Patents Represented by Attorney Herman O. Bauermeister
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Patent number: 4268688Abstract: This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g.Type: GrantFiled: February 16, 1973Date of Patent: May 19, 1981Assignee: Monsanto CompanyInventors: Harold B. Tinker, Arthur J. Solodar
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Patent number: 4164600Abstract: Melt blended fibers of lactam-polyol-polyacyl lactam or acyl polylactam terpolymers together with polyesters are thermally bonded at temperatures below the bonding temperatures of either the crystalline polyester or the terpolymer, resulting in thermally stable fabrics that have bond strength greater than the individual polyester or terpolymer webs bonded at the same temperature.Type: GrantFiled: December 27, 1977Date of Patent: August 14, 1979Assignee: Monsanto CompanyInventors: Kai-Lim W. Yung, Bernard Silverman, Virginia C. Menikheim
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Patent number: 4163819Abstract: The present invention relates to non-woven fabrics characterized by excellent drapeability, very pleasant handle and good tensile properties. The fabrics are made from melt blends of a polyamide together with lactam-polyol-polyacyl lactam or acyl-polylactam terpolymers.The production of the non-woven webs or fabrics from melt blended fibers of polyamide with lactam-polyol-polyacyl lactam or acyl-polylactam terpolymers is achieved by contact or thermal bonding of melt spun fibers. In one embodiment of the invention, the webs are formed from fibers in the nascent condition as freshly extruded, e.g., they are substantially amorphous. Such amorphous fibers are readily bonded even at room temperature, resulting in autogenous self-bonding, with only little pressure being imposed. If desired these fibers may be bonded at temperatures of up to 210.degree. C.Type: GrantFiled: December 27, 1977Date of Patent: August 7, 1979Assignee: Monsanto CompanyInventors: Kai-Lim W. Yung, Bernard Silverman
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Patent number: 4150674Abstract: The production of compatible polymeric compositions, fibers and nonwoven webs from three-component blends of a polyamide, a polyester, and a terpolymer of lactam-polyolpolyacyl lactam or lactam-polyol-acyl-polylactam is described in the present patent application.The products of this invention are characterized by having well balanced properties such as dimensional stability to moisture, moisture transport properties, antistatic and tensile properties. The compatible polymeric compositions of the invention are useful in general textile applications such as fibers, woven and nonwoven fabrics, apparel, carpeting, draperies and various industrial forms e.g. articles such as films.Type: GrantFiled: December 27, 1977Date of Patent: April 24, 1979Assignee: Monsanto CompanyInventor: Kai-Lim W. Yung
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Patent number: 4145296Abstract: Concentrated ammonium salt compositions containing a binder and a viscosity control agent, when utilized in aqueous dispersion, are stabilized against gelation by addition of an inhibitor. The aqueous dispersion is applied to foliage, vegetation, logging slash and the like to hinder or prevent wildfires during prolonged weather exposure. Typical gelation inhibitors are morpholine, ethylenediamine and monoethanolamine.Type: GrantFiled: December 29, 1977Date of Patent: March 20, 1979Assignee: Monsanto CompanyInventors: Thomas U. Fox, Nelson H. Kasten
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Patent number: 4145281Abstract: Process for the removal of chromium and zinc corrosion inhibitor compounds from cooling tower blowdown streams, comprising contacting the water of said streams first with a weakly basic anion exchange resin and then with a weakly acidic cation exchange resin.Type: GrantFiled: December 20, 1976Date of Patent: March 20, 1979Assignee: Monsanto CompanyInventors: Michael F. Weishaar, F. Leon Ballard
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Patent number: 4124526Abstract: Oil droplets are encapsulated by forming a dispersion of the droplets in an aqueous alkaline liquid medium containing a water-soluble salt of a polycarboxylate polymer and acidifying the medium to a pH in the range of 5 to 8 whereby the polycarboxylate polymer precipitates to form walls around the droplets.Type: GrantFiled: June 13, 1977Date of Patent: November 7, 1978Assignee: Monsanto CompanyInventors: Pierre J. Allart, Henri B. May
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Patent number: 4108949Abstract: The invention relates to o-hydroxy(or alkyloxy)-phenythiomethylenedi(organophosphorus) compounds and to processes for making the same. The compounds have the general formula ##STR1## where L is H or R',R' is alkyl of 1 to 6 carbon atomsM is H, Cl or Br,X is Br, Cl, F, CF.sub.3, NO.sub.2, CN, CO.sub.2 R', SO.sub.2 R', or ##STR2## and R is phenyl, alkyl of 1 to 3 carbon atoms, or OR'.The compounds of the invention have utility as corrosion inhibitors, oil additives and flame retardants.Type: GrantFiled: January 3, 1977Date of Patent: August 22, 1978Assignee: Monsanto CompanyInventor: Gail H. Birum
