Patents Represented by Attorney Charles J. Enright
  • Patent number: 4728696
    Abstract: The invention comprises a composition comprising at least one compound defined by the formula ##STR1## wherein R is hydrogen, C.sub.1-4 alkyl or a group ##STR2## wherein G is a divalent hydrocarbyl-linking group and J, D, E and F are hereinafter defined; wherein J and E independently are divalent linking groups selected from ##STR3## wherein R' is hydrogen or C.sub.1-4 alkyl; D is a divalent hydrocarbyl group which lends hydrophobicity to the compound; and F is a monovalent hydrocarbyl group which lends hydrophilicity to the compound. Such compositions are useful as comonomers with water-soluble monomers such as acrylamide and acrylic acid which form water-dispersible thickening agents which are resistant to shear degradation and heat and have a broad range of salt tolerance. Aqueous solutions thickened with such copolymers are useful in enhanced oil recovery processes as fluid mobility control agents, as fracturing fluids and drilling muds as well as hydraulic fluids and lubricants in many applications.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: March 1, 1988
    Assignee: The Dow Chemical Company
    Inventors: Kien Van Phung, Syamalarao Evani
  • Patent number: 4713363
    Abstract: Novel supported noble metal catalysts have high metal loadings and dispersions and are particularly effective catalysts in the conversion of 2-chloropropene to methyl methacrylate by vapor phase reaction with methanol and carbon monoxide.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventor: Dennis A. Hucul
  • Patent number: 4675344
    Abstract: A method for controlling the ratio of methanol to higher alcohols produced in a process for making mixed alcohols by contacting a hydrogen- and carbon monoxide-containing feed with a molybdenum- or tungsten-containing catalyst, said method comprising adjusting a concentration of a sulfur releasing substance in the feed.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: June 23, 1987
    Assignee: The Dow Chemical Company
    Inventors: Mark M. Conway, Craig B. Murchison, Rex R. Stevens
  • Patent number: 4543414
    Abstract: 2-Substituted-2-oxazolines are prepared by contacting N-(2-hydroxyalkyl)carboxamides with a small but catalytic amount of a cadmium or zinc salt at an elevated temperature.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: September 24, 1985
    Assignee: The Dow Chemical Company
    Inventor: David L. Larson
  • Patent number: 4539334
    Abstract: A Fischer-Tropsch process comprises contacting hydrogen and carbon monoxide in the presence of a conventional Fischer-Tropsch catalyst in combination with an amount of phosphorus effective to selectively poison the Fischer-Tropsch catalyst so as to improve the selectivity of said catalyst to C.sub.2 -C.sub.4 olefins.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: September 3, 1985
    Assignee: The Dow Chemical Company
    Inventor: Craig B. Murchison
  • Patent number: 4539416
    Abstract: A process for making N-furfurylthioalkyl carboxamide by reacting an oxaz(ol)ine with furfurylmercaptan in the absence of a transition metal catalyst. The carboxamide may then be hydrolyzed to form the 2-furfurylthioalkylamine.
    Type: Grant
    Filed: June 10, 1983
    Date of Patent: September 3, 1985
    Assignee: The Dow Chemical Company
    Inventors: Harold G. Fravel, Jr., Michael J. Fazio
  • Patent number: 4500728
    Abstract: The title salts are prepared in high purity by contacting in an aqueous reaction medium (a) 2-isopropenyl-2-oxazoline present in its free form in low concentration and (b) an acid selected from the group consisting of hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, organic carboxylic acids, alkyl or aryl sulfonic acids and mixtures thereof. The low concentration of 2-isopropenyl-2-oxazoline (IPO) in its free form can be achieved by adding the IPO slowly to the reaction mixture so that it does not accumulate or by maintaining a pH of less than about 2.5 in the reaction mixture so that nearly all of the IPO will be protonated.
    Type: Grant
    Filed: April 8, 1980
    Date of Patent: February 19, 1985
    Assignee: The Dow Chemical Company
    Inventors: Michael J. Fazio, Kirk E. Paisley
  • Patent number: 4481167
    Abstract: The title complexes comprise (a) a poly-2-oxazoline or poly-2-oxazine, such as the homopolymers of polymerized 2-ethyl-2-oxazoline or 2-ethyl-2-oxazine, and (b) IBrCl.sup.- or polyhalide anion of the formula (XY.sub.2n).sup.- where X and Y are individually chloride, bromide or iodide, but not both chloride, and n is 1, 2 or 3, and an independently supplied cation selected from the group consisting of alkali metals, alkaline earth metals, hydrogen and mixtures thereof. These complexes are readily prepared in either an aqueous or anhydrous environment at room temperature and are significantly more stable than either complexes of polyoxazolines or polyoxazines and halogen or interhalogen; or complexes of polyvinylpyrrolidone and polyhalide anions.
