Patents Represented by Attorney John Kekich
  • 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: 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: 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: 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: 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: 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: 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: 4228053
    Abstract: The structural strength properties of concrete and its resistance to sealing are improved by incorporating into the concrete-forming mixture an aqueous solution 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 solution so obtained in an amount less than that required to react with all the excess isocyanate groups.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: October 14, 1980
    Assignee: The Upjohn Company
    Inventors: Alexander McLaughlin, Reinhard H. Richter, Harold E. Reymore, Jr.
  • Patent number: 4226958
    Abstract: A process is described for the preparation of a polymer having a recurring unit of the formula: ##STR1## where R is hydrogen or methyl, C.sub.n H.sub.2n is lower-alkylene, R.sub.1 and R.sub.2 are aryl or lower-alkyl, and x is 0 or 1. A polymer having a recurring unit of the formula: ##STR2## where X is chloro, bromo, iodo, chloroalkyl, bromoalkyl or iodoalkyl, is reacted with the appropriate aryl or alkyl chloride or bromide and arsenic trichloride, arsenic tribromide or arsenic trioxide in the presence of sodium, magnesium, or lithium metal. The resulting polymer is an intermediate in the preparation, by oxidation, of the corresponding As-oxide which polymer is useful as a catalyst for the conversion of isocyanates to the corresponding carbodiimides.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: October 7, 1980
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, George H. Temme
  • Patent number: 4223111
    Abstract: A process is described for the preparation of a polymer having a recurring unit of the formula: ##STR1## where R is hydrogen or methyl, C.sub.n H.sub.2n is lower-alkylene, R.sub.1 and R.sub.2 are aryl and x is 0 or 1. A polymer having a recurring unit of the formula: ##STR2## where X is chloro, bromo, iodo, chloroalkyl, bromoalkyl or iodoalkyl, is reacted with a triarylarsine in the presence of lithium or sodium-potassium alloy. The resulting polymer is an intermediate in the preparation, by oxidation, of the corresponding As-oxide. The latter is useful as a catalyst for the conversion of isocyanates to the corresponding carbodiimides.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: September 16, 1980
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, George H. Temme
  • Patent number: 4218289
    Abstract: An improved fractional distillation column, especially adapted for use in fractional distillation of heat-sensitive materials under low pressure, is described. The improvement comprises a partial condenser disposed above the packing in the column. The partial condenser is a grid of hollow tubes mounted horizontally and extending through the side walls of the column. Heat exchange fluid at controlled temperature lower than the outer condensing vapor temperature is circulated through the tubes. The outer surfaces of the tubes within the column are provided with drip sites to facilitate uniform distribution of condensed liquid falling from condenser tubes to the packing below.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: August 19, 1980
    Assignee: The Upjohn Company
    Inventors: James D. Hajek, Earl E. McReynolds
  • Patent number: 4207265
    Abstract: A process is provided for the preparation of hydroquinone by oxidizing a phenol having in the paraposition a 1-cycloalkenyl or .alpha.-methylene-(alkyl or aralkyl) group. The oxidation is carried out using hydrogen peroxide or a hydrocarbyl peroxide in the presence of an inert solvent and a catalytic amount of a strong acid which is not oxidized by the peroxide. The other product of the reaction is the ketone derived by oxidation of the para-substituent in the starting phenol, e.g. p-isopropenylphenol gives hydroquinone and acetone. The reaction forms a particularly convenient route for conversion of phenol to hydroquinone in that phenol is condensed with acetone to bisphenol A, the latter is degraded by alkaline hydrolysis to a mixture of phenol and p-isopropenylphenol, which latter is subjected, without separation, to the above process to give a mixture of hydroquinone, phenol, and acetone.
    Type: Grant
    Filed: March 31, 1975
    Date of Patent: June 10, 1980
    Assignee: The Upjohn Company
    Inventor: Peter S. Carleton
  • Patent number: 4202779
    Abstract: Bis(2-hydroxyalkyl) N,N-di(lower-alkyl)aminomethyl-phosphonates 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: June 28, 1978
    Date of Patent: May 13, 1980
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4202946
    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: June 28, 1978
    Date of Patent: May 13, 1980
    Assignee: The Upjohn Company
    Inventors: Curtis P. Smith, Henri Ulrich
  • Patent number: 4202957
    Abstract: Polyurethane polyether-based elastomers are described which are thermoplastic, recyclable and have increased high temperature resistance which permits fabrication by injection molding. The elastomers are the product of reaction of 4,4'-methylenebis(phenyl isocyanate), a particular group of polypropylene oxide-polyethylene oxide block copolymers and an extender [straight chain aliphatic diols C.sub.2-6 or the bis(2-hydroxyethyl ether) of hydroquinone or resorcinol]. The block copolymers have at least 50 percent primary hydroxyl groups, a pH in the range of 4.5 to 9, a content of alkali metal ion less than 25 ppm and a molecular weight of 1000 to 3000. The minimum ethylene oxide (E.O.) residue content (percent by weight) of the polyether for any molecular weight (M.W.) is governed by the equation: ##EQU1## In a particularly preferred embodiment the elastomers are prepared by replacing up to 25 percent by equivalents of the extender by certain diols (polyethylene glycols up to 1500 M.W. preferred).
    Type: Grant
    Filed: April 29, 1975
    Date of Patent: May 13, 1980
    Assignee: The Upjohn Company
    Inventors: Henry W. Bonk, Tilak M. Shah
  • Patent number: 4201722
    Abstract: A process is described for the isolation of 4,4'-diaminodiphenylmethane in substantially pure form (of the order of 99% purity) from admixtures thereof with the corresponding 2,4'-isomer and 2,2'-isomer. The dihydrochloride of the isomeric mixture of diamines is heated in the presence of an inert organic solvent with a mixture of isomers of the free diamine, in which the amount of the 4,4'-isomer is at least equal to that of the 2,4'-isomer in the dihydrochloride isomeric mixture. The isomeric mixture of the diamines may be employed in the form of a mixture of polymethylene polyphenyl polyamines containing a major portion of said diamines. The reaction product consists of the insoluble dihydrochloride of substantially pure 4,4'-diaminodiphenylmethane and a solution which is enriched in 2,4'-isomer as compared with the starting mixture of diamines.
    Type: Grant
    Filed: June 4, 1976
    Date of Patent: May 6, 1980
    Assignee: The Upjohn Company
    Inventor: Kwok K. Sun
  • Patent number: 4179094
    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: May 26, 1978
    Date of Patent: December 18, 1979
    Assignee: The Upjohn Company
    Inventors: John N. Curtiss, Charles E. Koehler, Pat L. Murray
  • Patent number: 4177211
    Abstract: An improved process is described for the preparation of bis(aminophenyl)alkanes which comprises heating the corresponding bis(di-alkoxyphenyl)alkane or corresponding cyclic ethers of bis(phenyl)alkanes with an at least stoichiometric proportion of an aniline acid addition salt, optionally in the presence of an inert organic solvent.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: December 4, 1979
    Assignee: The Upjohn Company
    Inventor: Kwok K. Sun