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Patent number: 4101587Abstract: Substituted phosphonium salts such as tetrakis(hydroxymethyl)phosphonium chloride are prepared by reacting a metal phosphide selected from the group consisting of lithium phosphide, sodium phosphide, potassium phosphide, beryllium phosphide, magnesium phosphide, calcium phosphide, strontium phosphide, barium phosphide, boron phosphide, aluminum phosphide, gallium phosphide, and zinc phosphide, with an aldehyde having from 1 to 12 carbon atoms, the proportion of the aldehyde being at least 4 moles per gram atom of the phosphorus in the said phosphide. The reaction is conducted with at least one and a half moles of water per gram atom of phosphorus in the said phosphide and at least one mole of mineral acid being present per gram atom of phosphorus in the said phosphide, with or without a catalyst, and in the presence of an inert gas atmosphere. The products are fire retardants.Type: GrantFiled: December 15, 1975Date of Patent: July 18, 1978Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4087403Abstract: The invention relates to novel phosphinate polymers having the formula ##STR1## WHEREIN R is a phenylene or naphthylene group in which the O substituent is nonvicinal to the ##STR2## group, R' is an alkyl group of 1 to 15 carbon atoms or an aryl group of 6 to 15 carbon atoms, and n is from 5 to 50 units. The invention also relates to a process for the production of the novel polymeric phosphinate resins, and to combinations of such polymeric phosphinates with organic polymers such as polyesters, e.g., polyethylene terepthalate, and polyamides, e.g., hexamethylene adipamide. The combination of the present polymeric phosphinates with the organic polymers makes it possible to obtain flame retardant products, for example fibers suitable for carpeting and clothing.Type: GrantFiled: March 1, 1976Date of Patent: May 2, 1978Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4087408Abstract: Polyesters containing bromine and phosphorus are provided by the copolymerization of a ternary system based upon an alcoholic component and an acidic component. The third component is a bromo bisphenol alkyl or aryl phosphine oxide ##STR1## The hydroxyl groups are present in either the para or meta positions, m plus n is from 1 to 8, preferably 1 to 4 and R is an alkyl radical of 1-10 carbon atoms, or an aryl radical of 6-10 carbon atoms. The polyesters which are obtained have flame retardant properties.Type: GrantFiled: December 15, 1976Date of Patent: May 2, 1978Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4086205Abstract: The present invention relates to cyclic phosphorus compounds and processes for the preparation thereof.The present invention relates to a process for the preparation of certain derivatives of cyclic hydrogenphosphonates which are diisocyanate derivatives formed as adducts or as polymers.The cyclic phosphorus compounds are useful as flame retardants with organic polymers, such as polyurethanes, polyesters, and polyamides.Type: GrantFiled: September 3, 1976Date of Patent: April 25, 1978Assignee: Monsanto CompanyInventor: Gail H. Birum
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Patent number: 4081463Abstract: 2-Carboxyethyl(phenyl)phosphinic acid is prepared in two stages by first reacting dichloro(phenyl)phosphine with acrylic acid employed at a molar excess of 25% to 45% to form a mixture of three intermediates, namely 3-(chlorophenylphosphinyl)propionyl chloride, the cyclic anhydride of 2-carboxyethyl(phenyl)phosphinic acid and the mixed anhydride of acrylic acid with 3-chlorocarbonylethyl(phenyl)phosphinic acid. The second stage of the process is the hydrolysis of the mixture of three intermediates set forth above to obtain the desired product. The product is useful as a flame retardant material when used with organic polymers such as polyesters.Type: GrantFiled: December 27, 1976Date of Patent: March 28, 1978Assignee: Monsanto CompanyInventors: Gail H. Birum, Richard F. Jansen
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Patent number: 4073767Abstract: The present invention relates to cyclic phosphorus compounds and processes for the preparation thereof.The present invention relates to a process for the preparation of certain derivatives of cyclic hydrogenphosphonates. Azomethine, sulfonyl isocyanate, isocyanate, and isothiocyanate derivatives are a part of the present invention.The cyclic phosphorus compounds are useful as flame retardants with organic polymers, such as polyurethanes, polyesters, and polyamides.Type: GrantFiled: September 3, 1976Date of Patent: February 14, 1978Assignee: Monsanto CompanyInventor: Gail H. Birum
