Patents by Inventor Charles R. Frihart

Charles R. Frihart 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).

  • Publication number: 20210284889
    Abstract: Methods of making and using adhesive compositions based on oilseed solids are provided. Also provided are adhesive compositions made using the methods. The adhesive compositions are made by mixing defatted oilseed solids with a polyisocyanate to form a non-aqueous adhesive composition and, subsequently, mixing the non-aqueous adhesive composition with water to form an aqueous adhesive composition.
    Type: Application
    Filed: March 10, 2021
    Publication date: September 16, 2021
    Inventors: Charles R. Frihart, Linda F. Lorenz
  • Patent number: 7651582
    Abstract: A bioadhesive composition for bonding together adjacent surfaces of wood comprises a microbially-produced fermentation residue containing adherent microbial cells and glycocalyx. This residue finds particular application as a replacement for a significant amount of phenol-formaldehyde (PF) or other conventional adhesive component commonly used in the production of plywood and other wood products.
    Type: Grant
    Filed: May 6, 2008
    Date of Patent: January 26, 2010
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
  • Publication number: 20080202684
    Abstract: A bioadhesive composition for bonding together adjacent surfaces of wood comprises a microbially-produced fermentation residue containing adherent microbial cells and glycocalyx. This residue finds particular application as a replacement for a significant amount of phenol-formaldehyde (PF) or other conventional adhesive component commonly used in the production of plywood and other wood products.
    Type: Application
    Filed: May 6, 2008
    Publication date: August 28, 2008
    Applicant: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
  • Patent number: 7345136
    Abstract: Water-resistant, protein-based adhesive dispersion compositions and methods for preparing them are provided. The adhesive dispersions are prepared by copolymerizing a denatured vegetable protein, such as soy flour, that has been functionalized with methylol groups with one or more reactive comonomers, and preparing an acidic dispersion of the adhesive. The adhesive dispersions exhibit superior water resistance, and can be used to bond wood substrates, such as panels or laminate, or in the preparation of composite materials.
    Type: Grant
    Filed: April 4, 2005
    Date of Patent: March 18, 2008
    Assignees: Heartland Resource Technologies LLC, USDA
    Inventors: James M. Wescott, Charles R. Frihart
  • Publication number: 20040259218
    Abstract: A bioadhesive composition for bonding together adjacent surfaces of wood comprises a microbially-produced fermentation residue containing adherent microbial cells and glycocalyx. This residue finds particular application as a replacement for a significant amount of phenol-formaldehyde (PF) or other conventional adhesive component commonly used in the production of plywood and other wood products.
    Type: Application
    Filed: May 4, 2004
    Publication date: December 23, 2004
    Inventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
  • Patent number: 6562888
    Abstract: Rosin esters that are both light-colored and color stable may be produced by reacting rosin with an organic compound containing two or more hydroxyl groups each separated from each other by at least four carbon atoms. With appropriate choices for the esterification catalyst and antioxidant(s), the rosin ester may be useful as a tackifier, and can be formulated into an adhesive composition. The adhesive compositions will further comprise an appropriate adhesive polymer.
    Type: Grant
    Filed: July 27, 1998
    Date of Patent: May 13, 2003
    Assignee: Arizona Chemical Company
    Inventors: Charles R. Frihart, Nelson E. Lawson, Brett A. Neumann
  • Patent number: 6242509
    Abstract: An ester-terminated dimer acid-based polyamide may be blended with a solvent to form a gel. The solvent may be flammable, and a wick may be added to the resulting gel so as to form a candle. Depending on the composition, the candle may be formed into a free standing pillar, or may be better suited to being placed in a container. The solvent may be mineral oil. A solid coating may be placed around the candle, for advantages including to enhance the clarity and/or mechanical stability of the gelled body, and to eliminate the tendency of a gel to have an oily feel and to accept noticeable fingerprints. The ester-terminated dimer acid-based polyamide may also be combined with an active ingredient, such as a fragrance, colorant, insect-repellant, insecticide, bioactive ingredient or the like, to afford a delivery vehicle for the active ingredient.
