Patents Represented by Attorney Denis A. Firth
  • Patent number: 4017459
    Abstract: Polyamide-imides are described which are derived by conventional procedures from 2,2-bis[4-(p-aminophenoxy)-phenyl]propane (or the corresponding diisocyanate) and trimellitic acid (preferably through the anhydride acid chloride). Copolyamide-imides derived from trimellitic acid, the above diamine (or diisocyanate) and certain other aromatic diamines or diisocyanates (4,4'-diaminodiphenyl ether, m-phenylene diamine and corresponding diisocyanates are preferred) are also described. The above polyamide-imides are engineering thermoplastics which, unlike closely related polyamides and polyimides, can be extruded and injection molded to form parts having good mechanical properties.
    Type: Grant
    Filed: September 19, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • Patent number: 4017572
    Abstract: An improved molding apparatus is described for use with relatively light weight molds, particularly molds for articles having a plurality of voids therein. A light weight two-piece mold, one-half being substantially rigid and the other relatively flexible, is disposed in a jig. The two halves of the mold are held in sealing relationship by inserting a hollow inflatable bag between the exterior of the relatively flexible mold piece and the interior wall of the adjacent jig member and inflating said bag to a pressure superior to that exerted by the expanding foam mix in the mold.The use of the improved apparatus obviates the need for molds of high structural strength (and hence excessive weight) and gives molded articles, particularly those of complex configuration, which are free from flashing.
    Type: Grant
    Filed: April 15, 1975
    Date of Patent: April 12, 1977
    Assignee: The Upjohn Company
    Inventors: Raymond L. Magone, Samir N. Saaty
  • Patent number: 4016227
    Abstract: A process is described for the isolation, in a solid state, of polyimides particularly those prepared by interaction of a polyisocyanate and a polycarboxylic anhydride in an organic solvent. A solution of the polyimide is passed into water preferably in the form of droplets or as extruded thin strands. The droplets or strands can be chopped, ground or otherwise comminuted after solidification. The process is particularly applicable to the isolation of solvent-soluble polyimides prepared by reaction of benzophenone tetracarboxylic dianhydride with a mixture of methylenebis(phenyl isocyanate) and toluene diisocyanate.
    Type: Grant
    Filed: February 7, 1972
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventors: Gregory L. Lines, Alec Odinak
  • Patent number: 4016144
    Abstract: Novel oligomeric poly N-carboxylic anhydrides having the following structure are disclosed. ##STR1## The unit Ar represents arylene and x represents an integer from 1 to 10 and y represents a number having an average value from 0 to 4. The polyanhydrides serve as useful storage stable intermediates for the production of polyamides to which they are easily converted by the elimination of carbon dioxide. A process for the preparation of the polyanhydrides from arylene diisocyanates and .alpha.,.omega.-alkylene dicarboxylic acids is disclosed. Processes for the conversion of the polyanhydrides to the corresponding polyamides are also disclosed.
    Type: Grant
    Filed: September 5, 1975
    Date of Patent: April 5, 1977
    Assignee: The Upjohn Company
    Inventor: James N. Tilley
  • Patent number: 4011180
    Abstract: A novel catalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises (i) an alkali metal salt of an N-substituted amide, (ii) an alkali metal salt of an N-(2-hydroxyphenyl)methyl glycine, and optionally a tertiary amine trimerization catalyst. The use of these catalyst combinations in the preparation of polyisocyanurate foams results in the facile continuous formation of laminate board stock. The polyisocyanurate foams produced using the novel catalyst combinations of the invention are characterized by having high resistance to heat distortion and volume change.
    Type: Grant
    Filed: May 2, 1975
    Date of Patent: March 8, 1977
    Assignee: The Upjohn Company
    Inventors: Robert J. Lockwood, Harold E. Reymore, Jr., Edward J. Thompson
  • Patent number: 4010209
    Abstract: A process is described for the preparation of phospholene-1-oxides and 1-sulfides having an aliphatic substituent in the 1-position, a double bond at the 2- or 3-positions and, optionally, having additional substituents at one or more of positions 2, 3, 4 or 5. The process comprises the reaction of a 1-(2-chloroalkoxy)-phospholene with the appropriate aliphatic alcohol or thiol optionally in the presence of an alkylation catalyst. Use of an aliphatic alcohol gives rise to a phospholene oxide while use of the corresponding thiol gives rise to a phospholene sulfide. The phospholene-1-oxides and 1-sulfides so obtained are useful as catalysts for the conversion of isocyanates to carbodiimides.
    Type: Grant
    Filed: December 15, 1975
    Date of Patent: March 1, 1977
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4008275
    Abstract: 2,2'- AND 2,4'-DIAMINODIPHENYLMETHANE ARE SELECTIVELY REMOVED FROM ADMIXTURES THEREOF WITH THE 4,4'-ISOMER BY HEATING THE ISOMER MIXTURE AT 30.degree. TO 100.degree. C in the presence of styrene, .alpha.-alkylstyrenes, or the mono- or diamino nuclear substituted derivatives thereof and a catalyst (mineral acid, clays, diatomaceous earth, zeolites). The styrene or .alpha.-alkylstyrene can be employed as such or generated in situ from a precursor therefor. The process is particularly useful in facilitating the isolation of substantially pure 4,4'-diaminodiphenylmethane from the polyamine mixture obtained by condensation of aniline and formaldehyde.
