Patents Assigned to DeSoto, Inc.
  • Patent number: 4657779
    Abstract: An ultraviolet-curable liquid coating composition which possesses minimal substrate deformational shrinkage on cure is disclosed in which (A) a cationically curable polyepoxide having a 1,2-epoxy equivalency of at least 1.3 is used in admixture with (B) an acrylate-functional compound which is either (1) a monoacrylate-functional compound carrying at least two primary hydroxy groups; or (2) an epoxy-functional monoacrylate in admixture with a compound carrying a plurality of primary hydroxyl groups. An acrylate-functional liquid (C), preferably a monoacrylate, is used to provide coating viscosity, and a catalyst component capable of initiating, on ultraviolet exposure, both the conventional free-radical polymerization of ethylenically unsaturated monomers, and the cationic polymerization of polyepoxides in the presence of a compound carrying the primary hydroxy group.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: April 14, 1987
    Assignee: DeSoto, Inc.
    Inventor: Joseph E. Gaske
  • Patent number: 4654083
    Abstract: A concrete mix comprises a cementing agent and aggregate, the aggregate comprising vesiculated beads of cross-linked resin which beads contain an average of at least 2 thin-walled foraminous cells to provide communication between the vesicles within said bead and the exterior of said beads to allow water to move into and out of said beads. This reduces the density of the concrete and the beads hold water to help control the cure.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: March 31, 1987
    Assignee: DeSoto, Inc.
    Inventor: John T. Vandeberg
  • Patent number: 4649045
    Abstract: The present invention relates to coating compositions that include an admixture or blend of at least two solution copolymers that provide combinations of properties which are not possessed by coating compositions that include only one of the copolymers. Each solution copolymer contains at least one aromatic monoethylenic monomer and at least one monoethylenic ester in amounts sufficient to provide a first solution copolymer having a glass transition temperature between about 40 and 70 degrees Centigrade and a second solution copolymer having a glass transition temperature between about -10 and +10 degrees Centigrade. Pigments can be readily wetted and dispersed in the copolymer blend to provide stable pigment concentrates that are useful in the preparation of coating compositions suitable for use on human fingernails.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: March 10, 1987
    Assignee: DeSoto, Inc.
    Inventors: Joseph E. Gaske, Edwin A. Zychowski
  • Patent number: 4629287
    Abstract: An ultraviolet curing liquid coating composition is disclosed which, when cured with ultraviolet light in the presence of a photoinitiator, provides a buffer coating for optical glass fiber having adequate strength at room or expected elevated temperature and stability at such elevated temperature, a high index of refraction above 1.48, and a low tensile modulus which remains low to resist microbending difficulties down to around -60.degree. C. This coating composition consists essentially of a linear polyacrylate-terminated polyurethane oligomer in admixture with a liquid linear aliphatic diacrylate in which the two acrylate groups are separated by a molecular weight of at least 400 up to about 4000, said liquid linear diacrylate providing said coating composition with a viscosity suitable for coating application.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: December 16, 1986
    Assignee: DeSoto, Inc.
    Inventor: Timothy E. Bishop
  • Patent number: 4624994
    Abstract: A radiation-curable liquid coating composition which cures on radiation exposure to form a soft and tough coating and which is adapted for coating optical fiber is disclosed. This composition comprises a polyurethane, polyamide or polyurea oligomer having (1) a molecular weight in the range of about 2000 to about 8000; (2) amide, urea or urethane groups in an amount of one such group for every 300 to 900 units of weight; and (3) polyalkylene polyether, polyalkylene polysulfide or polyalkylene polyester groups in which the alkylene moiety contains 2-6 carbon atoms. The polyether, polysulfide or polyester constitutes about 40% to about 90% by weight of the oligomer, and each end of the oligomer is terminated with a monoethylenically unsaturated addition polymerizable group. From 20% to 50% of the weight of the composition is a radiation-curable monoethylenically unsaturated monomer having a T.sub.g below about 10.degree. C.
    Type: Grant
    Filed: July 18, 1980
    Date of Patent: November 25, 1986
    Assignee: DeSoto, Inc.