    Type: Grant
    Filed: April 15, 1999
    Date of Patent: June 5, 2001
    Assignees: International Paper Company, Bush Boake Allen Inc.
    Inventors: Vivian Berger, Jochen Heydel, Virgil A. G. Williams, Charles R. Frihart, Ronald L. Gordon, Richard C. MacQueen, Mark S. Pavlin
  • Patent number: 6111055
    Abstract: An ester-terminated dimer acid-based polyamide may be blended with a solvent to form a gel. The solvent may be flammable, and a wick may be added to the resulting gel so as to form a candle. Depending on the composition, the candle may be formed into a free standing pillar, or may be better suited to being placed in a container. The solvent may be mineral oil. A solid coating may be placed around the candle, for advantages including to enhance the mechanical stability of the gelled body, and to eliminate the tendency of a gel to have an oily feel and to accept noticeable fingerprints. The solvent which, in combination with the ester-terminated dimer acid-based polymer forms a gel, may be or include a fragrance material, an insecticide or an insect repellent. A wick may or may not be present in this gel, but in any event, the composition provides for the release of the fragrance, insecticide or insect-repellent.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: August 29, 2000
    Assignees: Union Camp Corporation, Bush Boake Allen
    Inventors: Vivian Berger, Charles R. Frihart, Ronald L. Gordon, Jochen Heydel, Richard C. MacQueen, Mark S. Pavlin, Virgil Williams
  • Patent number: 6022947
    Abstract: Light-colored phenolic-modified rosin esters, suitable for use as, for example, tackifiers in adhesive compositions, are prepared by reacting together rosin, a phenolic compound, formaldehyde or a reactive equivalent thereof, and a non-phenolic hydroxyl-containing organic compound in the presence of at least one lightening agent selected from phenol sulfide compounds, phosphorous acid, esters of phosphorous acid, and hypophosphite salts. The formaldehyde or reactive equivalent is present in an amount ranging from about 1.1 to about 3.5 equivalents of --CHO moieties per 1 equivalent of Ar--OH moiety of the phenolic compound, in order to obtain rosin esters having desirably low color, and adequately low molecular weight to effectively function as tackifiers.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: February 8, 2000
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Kenneth E. Krajca, Brett A. Neumann
  • Patent number: 5612448
    Abstract: Hot melt adhesive compositions containing amine and acid terminated polyamide resins, optionally curable when combined with epoxy resins, wherein the amine component of the polyamide resin contains (i) 1,2-diaminopropane, (ii) a piperazine-containing diamine, and optionally, (iii) polyetherdiamines; the polyamide resins may be acid or amine terminated, and are characterized by having an acid plus amine number of up to 40, preferably up to 30, and more preferably up to 20; the adhesive compositions are useful in a number of applications and have good strength while exhibiting flexibility and low tackiness.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: March 18, 1997
    Assignee: Union Camp Corporation
    Inventor: Charles R. Frihart
  • Patent number: 5539025
    Abstract: Stable, one-component, curable epoxy resin and polyamide resin dispersions and methods for the preparation of the same are described, wherein the polyamide resin dispersion has a stability enhancing, water soluble, dipolar chemical moiety.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: July 23, 1996
    Assignee: Union Camp Corporation
    Inventors: George A. Smith, Charles R. Frihart
  • Patent number: 5428083
    Abstract: Stable, one-component, curable epoxy resin and polyamide resin dispersions and methods for the preparation of the same are described, wherein the polyamide resin dispersion has a stability enhancing, water soluble, dipolar chemical moiety.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: June 27, 1995
    Assignee: Union Camp Corporation
    Inventors: George A. Smith, Charles R. Frihart
  • Patent number: 5424371
    Abstract: A thermoset adhesive composition comprising a thermoplastic, substantially amine terminated piperazine-containing and/or polyetherdiamine-containing polyamide resin, and further comprising an epoxy resin.
