Patents Represented by Attorney Denis A. Firth
  • Patent number: 4105643
    Abstract: Homopolymers of the diacrylates, dimethacrylates, di(2-haloacrylates) and di(2-cyanoacrylates) of 1-dialkanolaminophospholene-1-oxides and the copolymers of the above esters with lower-alkyl acrylates, meth-acrylates, 2-chloroacrylates and 2-cyanoacrylates are described. These polymers are useful as catalysts in the conversion of organic isocyanates to the corresponding carbodiimides.
    Type: Grant
    Filed: November 1, 1977
    Date of Patent: August 8, 1978
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith
  • Patent number: 4104346
    Abstract: A mold is described for the molding of substantially isotropic isocyanate-based polymer foam buns. The mold is a box mold which has sidewalls of which at least one pair disposed in parallel relationship is adapted to move outwardly when subjected to pressure exerted by the expanding foam during the molding operation. The outward movement of the sidewalls is controlled by stops provided on the periphery of the mold floor, said sidewalls being free to slide over the surface of the floor. The lid of the mold is supported in sliding engagement with the upper edges of the sidewalls. The mold and the process of fabricating foam buns therewith is particularly suitable for use in situations (e.g. operation in the field) in which it is not possible or practicable to employ continuous bunstock machines. The mold is relatively inexpensive and readily dismantled for transportation to a fabrication site.
    Type: Grant
    Filed: July 29, 1976
    Date of Patent: August 1, 1978
    Assignee: The Upjohn Company
    Inventors: John N. Curtiss, Charles E. Koehler, Pat L. Murray
  • Patent number: 4101465
    Abstract: A novel cocatalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises: (a) alkali metal glycine salts, (b) hydroxyalkyltrialkylammonium carboxylate salts, and (c) alkali metal salts selected from the group consisting of (i) alkali metal salts of N-phenyl aliphatic amides, and (ii) alkali metal salts of aliphatic carboxylic acids. The use of the cocatalyst combination provides for the facile formation of polyisocyanurate foam laminate boardstock which is characterized by good fire resistance and good physical properties.
    Type: Grant
    Filed: October 6, 1976
    Date of Patent: July 18, 1978
    Assignee: The Upjohn Company
    Inventors: Robert J. Lockwood, Alexander McLaughlin, Harold E. Reymore, Jr.
  • Patent number: 4098775
    Abstract: Polyamideimides are described which are derived by conventional procedures from particular 1,1-cycloaliphatic bis(phenylamine) compounds (or the corresponding diisocyanates) and trimellitic acid (preferably through the anhydride acid chloride). The polyamideimides are engineering thermoplastics characterized by the combined properties of solubility, melt processability, and resistance to thermal oxidation.
    Type: Grant
    Filed: November 15, 1976
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventor: Kemal B. Onder
  • Patent number: 4098973
    Abstract: Modified polystyrenes are described which are catalysts for the conversion of organic isocyanates to the corresponding carbodiimides. The modified polystyrenes are characterized by the presence of recurring units of the formula: ##STR1## R.sub.1 and R.sub.2 are hydrocarbyl which is free of substituents reactive with isocyanate groups, R.sub.3 is hydrogen, chloro or methyl, R.sub.4 is hydrogen or methyl, and n is 0 or 1.The use of the above polymers to catalyze the formation of carbodiimides from organic isocyanates is also disclosed.
    Type: Grant
    Filed: January 31, 1977
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith
  • Patent number: 4098772
    Abstract: The processing temperatures of thermoplastic polyurethane elastomers are reduced, and the extrudability and the sensitivity to degradation by shear and by moisture are improved, by including a minute proportion (from 0.0005 to 0.05 equivalents, per equivalent of isocyanate) of a monohydric aliphatic alcohol in the reaction mixture (diisocyanate, polymeric diol and difunctional extender) employed to prepare thermoplastic polyurethane elastomers by the one-shot procedure.
