Polyoxy Alcohol Moiety Patents (Class 560/26)
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4251667Abstract: A process for the preparation of aromatic urethanes by reacting an aromatic amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: February 17, 1981Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4250322Abstract: A method for preparing oligourethanacrylates having the general formula ##STR1## where ##STR2## is a radical of a telogen; X is H, CH.sub.Type: GrantFiled: August 10, 1979Date of Patent: February 10, 1981Inventors: Alexei V. Efimov, Alfred A. Berlin, Tamara Y. Kefeli, Nina V. Varlamova, Grigory M. Strongin, Judif M. Altshuler, Boris I. Kolomazov
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Patent number: 4247653Abstract: A process is disclosed for preparing mixtures of low molecular weight polyhydroxyl compounds and hydroxyaldehydes and hydroxyketones by condensing formaldehyde hydrate with itself in the presence of (I) as catalyst a soluble or insoluble compound of a metal of the first to eighth sub-group or second to fourth main group of the Periodic System of Elements, optionally bound to a high molecular weight carrier, and (II) more than 10% by weight, based on formaldehyde, of one or more dihydric or higher hydric low molecular weight alcohols and/or higher molecular weight polyhydroxyl compounds. The pH of the reaction mixture is held at 5.5 to 9.0 until 5-40% conversion has occurred and is then lowered to between 4.5 and 8.0 (0.5-2.0 pH units lower). The reaction is then stopped by inactivating the catalyst.Type: GrantFiled: August 30, 1977Date of Patent: January 27, 1981Assignee: Bayer AktiengesellschaftInventor: Kuno Wagner
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Patent number: 4246260Abstract: The invention relates to new substituted o-phenylenediamine derivatives of the general formula ##STR1## in which R represents optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkinyl,X represents O, S, SO or SO.sub.2 andR.sup.1 and R.sup.2 are different from one another and individually represent ##STR2## in which R.sup.3 and R.sup.4 are identical or different and represent alkyl andR.sup.5 represents hydrogen, optionally substituted alkyl or optionally substituted alkoxy, and salts thereof.Also included in the invention are (1) methods for preparing the above-described compounds, (2) compositions containing the above-described compounds and (3) methods for the treatment of helminthiasis.Type: GrantFiled: March 19, 1979Date of Patent: January 20, 1981Assignee: Bayer AktiengesellschaftInventors: Heinrich Kolling, Ekkehard Niemers, Hartmund Wollweber, Herbert Thomas
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Patent number: 4246391Abstract: Radiation-curable acrylated urethanes having a lower viscosity than heretofore achievable without dilution are produced by an improved process that involves first reacting a monohydroxy-functional acrylate with a polyisocyanate followed by the reaction of the product mixture produced with a polyol. The acrylated urethanes so produced are useful in radiation-curable coatings.Type: GrantFiled: June 26, 1979Date of Patent: January 20, 1981Assignee: Union Carbide CorporationInventor: Stuart L. Watson, Jr.
