Patents Represented by Attorney John Kekich
  • Patent number: 4173602
    Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorous-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: November 6, 1979
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4156065
    Abstract: An improved process is described for the reaction of an isocyanate (mono or poly) with a carboxylic acid or anhydride (mono or poly) to form the corresponding imide, amide or amide-imides. The improvement lies in using as the catalyst the 1-oxide, 1-sulfide or 1-hydrocarbylimino derivative of a phospholene, phospholane or phosphetane. The latter compounds are also substituted in the 1-position by a hydrocarbyl (C.sub.1-12) or halohydrocarbyl (C.sub.1-12) and may additionally carry one or more halo, lower-alkoxy, phenoxy, lower-hydrocarbyl or halo-substituted hydrocarbyl groups on the ring carbon atoms.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: May 22, 1979
    Assignee: The Upjohn Company
    Inventors: Kemal B. Onder, Curtis P. Smith
  • Patent number: 4152349
    Abstract: The reactivity of polymethylene polyphenyl isocyanates containing 20 to 90 percent of methylenebis(phenyl isocyanates) is improved, and stabilized against a decline on storage, by incorporating therein very small amounts of a compound of the formula ##STR1## wherein R.sub.1 =alkyl, aryl; R.sub.2 =alkyl; R.sub.3 =H, alkyl or aralkyl; and R.sub.1 and R.sub.2 taken together represent the residue of an oxazoline or oxazine. 2-Ethyloxazoline is the preferred compound for incorporation in the polyisocyanate.
    Type: Grant
    Filed: February 22, 1978
    Date of Patent: May 1, 1979
    Assignee: The Upjohn Company
    Inventor: Warren J. Rabourn
  • Patent number: 4152348
    Abstract: Color stabilized isocyanates, particularly methylene-bridged aromatic isocyanates [methylenebis(phenyl isocyanate) and prepolymers thereof], are derived by incorporating in the isocyanate a color stabilizing amount of a compound of the formula ##STR1## wherein R.sub.1 =alkyl, aryl; R.sub.2 =alkyl; R.sub.3 =H, alkyl or aralkyl; and R.sub.1 and R.sub.2 taken together represent the residue of an oxazoline or oxazine. 2-Ethyloxazoline is a preferred color stabilizing compound. The above compounds can also be used to discharge undesirable colors which have developed in such isocyanates on storage.
    Type: Grant
    Filed: February 22, 1978
    Date of Patent: May 1, 1979
    Assignee: The Upjohn Company
    Inventor: Warren J. Rabourn
  • Patent number: 4143063
    Abstract: A process is described for converting organic polyisocyanates to carbodiimide-containing polyisocyanates by heating said organic polyisocyanates in the presence of an organoarsine-substituted polystyrene carbodiimide-forming catalyst until a desired level of conversion is achieved, followed by separation of catalyst from product. It is thus possible to obtain a carbodiimide-containing polyisocyanate which is free from catalyst and hence free from the possibility that carbodiimide formation can continue on storage of the product. In a particular embodiment the process is employed to convert methylenebis(phenyl isocyanate), which is normally solid at ambient temperatures, to a storage stable liquid product. The polymeric catalysts employed in the process are characterized by a recurring unit of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrocarbyl, R.sub.3 is hydrogen, chloro or methyl, R.sub.4 is hydrogen or methyl and n is 0 or 1.
    Type: Grant
    Filed: April 10, 1978
    Date of Patent: March 6, 1979
    Assignee: The Upjohn Company
    Inventors: Louis M. Alberino, Curtis P. Smith
  • Patent number: 4143014
    Abstract: Storage stable aqueous solutions derived from polymethylene polyphenyl polyisocyanates are described, which solutions are useful as sealant coating compositions for wood and other substrates and, in the form of emulsions with polyisocyanates, as improved particle board binders. The storage stable aqueous solutions are obtained by admixing polymethylene polyphenyl polyisocyanates with less than a stoichiometric amount of a polyethylene glycol (MW 600 to 3000) or polypropylene glycol tipped with 15 to 85 percent ethylene oxide (MW 1000 to 3500) and, within a short time of completing the admixture but during the period where said mixture is completely soluble in water, dissolving said mixture in water. Optionally, a difunctional extender is added to the resulting solution in amount less than that required to react with all the isocyanate groups.