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Patent number: 4073829Abstract: The present invention relates to phosphorus-containing compositions which are polymeric esters having flame retardant properties and also a process for the production thereof, as well as the combinations of such phosphorus compositions with otherwise combustible base materials exemplified by various organic polymers, for example polyamides or polyesters.The phosphorus compositions of the present invention are polymeric esters having as moieties thereof, (A) an aliphatic alcoholic moiety of an alcoholic reactant of 5 to 20 carbon atoms, and from 2 to 10 or preferably 2 to 6 hydroxyl functional groups, with the proviso that there is no hydrogen atom on the carbon atoms which are beta to the hydroxyl oxygen, (B) a moiety of a phosphorus-containing acid halide, ester or amide reactant of 0 to 20 carbon atoms, and having from 1 to 4 functional groups selected from the group consisting of halogen, ester (--OR) and amide (--NR.sub.Type: GrantFiled: June 14, 1976Date of Patent: February 14, 1978Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4072653Abstract: Polymeric phosphine oxides having the formula ##STR1## WHERE R is an alkyl group of from 1 to 20 carbon atoms, or an aryl group of from 6 to 20 carbon atoms, R' is a phenylene or naphthylene group, and n is from 2 to 50 or preferably 5 to 25. The invention also relates to compositions of such polymeric phosphine oxides with organic polymers such as polyesters, e.g. ethylene terephthalate and polyamides, e.g. hexamethylene adipamide. The combination of the present polymeric phosphine oxides with the organic polymers makes it possible to obtain flame retardant products useful in many applications such as for carpeting and clothing.Type: GrantFiled: May 20, 1976Date of Patent: February 7, 1978Assignee: Monsanto CompanyInventor: Kurt Moedritzer
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Patent number: 4071584Abstract: The present invention relates to a new hydroxyphenylthiophosphoranylidene organophoshorus compounds and to a process involving an unusual phenyl migration for their preparation. The general reaction for the preparation of the products of the present invention is set forth below: ##STR1## WHERE X is halogen (F, Cl, Br), NO.sub.2, CN, CO.sub.2 R', SO.sub.2 R', CF.sub.3 or ##STR2## R is phenyl, alkyl of 1 to 3 carbon atoms, or OR', and R' is alkyl of 1 to 6 carbon atoms.The compounds of the invention are useful as flame retardants, lubricating oil additives and as corrosion inhibitors.Type: GrantFiled: January 3, 1977Date of Patent: January 31, 1978Assignee: Monsanto CompanyInventor: Gail H. Birum
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Patent number: 4070336Abstract: The present invention relates to cyclic phosphorus compounds including cyclic hydrogen phosphonates and processes for the preparation thereof.The present invention relates to an improved process for the preparation of cyclic hydrogenphosphonates, which comprises the reaction of phosphorochloridites with formic acid in accordance with the general reaction set forth below: ##STR1## where R is an alkylene or haloalkylene group of a 1,2-glycol having from two to six carbon atoms, or a 1,3-glycol having from three to eight carbon atoms, and Z is Cl or Br. Ketone and sulfenyl derivatives are also a part of the present invention.The cyclic phosphorus compounds are useful as flame retardants with organic polymers, such a polyurethanes, polyesters and polyamides.Type: GrantFiled: September 3, 1976Date of Patent: January 24, 1978Assignee: Monsanto CompanyInventor: Gail H. Birum
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Patent number: 4067934Abstract: The present invention relates to novel oligomeric and polymeric condensation products of phosphine oxides, such as bis(p-hydroxyphenyl)alkyl or aryl phosphine oxides condensed with alkyl or arylphosphonic dihalides or diphenoxides, and to processes of preparing the present novel compositions of matter. The invention also includes a process of imparting fire-retardant properties to combustible materials by treatment with the condensation products of the present invention, as well as novel compositions composed of otherwise combustible base materials such as various organic polymers for example Nylon or polyethylene terephthalate having combined therewith the present condensation products.Type: GrantFiled: May 20, 1976Date of Patent: January 10, 1978Assignee: Monsanto CompanyInventors: Kurt Moedritzer, Eugene L. Ringwald
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Patent number: 4036913Abstract: The present invention relates to new nitrogen-containing organophosphorus compounds having aryloxy substituents bonded to phosphorus in ester structures. ##STR1## R' is aryl of 6 to 10 carbon atoms, R" is hydrogen, alkyl, aryl or haloaryl of 1 to 15 carbon atoms, or no more than one carboethoxymethyl group, and where the halogen on the aryl group is bromine, chlorine or fluorine,R'" is alkyl, alkenyl or aryl groups of 1 to 15 carbon atoms and substituted aryl forms where the subtituent is fluorine, chlorine, bromine, nitro, cyano, hydroxyl, alkyloxy or mixtures of such substituents, andZ is CO, CS or SO.sub.2.The phosphorus compounds have utility as fire retardants and as biologically active materials.Type: GrantFiled: July 14, 1975Date of Patent: July 19, 1977Assignee: Monsanto CompanyInventor: Gail H. Birum