Patents by Inventor Charles M. Orlando

Charles M. Orlando 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: 4460798
    Abstract: Asymmetrical bisphenols such as 2-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)propane are prepared by an improved process wherein a hydroxyphenyldialkylcarbinol is reacted with a phenol in the presence of a hydrogen halide catalyst. According to the improved process, the carbinol is added to a mixture of the phenol and hydrogen halide under conditions maintaining a low carbinol concentration in the reaction mixture. This low concentration is preferably maintained by adding the carbinol in the form of a solution in a portion of the phenol.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: July 17, 1984
    Assignee: General Electric Company
    Inventors: Howard J. Klopfer, Charles M. Orlando
  • Patent number: 4460800
    Abstract: The preparation of hydroxyaryldialkylcarbinols by the reaction of hydroxyaryl alkyl ketones or alkyl hydroxyarenecarboxylates with Grignard reagents in a mixed ether-aromatic hydrocarbon solvent is frequently difficult on a large-scale basis because of formation of a voluminous precipitate of mixed magnesium salt. In an improvement in this process, a solution of the ketone or ester in an ether is added to the solution of the Grignard reagent.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: July 17, 1984
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Howard J. Klopfer
  • Patent number: 4391996
    Abstract: A method is described for dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane employing a refluxing dipolar aprotic solvent, such as dimethylformamide, containing a lithium halide catalyst to produce a crystalline product consisting essentially of 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene. The crystalline product can be isolated in substantially pure form and converted to a high impact, flame retardant polycarbonate.
    Type: Grant
    Filed: November 16, 1981
    Date of Patent: July 5, 1983
    Assignee: General Electric Company
    Inventors: Cleveland William K. S., Jimmy L. Webb, Charles M. Orlando
  • Patent number: 4294954
    Abstract: Polycarbonate copolymers are provided consisting essentially of chemically combined bisphenol carbonate units and having from about 5 to 70 mole percent of such chemically combined bisphenol carbonate units in the form of o,p'-bisphenol dichloroethylene carbonate units. The polycarbonate copolymers have been found to possess valuable flame retardant properties and improved processability.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: October 13, 1981
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, George R. Loucks
  • Patent number: 4221901
    Abstract: A method is described for dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane employing a refluxing dipolar aprotic solvent, such as dimethylformamide, containing a lithium halide catalyst to produce a crystalline product consisting essentially of 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene. The crystalline product can be isolated in substantially pure form and converted to a high impact, flame retardant polycarbonate.
    Type: Grant
    Filed: June 27, 1978
    Date of Patent: September 9, 1980
    Assignee: General Electric Company
    Inventors: William K. S. Cleveland, Jimmy L. Webb, Charles M. Orlando
  • Patent number: 4178466
    Abstract: Phenyl trichloro-ethanes can be prepared by reacting chloral with a phenol compound, such as phenol itself or 2,6-xylenol in HF, which acts both as a catalyst and solvent medium.
    Type: Grant
    Filed: March 15, 1978
    Date of Patent: December 11, 1979
    Assignee: General Electric Company
    Inventors: Russell A. Gardner, Charles M. Orlando
  • Patent number: 4170711
    Abstract: Monomeric and polymeric halogenated organic compounds derived from 2,2',6,6'-tetrabromo-3,3',5,5' -tetraalkyl-4,4'-biphenols are described. The derivatives are useful in their monomeric and polymeric form as flame retardant additives and/or concentrates for normally flammable resinous materials. The thermal stability at elevated temperatures of the brominated biphenol derivatives advantageously benefits polymeric compositions containing the brominated biphenol derivatives especially when the polymeric compositions are molded into three dimensional articles, or formed into films, sheeting or shaped into fibers, laminates or reinforced plastics by conventional techniques.
    Type: Grant
    Filed: September 27, 1976
    Date of Patent: October 9, 1979
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Francois A. Lavallee
  • Patent number: 4117018
    Abstract: A method is described for dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane employing a refluxing dipolar aprotic solvent, such as dimethylformamide, containing a lithium halide catalyst to produce a crystalline product consisting essentially of 1,1-dichloro-2,2-bis(4-hydroxyphenyl) ethylene. The crystalline product can be isolated in substantially pure form and converted to a high impact, flame retardant polycarbonate.
    Type: Grant
    Filed: February 4, 1977
    Date of Patent: September 26, 1978
    Assignee: General Electric Company
    Inventors: William K. S. Cleveland, Jimmy L. Webb, Charles M. Orlando
  • Patent number: 4058570
    Abstract: Brominated biphenols are produced by a bromination process which comprises reacting bromine with a 3,3', 5,5'-tetrasubstituted diphenoquinone at a temperature below about +20.degree. C. in the presence of an inert diluent, evolving hydrogen bromide gas at a temperature of about +20.degree. C. or lower, heating the resulting reaction mixture at elevated temperatures to complete the bromination reaction and recovering the desired 2,2',6,6'-tetrabromo-3,3',5,5'-tetrasubstituted-4,4'-biphenol. The biphenol products of the process can be used as antioxidants, as monomeric starting materials for polymeric halogenated organic compounds which are fire retardant as well as monomeric flame retardant additives for polymeric compositions useful in molding, coating and insulating various articles of manufacture.
    Type: Grant
    Filed: May 7, 1976
    Date of Patent: November 15, 1977
    Assignee: General Electric Company
    Inventors: Philip L. Kinson, Charles M. Orlando
  • Patent number: 3989531
    Abstract: Bromobiphenols comprising 2,2' ,6,6'-tetraalkyl-3,3',5,5'-tetrabromo-1,1'-biphenols and derivatives thereof are employed as fire-retardant additives for normally flammable resins yielding fire-retardant polymeric compositions. These fire-retardant compositions are thermally stable and can be molded or formed into fire-retardant articles, such as films, sheeting, fibers, laminates, or reinforced plastics by conventional techniques.
    Type: Grant
    Filed: March 12, 1974
    Date of Patent: November 2, 1976
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Francois A. Lavallee
  • Patent number: 3956403
    Abstract: Bromobiphenols containing at least two bromine atoms meta to the phenolic hydroxyl groups can be produced from 3,3',5,5'-tetra-substituted diphenoquinones by reacting the latter with bromine. The reaction can be controlled to produce little, if any, by-product. The products obtained are dependent to some extent on the substituents in the four positions ortho to the hydroxyl groups. The biphenols can be used as antioxidants or as starting materials for preparation of flame-retardent polymeric compositions useful in the molding, coating and insulating arts.
    Type: Grant
    Filed: August 18, 1975
    Date of Patent: May 11, 1976
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Francois A. Lavallee