    Inventor: Robert E. Ansel
  • Patent number: 4619051
    Abstract: A process for drying a water-wet paste containing polymeric beads without agglomeration is disclosed in which there is added to the wet paste a proportion of an organic solvent which forms an azeotrope with water, such as methyl isobutyl ketone, in an amount providing a stirrable mixture, and the solvent-containing aqueous paste is heated to remove the water as an azeotrope with the solvent and to produce a water free suspension of the beads in organic solvent. The proportion of azeotropic solvent can be minimized by adding a resinous vehicle in organic solvent solution to the solvent-containing aqueous paste after substantially all the water has been removed, and continuing the application of heat to remove undesired organic solvent and thereby increase the solids content.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: October 28, 1986
    Assignee: DeSoto, Inc.
    Inventors: Laura M. Wells, Fred D. Hawker, Maryam L. Dachniwskyj, Charles W. Strobel
  • Patent number: 4618657
    Abstract: A heat curable coating composition which deposits a release coating containing a smaller proportion of silicone release material is disclosed. This composition comprises (1) an hydroxy-functional resin which is preferably a polyester resin; (2) a cross-linking agent for the polyester, such as an aminoplast resin; and (3) at least one and preferably a mixture of at least two reactive silicones which are preferably polysiloxanes. These two polysiloxanes comprise: (A) a hydrogen- or alkoxy-functional polysiloxane; and (B) an elastomeric polysiloxane reactive with the hydrogen- or alkoxy-functional polysiloxane to provide release properties. Either or both of the polysiloxanes are reactive with the hydroxy-functional resin or the cross-linking agent. Components (1), (2) and (3) are compatible in a liquid admixture which may contain a volatile inert organic solvent or which may be solvent-free.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: October 21, 1986
    Assignee: DeSoto, Inc.
    Inventors: John Katchko, Thomas H. Plaisance, Karel Kriz
  • Patent number: 4617364
    Abstract: Monoethylenically unsaturated copolymerizable monomers are disclosed which improve the adhesion of copolymers (especially those produced by aqueous emulsion copolymerization to provide latex paint). These monomers are the reaction product of one equivalent of a monoethylenically unsaturated compound which resists homopolymerization and which carries a single isocyanate-reactive hydrogen atom, such as 2-hydroxypropyl monobutyl maleate, one mole of an organic polyisocyanate, such as 2,4-toluene diisocyanate, and sufficient alkyl alkylene urea carrying a single isocyanate-reactive hydrogen atom on the alkyl group, such as 2-hydroxyethyl ethylene urea, to consume the remaining isocyanate functionality on the polyisocyanate. An improved method of producing these monomers from a mixture of all three reactants is also disclosed.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: October 14, 1986
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4609718
    Abstract: An ultraviolet curing liquid coating composition is provided which, when cured with ultraviolet light in the presence of an appropriate photoinitiator, provides a buffer coating for optical glass fiber having adequate strength at room or expected elevated temperature and stability at such elevated temperature, a high index of refraction above 1.48, and a low tensile modulus which remains low to resist microbending difficulties down to around -60.degree. C. This coating composition consists essentially of a linear acrylate-terminated polyurethane oligomer including urea groups introduced by the presence in the oligomer of the reaction product with isocyanate functionality of about 30% to about 90% by weight of the acrylate-terminated oligomer of a polyoxyalkylene diamine having a molecular weight in the range of from about 1000 to about 8000 in which the alkylene group contains from 2-4 carbon atoms.
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: September 2, 1986
    Assignee: DeSoto, Inc.
    Inventors: Timothy E. Bishop, Clive J. Coady, John M. Zimmerman
  • Patent number: 4608409
    Abstract: An ultraviolet curing liquid coating composition is disclosed which, when cured with ultraviolet light in the presence of an appropriate photoinitiator, provides buffer coatings for optical glass fiber having adequate strength at room or expected elevated temperature and stability at such elevated temperature, a high index of refraction above 1.48, and a low tensile modulus which remains low to resist microbending difficulties down to around -60.degree. C. This coating composition consists essentially of a linear polyacrylate-terminated polyurethane or polyurea oligomer having a room temperature tensile modulus of at least 100 psi., and a tensile modulus at -60.degree. C. which is less than 175,000 psi., when capped with 2-hydroxyethyl acrylate and cured with ultraviolet light, in admixture with a liquid acrylate-functional material which does not increase the low temperature hardness and which provides the liquidity needed for coating application.