    Type: Grant
    Filed: August 18, 1975
    Date of Patent: February 15, 1977
    Assignee: The Upjohn Company
    Inventors: Adnan A. R. Sayigh, Kwok K. Sun, Henri Ulrich
  • Patent number: 4006122
    Abstract: Poly(ester amides) are obtained by heating a hydroxyl-containing or hydroxyl-free polyester of malonic acid with an organic polyisocyanate in the presence of a basic catalyst. Crosslinking of the polyester takes place by reaction of the isocyanate with the active hydrogen of the CH.sub.2 group of the malonate to give amide linkages, in addition to formation of urethane linkages in the case where the polyester contains free hydroxyl groups. The products range from elastomeric materials, where the isocyanate is in the form of an isocyanate-terminated prepolymer derived by reaction of an organic polyisocyanate with a polyol, to more rigid plastics where the isocyanate is a "simple" isocyanate, i.e. not in prepolymer form.
    Type: Grant
    Filed: March 11, 1974
    Date of Patent: February 1, 1977
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, William J. Farrissey, Jr.
  • Patent number: 4003859
    Abstract: A novel catalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises (i) a tertiary amine trimerization catalyst, (ii) an alkali metal salt of an N-substituted amide, and (iii) a dibutyl tin di(alkanoate) compound. The use of this catalyst combination in the preparation of polyisocyanurate spray foams enables the systems to be sprayed in either a 1:1 or 2:1 by volume ratio, or ratios between these limits interchangably with no alterations being required in reactant formulations. The polyisocyanurate foams produced using the novel catalyst combination of the invention are characterized by having high resistance to flame and heat distortion.
    Type: Grant
    Filed: May 19, 1975
    Date of Patent: January 18, 1977
    Assignee: The Upjohn Company
    Inventors: Harold E. Reymore, Jr., John K. Zane
  • Patent number: 4001186
    Abstract: The use of certain catalysts provide for an improved process for the preparation of soluble polyimides, polyamides, and polyamideimides. The catalysts are alkali metal salts of formula MOR, wherein R represents alkyl or aryl and M represents an alkali metal. 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: November 7, 1974
    Date of Patent: January 4, 1977
    Assignee: The Upjohn Company
    Inventor: Besir K. Onder
  • Patent number: 4000117
    Abstract: Two solvent soluble thermoplastic polyurethane elastomers and blends thereof are characterized by a hardness from about 67 Shore A to about 58 Shore D. The softer of the two elastomers is derived from the reaction of 4,4'-methylenebis(phenylisocyanate) and a poly(1,4-butylene adipate) which has a molecular weight of 600-750. The harder of the two elastomers is derived from the reaction of the same isocyanate and a combination of a major portion of poly(neopentylene adipate) of M.W. circa 450-550 and a minor portion of a poly(1,4-butylene adipate) of M.W. circa 300-360. The elastomers find particular utility as solution grade materials for various types of coatings and the like.
    Type: Grant
    Filed: March 31, 1975
    Date of Patent: December 28, 1976
    Assignee: The Upjohn Company
    Inventor: Tilak M. Shah
  • Patent number: 3991252
    Abstract: Novel fire resistant insulating structural building elements are provided which are comprised of unitized structures such as walls, roofs, ceilings, and floors in combination with a layer of plastic foam insulation to which is in turn bonded a coating of gypsum plaster by a layer of bonding agent. The novel elements of the invention find particular utility in the rapid and economic construction of thermally insulated and fire resistant buildings. Additionally, a method is disclosed for a facile and economic way of providing thermal barrier protection for exposed plastic foam insulation in existing buildings by the application of a bonding agent and a plaster coat on said foam.
    Type: Grant
    Filed: April 29, 1975
    Date of Patent: November 9, 1976
    Assignee: The Upjohn Company
    Inventors: Richard A. Kolakowski, Harold E. Reymore, Jr., Richard H. Roess
  • Patent number: 3989651
    Abstract: A novel process for the preparation of polyisocyanurate spray foams is disclosed. The catalyst combination comprises (i) N,N-dimethylcyclohexylamine, and (ii) a tetra (lower-alkyl) quaternary ammonium salt of an alkanoic acid. The use of this catalyst combination in the preparation of polyisocyanurate spray foams enables the systems to be sprayed under conditions of low ambient temperature upon cold substrates and to achieve good adhesion between the foam and substrate under such conditions. The polyisocyanurate foams produced using the novel catalyst combination of the invention are characterized by having high resistance to flame and heat distortion.
    Type: Grant
    Filed: July 9, 1974
    Date of Patent: November 2, 1976
    Assignee: The Upjohn Company
    Inventors: Robert J. Lockwood, Richard H. Roess
  • Patent number: 3986991
    Abstract: A novel catalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises (i) a tertiary amine trimerization catalyst containing a dimethylamino moiety, (ii) an alkali metal salt of an N-(2-hydroxyphenyl)methyl glycine, and (iii) a monomeric epoxide. The use of these catalysts in the preparation of polyisocyanurate foams results in facile machine preparation of bun stock foam without incurring the processing problems that arise from the prior art method. The polyisocyanurate foams produced using the novel catalyst combination of the invention are characterized by a reduced level of smoke generated on combustion.