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Patent number: 4242520Abstract: A process for the production of carbamates is provided which comprises contacting an organic primary or secondary amine with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of a catalyst for the reaction and in the presence of at least one member selected from the group consisting of disulfides of the formulaR.sup.1 --S--S--R.sup.2wherein R.sup.1 and R.sup.2 comprise members selected from the group consisting of alkyl, aryl, cycloalkyl, alkaryl, aralkyl, heterocyclic, alkenyl, alkynyl, alkanoyl, aranoyl, halogenated derivatives of the foregoing groups, and derivatives of the foregoing groups in which one or more carbon atoms is replaced by an oxygen atom.Type: GrantFiled: January 29, 1979Date of Patent: December 30, 1980Assignee: Halcon Research & Development CorporationInventor: David Moy
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Patent number: 4230552Abstract: A polymeric product suitble for use as a pigment grinding vehicle is disclosed. The polymeric product is the reaction product of an organic polyepoxide and an organic amine containing an alkylarylpolyether moiety.Type: GrantFiled: July 20, 1979Date of Patent: October 28, 1980Assignee: PPG Industries, Inc.Inventors: Karl F. Schimmel, Lance C. Sturni, Martin J. Robles
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4229207Abstract: Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid are effective plant growth regulating agents. They are useful for controlling wild oats in cereal cultures and for growth inhibition in different cultures, e.g. for the inhibition of suckers in tobacco plants.Type: GrantFiled: June 22, 1978Date of Patent: October 21, 1980Assignee: Ciba-Geigy CorporationInventors: Verena Laanio, Werner Fory, Rolf Schurter
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Patent number: 4227007Abstract: New and valuable diurethanes having a good herbicidal action, herbicides containing these compounds, and a process for controlling the growth of unwanted plants with these compounds.Type: GrantFiled: January 13, 1978Date of Patent: October 7, 1980Assignee: BASF AktiengesellschaftInventors: Ulrich Schirmer, Wolfgang Rohr, Bruno Wuerzer, Kurt Fett
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Patent number: 4227008Abstract: Aromatic urethanes can be produced by interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system composed of a platinum group metal and/or a compound thereof serving as catalyst and a Lewis acid and/or a compound thereof as promoter under high temperature and high pressure conditions. For instance, the interaction of 2-amino-4-nitrotoluene, ethanol and carbon monoxide in the presence of palladium chloride and a ferrous chloride-pyridine complex under high temperature and high pressure conditions can yield 2,4-diethylcarbamatetoluene.Type: GrantFiled: July 25, 1978Date of Patent: October 7, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Katsuharu Miyata, Makoto Aiga, Seiji Hasegawa
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Patent number: 4224454Abstract: Acyloin urethans can be employed to effect photopolymerization of free radical-polymerizable compositions in inert and oxygen-containing atmospheres.Type: GrantFiled: October 13, 1978Date of Patent: September 23, 1980Assignee: Lord CorporationInventors: John R. McDowell, Dennis D. Howard, Vincent J. Pascarella
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Patent number: 4219661Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.Type: GrantFiled: April 23, 1979Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
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Patent number: 4212901Abstract: A method is provided for treating a substrate with a radiation curable coating composition based on a polyester resin esterified with acrylic acid or methacrylic acid and having a hydroxyl number in the range of from 50 to 250 and an ethylenic unsaturation equivalent weight of from 200 to 10,000 grams and on a polyisocyanate that is present in an amount of 0.7 to 1.3 equivalents of isocyanate per equivalent of hydroxyl contained in the composition. The curing of the coating composition is effected in a first stage by subjecting the composition to radiation having a wave length of 200 to 600 nm and in a second stage by reaction between the isocyanate groups of the polyisocyanate and the hydroxyl groups of the polyester resin.Type: GrantFiled: July 10, 1978Date of Patent: July 15, 1980Assignee: Akzo N.V.Inventors: Abraham van Neerbos, Adrianus C. J. van Oosterhout
