the product of the transesterification is a polyurethane. Since urethanes can be generated from amines and organic carbonates using the methods of the prior art, the present invention provides processes for the manufacture of polyurethanes from amines which avoid the use of either phosgene or isocyanates both of which are extremely toxic.
    Type: Grant
    Filed: January 30, 1985
    Date of Patent: May 5, 1987
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4661288
    Abstract: Water-soluble zwitterionic compounds having clay soil removal/anti-redeposition properties. The zwitterionic compounds are selected from monozwitterionic compounds, dizwitterionic compounds, polyzwitterionic compounds, and zwitterionic polymers. These zwitterionic compounds are useful in detergent compositions at from about 0.05 to about 95% by weight. In addition to the zwitterionic compounds, the detergent compositions further comprise from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant or mixture thereof.
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: April 28, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Donn N. Rubingh, Eugene P. Gosselink
  • Patent number: 4659733
    Abstract: Disclosed are 2,3-diamino-1,4-butanedithiol; 4,5-diamino-1,2-dithiane; and their N-acyl and N-alkyl derivatives. Also disclosed are processes for preparing the disclosed compounds; pharmaceutical compositions comprising such compounds; and a method of treatment comprising administering such compounds and compositions when an antihypertensive effect or radioprotective effect is indicated.
    Type: Grant
    Filed: December 6, 1984
    Date of Patent: April 21, 1987
    Assignee: Alcon Laboratories, Inc.
    Inventors: Mark T. DuPriest, Billie M. York, Jr.
  • Patent number: 4659802
    Abstract: Water-soluble cationic compounds having clay soil removal/anti-redeposition properties. The cationic compounds are selected from ethoxylated cationic diamines, ethoxylated cationic polyamines, ethoxylated cationic polymers and mixtures thereof. These cationic compounds are useful in detergent compositions.
    Type: Grant
    Filed: November 22, 1983
    Date of Patent: April 21, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Donn N. Rubingh, Eugene P. Gosselink
  • Patent number: 4644036
    Abstract: Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing double bonds capable of undergoing Michael addition are suitable for use as a curing component for synthetic resins containing groups capable of amide formation and/or ester formation with carboxylic acids. In particular, the Michael addition products of acetoacetic esters or malonic esters with esters, amides or urea derivatives of .alpha., .beta.-unsaturated monocarboxylic or dicarboxylic acids are used. The structure and the functionality of the curing component can be varied in many ways. It can be attached directly to the synthetic resin molecule, so that self-curing synthetic resins are obtained.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: February 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Walz, Ernst-August Theiling
  • Patent number: 4640849
    Abstract: Polyfunctional cationically polymerizable styryloxy compounds of the formula ##STR1## where R.sup.1 is H or methyl; R.sup.2 is hydrocarbyl, hydrocarbyl interrupted by ether oxygen atoms, or halo substituted hydrocarbyl; R.sup.3 is H, lower alkyl, or alkoxy; G is any multivalent organic or inorganic radical free of amino or aliphatic thiol groups; and n is an integer of two or more.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: February 3, 1987
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, John M. Rooney
  • Patent number: 4629804
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: December 16, 1986
    Assignee: Catalytica Associates
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4621149
    Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: November 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono
  • Patent number: 4609718
    Abstract: An ultraviolet curing liquid coating composition is provided which, when cured with ultraviolet light in the presence of an appropriate photoinitiator, provides a buffer coating for optical glass fiber having adequate strength at room or expected elevated temperature and stability at such elevated temperature, a high index of refraction above 1.48, and a low tensile modulus which remains low to resist microbending difficulties down to around -60.degree. C. This coating composition consists essentially of a linear acrylate-terminated polyurethane oligomer including urea groups introduced by the presence in the oligomer of the reaction product with isocyanate functionality of about 30% to about 90% by weight of the acrylate-terminated oligomer of a polyoxyalkylene diamine having a molecular weight in the range of from about 1000 to about 8000 in which the alkylene group contains from 2-4 carbon atoms.
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: September 2, 1986
    Assignee: DeSoto, Inc.
    Inventors: Timothy E. Bishop, Clive J. Coady, John M. Zimmerman
  • Patent number: 4608420
    Abstract: Process for the preparation of acylurethanes by reacting a urethane with compounds containing hydroxyl groups, which comprises reacting a hydroxy compound (A) with a urethane (B) in the form of an imide of the formula ##STR1## to give an acylurethane containing at least one grouping of the formula --CO--R--CO--NH--COOR.sup.1 (II). In these formulae,R denotes the hydrocarbon radical of an optionally .alpha.,.beta.-ethylenically unsaturated, aliphatic, cycloaliphatic or aromatic dicarboxylic acid or endomethylene derivatives thereof, andR.sup.1 denotes alkyl, alkoxy, alkoxyalkyl, cycloalkyl or benzyl.These acylurethanes are suitable for use as self-crosslinking curing agents or as curing agents for polyhydroxy compounds for the production of shaped articles and/or coatings.