    Type: Grant
    Filed: March 11, 1976
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventors: Henry W. Bonk, Benjamin S. Ehrlich, Joseph Pleckaitis
  • Patent number: 4094866
    Abstract: The use of certain catalysts provide for an improved process for the preparation of soluble polyimides, polyamides, and polyamideimides. The catalysts are compounds of formula ##STR1## wherein M represents an alkali metal, and n is an integer from 2 to 5 inclusive. The improved process comprises reacting organic diisocyanates with polycarboxylic compounds consisting of tetracarboxylic acids or the intramolecular dianhydrides thereof, tricarboxylic acids or the monoanhydrides thereof, dicarboxylic acids, and mixtures thereof, in the presence of said catalysts. The polymers are obtained in solution at low reaction temperatures and short reaction times thereby avoiding side-reactions which otherwise would be detrimental to polymer molecular weight and ultimate polymer properties.
    Type: Grant
    Filed: February 17, 1977
    Date of Patent: June 13, 1978
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • Patent number: 4094864
    Abstract: The use of certain catalysts provide for an improved process for the preparation of soluble polyimides, polyamides, and polyamideimides. The catalysts are compounds of formula ##STR1## WHEREIN M represents an alkali metal, and n is an integer from 2 to 5 inclusive. The improved process comprises reacting organic diisocyanates with polycarboxylic compounds consisting of tetracarboxylic acids or the intramolecular dianhydrides thereof, tricarboxylic acids or the monoanhydrides thereof, dicarboxylic acids, and mixtures thereof, in the presence of said catalysts. The polymers are obtained in solution at low reaction temperatures and short reaction times thereby avoiding side-reactions which otherwise would be detrimental to polymer molecular weight and ultimate polymer properties.
    Type: Grant
    Filed: February 17, 1977
    Date of Patent: June 13, 1978
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • Patent number: 4093604
    Abstract: Random copolymers of polyparabanic acids and polyamides are described. The copolymers are highly useful engineering thermoplastics which, unlike the corresponding polyparabanic acids alone, are readily moldable by extrusion, injection molding and like techniques. The copolymers are readily prepared by a one-shot reaction of (i) bis(alkoxyoxalyl)amides of aliphatic, araliphatic or aromatic diamines, (ii) aromatic or aliphatic dicarboxylic acids, and (iii) organic diisocyanates.
    Type: Grant
    Filed: July 5, 1977
    Date of Patent: June 6, 1978
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, Kemal B. Onder
  • Patent number: 4092752
    Abstract: An improved combination of box spring and mattress is provided. The mattress has a core of a particular class of flame-retarded flexible polyurethane foam and, optionally, has an outer layer of flexible polyimide foam fabricated to surround said core. The foam core, optionally with outer layer of polyimide foam, is enclosed in a flame retardant or retarded ticking (flame retarded cotton, polyvinyl chloride, fiber glass cloth, high temperature resistant polymeric fiber cloth). The box spring has a non-combustible frame and, optionally, is padded with a flame retarded flexible polyurethane foam, such as that used in the aforesaid mattress, or a flexible polyimide foam.The box spring and mattress combination meets the requirements of present institutional fire codes and the like and represents a significantly improved product for commercial and domestic household use.
    Type: Grant
    Filed: November 29, 1976
    Date of Patent: June 6, 1978
    Assignee: The Upjohn Company
    Inventor: Thomas P. Dougan
  • Patent number: 4092343
    Abstract: A process is described for the preparation of polymethylene polyphenyl polyamines containing from 40 to 60 percent by weight of diamine and also containing markedly less high molecular weight polyamines than products hitherto available. Phosgenation of the polyamines gives the corresponding mixture of polymethylene polyphenyl polyisocyanates of markedly lower viscosity and lighter color than products hitherto available, and yielding polymer foams which are substantially white in color.The process comprises condensing aniline and formaldehyde (molar ratio 4-10:1) in the absence of catalyst, separating water from the resulting aminal mixture, contacting the aminals at 20.degree. C to 60.degree. C with a solid catalyst (diatomaceous earths, clays, zeolites) until formation of benzylamines is substantially complete, distilling aniline from the resulting benzylamines under reduced pressure and below 150.degree.
