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: 4810261
    Abstract: A novel gasoline-soluble reaction product, a concentrate comprising the reaction product dissolved in a hydrocarbon solvent, and a haze-free, deposit-resistant and ORI-inhibited motor fuel composition comprising the reaction product is described. The reaction product is obtained by reacting a dibasic acid anhydride, a novel diamine containing block copolymers with polyoxyalkylene backbones, and a hydrocarbyl polyamine. Motor fuel compositions containing the reaction product additive of the instant invention are haze-free and show improved deposit-resistance and ORI control in comparison with motor fuels without the reaction product. Motor fuel compositions of the instant invention may optionally comprise a polyolefin polymer/copolymer component having a molecular weight range of about 500-3500.
    Type: Grant
    Filed: February 19, 1988
    Date of Patent: March 7, 1989
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
  • Patent number: 4789689
    Abstract: Covers a method of producing a polyurethane by utilizing specific amine compounds of high activity as a catalyst in reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of said catalyst. Said amines fall within the following structural formula: ##STR1## where R.sub.1 and R are lower alkyl and x is 2-4.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: December 6, 1988
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Terry L. Renken
  • Patent number: 4769438
    Abstract: Diamines of the formula:H.sub.2 N(CH(CH.sub.3)CH.sub.2 O).sub.x nC.sub.4 H.sub.8 OCH.sub.2 CH(CH.sub.3)NH.sub.2are modified with 5 to 50 wt % of a diglycidyl ether of bisphenol A to form a prepolymer. When reacted with an epxoy resin, these modified diamines impart improved properties to the cured resin compared with the unmodified amine. Improved rate of cure and greater thermal shock resistance were achieved.The cured resin products are useful for coatings, adhesives, encapsulations, laminates and composite fabrications.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: September 6, 1988
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Harold G. Waddill, Kathy B. Sellstrom
  • Patent number: 4747851
    Abstract: A novel gasoline-soluble polyoxyalkylene diamine compound, a concentrate comprising the compound dissolved in a hydrocarbon solvent, and a haze-free, deposit-resistant and ORI-inhibited motor fuel composition comprising the compound is described. Motor fuel compositions comprising the novel polyoxyalkylene diamine compound of the instant invention are haze-free and show improved ORI control and carbonaceous deposit inhibition in comparison with conventional motor fuels. Motor fuel compositions of the instant invention may optionally comprise a polyolefin polymer/copolymer component having a molecular weight range of about 500-3500.
    Type: Grant
    Filed: January 2, 1987
    Date of Patent: May 31, 1988
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Milton D. Behrens, Michael A. Caggiano, John F. Knifton, John M. Larkin, Robert L. Zimmerman
  • Patent number: 4742168
    Abstract: The use of certain oxyalkyl amines as anti-caking agents for triethylenediamine (TEDA) is disclosed. The anti-caking agent comprises polyoxypropylene amines or their amides, the amines having the formula: ##STR1## wherein X is hydrogen, a methyl radical or an ethyl radical, Z is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 external ether linkages; n is a number from 1 to about 40 and r is a number from 2 to 4.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: May 3, 1988
    Assignee: Texaco Inc.
    Inventor: Robert L. Zimmerman
  • Patent number: 4698428
    Abstract: It has been surprisingly discovered in accordance with the present invention that N-methylethanolamine may be converted to N,N'-dimethylpiperazine when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 6, 1987
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Steven H. Vanderpool
  • Patent number: 4647664
    Abstract: N-alkylmorpholines are prepared by passing a reaction mixture over a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages, the reaction mixture being composed of a C.sub.1 -C.sub.4 primary alkyl alcohol and a feedstock selected from the class consisting of morpholine, diethanolamine and bis-aminoethylether.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Steven H. Vanderpool, Robert L. Zimmerman
  • Patent number: 4615771
    Abstract: A method for the separation of bis-(2-aminoethyl)ether from N-(2-methoxyethyl)morpholine via azeotropic distillation using an entrainer such as monoethanolamine is described. The N-(2-methoxyethyl)morpholine is selectively removed by the monoethanolamine. The N-(2-methoxyethyl)morpholine is then separated from the monoethanolamine by liquid-liquid extraction using a non polar hydrocarbon or aromatic extraction solvent and distillation.The N-(2-methoxyethyl)morpholine-monoethanolamine stream previously had no economic use. The separation is now economically effected and the N-(2-methoxyethyl)morpholine used as a polyurethane catalyst.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: October 7, 1986
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Roger G. Duranleau
  • Patent number: 4579630
    Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via azeotropic distillation using an entrainer such as monoethanolamine is described. The N-(2-methoxyethyl) morpholine is selectively removed by the monoethanolamine. Surprisingly, a number of structurally similar compounds, such as ethylenediamine, methylethanolamine, water, ethylene glycol and isopropanolamine were discovered to be unsuitable azeotropic distillation agents either because they did not form azeotropes or for other reasons.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: April 1, 1986
    Assignee: Texaco Inc.
    Inventor: Robert L. Zimmerman
  • Patent number: 4487912
    Abstract: The invention relates to reaction injection molded elastomers derived from high molecular weight active hydrogen containing materials, a chain extender, a polyisocyanate and an acid amide as an internal mold release agent imparting superior hot tear strength. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.
