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).
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Publication number: 20210284889Abstract: 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: ApplicationFiled: March 10, 2021Publication date: September 16, 2021Inventors: Charles R. Frihart, Linda F. Lorenz
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Patent number: 7651582Abstract: 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: GrantFiled: May 6, 2008Date of Patent: January 26, 2010Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
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Publication number: 20080202684Abstract: 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: ApplicationFiled: May 6, 2008Publication date: August 28, 2008Applicant: The United States of America, as represented by the Secretary of AgricultureInventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
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Patent number: 7345136Abstract: 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: GrantFiled: April 4, 2005Date of Patent: March 18, 2008Assignees: Heartland Resource Technologies LLC, USDAInventors: James M. Wescott, Charles R. Frihart
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Publication number: 20040259218Abstract: 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: ApplicationFiled: May 4, 2004Publication date: December 23, 2004Inventors: Paul J. Weimer, Linda F. Lorenz, Anthony H. Conner, Charles R. Frihart
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Patent number: 6562888Abstract: 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: GrantFiled: July 27, 1998Date of Patent: May 13, 2003Assignee: Arizona Chemical CompanyInventors: Charles R. Frihart, Nelson E. Lawson, Brett A. Neumann
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Patent number: 6242509Abstract: 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: GrantFiled: April 15, 1999Date of Patent: June 5, 2001Assignees: 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
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Patent number: 6111055Abstract: 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: GrantFiled: September 26, 1997Date of Patent: August 29, 2000Assignees: Union Camp Corporation, Bush Boake AllenInventors: Vivian Berger, Charles R. Frihart, Ronald L. Gordon, Jochen Heydel, Richard C. MacQueen, Mark S. Pavlin, Virgil Williams
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Patent number: 6022947Abstract: 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: GrantFiled: September 18, 1998Date of Patent: February 8, 2000Assignee: Union Camp CorporationInventors: Charles R. Frihart, Kenneth E. Krajca, Brett A. Neumann
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Patent number: 5612448Abstract: 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: GrantFiled: April 21, 1995Date of Patent: March 18, 1997Assignee: Union Camp CorporationInventor: Charles R. Frihart
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Patent number: 5539025Abstract: 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: GrantFiled: March 16, 1995Date of Patent: July 23, 1996Assignee: Union Camp CorporationInventors: George A. Smith, Charles R. Frihart
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Patent number: 5428083Abstract: 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: GrantFiled: August 20, 1993Date of Patent: June 27, 1995Assignee: Union Camp CorporationInventors: George A. Smith, Charles R. Frihart
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Patent number: 5424371Abstract: 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: GrantFiled: February 17, 1994Date of Patent: June 13, 1995Assignee: Union Camp CorporationInventors: Charles R. Frihart, Ronald L. Gordon
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Patent number: 5385986Abstract: 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: GrantFiled: May 5, 1994Date of Patent: January 31, 1995Assignee: Union Camp CorporationInventors: Charles R. Frihart, Ronald L. Gordon
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Patent number: 5296557Abstract: 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: GrantFiled: July 2, 1992Date of Patent: March 22, 1994Assignee: Union Camp CorporationInventor: Charles R. Frihart
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Patent number: 5296556Abstract: 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: GrantFiled: August 9, 1991Date of Patent: March 22, 1994Assignee: Union Camp CorporationInventor: Charles R. Frihart
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Patent number: 5194638Abstract: 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: GrantFiled: April 23, 1991Date of Patent: March 16, 1993Assignee: Union Camp CorporationInventors: Charles R. Frihart, Mark S. Pavlin
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Patent number: 5155177Abstract: 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: GrantFiled: March 18, 1991Date of Patent: October 13, 1992Assignee: Union Camp CorporationInventor: Charles R. Frihart
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Patent number: 5109053Abstract: 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: GrantFiled: June 21, 1990Date of Patent: April 28, 1992Assignee: Union Camp CorporationInventors: George A. Smith, Daniel T. Rumack, Charles R. Frihart
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Patent number: 4987160Abstract: 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: GrantFiled: January 31, 1989Date of Patent: January 22, 1991Assignee: Union Camp CorporationInventors: Charles R. Frihart, Ronald J. Wroczynski