    Type: Grant
    Filed: June 9, 1975
    Date of Patent: October 19, 1976
    Assignee: The Upjohn Company
    Inventors: Richard A. Kolakowski, Harold E. Reymore, Jr., Adnan A. R. Sayigh
  • Patent number: 3985934
    Abstract: High temperature resistant aromatic copolyimide fibers are disclosed together with processes for their preparation by wet and dry spinning techniques from solvent soluble copolyimides. The latter are prepared from benzophenone-3,3',4,4'-tetracarboxylic acid dianhydride and a mixture of 4,4'-methylenebis(phenyl isocyanate) and toluene diisocyanate (2,4-, or 2,6-isomer, or mixtures thereof). The wet spinning process can be stopped at any one of the stages taught, to yield useful fibers. The choice of coagulant fluid in the spin bath controls the fiber cross-section which in turn controls certain fiber characteristics. When glycerine or a low molecular weight aliphatic glycol is employed as coagulant fluid, the high temperature fiber obtained has advantageous properties which are otherwise difficult or impossible to obtain.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: October 12, 1976
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., Besir K. Onder
  • Patent number: 3984490
    Abstract: A process is described for recovering phenylcyclohexane as principal product from dicyclohexylbenzenes by heating the latter in the presence of at least an equal amount by weight of benzene and an acid clay or zeolite catalyst at a temperature of 190.degree. - 400.degree.C. The period of heating is preferably controlled so that no significant cracking of the phenylcyclohexane is caused. The process is a useful adjunct to the known methods of production of phenylcyclohexane by hydrodimerization by benzene. The latter process gives significant amounts of dicyclohexylbenzenes as by-product. The present process enables this generally undesirable by-product to be converted to phenylcyclohexane thus increasing the overall yield of phenylcyclohexane from benzene in the hydrodimerization process.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: October 5, 1976
    Assignee: The Upjohn Company
    Inventors: Tae H. Chung, Chandrakant A. Patel, Adnan A. R. Sayigh
  • Patent number: 3983087
    Abstract: A process is described for converting scrap flexible polyurethane foam, derived from a polyether polyol, to a homogeneous mixture of polyols which can be used, alone or as a blend with other polyols, in the preparation of polyurethane foams. The process comprises heating the scrap foam with not more than its own weight of an aliphatic diol which has at least one alkyl substituent in the alkylene chain, and which optionally contains an oxygen atom in the alkylene chain. The scrap flexible foam can contain up to about 75 percent of scrap rigid or semi-flexible foam, if desired.
    Type: Grant
    Filed: July 25, 1975
    Date of Patent: September 28, 1976
    Assignee: The Upjohn Company
    Inventors: Benjamin Tucker, Henri Ulrich
  • Patent number: 3954684
    Abstract: A novel catalyst combination for the trimerization of polyisocyanates to polyisocyanurates is disclosed. The catalyst combination comprises (i) a tertiary amine trimerization catalyst, and (ii) a quaternary ammonium salt of an alkanoic acid. The use of this catalyst combination in the preparation of polyisocyanurate foams enables the foaming speeds to be varied from relatively slow to fast in the absence of foam shrinkage. The foams produced in accordance with the present invention are useful in applications calling for relatively fast rise characteristics such as in laminate production.
    Type: Grant
    Filed: July 9, 1974
    Date of Patent: May 4, 1976
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., Abdul-Munim Nashu
  • Patent number: 3951657
    Abstract: A photopolymerizable element for the preparation of relief printing plates. The element comprises an addition polymerizable monomer (e.g. trimethylolpropane trimethacrylate), a free radical initiator for polymerizing the monomer (e.g. benzophenone) and a polyester-based polyurethane binding agent which is the reaction product of 4,4'-methylenebis(phenyl isocyanate), a polycaprolactone diol having a molecular weight in the range of 1,000 to 2,500, and a mixture of at least two aliphatic diol extenders. Optionally the photopolymerizable element is provided with a support layer such as a polyester film or paper.Processes for the preparation of relief printing plates from said elements are also disclosed.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: April 20, 1976
    Assignee: The Upjohn Company
    Inventors: Frank P. Recchia, Tilak M. Shah
  • Patent number: 3951922
    Abstract: The compounds 4-azidocarbonylphthalic anhydride, 4-isocyanatophthalic anhydride, and the lower-alkyl carbamates obtained by reacting the latter isocyanate with a lower-aliphatic alcohol, are described. A process for the preparation of a polyimide by heating these compounds alone or in admixture with other polyisocyanates is also described. The 4-azidocarbonylphthalic anhydride is an intermediate for the 4-isocyanatophthalic anhydride.
    Type: Grant
    Filed: June 10, 1974
    Date of Patent: April 20, 1976
    Assignee: The Upjohn Company
    Inventors: Reinhard H. Richter, Henri Ulrich