    Type: Grant
    Filed: May 16, 1977
    Date of Patent: May 30, 1978
    Assignee: The Upjohn Company
    Inventors: Floro F. Frulla, Adnan A. R. Sayigh, Henri Ulrich, Peter J. Whitman
  • Patent number: 4089843
    Abstract: A process is described for the conversion of solid polymers to powders in which the particles are substantially spherical and uniform in size. The polymer is dissolved in an aprotic solvent which is at least partially miscible with water but immiscible with mineral oil, the resulting solution is emulsified in mineral oil, and a minor amount of water or a glycol is added with agitation. The powdered polymer separates and is isolated by filtration, centrifugation and the like. Alternatively, when the precipitant is a glycol having a boiling point higher than the aprotic solvent in which the polymer is initially dissolved, the powdered polymer is isolated by filtration, centrifugation and the like after first removing the aprotic solvent and glycol by distillation. The process is applicable to a wide variety of polymers (polyimide, polyamides, polyamideimides, polyurethanes) which are soluble in aprotic solvents.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: May 16, 1978
    Assignee: The Upjohn Company
    Inventor: Karl W. Rausch, Jr.
  • Patent number: 4087481
    Abstract: Novel copolyamides having the recurring unit ##STR1## are disclosed wherein, in about 30 percent to about 60 percent of the recurring units, R is --CH.sub.2).sub.x wherein x is an integer from 7 to 12 inclusive, and, in about 40 percent to about 70 percent of the recurring units, R is m-phenylene; Ar in about 70 percent to about 95 percent of the recurring units is 4,4'-methylenebis(phenylene) and in the remaining 5 to 30 percent is a tolylene radical; and provided that when at least about 50 percent of R is m-phenylene Ar is at least 10 percent tolylene and further provided that said tolylene radicals are present in said copolyamide substantially as polyamide blocks with at least said m-phenylene radicals.The copolyamides are highly amorphous and characterized by high glass transition temperatures. They are easily injection molded with no brittle fracture occurring and yield polymer articles, having high impact and tensile strengths along with excellent elongation and clarity.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: May 2, 1978
    Assignee: The Upjohn Company
    Inventor: Kemal B. Onder
  • Patent number: 4083815
    Abstract: Polyurethane elastomers are described which are not themselves soluble in organic polar solvents at ambient temperatures but which, upon heating to 140.degree. - 180.degree. C in the presence of said solvents, form solutions which are stable at ambient temperatures. The elastomers are obtained by reacting 4,4'-methylenebis(phenyl isocyanate) with a polyester of polyether diol (M. W. = 750 to 2000) and diol extender in the presence of a monohydric alcohol (M. W. = 32 to 500). The elastomers generally have softening points in the range of 140.degree. C to 180.degree. C.Coating compositions derived from the above elastomers are also described.
    Type: Grant
    Filed: March 11, 1976
    Date of Patent: April 11, 1978
    Assignee: The Upjohn Company
    Inventor: Edward J. Thompson
  • Patent number: 4080314
    Abstract: The processing temperatures of thermoplastic polyurethane elastomers are reduced, and the extrudability and sensitivity to shear and moisture are improved, by employing as the diisocyanate, in the preparation of said elastomers, the product obtained by reacting 4,4'-methylenebis(phenyl isocyanate) with a monohydric aliphatic alcohol. Use of the latter also counteracts batch-to-batch variations in reactivity of 4,4'-methylenebis(phenyl isocyanate).