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Patent number: 4204010Abstract: This invention relates to an ethylenically unsaturated reactive thixotropic agent for use in radiation curable compositions, e.g., overprint varnishes, formed by reacting a hydroxyl-containing fatty acid ester with an ethylenically unsaturated isocyanate. The agent not only performs its thixotropic function in the uncured state but also forms part of the cured product on exposure to radiation, e.g., UV radiation due to its substantially similar reactivity.Type: GrantFiled: December 21, 1978Date of Patent: May 20, 1980Assignee: W. R. Grace & Co.Inventors: David E. Kramm, Arthur D. Ketley
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Patent number: 4202956Abstract: Liquid thixotropic isocyanate-terminated prepolymers are prepared by the reaction of a polyarylene polyalkylene polyisocyanate or diphenylmethane diisocyanate with certain graft polyols. The resulting prepolymers are particularly useful in the preparation of polyurethane coating compositions.Type: GrantFiled: November 13, 1978Date of Patent: May 13, 1980Assignee: BASF Wyandotte CorporationInventor: James D. Taylor
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Patent number: 4200762Abstract: Prepolymers having at least one functional group capable of absorbing actinic radiation resulting in electronic excitation of the molecule, leading to free radical type cure of systems containing these prepolymers and prepolymers capable of curing by a free radical mechanism are disclosed.Type: GrantFiled: September 1, 1978Date of Patent: April 29, 1980Assignee: Thiokol CorporationInventor: Claude J. Schmidle
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Patent number: 4192925Abstract: This invention relates to new polyols modified by guanidine groups, to a process for the preparation thereof and to the use thereof as starting component for the preparation of preferably foamed polyurethane plastics. The process involves (A) reacting diisocyanato-carbodiimides corresponding to the following general formula:OCN--(R.sup.2 -N=C=N).sub.m R.sup.2 --NCOat a temperature of from about 25.degree. to 130.degree. C., optionally in the presence of an inert solvent, with polyhydroxyl compounds corresponding to the following general formula:A--OH).sub.nin an OH/NCO-ratio of from 1.2:1 to 30:1 to form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partly reacting, at a temperature of from 0.degree. to 150.degree. C., the remaining carbodiimide groups remaining in the production of Step (A), optionally in the presence of an inert solvent, with an amine, amide or hydrazide corresponding to the following general formula:R.sup.3 --NR.sup.1 H).sub.Type: GrantFiled: April 16, 1979Date of Patent: March 11, 1980Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
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Patent number: 4192926Abstract: New polyols modified by acyl urea groups, process for the preparation thereof and use thereof as starting component for the preparation of preferably foamed polyurethane plastics. The process involves (A) reacting diisocyanatocarbodiimides corresponding to :OCN--R.sup.2 --N.dbd.C.dbd.N .sub.M --R.sup.2 --NCOwith polyhydroxyl compounds corresponding to:A--OH).sub.nto form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partially reacting, the carbodiimide groups remaining in the product of step (A), with a carboxylic acid corresponding to the following general formula: ##STR1## to form acyl urea groups, and (C) distilling off the inert solvent, if used; whereinm represents a number of from 1 to 10;s represents an integer of from 1 to 3; andR.sup.1 represents hydrogen or a monofunctional or--in the form of a bridge to further acyl groups--a di- or trifunctional C.sub.1 -C.sub.18 aliphatic, C.sub.4 -C.sub.15 cycloaliphatic, C.sub.6 -C.sub.Type: GrantFiled: April 16, 1979Date of Patent: March 11, 1980Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
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Patent number: 4190711Abstract: Thermoplastic polyether polyurethane elastomers are provided by reacting and forming: (a) a novel liquid polyurethane quasi-prepolymer having a free NCO content of from about 16 percent to about 25 percent; (b) a reactive poly(oxypropylene-oxyethylene) diol; and (c) as an extender, a short chain diol in the presence of (d) a catalyst. The elastomers can be either solid or microcellular, and they are suitable for production using Reaction Injection Molding (RIM) or conventional casting technology. The elastomers are useful in the production of automotive body panels, gears, seals and the like, and, since the elastomers are thermoplastic, any excess elastomer ("scrap") can be reused.Type: GrantFiled: September 29, 1977Date of Patent: February 26, 1980Assignee: Union Carbide CorporationInventors: Richard J. Zdrahala, Frank E. Critchfield
