Patents Represented by Attorney Charlotte M. Kraebel
  • Patent number: 5349095
    Abstract: A process for preparing a substituted or unsubstituted 3- or 4-hydroxyalkylbenzocyclobutene compound comprises reducing a corresponding 3- or 4-formyl or ketobenzocyclobutene compound with a hydride at a temperature below that at which dimerization or oligomerization of the formyl- or ketobenzocycloutene compound or the thus-produced hydroxyalkylbenzocyclobutene compound is a significant side reaction, for a time sufficient to convert the formyl- or ketobenzocyclobutene compound to the hydroxyalkylbenzocyclobutene compound. In a two-step process, formylbenzocyclobutenes are prepared from bromobenzocyclobutenes in 90% yield or from benzocyclobutenes in a 70% yield, and then converted to hydroxymethylbenzocyclobutenes for an overall yield of about 85% from a bromobenzocyclobutene or of about 65% from a benzocyclobutene.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: September 20, 1994
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 5274135
    Abstract: A process for preparing a 3- or 4-aminobenzocyclobutene comprises aminating a 3- or 4-halo- or sulfonyloxybenzocyclobutene reactant with an aminating agent by heating at a temperature from about 80.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to aminate the halo- or sulfonyloxybenzocyclobutene reactant. In another aspect, this invention relates to a process for making a 3- or 4-phthalimido- or maleimidobenzocyclobutene, comprising reacting a 3- or 4-halobenzocyclobutene reactant with a phthalimide or maleimide compound in the presence of a metal-containing catalyst. The resulting phthalimido- or maleimidobenzocyclobutene can be hydrolyzed to a 3- or 4-aminobenzocyclobutene.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: December 28, 1993
    Assignee: The Dow Chemical Company
    Inventors: Kenneth J. Bruza, Arnold E. Young, Kurt A. Bell
  • Patent number: 5264613
    Abstract: A process for preparing carboxylic acid esters of of the formulaX--(COOCH.sub.2 A).sub.nwherein A is the residue of a substituted or unsubstituted 3- or 4-benzocyclobutene compound, X is an n-valent organic bridging group, and n is 2,3, or 4, comprises reacting a substituted or unsubstituted 3- or 4-hydroxymethylbenzocyclobutene compound with a compound of the formula X--(COY).sub.n, wherein X is an n-valent organic bridging group and Y is Cl or Br. Esters of inorganic acids of the formulaX'(OCH.sub.2 A).sub.nwherein X' is a residue of an inorganic acid halide, n is 2 or 3, and A is the residue of a substituted or unsubstituted 3- or 4-benzocyclobutene compound, are prepared by reacting an inorganic halide of the formula X'Y.sub.n, wherein Y is Br or Cl, with a substituted or unsubstituted 3- or 4-hydroxymethylbenzocyclobutene compound. Biscarbonates of the formula X"[OC(.dbd.O)CH.sub.2 A].sub.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: November 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 5264646
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an organic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from organosilicon compounds, hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: November 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Gregory F. Schmidt, Hughie R.* Frick, Bonnie Frick
  • Patent number: 5243068
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Hughie R. Frick, deceased
  • Patent number: 5227536
    Abstract: A process for preparing a 3- or 4-hydroxybenzocyclobutene comprises reacting a 3- or 4-halogenzocyclobutene reactant with an alkali metal hydroxide by heating in an aqueous alcohol medium at a temperature from about 50.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to convert the halobenzocyclobutene reactant to the hydroxybenzocyclobutene product.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: July 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Pulikkottil J. Thomas, Robert A. DeVries, R. Garth Pews, Daniel A. Batzel
  • Patent number: 5210339
    Abstract: An improved process for the nitration of a substituted or unsubstituted benzocyclobutene compound in a reaction mixture comprising a nitrating agent, an unhalogenated carboxylic acid anhydride, clay and a solvent to produce a corresponding nitrobenzocyclobutene compound, is that wherein:(a) the solvent has a density above that of the nitrating agent or an extractable precursor thereof;(b) the reaction mixture is heated at a temperature such that solvent is removed from the reaction mixture to a site outside the reaction mixture to extract nitrating agent or extractable precursor thereof; and(c) the thus-extracted nitrating agent or precursor thereof is fed into the reaction mixture to nitrate the benzocyclobutene compound.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 5138081
