Patents Represented by Attorney Denis A. Firth
  • Patent number: 4334106
    Abstract: An improved process is provided for the preparation of a certain class of hydroxyphenyl-indanol compounds by the cyclization of a phenol selected from the group consisting of an isopropenylphenol, oligomers thereof, and mixtures of any of said group in any combination and proportion, by dissolving said phenol in a stoichiometric excess of an organic acid selected from the group consisting of trifluoroacetic acid, trichloroacetic acid, difluoroacetic acid, dichloroacetic acid, fluoroacetic acid, chloroacetic acid, formic acid, and mixtures thereof at a temperature falling within a range of from about 0.degree. C. to about 90.degree. C. to form a solution; and maintaining said solution at a temperature falling within the above said range until the formation of said indanol is substantially complete.The dihydroxy compounds produced by the present method are useful in the preparation of epoxy, alkyd, and urethane resins in particular.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: June 8, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4328361
    Abstract: A process is disclosed for converting p-isopropenylphenol and derivatives thereof and, more particularly, oligomers of p-isopropenylphenol and derivatives thereof, to hydroquinone via monomeric intermediates [e.g. p-(2-haloisopropyl)phenol in the case of p-isopropenylphenol and oligomers thereof]. The process involves reacting the starting materials with a hydrogen halide (e.g. gaseous hydrogen chloride) in the presence of an organic solvent and subjecting the product so obtained to oxidation with hydrogen peroxide or an organic hydroperoxide.
    Type: Grant
    Filed: January 16, 1981
    Date of Patent: May 4, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4328331
    Abstract: Segmented thermoplastic polyester-amides are described which are prepared by reacting a polymeric diol (molecular weight in the range of 400 to 4000) with a carboxylic acid terminated prepolymer obtained by reacting an aliphatic ether diamine, optionally in admixture with a minor proportion (based on equivalents) of an alkylene diamine, with an excess of dicarboxylic acid (aromatic or aliphatic). The polyester-amides, which can be prepared preferably by the melt condensation method, have excellent physical properties and resistance to degradation by heat.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: May 4, 1982
    Assignee: The Upjohn Company
    Inventors: Augustin T. Chen, Robert G. Nelb, II, Kemal B. Onder
  • Patent number: 4321333
    Abstract: Polyurethane polymers comprising the reaction product of an organic polyisocyanate (A), an organic polyol (B), & a difunctional extender (C) wherein the improvement comprises employing as the polyisocyanate (A) a composition comprising a bond of, (a) a prepolymer comprising the reaction product of methylenebis (phenyl isocyanate) with a polyol mixture comprising:(1) polyol having a molecular weight of at least 1,000, &(2) polyol having a molecular weight of about 115 to 300 & (b) a liquefied methylenebis (phenyl isocyanate). Also disclosed are blends of (a) & (b).
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: March 23, 1982
    Assignee: The Upjohn Company
    Inventors: Louis M. Alberino, Robert J. Lockwood
  • Patent number: 4315078
    Abstract: Flexible polyurethane foams are described which are the product of reaction under foam producing conditions of a combination of (a) an aromatic polyisocyanate; (b) a polyether polyol with the optional use of a minor amount of a cross-linking polyol; (c) antimony oxide; (d) a polyhalogenated aromatic compound; and (e) a hydrated inorganic salt.The foams have flame retardant properties superior to those of the prior art while at the same time having physical properties equal or superior to the prior art materials. Accordingly, the foams of the invention meet very stringent tests for fire retardance required of seat cushioning, mattresses, and like materials in aircraft, institutions such as hospitals, convalescent homes, and the like.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: February 9, 1982
    Assignee: The Upjohn Company
    Inventor: Carlos J. Anorga
  • Patent number: 4306052
    Abstract: Novel thermoplastic polyester polyurethanes are disclosed which are obtained by reacting a polyester diol, a difunctional extender, a methylenebis(phenyl isocyanate), and from about 0.0025 mole to about 0.03 mole per equivalent of isocyanate of a monocarbodiimide product derived from a methylenebis(phenyl isocyanate) or the corresponding uretidinedioneimine adduct thereof with said latter methylenebis(phenyl isocyanate).The polyester polyurethanes are characterized by a combination of thermoplasticity, extremely good hydrolytic stability which cannot be diminished by solvent action, good physical properties, particularly tensile strength and elongation, and enhanced clarity of molded articles.