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Patent number: 4186269Abstract: An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration.Type: GrantFiled: December 31, 1975Date of Patent: January 29, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyate, Makoto Aiga
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Patent number: 4186124Abstract: A polymeric product suitable for use as a pigment grinding vehicle is disclosed. The polymeric product is the reaction product of an organic polyepoxide and an organic amine containing an alkylarylpolyether moiety.Type: GrantFiled: January 13, 1978Date of Patent: January 29, 1980Assignee: PPG Industries, Inc.Inventors: Karl F. Schimmel, Lance C. Sturni, Martin J. Robles
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Patent number: 4182898Abstract: Polyurethanes having improved properties are obtained from polyester-polyether co-prepolymers. These co-prepolymers are homogeneous, clear liquids of varying viscosity and can be reacted with curing agents to yield clear homogeneous elastomers of various hardness. Cast elastomers prepared from such co-prepolymers have physical properties at least as good as premium polyester urethanes currently available, and have hydrolytic stability and low temperature properties better than such premium polyester urethanes and comparable to premium polyether urethanes, with the cost being comparable to the lower cost of the conventional polyester systems.Type: GrantFiled: January 20, 1978Date of Patent: January 8, 1980Assignee: Anderson Development CompanyInventors: Edward J. Fujiwara, Michelle D. Pate
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Patent number: 4180673Abstract: Electron-beam sensitive monomers contain two to three terminal acryloxy and one intermediate divalent or trivalent hydrocarbylene group the valences of which are respectively linked in each case by at least one of acyloxylene and alkoxycarbonylamidolene units.Type: GrantFiled: May 10, 1976Date of Patent: December 25, 1979Assignee: Minnesota Mining and Manufacturing CompanyInventor: Mario D. Burguette
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Patent number: 4177206Abstract: The present invention is directed to polyisocyanate mixtures which are liquid at room temperature and which(a) contain from 10 to 42% by weight of aromatically-bound isocyanate groups, which may be partly in the form of carbamic acid chloride;(b) contain from 0.5 to 5% by weight of sulphur in the form of sulphonic acid groups which may be at least partly neutralized or esterified;(c) contain from 0.5 to 5% by weight of phosphorus in the form of phosphonic acid alkyl ester groups or phosphonic acid aralkyl ester groups and(d) have a viscosity of from 10 to 50,000 cP at 25.degree. C.Type: GrantFiled: May 19, 1978Date of Patent: December 4, 1979Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Dieter Dieterich
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Patent number: 4177205Abstract: Highly stable liquid 4,4'-diphenylmethane diisocyanate (MDI) containing MDI-carbodiimide adducts are prepared by (a) heating MDI at a temperature of from 60.degree. C. to 120.degree. C. for a period of from one hour to ten hours in the presence of tris(chloromethyl)phosphine oxide, (b) stopping the carbodiimide formation by adding thereto a quenchant selected from the group consisting of magnesium chloride hydrate, stannous chloride and trichlorosilane, (c) heating the reaction mixture at a temperature between 60.degree. C. and 120.degree. C. for a period of from 0.5 hour to 6.0 hours, and (d) cooling to room temperature. The resulting compositions are highly stable and may be advantageously employed in the preparation of polyurethane compositions.Type: GrantFiled: November 20, 1978Date of Patent: December 4, 1979Assignee: BASF Wyandotte CorporationInventors: Robert L. Schaaf, Peter T. Kan, Moses Cenker
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Patent number: 4176212Abstract: Coating compositions which are curable by simultaneous or sequential exposure to radiation and moisture. In the case of pigmented compositions, rapid curing is initiated by exposure to moderate radiation and the cure completed by exposure to moisture. The various compositions include radiation reactive groups and moisture reactive oxazolidine and isocyanate groups. The moisture reactive and radiation curable groups preferably are interpolymerized during the curing process.Type: GrantFiled: January 25, 1978Date of Patent: November 27, 1979Assignee: Design Cote CorporationInventor: Karl Brack
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Patent number: 4174433Abstract: This invention relates to new polyols modified by guanidine groups, to a process for the preparation thereof and to the use thereof as starting component for the preparation of preferably foamed polyurethane plastics. The process involves (A) reacting diisocyanato-carbodiimides corresponding to the following general formula:OCN--R.sup.2 -N.dbd.C.dbd.N).sub.m R.sup.2 -NCOat a temperature of from about 25.degree. to 130.degree. C., optionally in the presence of an inert solvent, with polyhydroxyl compounds corresponding to the following general formula:A--OH).sub.nin an ON/NCO-ratio of from 1.2:1 to 30:1 to form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partly reacting, at a temperature of from 0.degree. to 150.degree. C., the remaining carbodiimide groups remaining in the production of Step (A), optionally in the presence of an inert solvent, with an amine, amide or hydrazide corresponding to the following general formula:R.sup.3 --NR.sup.1 H).sub.Type: GrantFiled: March 23, 1978Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
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Patent number: 4173682Abstract: A process is disclosed for coating a substrate with a radiation curble coating composition, characterized in that the composition comprises (A) an at least one isocyanate group-containing adduct of (a) an acrylic or methacrylic hydroxy ester with 5 to 20 carbon atoms and (b) a polyisocyanate with 4 to 40 carbon atoms and with 2 to 4 isocyanate groups per molecule, (B) a polyfunctional hydroxy compound having a molecular weight of 178 to 12,000 and a hydroxyl content of 0.5 to 30% by weight in an amount of 0.5 to 1.5 equivalents of hydroxy per equivalent of isocyanate of component A, and (C) a photoinitiator in an amount of 0.1 to 10% by weight of component A. The curing takes place in a first stage by radiation having a wavelength of 90 to 600 nm and in a second stage by reaction of the isocyanate groups of component A with water vapor and the hydroxyl groups of the polyfunctional hydroxy compound.Type: GrantFiled: March 8, 1978Date of Patent: November 6, 1979Assignee: Akzo N.V.Inventors: Arie Noomen, Johannes M. P. van der Geest, Cornelis de Jong, Dick Van Santen
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Patent number: 4172936Abstract: This invention relates to new polyols modified by acyl urea groups, to a process for the preparation thereof and to the use thereof as starting component for the preparation of preferably foamed polyurethane plastics. The process involves (A) reacting diisocyanatocarbodiimides corresponding to the following general formula:OCN--R.sup.2 --N.dbd.C.dbd.N).sub.m R.sup.2 --NCOat a temperature of from about 25.degree. to 130.degree. C., optionally in the presence of an inert solvent, with polyhydroxyl compounds corresponding to the following general formula:A--OH).sub.nin an OH/NCO-ratio of from 1.2:1 to 30:1 to form a polyhydroxyl compound containing carbodiimide groups and (B) completely or partially reacting, the carbodiimide groups remaining in the product of step (A) at a temperature of from 25.degree. to 100.degree. C.Type: GrantFiled: March 23, 1978Date of Patent: October 30, 1979Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen
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Patent number: 4170708Abstract: Aromatic urethanes are produced by interacting an aromatic nitro compound, an organic compound containing hydroxyl groups and carbon monoxide in the presence of a catalyst composed of elemental selenium or a selenium compound and of a promoter composed of a bicyclic amidine together with a phenolic compound or a carboxylic acid. The interaction proceeds smoothly with the aid of a small amount of the promoter, attended with secondary production of amino compounds only in small amounts. For instance, 2,4-diethyldicarbamatetoluene is obtained at a yield of 87% by interacting 2,4-dinitrotoluene, ethanol and carbon monoxide in the presence of a catalytic system composed of metallic selenium, 1,8-diazabicyclo(5,4,0)-undecene-7 and acetic acid.Type: GrantFiled: March 8, 1976Date of Patent: October 9, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyata, Seiji Hasegawa