    Type: Grant
    Filed: November 9, 1977
    Date of Patent: March 6, 1979
    Assignee: The Upjohn Company
    Inventors: Alexander McLaughlin, Harold E. Reymore, Jr., Reinhard H. Richter
  • Patent number: 4137386
    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: May 3, 1978
    Date of Patent: January 30, 1979
    Assignee: The Upjohn Company
    Inventor: Curtis P. Smith
  • Patent number: 4129715
    Abstract: Substantially linear, segmented polyester amides are described which contain aromatic residues in the "hard" segments but which still possess sufficiently low melt properties to be injection moldable. The polyester amides are obtained by reacting a carboxylic acid-terminated prepolymer (derived by reacting an excess of a dicarboxylic acid with a polymeric diol of molecular weight 400 to 4000) with a stoichiometric amount of methylenebis(phenyl isocyanate) or toluene diisocyanate or mixtures of these isocyanates and, optionally, a dicarboxylic acid.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: December 12, 1978
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, William J. Farrissey, Jr., Robert G. Nelb, II
  • Patent number: 4128611
    Abstract: A process and apparatus are described for the preparation of continuous polymer foam bunstock having substantially rectangular cross-section. The novel feature comprises a panel member having its downstream end pivotally mounted above a conventional moving trough-shaped mold, the underside of said panel member floating freely in tangential contact with the rising foam in the area immediately following the gel point of said foam but before the point at which the foam is no longer sufficiently mobile to be molded without distortion of the cells thereof.
    Type: Grant
    Filed: April 7, 1977
    Date of Patent: December 5, 1978
    Assignee: The Upjohn Company
    Inventors: Richard A. Kolakowski, Richard M. Stroud
  • Patent number: 4123466
    Abstract: An improved process for the nitration of aromatic hydrocarbons is described. The aromatic hydrocarbon (benzene, toluene of particular interest) is reacted with gaseous nitrogen dioxide in the presence of a catalytic amount of sulfuric acid and in the absence of oxygen. The process is highly selective and avoids the formation of undesired by-products. The acid employed as catalyst can be recovered and recycled after removal of water of condensation liberated in the reaction.
    Type: Grant
    Filed: December 12, 1977
    Date of Patent: October 31, 1978
    Assignee: The Upjohn Company
    Inventors: Chung-Yuan Lin, Fred A. Stuber, Henri Ulrich
  • Patent number: 4112014
    Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethylphosphonates are described. These phosphorus-containing polyols can be incorporated into polyurethane foams to render the latter fire retardant. They have the advantage over closely related phosphorus-containing polyols that they are autocatalytic in the polyurethane foam forming reaction and that they can be mixed with the polyol component of the polyurethane foam forming composition to give a mixture (premix) which can be maintained in storage for prolonged periods without showing any signs of deterioration.
    Type: Grant
    Filed: April 11, 1977
    Date of Patent: September 5, 1978
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4108843
    Abstract: Random copolymers of polyparabanic acids and polyamide-imides are described. The copolymers are highly useful engineering thermoplastics which, unlike the corresponding polyparabanic acid homopolymers, are readily moldable by compression molding and like techniques. The copolymers are readily prepared by the one-shot reaction of bis(alkoxyoxalyl)amides of aliphatic, araliphatic or aromatic diamines, with organic diisocyanates and trimellitic anhydride.
    Type: Grant
    Filed: July 5, 1977
    Date of Patent: August 22, 1978
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, Kemal B. Onder
  • 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: 4105642
    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 (C.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 isocyanate.
    Type: Grant
    Filed: October 31, 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: 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: 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