    Type: Grant
    Filed: September 25, 1980
    Date of Patent: December 15, 1981
    Assignee: The Upjohn Company
    Inventors: Henry W. Bonk, Richard W. Oertel
  • Patent number: 4296212
    Abstract: Elastomeric polyurethane-polyurea polymers are disclosed that are derived from the reaction of organic polyisocyanates with A. primary hydroxyl polyols having a functionality of 2 to 4 and a molecular weight from 1500 to 12000, and B. extender mixtures comprised of 1. an aromatic diamine wherein at least one of the positions ortho to each amine group is substituted by a lower alkyl group, and 2. a lower molecular weight diol, provided that the aromatic diamine comprises from 5 to 45 percent by weight of the extender mixture and the balance comprises the diol.The polymers find particular utility in the preparation of reaction injection molded parts, particularly, automotive parts because of their excellent flexural modulus, tensile, and tear properties.
    Type: Grant
    Filed: August 27, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventors: James H. Ewen, Thomas R. McClellan
  • Patent number: 4294987
    Abstract: An improvement is described in the process of preparing polymethylene polyphenyl polyamines by condensing aniline and formaldehyde in the presence of an acid catalyst in the initial condensation. The improvement enables the amount of acid which has to be neutralized at the end of the reaction to be substantially reduced or eliminated entirely. This is accomplished without sacrifice of the high level of 4,4'-isomer of di(aminophenyl)methane normally present in the diamine content of the polyamines when a mineral acid catalyst is employed in the condensation.
    Type: Grant
    Filed: December 31, 1979
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, Nirad N. Shah
  • Patent number: 4289732
    Abstract: An apparatus is described for intimately admixing two liquid components which react chemically with each other immediately after mixing (the mixing of phosgene and polyamines is an example). The mixing is accomplished by introducing one component in the form of a fan shaped spray into a mixing chamber, and causing this spray to intersect with twin fan-shaped sprays of the second component which latter sprays are introduced into the mixing chamber from preferably diametrically opposed locations in a direction substantially perpendicular to the direction of the first component spray. The process and apparatus in question provide improved mixing, substantially reduce problems of solids deposition hitherto encountered in similar processes, and give products of greater uniformity and improved physical properties.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventors: John R. Bauer, Robert W. Byars, Robin L. Grieve
  • Patent number: 4289858
    Abstract: Disclosed are novel polyol blends comprising from about 20 percent to about 85 percent by weight of said blend of an amine triol, or mixture of amine triols selected from the formula ##STR1## wherein R is an aliphatic radical having from 8 to 18 carbon atoms, inclusive, each R.sub.1 is independently selected from the group consisting of hydrogen or methyl, x, y, and z each independently have an average value from about 1 to about 5 inclusive, n is 2 or 3; and from about 15 percent to about 80 percent by weight of a primary hydroxyl polyol characterized by a molecular weight of from about 60 to about 1000.The polyol blends are miscible with fluorocarbon blowing agents and water and other adjuvants including trimerization catalysts.The novel blends are particularly useful in an improved process for the preparation of polyisocyanurate foams. The foams are characterized by high reaction exotherms making such foams particularly suited to the preparation of polyisocyanurate foam laminates.