    Type: Grant
    Filed: February 13, 1984
    Date of Patent: December 11, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Richard J. G. Dominguez
  • Patent number: 4482743
    Abstract: A process for manufacturing hydroxyalkyl bis(dialkylaminoalkyl)amine is disclosed wherein dialkylaminopropylaminopropionitrile is separated from a mixture of dialkylaminopropylaminopropionitrile and bis(dialkylaminoalkyl)amine by adding to the mixture under alkoxylation conditions alkylene oxide sufficient to react with substantially all of the bis(alkylaminoalkyl)amine and then separating the reacted materials by distillation. This process yields very pure hydroxyalkyl bis(dialkylaminoalkyl)amine which is useful as a urethane catalyst.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: November 13, 1984
    Assignee: Texaco Inc.
    Inventors: Ernest L. Yeakey, Robert L. Zimmerman
  • Patent number: 4470782
    Abstract: An apparatus for producing custom orthotics includes a boundary wall encompassing a substrate pad and an overlying elastic skin to form an expandable interior chamber into which high density molding material is injected. A matrix of axially movable drive pins project through the pad and are urged upwardly into contact with the arch of the individual's foot to maintain the foot in properly aligned position during fabrication of the orthotic, the drive pins carrying a support bridge driven into conforming contact against the arch of the foot.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: September 11, 1984
    Inventors: Robert L. Zimmerman, Jr., Elliot G. Swan
  • Patent number: 4469823
    Abstract: A method for producing a flexible polyurethane foam from reacting a polyol blend with a polyisocyanate in the presence of a polyurethane formation catalyst is described. The polyol blend contains from 0.5 to 10 wt. % of an aromatic polyester polyol extender typically used in rigid foams. The polyol extender is made from dibasic acids, alkylene glycols and recycled polyethylene terephthalate. Commercial extenders cause flexible foams to shrink, a problem not found in the foams of this invention.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: September 4, 1984
    Assignee: Texaco Inc.
    Inventors: Ernest L. Yeakey, Robert L. Zimmerman, Michael E. Brennan
  • Patent number: 4464488
    Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydration catalyst to produce compounds of the formula ##STR1## where R is hydrogen or lower alkyl of 1 to 4 carbon atoms and R" is methyl or ##STR2## where R is as above. Monocarboxylic acid salts of these compounds show unexpectedly high efficiency as polyurethane catalysts. Smaller amounts of this amine are required to produce foams having the same reaction profile as foams made with prior art amine salt catalysts.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: August 7, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Bruce W. Peterson
  • Patent number: 4463050
    Abstract: A method for making polyurethanes in a mold that is cooler than usual; i.e., at a temperature less than 120.degree. F., is described. Normally, polyurethanes made in relatively "cold" molds contain numerous surface voids. However, N-alkylmorpholines have been discovered to be effective "cold sink" catalyst additives which permit void-free polyurethane formation even in cooler than average molds. The additive should comprise from about 10 to about 30 wt. % of the entire catalyst portion of the polyurethane formulation.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: July 31, 1984
    Assignee: Texaco Inc.
    Inventor: Robert L. Zimmerman
  • Patent number: 4454297
    Abstract: Bis(aminoethyl) ether is reacted with an alkylene oxideto form a 2-[2-aminoethoxy-2-ethylamino]alkanol which is useful as an epoxy curative.The curative is cured with a polyepoxide to form an epoxy resin useful for such applications as decorative coatings, encapsulations, adhesives, laminates, potting compounds, etc.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: June 12, 1984
    Assignee: Texaco Inc.
    Inventors: Harold G. Waddill, Robert L. Zimmerman
  • Patent number: 4452922
    Abstract: A polyamide co-polymer polyol made by the reaction of a dicarboxylic acid diester with a diamine in the presence of a polyether polyol is described. The nylon formed should be present in the polyol in an amount of from 1 to 30 wt. %. The polyether polyol may have a molecular weight of about 2,000 to 8,000. This polyamide co-polymer polyol may be used in the manufacture of elastomers and flexible polyurethane foams which are characterized by good load bearing properties.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: June 5, 1984
    Assignee: Texaco Inc.
    Inventors: George P. Speranza, Robert L. Zimmerman
  • Patent number: 4442237
    Abstract: Mixtures of aromatic polyols containing tertiary amine and ester functionalities suitable for use in rigid foams prepared by reacting a phthalic acid residue with an alkylene glycol and an amino alcohol are described. These novel polyols may be blended with conventional polyols to yield rigid polyurethane foams with better flammability resistance as compared with foams made from conventional polyols alone.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 10, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Kenneth G. McDaniel
  • Patent number: 4442238
    Abstract: Mixtures of aromatic polyols containing amide and ester functionalities suitable for use in rigid foams prepared by reacting a phthalic acid residue with an amino alcohol and subsequent alkoxylation are described. These novel polyols may be blended with conventional polyols to yield rigid foams with better flammability resistance as compared with foams made from conventional polyols alone.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 10, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, George P. Speranza
  • Patent number: 4433170
    Abstract: The alkylene oxide adduct of bis(aminoethyl)ether may be reacted with formaldehyde in the presence of hydrogen and a hydrogenation-dehydrogenation catalyst to produce new compounds of the formula ##STR1## where R is hydrogen or lower alkyl and R" is methyl or ##STR2## These compounds show unexpectedly high efficiency as polyurethane catalysts. Fewer equivalents of this amine are required to produce foams having the same reaction profile as foams made with piror art amine catalysts.
    Type: Grant
    Filed: July 20, 1981
    Date of Patent: February 21, 1984
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Ernest L. Yeakey