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: August 26, 1986
    Assignee: DeSoto, Inc.
    Inventors: Clive J. Coady, John J. Krajewski, Timothy E. Bishop
  • Patent number: 4607068
    Abstract: Radiation curable coating compositions, and especially electron beam-curable coating compositions, are disclosed in which magnetizable particles are dispersed in a liquid vehicle comprising a polyethylenically unsaturated polyurethane oligomer which includes a polycarbonate diol, and from 5% to 50%, based on the total weight of unsaturated material, of a polyethylenically unsaturated isocyanurate, such as a triacrylate of tris(2-hydroxyethyl) isocyanurate.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: August 19, 1986
    Assignee: DeSoto, Inc.
    Inventor: Robert E. Ansel
  • Patent number: 4601757
    Abstract: Nonvolatile plasticizers are provided which are the carboxyl-functional amide reaction product of: (1) a secondary amine-functional adduct of an acrylate compound, like 2-hydroxyethyl acrylate or a monohydric caprolactone monoacrylate, and about one amine equivalent per acrylate group in the acrylate compound, of an organic primary amine such as a polyoxypropylene monoprimary amine having a molecular weight in the range of about 50 to about 8000; with (2) a dicarboxylic acid anhydride, like phthalic anhydride. These plasticizers have improved wetting properties and are particularly useful in nitrocellulose compositions, such as nail polish.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: July 22, 1986
    Assignee: DeSoto, Inc.
    Inventors: Wallace H. Brown, Robert E. Ansel, Kevin P. Murray
  • Patent number: 4600649
    Abstract: Ultraviolet-curable, liquid coating compositions are disclosed which are resistant to abrasion and which are strongly adherent to basic plastic surfaces. These compositions comprise one or more polyacrylates or polymethacrylates, preferably including from 70% to 85% of trimethylol propane triacrylate, from 5% to 15% of a carboxylic acid which contains acrylic or methacrylic unsaturation, preferably acrylic acid itself, and photoinitiators (which are preferably ketonic and which desirably comprise a substituted acetophenone and benzophenone) are used to render the composition sensitive to ultraviolet light. The polyacrylate component preferably includes from 1% to 12% of a diacrylate or dimethacrylate of a diglycidyl ether of a bisphenol in which the molecular weight of the diglycidyl ether is less than about 600. The above proportions are based on the total weight of polymerizable material. The composition preferably also includes 0.5% to 2.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: July 15, 1986
    Assignee: DeSoto, Inc.
    Inventor: A. Frank Leo
  • Patent number: 4599807
    Abstract: A process for drying a water-wet paste containing polymeric beads without agglomeration is disclosed in which there is added to the wet paste a proportion of an organic solvent which forms an azeotrope with water, such as methyl isobutyl ketone, in an amount providing a stirrable mixture, and the solvent-containing aqueous paste is heated to remove the water as an azeotrope with the solvent and to produce a water free suspension of the beads in organic solvent. The proportion of azeotropic solvent can be minimized by adding a resinous vehicle in organic solvent solution to the solvent-containing aqueous paste after substantially all the water has been removed, and continuing the application of heat to remove undesired organic solvent and thereby increase the solids content.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: July 15, 1986
    Assignee: DeSoto, Inc.