    Type: Grant
    Filed: February 1, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventors: Charles E. Koehler, Thomas R. McClellan, Pat L. Murray
  • Patent number: 4284775
    Abstract: There is disclosed a novel process for the preparation of 1,4-diazabicyclooctane dihydrohalides having the formula ##STR1## wherein each R is independently selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl, and cycloalkyl, and X is chlorine or bromine, said process comprising heating at a temperature of at least about 100.degree. C. and in a dipolar aprotic solvent certain novel dihaloalkylene diamines. Neutralization of the dihydrohalides provides the corresponding 1,4-diazabicyclooctane free bases.Also disclosed are certain novel 1,4-diazabicyclooctane diammonium dihalides formed as intermediates in the above process and a process for their conversion to the 1,4-diazabicyclooctane dihydrohalides and free bases thereof.The 1,4-diazabicyclo compounds produced in accordance with the invention find particular utility as catalysts in the preparation of polyurethanes from organic polyols and polyisocyanates.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: August 18, 1981
    Assignee: The Upjohn Company
    Inventor: George H. Temme
  • Patent number: 4282383
    Abstract: Cyclohexylbenzene and dicyclohexylbenzenes are converted to the corresponding hydroperoxides in the presence of t-butyl, cumene, or p-diisopropylbenzene hydroperoxides and a free radical initiator. The use of the combination of hydroperoxide and free radical initiator enables the reaction to be carried out at lower temperatures (80.degree.-105.degree. C.) than can be employed with hydroperoxides or free radical initiators alone and gives high (90%) selectivity and good conversion (20% or higher).
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: August 4, 1981
    Assignee: The Upjohn Company
    Inventors: Sheng-Hong A. Dai, Chung-Yuan Lin, Fred A. Stuber
  • Patent number: 4267135
    Abstract: An improvement is described in a prior art process and apparatus for the preparation of continuous polymer bunstock having substantially rectangular cross-section which employs 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. The improvement, which is particularly designed for use in those cases (e.g.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventors: Richard M. Stroud, Richard A. Kolakowski
  • Patent number: 4260718
    Abstract: Novel liquid organic polyisocyanate compositions are disclosed which are obtained by reacting a carbodiimide-containing organic polyisocyanate with a carboxylic acid terminated butadiene-acrylonitrile low molecular weight copolymer in the proportions of from about 2 to about 30 parts of the copolymer per 100 parts of the polyisocyanate provided there is from about 0.01 to about 0.5 carboxylic acid equivalent per equivalent of carbodiimide.The liquid polyisocyanates are particularly useful in providing hard glassy polyurethanes having improved impact strengths.
    Type: Grant
    Filed: December 18, 1979
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., David J. Goldwasser, Kemal B. Onder
  • Patent number: 4257996
    Abstract: The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by utilizing, in association with the polyisocyanate to be used as binder, minor amounts of one or more phosphates or thiophosphates of the formula: ##STR1## where R=alkyl (C.sub.3 and higher), alkenyl (C.sub.3 and higher), aryl, alkyl-substituted aryl, ##STR2## (where R.sub.2 is alkyl, aryl, or alkyl-substituted aryl, A and B are H, methyl, chloromethyl, 2,2,2-trichloromethyl, m=1-25) and lower-alkyl substituted by from 1 to 2 acyloxy groups where acyl is the residue of an aliphatic carboxylic acid having at least 2 carbon atoms; R.sub.1 is Cl, Br, lower-alkoxy, lower-alkylmercapto, arylamino, mono(lower-alkyl)amino, di(lower-alkyl)amino, hydroxy(lower-alkylene)oxy, aryloxy, hydrocarbylureido, and an enol residue; X=O or S and n=1 or 2.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: William J. Farrissey, Jr., Alexander McLaughlin, Reinhard H. Richter, Curtis P. Smith, Benjamin W. Tucker
  • Patent number: 4257995
    Abstract: The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by incorporating minor amounts of a mixture of certain mono- and di- (saturated or unsaturated aliphatic) acid phosphates or the corresponding pyrophosphates, into the polyisocyanate to be used as binder. The polyisocyanates and the acid phosphates and or pyrophosphates, are applied to the particles separately, or after preblending one with the other. Whether the components are applied separately or in combination one with the other, they can each be applied either neat or in the form of an emulsion or emulsions.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: Alexander McLaughlin, Reinhard H. Richter, Harold E. Reymore, Jr.