    Type: Grant
    Filed: June 6, 1985
    Date of Patent: August 26, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Brindopke, Gerhard Johannes
  • Patent number: 4606737
    Abstract: Fluorochemical allophanates containing one or more monovalent fluoroaliphatic radicals having at least three fully fluorinated terminal carbon atoms and one or more allophanate moieties, the radicals and moieties bonded together by hetero atom-containing or organic linking groups are provided. These fluorochemical allophanates are useful in the form of aqueous dispersions or emulsions or organic solutions in the treatment of fibrous substrates, such as textile fibers, to impart oil and water repellency.
    Type: Grant
    Filed: June 26, 1984
    Date of Patent: August 19, 1986
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Richard M. Stern
  • Patent number: 4603216
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst comprising a bis phosphine ligand.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 29, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4600793
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a halide-free ruthenium catalyst is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a primary amine in the reaction solution.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 15, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine
  • Patent number: 4594441
    Abstract: A process for the preparation of urethanes. Urethanes having the general formula R.sub.1 (NHCOOR.sub.2).sub.n are reacted with an alcohol at a temperature of 120.degree. to 400.degree. C. in amounts such that, for every mol of the urethane, at least one mol of the alcohol is present. R.sub.1 is a radical obtained by removing the isocyanate groups from an n-functional organic isocyanate, which isocyanate has a boiling point greater than 100.degree. C. at atmospheric pressure. R.sub.2 is a radical obtained by removing the hydroxyl group from a monohydric alcohol which has a boiling point greater than 140.degree. C. at atmospheric pressure.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: June 10, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
  • Patent number: 4593117
    Abstract: Low molecular weight N- and O-substituted diurethanes and/or polyurethanes are prepared by reacting a diamine and/or polyamine containing a primary amino group with an N-aryl-0-alkyl urethane in the presence of at least one high boiling alcohol. This reaction may be carried out at a temperature of from 180.degree. to 350.degree. C. and a pressure of approximately 0.1 to 1,500 mbar. The arylamine corresponding to the N-ary-0-alkyl urethane which forms during this reaction is continuously removed from the reaction mixture.
    Type: Grant
    Filed: December 5, 1984
    Date of Patent: June 3, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Stefan Penninger, Gunther Hammen, Peter Heitkamper
  • Patent number: 4593116
    Abstract: Urethanes are made by reacting an organic nitro compound with an organic compound containing at least one hydroxyl group in the presence of carbon monoxide, hydrogen and a catalyst system. The carbon monoxide and hydrogen are used in quantities such that the molar ratio of CO to H.sub.2 is from 0.3:1 to 3:1. The catalyst system is made up of at least one noble metal or compound of a noble metal from Group VIIIB of the Periodic System of Elements, at least one organic nitrogen base and a co-catalyst combination of iron or copper oxidic or hydroxidic compound and a chloride compound. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: June 13, 1984
    Date of Patent: June 3, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
  • Patent number: 4587323
    Abstract: An improved hydroxyl functional urethane-extended polyester is based on the condensation reaction of fumaric acid, one or more non-aromatic polyols, azelaic acid and optionally one or more non-aromatic carboxylic acids including lauric acid or stearic acid. The hydroxylated polyester urethane oligomer possesses a molecular weight below 2600 and a mole ratio of hydroxyl groups to urethane linkage of from 0.5 to 6. Gel coats prepared from these oligomers exhibit superior water resistance and improved weathering characteristics.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: May 6, 1986
    Assignee: SCM Corporation
    Inventor: Perry A. Toman
  • Patent number: 4582923
    Abstract: Urethanes are made by reacting a primary amine with carbon monoxide and a compound containing at least one hydroxyl group in the presence of an oxidizing agent and a catalyst system. The catalyst system is made up of (i) a noble metal and/or a noble metal compound of a metal of the Eighth Secondary Group of the Periodic System of Elements and (ii) an oxidizing quinoid and/or a compound capable of being converted to an oxidizing quinoid compound under the reaction conditions. The catalyst system may optionally include (iii) metal compounds of elements of the Third to Fifth Main Groups and/or First to Eighth Secondary Groups of the Periodic System of Elements and/or (iv) a tertiary amine. This reaction is generally carried out at a temperature of from 100.degree. to 300.degree. C. and at a pressure of from 5 to 500 bars. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Robert Becker, Johann Grolig, Helmut Waldmann
  • Patent number: 4578506
    Abstract: The title compounds, having the formula (RO.sub.2 CNHCH.sub.2).sub.3 PY where Y=oxygen or sulfur, are prepared by reacting a tetrakis(N-carbalkoxylaminomethyl)phosphonium salt having the formula (RO.sub.2 CNHCH.sub.2).sub.4 P.sup.+ X.sup.- with ammonia or a primary or secondary amine, followed by an oxidizing or sulfurizing agent. The products, after methylolation with formaldehyde, are useful as finishing agents for imparting flame retardant properties to cotton fabrics.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: March 25, 1986
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Arlen W. Frank
  • Patent number: 4562241
    Abstract: Diurethane diureas of the formula ##STR1## wherein each R is a radical derived from a diisocyanate and having at most 20 C atoms, R' is a radical derived from a diol and having a molecular weight of at most 1500, and the radicals R" are each methyl or ethyl, or both radicals R" bound to the same N atom form together with the N atom the piperidino, morpholino or pyrrolidino radical, are valuable curing agents for epoxide resins, and are also suitable as accelerators for the hot-curing of epoxide resins with dicyandiamide, cyanoacetyl compounds and polycarboxylic acid anhydrides.
