Patents Represented by Attorney, Agent or Law Firm Lee G. Meyer
  • Patent number: 3972948
    Abstract: An improved process for preparing mono- and poly-glycol ethers by mixing and reacting an alkylene oxide and an alcohol in the presence of a catalyst containing alkali or alkaline earth cations at temperatures within the range of about 50.degree.to about 350.degree.C. under pressure of between about 30 to about 3,000 psig is disclosed. An anhydrous high boiling liquid residue, prepared by the concentration of the liquid reaction product effluent residue remaining after desired mono- and poly-glycol ethers have been separated therefrom has been found to be highly useful as the catalyst for the described process. The employment of the anhydrous high boiling liquid residue as a catalyst advantageously results in the production of liquid reaction product effluents containing relatively little, if any, undesirable glycol by-products which are difficult to separate from the desired mono- and poly-glycol ethers.
    Type: Grant
    Filed: November 29, 1974
    Date of Patent: August 3, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventors: George Joseph Laemmle, Kenneth Carol Rightmer
  • Patent number: 3971829
    Abstract: An improved process for the preparation of methylene-bridged polyphenylpolyamine mixtures having increased 4,4'-isomer content in the diaminodiphenylmethane portion by the catalyzed condensation reaction of aniline and formaldehyde is disclosed. Aniline and formaldehyde are mixed and reacted at an elevated temperature in the presence of up to about 3 weight percent of a co-catalyst system comprising about 0.1 to less than about 3.0 weight percent silica-alumina catalyst and from about 0.1 to less than about 3.0 weight percent oxalic acid, basis weight of aniline present. The novel process provides a resulting reaction product that can be easily filtered to remove the solid silica-alumina catalyst therefrom and a reaction product mixture of methylene-bridged polyphenylpolyamine mixtures having an increased 4,4'-isomer content in the diaminodiphenylmethane portion than heretofore obtained utilizing silica-alumina catalysts alone.
    Type: Grant
    Filed: November 18, 1974
    Date of Patent: July 27, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventor: Edward Thomas Marquis
  • Patent number: 3968089
    Abstract: Novel isocyanate-terminated polyether-based polymer prepolymers useful in urethane applications are produced by polymerization of one or more ethylenically unsaturated monomers in the presence of an isocyanate-terminated prepolymer obtained by reaction of an organic polyisocyanate with a polyhydroxy-containing adduct obtained by reacton of an alkylene oxide with a polyfunctional initiator containing two to six active hydrogen atoms. These isocyanate-terminated polyether-based polymers prepolymer compositions are useful in the preparation of flexible urethane foams and moisture-cured adhesives.
    Type: Grant
    Filed: November 18, 1974
    Date of Patent: July 6, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventors: Michael Cuscurida, George Phillip Speranza
  • Patent number: 3959374
    Abstract: A process is described for the preparation of mixed isomeric methylene-bridged polycyclohexylpolyamines wherein a mixed isomeric methylene-bridged polyphenyl polyamine mixture having a functionality of from about 2.0 to about 3.3 is pretreated by contacting the mixture and hydrogen with a nickel-containing hydrogenation catalyst at a temperature of from about 25.degree.C. to about 250.degree.C. under a pressure of about 500 to about 15,000 psig. The pretreated isomeric polyamine is then hydrogenated in the presence of ammonia under conventional hydrogenation conditions employing a ruthenium-containing hydrogenation catalyst. The pretreatment step allows the utilization of mixed isomeric methylene-bridged polyphenyl polyamine feed mixtures for the production of isomeric methylene-bridged polycyclohexylpolyamines in high yields without attendant deactivation of the ruthenium hydrogenation catalyst heretofore observed. The process is particularly applicable to continuous operation.
    Type: Grant
    Filed: May 30, 1974
    Date of Patent: May 25, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventors: Michael E. Brennan, Ernest L. Yeakey
  • Patent number: 3959370
    Abstract: Novel compounds, N-acetyl-polychlorobenzamides, are prepared by treating corresponding polychlorobenzonitrile compounds with acetic acid in a closed reactor at an elevated temperature above the boiling point of the acetic acid. These new compounds have been found to be useful biological chemicals, particularly in controlling undesirable vegetation, and also useful as chemical intermediates.
    Type: Grant
    Filed: July 16, 1973
    Date of Patent: May 25, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventor: Lewis William Watts, Jr.
  • Patent number: 3956180
    Abstract: Hydrocarbon-soluble molybdenum catalysts are prepared by reacting an ammonia-containing molybdate with a hydroxy compound, for example, an organic primary or secondary alcohol, a glycol or a phenol. The hydrocarbon-soluble molybdenum solutions are useful as homogeneous oxidation catalysts, particularly for the oxidation of olefins to olefin oxides. Olefin oxides are useful in the manufacture of non-toxic antifreeze, urethane-grade polyols and many other applications. The catalysts of the invention may also be used as metal-plating solutions, lubricant additives, pigments, ammoxidation catalysts, printing inks, or solution components for organic laser devices. They may also be used as catalysts or co-catalysts for various polymerization processes, such as homopolymerization of isocyanates, isocyanate-polyol reactions, or olefin oxide polymerization reactions.
    Type: Grant
    Filed: December 28, 1970
    Date of Patent: May 11, 1976
    Assignee: Texaco Development Corporation
    Inventor: Stanley Bruce Cavitt
  • Patent number: 3952068
    Abstract: Particular compositions of vinylidene alcohols are provided which are distinguishably characterized by their structure, their biodegradable nature, and by their very low pour point characteristics. These compositions can be used to provide useful surfactants and detergents and to form distinctive ethoxylate derivatives having unusual attributes, such as biodegradability, very high rates of water solubility, nongelling tendencies, and superior wetting ability; and certain of these ethoxylate compositions are synergistic in wetting ability and, unlike related ethoxylates of conventional alcohols, the ethoxylates of certain compositions possess cloud point temperatures within an especially desired range.
    Type: Grant
    Filed: July 17, 1975
    Date of Patent: April 20, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventors: Robert Malone Gipson, John Gordon Milligan, Floyd Edward Bentley
  • Patent number: 3948900
    Abstract: A process for the preparation of 1-methylpiperazine and 1,4-dimethylpiperazine as co-products is disclosed which provides a crude reaction product free of piperazine impurity. The process of the invention comprises mixing and reacting formaldehyde and piperazine at a molar ratio of more than 1.3 to less than about 2.0 and then hydrogenating the resulting reaction product carried in methanol as a major solvent in liquid phase at a temperature of about 60.degree.-130.degree.C. in the presence of a nickel or cobalt hydrogenation catalyst. The crude hydrogenated reaction product is free from piperazine impurity from which 1-methylpiperazine and 1,4-dimethylpiperazine can be readily separated in substantially pure form such as by simple fractional distillation.
    Type: Grant
    Filed: August 16, 1974
    Date of Patent: April 6, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventor: Philip Hotchkiss Moss
  • Patent number: 3943162
    Abstract: An improved process is disclosed for the production of cyanoethylated aromatic amines comprising contacting an aromatic amine with acrylonitrile in the presence of a silica-alumina catalyst in a liquid phase reaction at elevated temperature. Aromatic polyamines are cyanoethylated according to the process of this invention to form a reaction product comprising poly-(N-monocyanoethylated) aromatic amines and poly-(N-monocyanoethylated) aromatic amines additionally having at least one cyanoethyl group attached to the nucleus of the aromatic ring.
    Type: Grant
    Filed: April 16, 1975
    Date of Patent: March 9, 1976
    Assignee: Jefferson Chemical Co., Inc.
    Inventors: Michael E. Brennan, Ernest Leon Yeakey
  • Patent number: 3943104
    Abstract: Epoxy resins, of the polyglycidyl ether of a polyhydric phenol type, are cured by incorporating therein a polyoxyalkylenepolyamine and an accelerator combination of piperazine and an alkanolamine, the combination having a combined weight ratio of between about 1:8 to 1:1. The accelerator combination is synergistic for accelerating the curing of a polyglycidyl ether of a polyhydric phenol cured with a polyoxyalkylenepolyamine at ambient or elevated temperatures. The epoxy resin products are useful in protective coatings, adhesives, seamless and terrazzo flooring, castings, laminates, and in grouting, potting, encapsulating, caulking and sealing compositions.
    Type: Grant
    Filed: December 12, 1974
    Date of Patent: March 9, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventor: Harold George Waddill
  • Patent number: 3941711
    Abstract: A novel combination soap bar effective in hard water is disclosed which is comprised of a major amount of a fatty acid soap and a minor amount of an alkali metal, amine or ammonium salt of an N-2(2-hydroxyethoxy)ethyl fatty amide-H-sulfate containing about 12 to 18 carbons in the fatty amide chain. The inventive combination bar produces a stable lather when used in hard water, yet will not produce a scum or insoluble precipitates. The novel combination bar may also include other ingredients such as perfumes, deodorants, anti-microbial agents, emollients, and other surfactants and processing aids, such as fatty acids, starch, polyethylene glycol, and the like.
    Type: Grant
    Filed: January 24, 1974
    Date of Patent: March 2, 1976
    Assignee: Jefferson Chemical Company, Inc.
    Inventor: Robert Malone Gipson