    Type: Grant
    Filed: February 17, 1994
    Date of Patent: June 13, 1995
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Ronald L. Gordon
  • Patent number: 5385986
    Abstract: A hot-melt adhesive composition is prepared from (1) a thermoplastic amine-terminated piperazine containing polyamide resin derived from (a) a polymerized fatty acid, (b) an aliphatic polyamine, and (c) a piperazine-containing polyamine without primary amine groups and/or a polyetherdiamine, optionally with (d) a linear dicarboxylic acid and/or a monocarboxylic acid; and (2) an epoxy resin; wherein the epoxy:amine ratio is greater than about 1:1 to less than about 10:1.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: January 31, 1995
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Ronald L. Gordon
  • Patent number: 5296557
    Abstract: This invention relates to two-component curable hot-melt compositions comprising thermoplastic polyamide resins that are substantially free of piperazine-containing polyamines. In one preferred embodiment the polyamide resins are the reaction product of an acid component with an amine component, wherein the amine component consists essentially of about (i) 20 to 100 equivalent percent of one or more acyclic diamines selected from the group consisting of 2-methyl-1,5-pentanediamine, 1,3-pentanediamine, 1,3-propanediamine, 1,5-pentanediamine, 1,7-heptanediamine, 1,9-nonanediamine, methyl-1,9-nonanediamine, 1,2-propanediamine, and 2-methyl-1,2-diaminopropane, and (ii) about 0 to 80 equivalent percent of one or more polyamines selected from the group consisting of cyclic and acyclic polyamines other than those amines of (i). The compositions possess excellent heat resistance, flexibility, elasticity and resistance to solvents, including organic solvents and water.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: March 22, 1994
    Assignee: Union Camp Corporation
    Inventor: Charles R. Frihart
  • Patent number: 5296556
    Abstract: An improved thermoset adhesive composition comprising a thermoplastic, substantially amine-terminated polyamide resin, an epoxy resin, and a diluent, and methods for the preparation thereof.
    Type: Grant
    Filed: August 9, 1991
    Date of Patent: March 22, 1994
    Assignee: Union Camp Corporation
    Inventor: Charles R. Frihart
  • Patent number: 5194638
    Abstract: A resinous binder for use in hot melt ink compositions, which ink compositions may be used in hot melt ink jet printing applications, is disclosed. The resinous binder has a melt viscosity of 250 cps or less at 150.degree. C., is sufficiently transparent to allow a colorant to be distributed through the resinous binder in an amount effective to impart a pre-determined color to the resulting hot melt ink composition, and has a blocking temperature greater than 100.degree. C.
    Type: Grant
    Filed: April 23, 1991
    Date of Patent: March 16, 1993
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Mark S. Pavlin
  • Patent number: 5155177
    Abstract: This invention provides acrylate-modified polyamide resins comprising the Michael addition product of a mixture of a thermoplastic polyamide and reactive diluent with a polyol ester having a plurality of acrylate ester groups, wherein the mole ratio of the initial acrylate groups of the polyol ester to the initial amino groups of the polyamide ranges from about 0.5 to about 8.0, and wherein the reactive diluent's from about 1% to about 25% by weight polyamide. The diluent comprises mono- and di-substituted amines of 10 to 44 carbon atoms.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: October 13, 1992
    Assignee: Union Camp Corporation
    Inventor: Charles R. Frihart
  • Patent number: 5109053
    Abstract: Aqueous dispersions of acrylate-modified polyamide resin having unreacted acrylate functionality are provided. These acrylate-modified polyamide dispersions cure upon exposure to either ultraviolet radiation or thermal energy to form cross-linked films useful, for example, as adhesive coatings. In a preferred embodiment, acrylate-modified dispersions are formed by the addition of a polyol ester having a multiplicity of acrylate ester groups to a polyamide resin having a multiplicity of free amino groups under conditions effective to form the Michael addition product thereof.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: April 28, 1992
    Assignee: Union Camp Corporation
    Inventors: George A. Smith, Daniel T. Rumack, Charles R. Frihart
  • Patent number: 4987160
    Abstract: A radiation-curable resin useful as a hot melt adhesive is made by the Michael addition of the amino functional groups of an aminoamide thermoplastic polymer with a portion of the acrylate groups of a polyol acrylate. A photoinitiator is optionally added.
    Type: Grant
    Filed: January 31, 1989
    Date of Patent: January 22, 1991
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Ronald J. Wroczynski