    Type: Grant
    Filed: October 4, 1984
    Date of Patent: December 31, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Alfred Renner
  • Patent number: 4559383
    Abstract: High solids, solvent-based resin composition comprises novel chain-extendable, crosslinkable urethane modified polyhydroxy oligomers, crosslinking agent and, preferably, catalyst(s). The composition cures at elevated temperature to provide a coating on a substrate, such as steel, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate. The novel oligomers can be the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises three or more hydroxy, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with approximately one molar equivalent of a monofunctional blocking agent.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventors: Joseph W. Holubka, Ray A. Dickie
  • Patent number: 4554188
    Abstract: High solids, solvent-based resin composition comprises novel chain-extendable, crosslinkable urethane modified polyhydroxy oligomers, crosslinking agent and, preferably, catalyst(s). The composition cures at elevated temperature to provide a coating on a substrate, such as steel, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate. The novel oligomers can be the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises three or more hydroxy, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with approximately one molar equivalent of a monofunctional blocking agent.
    Type: Grant
    Filed: January 5, 1983
    Date of Patent: November 19, 1985
    Assignee: Ford Motor Company
    Inventors: Joseph W. Holubka, Ray A. Dickie
  • Patent number: 4543397
    Abstract: Polyfunctional cationically polymerizable styryloxy compound of the formula ##STR1## where R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 are H and the other is methyl; R.sup.3 and R.sup.4 are H, lower alkyl, or alkoxy if R.sup.2 is not methyl; R.sup.5 is a divalent hydrocarbon radical; G is any multivalent organic or inorganic radical free of amino, aliphatic hydroxyl, aliphatic thiol or other groups which interfere with cationic polymerization; and n is an integer of two or more.
    Type: Grant
    Filed: December 4, 1984
    Date of Patent: September 24, 1985
    Assignee: Loctite (Ireland) Ltd.
    Inventors: John Woods, John M. Rooney, Stephen J. Harris
  • Patent number: 4539008
    Abstract: Hydroxymethylated organic carbamates are reacted with water soluble alcohols to produce etherified hydroxymethylated carbamates which are used with an acid catalyst to treat cellulosic textiles for sufficient time and temperature to produce a durable press low formaldehyde release cellulosic textile. Carbamates from the group consisting of alkyl or alkoxyalkyl carbamates of less than six carbons can be used. Water soluble aliphatic monohydric and polyhydric alcohols of one to six carbons are also satisfactory. The hydroxymethylated carbamate is reacted with the alcohol at about 10.degree. C.-100.degree. C. for about 0.5 to 16 hours at a pH from about 1 to 6. Concentrations of acid catalyst range from 0.5 to 3.0% of the solution. Curing temperatures range from about 120.degree. C. to 160.degree. C. for about 0.5 to 10 minutes.
    Type: Grant
    Filed: August 8, 1984
    Date of Patent: September 3, 1985
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Bethlehem K. Andrews, Robert M. Reinhardt
  • Patent number: 4535167
    Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co. Inc.
    Inventor: Roger M. Freidinger
  • Patent number: 4528391
    Abstract: The reaction between a hydroxyl-containing material and an isocyanate-containing material is catalyzed by a pyrazino pyrazine compound such as 1,4,5,8-tetramethyldecahydropyrazino(2,3-b)pyrazine.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: July 9, 1985
    Assignee: The Dow Chemical Company
    Inventors: Duane S. Treybig, James L. Potter
  • 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: 4518778
    Abstract: A polymer polyol made by the reaction of an alkylene oxide adduct of a hydroxyl-containing amine, a polyether polyol of about 3000 to 8000 molecular weight and an organic polyisocyanate is disclosed. This polymer polyol may be used in the manufacture of flexible polyurethane foams. The polymer polyols are more stable than those made by other procedures.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: May 21, 1985
    Assignee: Texaco Inc.
    Inventor: Michael Cuscurida
  • Patent number: 4511710
    Abstract: Unwanted halogen values are removed from liquid resin, organic or hydrocarbon material by adding particulate crystalline lithium aluminate compounds to the liquid material to act as a halogen scavenger, then separating the crystalline aluminate compound from the liquid material.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: April 16, 1985
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Kyle B. Benkendorfer, John L. Burba, III
  • Patent number: 4508916
    Abstract: A class of substituted urethane acrylates and methacrylates having an aliphatic backbone is provided, the members of the class having at least one ether or polyether group with at least one pendent fluorinated organic group attached thereto. The novel compositions may be radiation polymerized, e.g., by electron beam, actinic light or heat, to a light transmissive material which is well suited to optical application, such as coupling optical fibers and light emitting diodes so as to transmit light therebetween.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: April 2, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Richard G. Newell, Stephen F. Wolf