    Inventors: Laura M. Wells, Fred D. Hawker, Maryam L. Dachniwskyj, Charles W. Strobel
  • Patent number: 4599417
    Abstract: Ureido-functional ethylenically unsaturated copolymerizable amide monomers are disclosed which are the adduct formed by reacting an aminoalkyl alkylene urea, preferably aminoethyl ethylene urea, with substantially a stoichiometric amount, based on the amine functionality present, of a maleic anhydride compound in solution in N-methyl pyrollidone. The reaction is carried out at a temperature in the range of 80.degree. C. to 130.degree. C. to form an unsaturated carboxyl-functional amide. To provide amide monomers which are particularly useful for improving the adhesion of aqueous emulsion copolymer used to form latex paints, the carboxyl functionality in the amide is consumed by esterification with an epoxide, such as propylene oxide, to provide an acid value of less than 10.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: July 8, 1986
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4598109
    Abstract: A process of producing a water dispersible epoxy phosphate-solvent mixture is disclosed which comprises heating the solvent with orthophosphoric acid to reaction temperature together with additional water so that the total amount of water is sufficient to hydrolyze at least about 50% of the oxirane functionality in the polyepoxide which is used, slowly adding a resinous polyepoxide to this heated mixture so that reaction with phosphoric acid and hydrolysis of the oxirane groups will occur simultaneously to minimize the concentration of oxirane functionality in the reaction mixture as the reaction proceeds, thus minimizing epoxy-epoxy reactions which tend to increase the molecular weight of the epoxy phosphate which is formed, and then adding volatile amine to destroy any remaining oxirane functionality and to neutralize the epoxy phosphate to provide a water dispersible epoxy phosphate-solvent mixture.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: July 1, 1986
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4590250
    Abstract: Radiation curable coating compositions, and especially electron beam-curable coating compositions, are disclosed in which magnetizable particles are dispersed in a liquid vehicle comprising an hydroxy functional polyethylenically unsaturated polyurethane having the following structural formula: ##STR1## in which X is an ethylenically unsaturated monomer initially carrying a single hydroxy group, R' is the residue of an at least trifunctional polyol or amino alcohol linking compound, s is a number of 0.8 to 10, t is a number from 1 to 15, and Z is a diisocyanate terminated polycarbonate diol polyurethane oligomer having the following structure: ##STR2## in which R is alkylene having from 1-20 carbon atoms, Q is the residue of an organic diisocyanate; y is at least 1, and R and y are selected to provide a molecular weight for the polycarbonate diol reactant of from 300 to 3000.
    Type: Grant
    Filed: July 12, 1985
    Date of Patent: May 20, 1986
    Assignee: DeSoto, Inc.
    Inventor: Robert E. Ansel
  • Patent number: 4588757
    Abstract: A method of forming an aqueous emulsion laminating adhesive having an extended pot life is disclosed in which monoethylenically unsaturated monomers are polymerized to form a copolymer having a glass transition temperature in the range of about -10.degree. C. to about -50.degree. C. The polymerization is carried out in aqueous emulsion in the presence of emulsified epoxy resin in an amount of from about 2% to about 60%, based on the weight of the monomers which are copolymerized. An aqueous emulsion of amine-functional resin is then mixed into aqueous emulsion containing copolymer and epoxy resin formed by the aqueous emulsion copolymerization to provide a weight ratio of amino hydrogen atoms to oxirane groups of from about 0.1 to about 1.0.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: May 13, 1986
    Assignee: DeSoto, Inc.
    Inventors: Ralph L. Minnis, Elias P. Moschovis, James J. Killeen
  • Patent number: 4588649
    Abstract: Dielectric coating compositions intended for application to conductive papers are disclosed. These coating compositions comprise a pigmented aqueous dispersion of a carboxyl-functional copolymer of copolymerized monoethylenically unsaturated monomers including form 8% to 18% by weight of monoethylenically unsaturated carboxylic acid, such as acrylic acid. The carboxyl-functional copolymer is dispersed in water with the aid of a volatile amine, such as ammonia, and the water dispersion is pigmented to contain calcium carbonate and/or clay in a pigment to binder weight ratio of from 0.5:1 to 6:1.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: May 13, 1986
    Assignee: DeSoto, Inc.
    Inventors: Karel Kriz, Ralph L Minnis
  • Patent number: 4585534
    Abstract: Freshly drawn optical glass fiber is protected by coating it with an ultraviolet-initiated, cationically curable liquid coating composition comprising a cationically curable polyepoxide, a polysiloxane carrying a plurality of hydroxyalkyl groups, and a photoinitiator and/or photosensitizer for an ultraviolet-activated cationic cure. The coatings are of low modulus and retain a low modulus at temperatures as low as -60.degree. C.
    Type: Grant
    Filed: April 29, 1983
    Date of Patent: April 29, 1986
    Assignee: DeSoto, Inc.
    Inventors: George Pasternack, Timothy E. Bishop, Orvid R. Cutler, Jr.