    Type: Grant
    Filed: March 11, 1976
    Date of Patent: March 21, 1978
    Assignee: The Upjohn Company
    Inventors: Henry W. Bonk, Benjamin S. Ehrlich, Joseph Pleckaitis
  • Patent number: 4077922
    Abstract: Syntactic foams are described which consist of a spherical filler (microballoons, microspheres) embedded in a polyimide which is characterized by solubility in polar organic solvents and by thermoplasticity. These syntactic foams possess high structural strength, high resistance to deformation upon exposure to heat, and the ability to be subjected to further molding, e.g. for shaping and/or increase in density, if desired. These properties render the materials useful for a wide variety of structural and insulative applications e.g. in the preparation of mechanical parts and, using microballoons, lightweight, substantially non-burning, structural panels.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: March 7, 1978
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., Karl W. Rausch, Jr.
  • Patent number: 4075139
    Abstract: Phenolic foams are disclosed which are obtained by conventional procedures from phenol-aldehyde resole resins and novel premixed catalyst combinations comprising (a) a phosphonate compound ##STR1## wherein R, R.sub.1 and R.sub.2 are independently selected from the class consisting of alkyl having from 1 to 8 carbon atoms, inclusive, aryl having from 6 to 12 carbon atoms, inclusive, and aralkyl having from 7 to 13 carbon atoms, inclusive; and (b) an aromatic sulfonic acid. The foams are characterized as non-punking, fire resistant, and fine celled foams which can be prepared at room temperature (about 20.degree. C) in thick sections without splitting or cracking. Furthermore, the foams do not require a heat curing treatment in order to achieve a thermoset state.
    Type: Grant
    Filed: February 22, 1977
    Date of Patent: February 21, 1978
    Assignee: The Upjohn Company
    Inventor: Richard L. Greer
  • Patent number: 4072665
    Abstract: Novel copolyamides having the recurring unit ##STR1## are disclosed wherein R, in 60 percent to 85 percent of the recurring units, is --CH.sub.2 --.sub.x wherein x is an integer from 7 to 12 inclusive, and, in 15 percent to 40 percent of the recurring units, R is m-phenylene; and Ar is an arylene radical. The copolyamides are characterized by ease of melt processing such as in molding, extruding, and injection molding, while at the same time possessing good high temperature stability, and being further characterized by unexpectedly high impact and flexural strengths.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: February 7, 1978
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • Patent number: 4068055
    Abstract: Modified polystyrenes are described which are catalysts for the conversion of organic isocyanates to the corresponding carbodiimides. The modified polystyrenes are characterized by the presence of recurring units of the formula: ##STR1## WHEREIN THE BROKEN LINES IN THE PHOSPHOLENE NUCLEUS INDICATE A DOUBLE BOND LOCATED BETWEEN THE CARBON ATOM AT POSITION 3 AND ONE OF THE CARBON ATOMS AT POSITIONS 2 AND 4, THE H atom is attached to whichever carbon atom at positions 2 and 4 is not part of said double bond, R is halogen, alkoxy (CH.sub.1-6), phenoxy, hydrocarbyl (C.sub.1-18), halohydrocarbyl (C.sub.1-18), m = 0-3; n = 0, 1; R.sub.1 is hydrogen or methyl; and R.sub.2 is hydrocarbyl free from substituents reactive with iosocyanate.
    Type: Grant
    Filed: January 31, 1977
    Date of Patent: January 10, 1978
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith
  • Patent number: 4068065
    Abstract: Homopolymers of the diacrylates, dimethacrylates, di(2-haloacrylates) and di(2-cyanoacrylates) of 1-dialkanolaminophospholene-1-oxides and the copolymers of the above esters with lower-alkyl acrylates, methacrylates, 2-chloroacrylates and 2-cyanoacrylates are described. These polymers are useful as catalysts in the conversion of organic isocyanates to the corresponding carbodiimides.
    Type: Grant
    Filed: January 31, 1977
    Date of Patent: January 10, 1978
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith