Patents by Inventor Robert L. Zimmerman

Robert L. Zimmerman has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5286267
    Abstract: The present invention provides a novel class of compounds, useful as gasoline detergent additives, which is a polyether hydroxyethylaminoethyl oxalamide represented by the formula ##STR1## where R is a (C.sub.5 -C.sub.25) alkyl group and n is an integer between about 5 and about 20.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: February 15, 1994
    Assignee: Texaco Inc.
    Inventors: Wei-Yang Su, Sheldon Herbstman, Robert L. Zimmerman, Michael Cuscurida
  • Patent number: 5254737
    Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a reduction, hydrogenation catalyst, such as nickel or cobalt, in two steps has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The first step of the reaction is conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion is increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: October 19, 1993
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5241016
    Abstract: The invention is an epoxy resin adhesive composition. The composition comprises:A. An epoxy resin component; andB. A curative component comprising:a curing amount of a polyamine curing agent and 2 to 30 phr. of an adhesion enhancer of comprising a partially hindered polyetherpolyamine.The fast curing adhesive offers high lap shear strength and relatively high peel strength.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: August 31, 1993
    Assignee: Texaco Chemical Company
    Inventors: Harold G. Waddill, Robert A. Grigsby, Jr., Michael Cuscurida, Robert L. Zimmerman
  • Patent number: 5239041
    Abstract: A process for preparing a polyurea reaction injection molded (RIM) elastomer is described. A hindered polyetherpolyamine is first obtained by reacting a polyol having two or more hydroxyl groups with an effective amount of long chain alkyl epoxide to give an at least partially hindered intermediate having hydroxyl terminations; and then aminating at least one of the hydroxyl terminations on the intermediate to primary amine groups to give an at least partially hindered polyetherpolyamine. The hindered polyetherpolyamine is then reacted with a polyisocyanate in the optional presence of a catalyst to give a polyurea RIM elastomer. The long chain alkyl group provides steric hindrance to the primary aliphatic amine group, which slows down the reactivity of the amine. The slower reactivity of the amine group is useful in RIM and RRIM compositions since it allows for longer shot or flow times, which in turn permit larger parts to be made from existing equipment.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: August 24, 1993
    Assignee: Texaco Chemical Company
    Inventors: Robert A. Grigsby, Jr., Michael Cuscurida, Robert L. Zimmerman, George P. Speranza
  • Patent number: 5234478
    Abstract: An amido alkanolamine composition obtained by reacting, at a temperature of 10.degree. C.-200.degree. C.:(a) a 4-alkyl-2-morpholinone represented by the formula: ##STR1## in which R represents a monovalent aliphatic radical having from 1 to 10 carbon atoms, and(b) an alkylphenoxypolyoxyalkylene amine represented by the formula: ##STR2## in which R' represents a hydrocarbyl radical having from 4 to 30 carbon atoms, x has a value from 5 to 50, and R" represents a methyl radical or a mixture of hydrogen and methyl radicals is provided.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: August 10, 1993
    Assignees: Texaco Inc., Texaco Chemical Co.
    Inventors: Wei-Yang Su, Sheldon Herbstman, Robert L. Zimmerman, Michael Cuscurida, Wheeler C. Crawford, Daniel T. Daly
  • Patent number: 5218005
    Abstract: Low molecular weight, polyoxyalkylene polyamine reacts with carbonyl compound making polyamine adduct used as chain extender in preparing tack-free, smooth polyurea elastomers, useful in solventless spray coatings.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: June 8, 1993
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, Dudley J. Primeaux
  • Patent number: 5216154
    Abstract: N-methylmorpholine oxide which is essentially free from nitrosamine contaminants is prepared by oxidizing a feedstock consisting essentially of N-methylmorpholine with an oxidant consisting essentially of aqueous hydrogen peroxide in an atmosphere consisting essentially of carbon dioxide to thereby form a nitrosamine-free reaction product from which N-methylmorpholine oxide essentially free from nitrosamine can be recovered.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: June 1, 1993
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5203879
    Abstract: An amido alkanolamine composition obtained by reacting, at a temperature of 10.degree. C.-200.degree. C.:(a) a 4-alkyl-2-morpholinone represented by the formula: ##STR1## in which R represents a monovalent aliphatic radical having from 1 to 10 carbon atoms, and(b) a hydrocarbyl oxypolyoxyalkylene amine represented by the formula: ##STR2## in which R' represents an alkyl, an alicyclic, or a alkylalicyclic radical having from 8 to 30 carbon atoms, x has a value from 5 to 50, and R" represents a methyl radical or a mixture of hydrogen and methyl radicals is provided.
    Type: Grant
    Filed: September 1, 1992
    Date of Patent: April 20, 1993
    Assignee: Texaco Inc.
    Inventors: Wei-Yang Su, Sheldon Herbstman, Joseph M. Russo, Robert L. Zimmerman, Michael Cuscurida
  • Patent number: 5189221
    Abstract: A mixture of C.sub.1 -C.sub.4 mono-, di- and trialkylamines is separated by adding at least about an equimolar amount, based on the amine mixture, of a formyldialkanolamine selected from the group consisting of formyldiethanolamine, formyl aminoethylethanolamine and formyl 2-(2-aminoethylamino)-ethanol to the alkyl amine mixture, at a temperature of about 120.degree. to about 160.degree. C. and a pressure of about 500 to about 3,000 psig to provide a reaction mixture comprising the trialkylamine, the formyl dialkylamine and the formyl monoalkylamine, together with unreacted formyldialkanolamine and the corresponding alkanolamine, by separately recovering the trialkyl amine, the formyl dialkylamine and the formyl monoalkylamine from the reaction mixture, by reacting the dialkyl amine with said alkanolamine at atmospheric pressure at temperature of about 120.degree. to about 140.degree. C.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 23, 1993
    Assignee: Texaco Chemical Company
    Inventors: Roger G. Duranleau, Robert L. Zimmerman
  • Patent number: 5189075
    Abstract: Polyurea elastomers, made using low molecular weight polyoxyalkylene polyamines, like aminated, propoxylated .alpha.-methyl glucoside, as chain extenders for reactions of polyoxyalkylene polyamine with polyisocyanate, have improved spray and foam properties, including faster cure and foam stability.
    Type: Grant
    Filed: February 21, 1992
    Date of Patent: February 23, 1993
    Assignee: Texaco Chemical Co.
    Inventors: Robert L. Zimmerman, Dudley J. Primeaux
  • Patent number: 5140097
    Abstract: Polyamide reaction products comprising: a dicarboxylic acid and a diamine component comprising a mixture of poly(oxytetramethylene) diamines and oligomers of said poly(oxytetramethylene) diamines,said mixture containing from about 85 to about 99.5 wt. % of said poly(oxytetramethylene) diamines and, correspondingly, from about 15 to about 0.5 wt. % of said oligomers,said poly(oxytetramethylene) diamines having the formula: ##STR1## wherein n represents 0 or a positive number having a value of 1 to about 30,said oligomers having the formula: ##STR2## wherein n represents 0 or a positive number having a value of 1 to about 30.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: August 18, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Wei-Yang Su, Robert L. Zimmerman, Donald H. Champion
  • Patent number: 5130491
    Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a nickel catalyst promoted with copper, chromium and molybdenum has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The reaction may be conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion may be increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia. The same catalyst may be used in both steps if a two stage process is used.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: July 14, 1992
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5091585
    Abstract: A method for continuous production of tertiary aliphatic methyl amines, particularly fatty aliphatic methyl amines such as di-hydrogenated tallow methyl amine from fatty alkyl amines, such as di-hydrogenated tallow amine over a nickel catalyst has been discovered. The reaction gives high selectivity of tertiary methyl amine over the coproduced secondary amines. The reaction may be conducted continuously in the presence of hydrogen and a formaldehyde source. The formaldehyde source may be selected from the group consisting of formaldehyde alone, formalin, a solution of mixed formaldehyde and paraformaldehyde in methanol and water, trioxane and mixtures thereof. The nickel catalyst may be promoted with copper and/or chromium, in one embodiment.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: Wei-Yang Su, Robert L. Zimmerman
  • Patent number: 5075506
    Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a cobalt catalyst promoted with zirconium has been discovered. The catalyst may be supported on kieselguhr or other support. The reaction gives high selectivity or secondary amine over the coproduced primary and tertiary amines. The reaction may be conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion may be increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: December 24, 1991
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5037838
    Abstract: N-hydroxyethyl piperazine is converted to triethylenediamine using a titania-supported tungstopyrophosphate catalyst.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: August 6, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John F. Knifton
  • Patent number: 5013813
    Abstract: A polyurea elastomer which exhibits a rapid dry time is disclosed. The elastomer includes an isocyanate, an amine terminated polytetrahydrofuran and a chain extender. The isocyanate is preferably a quasi-prepolymer of an isocyanate and a material selected from at least one polyol, a high molecular weight polyoxyalkyleneamine or a combination thereof.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: May 7, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, Dudley J. Primeaux, II
  • Patent number: 5003107
    Abstract: Poly(oxytetramethylene) diamines useful in the preparation of polyamide and polyurea elastomers are prepared by the catalytic reductive amination of a poly(oxytetramethylene) glycol feedstock under reductive amination conditions in the presence of ammonia and hydrogen using a hydrogenation/dehydrogenation catalyst composed of, on an oxide-free basis, about 70 to 75 wt. % of nickel, about 20 to about 25 wt. % of copper, about 0.5 to 5 wt. % of chromium and about 1 to 5 wt. % of molybdenum.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: March 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John M. Larkin
  • Patent number: 4994621
    Abstract: Aminated, alkoxylated hydroxyl-terminated polymers are made by a process involving first polymerizing one or more unsaturated hydrocarbons, such as butadiene, to form a liquid polymer. Next, the liquid polymer is provided with terminal hydroxyl groups. Then, the hydroxylated liquid polymer is alkoxylated with one or more alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, and mixtures thereof, to provide secondary terminal hydroxyl groups. Finally, the alkoxylated liquid polymer is aminated over a transition metal oxide catalyst, such as a combination of nickel oxide/copper oxide/chromium oxide. If the alkoxylated, hydroxyl-terminated liquid polymer is terminated with primary hydroxyl groups, then the amination does not proceed well.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: February 19, 1991
    Assignee: Texaco Chemical Company
    Inventors: Ernest L. Yeakey, Robert L. Zimmerman, Michael Cuscurida
  • Patent number: 4826930
    Abstract: Novel melamine-poly(oxyethylene or oxypropylene) diamine condensates are prepared which have the formula: ##STR1## Wherein: R represents H or--NH--CHR'--(CH.sub.2).sub.x --[--O--CH.sub.2 --CHR"--].sub.n --O--(CH.sub.2).sub.x --CHR'--NH.sub.2R' represents H or --CH.sub.3,R" represents H or -CH.sub.3 or CH.sub.2 CH.sub.3,x represents an integer having a value of 1 or 2, andn is a number having an average value of about 1 to about 2.The melamine-poly(oxyethylene or oxypropylene) diamine condensates have utility as curing agents for epoxy resins.
    Type: Grant
    Filed: April 22, 1988
    Date of Patent: May 2, 1989
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, Harold G. Waddill, George P. Speranza
  • Patent number: 4825000
    Abstract: A series of polyoxyalkylene diamines modified with phenoxy groups is disclosed. This series of diamines is of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl of 1 to 4 carbon atoms, R.sub.3 is a alkyl of 1 to 4 carbon atoms, Ph is phenyl, x ranges from 2 to 40, y ranges from 1 to 20 and z ranges from 1 to 40.These diamines are cured with liquid epoxy resins. The cured resins demonstrated improved tensile strength and modulus, elongation and flexural strength and modulus over a commercially used curative.The diamines are also useful in RIM elastomers, in polyamides and as chain extenders in polyurethane foams.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: April 25, 1989
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Robert L. Zimmerman, Michael Cuscurida, Harold G. Waddill