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Patent number: 4163749Abstract: Dispersing agents comprising the adducts of one or more compounds from each of the following classes:(a) an organic compound containing two or more isocyanate groups,(b) an organic compound containing two or more groups which are reactive with isocyanate groups, and(c) a compound of the formula:Z--X--E (T--D).sub.n-1 QwhereinZ represents --OH or --NHR, wherein R is alkyl;X is optionally substituted alkylene;T is alkylene;N is a positive integer;Q is optionally substituted alkyl; andE is a ##STR1## group wherein R' is hydrogen or alkyl, and D is a ##STR2## group provided that only one of E and D is connected to T via the carbon atom of the carbonyl group present in D and E, and at least one of the group represented by X, T, Q, R and R.sup.1 contains a carbon chain having more than 4 carbon atoms, a process for the manufacture of the said dispersing agents, and their use in the preparation of finely divided dispersions of solids in organic liquids.Type: GrantFiled: November 25, 1974Date of Patent: August 7, 1979Assignee: Imperial Chemical Industries LimitedInventors: Frank Hauxwell, James F. Stansfield, Arthur Topham
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Patent number: 4152273Abstract: There are provided aqueous, heat curable compositions useful in the finishing of textile fabrics, the compositions comprising a diisophorone alkylene urea ethoxylate, a silanol end-stopped diorganopolysiloxane and a diorganopolysiloxane having an amino functionality. In preferred embodiments, the compositions also comprise a compound selected from among dimethylol dihydroxyethylene urea and dimethylol methoxy ethyl carbamate. The compositions, when applied to textile fabrics, result in improved wettability and soil releasability, without losses in hand modification and resistance to abrasion. Processes and articles are also provided.Type: GrantFiled: July 18, 1978Date of Patent: May 1, 1979Assignee: Arkansas Co., Inc.Inventor: Herman G. Weiland
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Patent number: 4152348Abstract: Color stabilized isocyanates, particularly methylene-bridged aromatic isocyanates [methylenebis(phenyl isocyanate) and prepolymers thereof], are derived by incorporating in the isocyanate a color stabilizing amount of a compound of the formula ##STR1## wherein R.sub.1 =alkyl, aryl; R.sub.2 =alkyl; R.sub.3 =H, alkyl or aralkyl; and R.sub.1 and R.sub.2 taken together represent the residue of an oxazoline or oxazine. 2-Ethyloxazoline is a preferred color stabilizing compound. The above compounds can also be used to discharge undesirable colors which have developed in such isocyanates on storage.Type: GrantFiled: February 22, 1978Date of Patent: May 1, 1979Assignee: The Upjohn CompanyInventor: Warren J. Rabourn
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Patent number: 4152349Abstract: The reactivity of polymethylene polyphenyl isocyanates containing 20 to 90 percent of methylenebis(phenyl isocyanates) is improved, and stabilized against a decline on storage, by incorporating therein very small amounts of a compound of the formula ##STR1## wherein R.sub.1 =alkyl, aryl; R.sub.2 =alkyl; R.sub.3 =H, alkyl or aralkyl; and R.sub.1 and R.sub.2 taken together represent the residue of an oxazoline or oxazine. 2-Ethyloxazoline is the preferred compound for incorporation in the polyisocyanate.Type: GrantFiled: February 22, 1978Date of Patent: May 1, 1979Assignee: The Upjohn CompanyInventor: Warren J. Rabourn
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Patent number: 4134880Abstract: An aromatic urethane of high quality and excellent heat stability can be produced in high yield by reacting an aromatic nitro compound, a hydroxyl group-containing organic compound and carbon monoxide in the presence of a catalytic system composed of (1) palladium, ruthenium, rhodium or a compound thereof, (2) a Lewis acid, and (3) ammonia. The use of such catalytic system can suppress undesirable side reactions to a satisfactory extent and ensures the reaction to proceed without causing any corrosion of a stainless steel reactor. If necessary, water may be added to the reaction system to increase the reaction velocity, by which the unit cost of the catalyst can be reduced.Type: GrantFiled: January 19, 1978Date of Patent: January 16, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Katsuharu Miyata, Yutaka Hirai, Hiroshi Yoshida