    Type: Grant
    Filed: July 1, 1981
    Date of Patent: November 6, 1984
    Assignee: The Dow Chemical Company
    Inventors: Sally P. Ginter, Percy J. Hamlin
  • Patent number: 4465601
    Abstract: A method is disclosed for servicing a wellbore comprising introducing into the wellbore a substantially solids-free fluid comprising an admixture of water, calcium bromide and methanol and wherein the admixture has a density of at least about 15 lb/gal (1.80 kg/l) and a crystallization point of no more than about 20.degree. C. The composition is also claimed.
    Type: Grant
    Filed: January 11, 1982
    Date of Patent: August 14, 1984
    Assignee: The Dow Chemical Company
    Inventor: Andrew J. Pasztor, Jr.
  • Patent number: 4458061
    Abstract: Novel monomers of the structure: ##STR1## wherein each R, which may be the same or different, is an alkyl group containing 1 to 3 carbon atoms; each R', which may be the same or different, is hydrogen or methyl, at least two R' are hydrogen; and x and y are independently 0, 1 or 2, are made and used to produce polyurethanes, polyureas and other useful polymers.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: July 3, 1984
    Assignee: The Dow Chemical Company
    Inventor: David W. Hughes
  • Patent number: 4447664
    Abstract: The disclosure describes a process for alkylating aromatics comprising the steps of:(1) contacting a mixture of hydrogen and carbon monoxide with a Fischer-Tropsch catalyst at conditions effective to form a first gas mixture containing an alkylating agent selected from ethylene or mixtures of ethylene and propylene;(2) removing from the first gas mixture components capable of alkylating aromatics and having boiling points higher than the selected alkylating agent to form a second gas mixture which contains less than about 10 mole percent of the selected alkylating agent and more than about 5 mole percent each of carbon monoxide and hydrogen;(3) combining the second gas mixture with sufficient alkylatable aromatic hydrocarbon to form a third mixture containing at least about a 1 to 1 aromatic to alkylating agent mole ratio; and(4) contacting the third mixture with a heterogeneous alkylation catalyst at conditions effective to alkylate the aromatic hydrocarbon.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: May 8, 1984
    Assignee: The Dow Chemical Company
    Inventors: Craig B. Murchison, Robert A. Stowe, Richard L. Weiss
  • Patent number: 4443611
    Abstract: 2-H-2-Oxazolines are prepared by contacting in liquid phase a N-(.beta.-hydroxyalkyl)formamide with a small but catalytic amount of an inorganic zinc salt at elevated temperatures. Similarly, 2-substituted-2-oxazolines are prepared by contacting N-(2-hydroxyalkyl)carboxamides with a small but catalytic amount of an inorganic zinc salt. As an example, 2-H-2-oxazoline was prepared in approximately 72 percent yield by warming a mixture of N-(.beta.-hydroxyethyl)formamide with a catalytic amount of zinc chloride at a temperature of from 180.degree. C. to 185.degree. C./50 mm Hg for 2.2 hours. In this reaction, the desired oxazoline product was recovered as a codistillate with water during the course of the reaction.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: April 17, 1984
    Assignee: The Dow Chemical Company
    Inventor: Mark E. Kaiser
  • Patent number: 4436789
    Abstract: Polyoxazolines, such as poly-2-ethyl-2-oxazoline, having a weight average molecular weight in the range of from about 1,000 to about 150,000, are effective as dispersing agents for particulate matter found in starch/clay coatings and protein/latex clay coatings for paper. Usually, 0.005 percent to about 2.0 percent polyoxazoline, based on the total weight of the binder, effectively reduces the viscosity of said paper coatings, allowing the use of higher solids in the coating composition.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: March 13, 1984
    Assignee: The Dow Chemical Company
    Inventors: Roy A. Davis, Norman L. Madison
  • Patent number: 4408001
    Abstract: A composition comprises(a) a polymer containing a characterizing amount of units of the formula ##STR1## wherein R.sub.1 -R.sub.4 are independently hydrogen, methyl or ethyl and wherein R.sub.5 is hydrogen or an alkyl radical containing 1 to 3 carbon atoms and x is 0 or 1;(b) IBr.sub.2.sup.-, IBrCl.sup.-, BrCl.sub.2.sup.- or mixtures thereof;(c) a cation selected from the group consisting of hydrogen ion, alkali metal ions, alkaline earth metal ions, ammonium ion and mixtures thereof; and(d) water; andwhich has been inhibited against degeneration by a degeneration inhibiting amount of an alcohol of the formulaR--(OCH.sub.2 CH.sub.2).sub.n --OHwherein R is hydrogen, an aliphatic radical containing 1 to 3 carbon atoms or a hydroxyl substituted aliphatic alkyl radical containing 2 or 3 carbon atoms and n is a number from 0 to 3 with the proviso that when R contains 3 carbon atoms and no hydroxyl groups, the n.noteq.0. The stabilized complexes are useful as sanitizers.