  • Patent number: 4258169
    Abstract: A process is disclosed for the preparation of liquid, storage-stable, polyisocyanate compositions containing a release agent formed in situ which compositions are useful, for example, as binder resins in the formation of particle boards which latter, because of the presence of the release agent, show no tendency to adhere to the face of metal platens used in their formation. The process comprises heating an organic polyisocyanate (polymethylene polyphenyl polyisocyanate preferred) with an acid phosphate (e.g. a mixture of mono- and di-alkyl acid phosphates) under conditions controlled as to time and temperature so as to yield a product which is storage stable and shows no tendency to deposit solid or to separate into two liquid phases.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn
  • Patent number: 4256802
    Abstract: Disclosed are novel polyol blends comprising from about 20 percent to about 85 percent by weight of said blend of an amine diol, or mixture of amine diols selected from the formula ##STR1## wherein R is an aliphatic radical having from 8 to 18 carbon atoms, inclusive, each R.sub.1 is independently selected from the group consisting of hydrogen or methyl, x and y each independently have an average value from about 4 to about 15 inclusive; and from about 15 percent to about 80 percent by weight of a primary hydroxyl polyol characterized by a molecular weight of from about 60 to about 1000.The polyol blends are miscible with fluorocarbon blowing agents and water and other adjuvants including trimerization catalysts.The novel blends are particularly useful in an improved process for the preparation of polyisocyanurate foams. The foams are characterized by high reaction exotherms making such foams particularly suited to the preparation of polyisocyanurate foam laminates.
    Type: Grant
    Filed: March 5, 1980
    Date of Patent: March 17, 1981
    Assignee: The Upjohn Company
    Inventors: Charles E. Koehler, Thomas R. McClellan, Pat L. Murray
  • Patent number: 4246364
    Abstract: Disclosed are novel polyol blends comprising from about 20 percent to about 85 percent by weight of said blend of an amide diol, or mixture of amide diols selected from the formula ##STR1## wherein R is an aliphatic radical having from 7 to 17 carbon atoms, inclusive, each R.sub.1 is independently selected from the group consisting of hydrogen or methyl, x and y each independently have an average value from about 1 to about 3 inclusive; and from about 15 percent to about 80 percent by weight of a primary hydroxyl polyol characterized by a molecular weight of from about 60 to about 1000.The polyol blends are miscible with fluorocarbon blowing agents and water and other adjuvants including trimerization catalysts.The novel blends are particularly useful in an improved process for the preparation of polyisocyanurate foams. The foams are characterized by high reaction exotherms making such foams particularly suited to the preparation of polyisocyanurate foam laminates.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: January 20, 1981
    Assignee: The Upjohn Company
    Inventors: Charles E. Koehler, Thomas R. McClellan, Pat L. Murray
  • Patent number: 4237238
    Abstract: Polyisocyanurate foams are disclosed which are characterized by a combination of a high degree of fire resistance with low smoke evolution, low foam friability yet high compressive strength, and, most unexpectedly, the formation of a protective intumescent char over unburnt foam when the foam is subjected to combustion.This combination of advantageous features is achieved by employing in the foam forming reaction a minor amount of a polyol mixture prepared by the transesterification, with a glycol of molecular weight from about 60 to about 400, of a residue obtained from the manufacture of dimethyl terephthalate.
    Type: Grant
    Filed: October 3, 1979
    Date of Patent: December 2, 1980
    Assignee: The Upjohn Company
    Inventors: David T. DeGuiseppi, Richard A. Kolakowski