    Abstract: A process for purifying an impure vinylically-unsaturated organosilicon product compound prepared by reaction between a vinylically-unsaturated organosilicon precursor and a halogenated organic compound in the presence of a homogeneous zerovalent palladium catalyst complex, the catalyst complex including an organophosphine or organoarsine ligand, in the presence of a hydrogen halide acceptor in an essentially anhydrous diluent, comprising treating a mixture containing the impure vinylically-unsaturated organosilicon product compound with a peroxide for a time sufficient to oxidize organophosphine or organoarsine impurities present in a mixture being treated. The peroxide can be selected from aqueous hydrogen peroxide or organic peroxides. The thus-treated mixture can be further treated by chromatography over silica gel or alumina. In optional embodiments, chromatography over silica gel or alumina can precede treatment with the peroxide.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: August 11, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Mary L. Ash, Hughie R. Frick, deceased
  • Patent number: 5136069
    Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, silicon atom or a combination thereof.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: August 4, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. DeVries, Hughie R. Frick, deceased
  • Patent number: 4822475
    Abstract: This invention relates to a process for determining the fouling tendency of a crude petroleum oil feed, comprising the steps of:(a) mixing a selected volume of crude petroleum oil sample with a selected volume of a solvent medium,(b) agitating the resulting mixture to solubilize fouling-determining materials in the solvent medium,(c) removing a sample of the resulting solvent medium,(d) determining absorbance of the resulting solvent medium at 230-270 nm and subtracting from the absorbance that of control solvent medium to obtain corrected absorbance of the resulting solvent medium and(e) determining the fouling tendency of the crude petroleum oil sample by correlating the corrected absorbance of the resulting solvent medium with calibration data specific for the solvent medium used, the ratio of oil sample to polar solvent and the wavelength at which absorbance is determined.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: April 18, 1989
    Assignee: Betz Laboratories, Inc.
    Inventors: Cato R. McDaniel, W. John Delaney, Bruce E. Wright
  • Patent number: 4449353
    Abstract: A natural gut string for sports rackets comprises at least two gut strands, each strand of which comprises a plurality of gut ribbons twisted together in a first direction, which strands are combined and re-twisted together in a direction opposite to the first direction. In a process for making the gut strings, the gut ribbons and gut strands are preferably twisted under tension.
    Type: Grant
    Filed: August 6, 1982
    Date of Patent: May 22, 1984
    Assignee: United States Tennis Gut Association, Inc.
    Inventor: Amad Tayebi
  • Patent number: 4391088
    Abstract: A string for sports rackets consists of a gut core covered with filamentary aramid and impregnated with at least one coating of water-resistant, vapor-impermeable, flexible smooth adhesive polymeric resin, which adheres the filamentary aramid to the gut core.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: July 5, 1983
    Assignee: United States Tennis Gut Association, Inc.
    Inventors: Jerome Salsky, Patrick K. Janis, Kenneth E. Branen
  • Patent number: 4319877
    Abstract: A non-discoloring palladium-based alloy, free of silver or gold, suitable for fusion to dental porcelain compositions consists essentially of 75-85% by weight of Pd, 5-10% by weight of In, 5-10.5% by weight of Sn, up to 7.5% by weight of Co, Cr or Ni and up to 0.25% by weight of Si. Inclusion of 0.2-0.7% by weight of Ru improves the physical and mechanical properties of the alloy.
    Type: Grant
    Filed: August 21, 1980
    Date of Patent: March 16, 1982
    Inventor: Benjamin K. Boyajian
  • Patent number: 4261744
    Abstract: A non-discoloring palladium-based alloy, free of silver or gold, suitable for fusion to dental porcelain compositions consists essentially of 75-85% by weight of Pd, 5-10% by weight of In, 5-10.5% by weight of Sn, up to 7.5% by weight of Co, Cr or Ni and up to 0.25% by weight of Si.
    Type: Grant
    Filed: October 10, 1979
    Date of Patent: April 14, 1981
    Inventor: Ben K. Boyajian