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Patent number: 4129455Abstract: Compositions of matter comprising a finely divided dispersion of a solid having a particle size of less than 20 microns in an organic liquid selected from the class consisting of hydrocarbons and halogenated hydrocarbons containing dissolved therein an adduct of one or more compounds from each of the following classes(a) an organic compound containing two or more isocyanate groups,(b) an organic compound containing two or more groups which are reactive with isocyanate groups, and(c) an addition polymer containing a hydroxy group, the amount of the adduct corresponding to between 5% and 100% by weight based on the weight of the solid, and the amount of the solid corresponding to between 5% and 70% by weight based on the total weight of the dispersion for use in the preparation of inks and paints.Type: GrantFiled: May 7, 1976Date of Patent: December 12, 1978Assignee: Imperial Chemical Industries LimitedInventors: Morice W. Thompson, Arthur Topham
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Patent number: 4120834Abstract: The present invention relates to modified polyols, and more particularly to polyols modified with polyisocyanates that can be employed, among other things, as components for formulations for polyurethanes or polyurethanes-isocyanurates.More particularly, the modified polyols of this invention consist of the reaction product of diols having an equivalent weight ranging from 30 to 150, with polyisocyanates having an equivalent weight ranging from 50 to 200, characterized in that said modified polyols exhibit a diol/isocyanate weight ratio comprised between 10 and 1, preferably between 5 and 1.6, and a OH/NCO equivalent ratio comprised between 3 and 50, preferably between 4 and 10.Type: GrantFiled: July 6, 1977Date of Patent: October 17, 1978Assignee: Montedison S.p.A.Inventor: Pierluigi Fatutto
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Patent number: 4117017Abstract: This invention relates to a process for preparing thiols and polythiols by the addition of a thiolcarboxylic acid, e.g., thiolacetic acid, to ethylenically unsaturated compounds in the presence of an initiator comprising a pinacol of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R.sub.2 and R.sub.4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy to obtain a thiol ester which is thereafter hydrolyzed to yield the corresponding thiol.Type: GrantFiled: April 18, 1977Date of Patent: September 26, 1978Assignee: W. R. Grace & Co.Inventors: Charles Robert Morgan, Richard Wayne Bush
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Patent number: 4115429Abstract: The instant invention is directed to novel low temperature, storage stable liquid diphenylmethane diisocyanates and to the method of their preparation. The diisocyanates of the instant invention are provided by reacting diphenylmethane diisocyanates having a specified 2,4'-isomer content with polyoxyethylene glycols having molecular weights of from 150 to 1500. It has been surprisingly found that the products of the instant invention are both stable and liquid at -5.degree. C for at least 48 hours. In fact, in many instances, the products of the instant invention show no tendency to crystallize even when stored at -22.degree. C for 100 hours.Type: GrantFiled: March 18, 1977Date of Patent: September 19, 1978Assignee: Mobay Chemical CorporationInventors: Helmut F. Reiff, Richard S. Pantone
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Patent number: 4104144Abstract: Radiation-curable coating compositions and inks which have as a component a polymerizable monomer or a mixture of polymerizable monomers, said monomer or monomers being represented by the formula: ##STR1## where Z represents a divalent aromatic, aliphatic or cycloaliphatic radical such as the following: ##STR2## and R is substantially an unsaturated monovalent organic radical of a polyfunctional polyethylenecally unsaturated ester.Type: GrantFiled: December 9, 1976Date of Patent: August 1, 1978Assignee: Kewanee IndustriesInventors: Marvin Weiss, Phillip Adams, Gerald I. Nass, Roland L. Leitner
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Patent number: 4098918Abstract: Novel diacrylates are prepared by reacting a monohydroxylated acrylic monomer with a polyisocyanate. The reaction product may be polymerized by subjecting to ionizing irradiation, actinic light or to free radical catalysis to form a useful coating material. The diacrylates may also be copolymerized with other radiation sensitive materials.Type: GrantFiled: April 21, 1976Date of Patent: July 4, 1978Assignee: PPG Industries, Inc.Inventor: Robert DeMajistre
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Patent number: 4094925Abstract: A condensation product of a polyepoxide with a monoalcohol or monocarboxylic acid is reacted with a monoisocyanatoallyl or methallyl carbamate to form a novel compound which can be mixed with a vinyl monomer to form a radiation hardenable lacquer composition.Type: GrantFiled: August 12, 1974Date of Patent: June 13, 1978Assignee: Rutgerswerke AktiengesellschaftInventors: Karl Jellinek, Rudi Oellig