    Type: Grant
    Filed: April 6, 1981
    Date of Patent: October 4, 1983
    Assignee: The Dow Chemical Company
    Inventors: Sally P. Ginter, Percy J. Hamlin
  • Patent number: 4399288
    Abstract: A 2-oxazoline is separated from an aqueous solution by contacting this solution with a membrane selectively permeable to the 2-oxazoline, removing the 2-oxazoline as a vapor on the other side of the membrane and recovering it by cooling. Polyethylene hollow fibers are particularly desirable membranes, which purify the 2-oxazoline as it is separated from the water.
    Type: Grant
    Filed: January 21, 1981
    Date of Patent: August 16, 1983
    Assignee: The Dow Chemical Company
    Inventor: John C. McClure
  • Patent number: 4393249
    Abstract: A process for removing alkynes from hydrocarbon mixtures, particularly those containing butadiene by reacting the alkynes with hydroxyl group containing organic compounds in the presence of a silver exchanged ion-exchange resin and separating the products formed from the unreacted components of said mixture.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: July 12, 1983
    Assignee: The Dow Chemical Company
    Inventors: Albert Heuvelsland, Fritz F. F. Jann, Greet de Block-Martens
  • Patent number: 4380589
    Abstract: In Fischer-Tropsch reaction to form hydrocarbons from hydrogen and carbon monoxide the use of a catalyst containing:(1) molybdenum in free or combined form;(2) a promoter comprising an alkali or alkaline earth metal in free or combined form; and(3) a binder comprising an iron-containing calcium aluminate cement.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: April 19, 1983
    Assignee: The Dow Chemical Company
    Inventors: Craig B. Murchison, Dewey A. Murdick
  • Patent number: 4376861
    Abstract: The process comprises the steps of:(A) reacting by contacting an anhydrous or substantially anhydrous 2-alkyl-2-oxazoline with formaldehyde in a molar ratio of at least about 1.5 moles of 2-alkyl-2-oxazoline per mole of formaldehyde, thereby forming 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline,(B) recovering the 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline from the reaction product of step (A), and(C) reacting by contacting the 2-(.alpha.-hydroxymethylalkyl)-2-oxazoline and step B with an alkali or alkaline earth metal hydroxide, thereby forming 2-alkenyl-2-oxazoline.As an example, step A was conducted by reacting 2-ethyl-2-oxazoline (4 moles) having less than 1,000 ppm of water with paraformaldehyde (1 mole) at a reaction temperature of 100.degree. C. for approximately 5.5 hours. The excess oxazoline reactant was removed along with water as "overheads" by fractional distillation of the reaction product, leaving the 2-(.alpha.-hydroxymethylethyl)-2-oxazoline in approximately 96 percent yield.
    Type: Grant
    Filed: December 3, 1981
    Date of Patent: March 15, 1983
    Assignee: The Dow Chemical Company
    Inventors: James W. Lalk, Gerald C. Kolb, Donald A. Tomalia, Peter W. Owen
  • Patent number: RE31356
    Abstract: .[.Aliphatic nitriles.]. .Iadd.Olefinic nitriles of three to six carbon atoms .Iaddend.are converted to the corresponding amides by contacting the nitrile in the presence of water with a cupreous catalyst containing copper prepared by reducing copper hydroxide or a copper salt.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: August 23, 1983
    Assignee: The Dow Chemical Co.
    Inventors: Clarence E. Habermann, Ben A. Tefertiller
  • Patent number: RE31430
    Abstract: Copper, copper oxide, copper-chromium oxide, copper-molybdenum oxide or mixtures thereof have been found to be excellent heterogeneous catalysts for the conversion of nitriles in the presence of water to the corresponding amides. Using one such catalyst in a continuous flow reactor, acrylonitrile was almost 100% converted to acrylamide during more than six weeks of continuous operation.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: October 25, 1983
    Assignee: The Dow Chemical Co.
    Inventors: Clarence E. Habermann, Ben A. Tefertiller