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Patent number: 4088665Abstract: The present invention relates to a new process for the partial carbodiimidization of the isocyanate groups of organic mono-, or di- and/or polyisocyanates, the mixtures which can be obtained by this process and the use of these mixtures as isocyanate components in the production of polyurethane plastics by the known isocyanate polyaddition process. In general, the process comprises:(a) mixing organic mono-, di- and/or polyisocyanates with 0.1 to 100 ppm of a phosphorus compound of the general formula ##STR1## wherein R represents a lower alkyl radical, a phenyl radical, an alkoxy radical, a hydrogen atom or an alkenyl radical; a, b, c and d each represent hydrogen, a halogen atom, a lower alkyl, lower alkenyl, phenyl, a cyclohexyl or a polymethylene group which together with two neighboring C-atoms of the heterocyclic ring forms a cycloaliphatic ring; and X represents an oxygen or sulphur atom; at a temperature from about 0.degree. to about 200.degree. C.Type: GrantFiled: August 17, 1976Date of Patent: May 9, 1978Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Kuno Wagner, Walter Schafer, Hans J. Hennig
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Patent number: 4082779Abstract: This invention relates to a novel carbamoylation method for the preparation of steroid phenolic N-disubstituted carbamate esters, and novel compounds in said method. Phenolic carbamate esters are useful for various purposes, for instance as pharmaceuticals, e.g. antitumor agents, as biocides, e.g. pesticides, and intermediates for preparing such useful compounds.Type: GrantFiled: June 24, 1976Date of Patent: April 4, 1978Assignee: Aktiebolaget LeoInventors: Hans Jacob Fex, Sten Krister Kristensson, Anders Robert Stamvik
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Patent number: 4078015Abstract: Useful copolymerizable compositions include 10 to 50 parts by weight of (I) a polymerizable diurethane monomer having the general formula ##STR1## wherein R.sub.1 is --H; or --CH.sub.3 ;R.sub.2 is --H; --CH.sub.3 ; or --C.sub.2 H.sub.5 ;R.sub.3 is an organic radical constituting the residue of a mono-hydroxy compound R.sub.3 OH having from one to twelve carbon atoms; andR.sub.4 is a divalent organic radical constituting the residue of an organic diisocyanate R.sub.4 -(NCO).sub.2 from which the two isocyanate radicals have been removed;And 90 to 50 parts by weight of (II) a polymerizable polyurethane monomer which is the reaction product of (a) an organic diisocyanate; (b) a beta-hydroxy alkyl ester of an acrylic acid; and (c) a polyol.Type: GrantFiled: December 17, 1976Date of Patent: March 7, 1978Assignee: Freeman Chemical CorporationInventors: Robert H. Leitheiser, John J. Szwarc
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Patent number: 4077989Abstract: The instant invention relates to a process for the production of novel modified polyisocyanates containing acylated urea groups and to the products obtained from this process. The process of the instant invention comprises reacting a compound containing isocyanate groups and carbodiimide groups with carboxylic acids in such quantities that from about 0.2 to about 1.2 gram equivalents of carboxyl groups are reacted per gram equivalent of carbodiimide groups.Type: GrantFiled: November 23, 1976Date of Patent: March 7, 1978Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner
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Patent number: 4065627Abstract: High molecular weight radiation curable ester-diethers, ester-monoethers and their diisocyanate derivatives.Type: GrantFiled: September 27, 1976Date of Patent: December 27, 1977Assignee: General Mills Chemicals, Inc.Inventor: Stuart A. Harrison
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Patent number: 4065630Abstract: Novel polyoxyalkylene fluoroalkyltrimellitate compounds are disclosed that are useful for improving the soil release properties of textiles. These compounds may be conveniently prepared by reacting a fluorinated alkyl thiol or amine with trimellitic anhydride monoacid chloride to form a fluorinated trimellitic anhydride intermediate product which is then reacted with a polyoxyalkylene derivative.Type: GrantFiled: September 10, 1976Date of Patent: December 27, 1977Assignee: Pennwalt CorporationInventor: Stanley Robert Sandler