Patents Represented by Attorney Denis A. Firth
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Patent number: 4228053Abstract: 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: GrantFiled: January 29, 1979Date of Patent: October 14, 1980Assignee: The Upjohn CompanyInventors: Alexander McLaughlin, Reinhard H. Richter, Harold E. Reymore, Jr.
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Patent number: 4226958Abstract: 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: GrantFiled: August 27, 1979Date of Patent: October 7, 1980Assignee: The Upjohn CompanyInventors: Curtis P. Smith, George H. Temme
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Patent number: 4225686Abstract: Novel polymer blends are disclosed comprising about 10 to 95 percent by weight of a copolyimide (A) 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) with the isocyanates used in a molar percent ratio from about 10/90 to 30/70 respectively; and from about 90 to 5 percent by weight of a copolyamideimide (B) prepared from 4,4'-methylenebis(phenyl isocyanate) and a mixture of trimellitic anhydride and isophthalic acid with the acid components used in a molar percent ratio from about 70/30 to 90/10 respectively.The novel blends may be used in the form of their dry blend or in solution and the films produced therefrom are characterized by improved elongation and tear strength values over those for the copolyimide (A) alone. Furthermore, the softening point of the blends is increased over the copolyamideimide alone.Type: GrantFiled: July 19, 1979Date of Patent: September 30, 1980Assignee: The Upjohn CompanyInventors: Kemal B. Onder, Frank P. Recchia
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Patent number: 4223111Abstract: 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: GrantFiled: August 27, 1979Date of Patent: September 16, 1980Assignee: The Upjohn CompanyInventors: Curtis P. Smith, George H. Temme
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Patent number: 4218289Abstract: 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: GrantFiled: March 8, 1976Date of Patent: August 19, 1980Assignee: The Upjohn CompanyInventors: James D. Hajek, Earl E. McReynolds
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Patent number: 4217436Abstract: Novel bis cyclic ureas are disclosed having the formula ##STR1## wherein C.sub.n H.sub.a n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide.The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.Type: GrantFiled: December 11, 1978Date of Patent: August 12, 1980Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4216322Abstract: 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: GrantFiled: October 30, 1978Date of Patent: August 5, 1980Assignee: The Upjohn CompanyInventor: George H. Temme
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Patent number: 4207265Abstract: 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: GrantFiled: March 31, 1975Date of Patent: June 10, 1980Assignee: The Upjohn CompanyInventor: Peter S. Carleton
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Patent number: 4202833Abstract: Isopropylphenyl esters are converted to di- or trihydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.Type: GrantFiled: May 11, 1979Date of Patent: May 13, 1980Assignee: The Upjohn CompanyInventor: Sheng-Hong A. Dai
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Patent number: 4202946Abstract: 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: GrantFiled: June 28, 1978Date of Patent: May 13, 1980Assignee: The Upjohn CompanyInventors: Curtis P. Smith, Henri Ulrich
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Patent number: 4202779Abstract: 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: GrantFiled: June 28, 1978Date of Patent: May 13, 1980Assignee: The Upjohn CompanyInventors: Curtis P. Smith, Henri Ulrich
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Patent number: 4202957Abstract: 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: GrantFiled: April 29, 1975Date of Patent: May 13, 1980Assignee: The Upjohn CompanyInventors: Henry W. Bonk, Tilak M. Shah
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Patent number: 4201722Abstract: 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: GrantFiled: June 4, 1976Date of Patent: May 6, 1980Assignee: The Upjohn CompanyInventor: Kwok K. Sun
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Patent number: 4200763Abstract: Isopropylphenyl esters are converted to di- or tri-hydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.Type: GrantFiled: May 11, 1979Date of Patent: April 29, 1980Assignee: The Upjohn CompanyInventor: Sheng-Hong A. Dai
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Patent number: 4190599Abstract: Novel bis cyclic ureas are disclosed having the formula ##STR1## wherein C.sub.n H.sub.2 n represents alkylene from 4 to 12 inclusive and provided there are at least 4 carbon atoms in succession in the chain and R is the residue obtained by the removal of both halogen atoms from a diacid halide.The bis cyclic ureas are easily converted to a novel class of aliphatic diisocyanates simply by heating. Alternatively, they are blended with polymeric polyols to form one-component storage stable compositions which are thermally converted to polyurethane resins without any significant volatile or side product formation.Type: GrantFiled: December 11, 1978Date of Patent: February 26, 1980Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4189544Abstract: Novel cellular and non-cellular polymers are provided in which the major recurring polymer unit is isocyanurate which polymer comprises the reaction product obtained by bringing together an aromatic polyisocyanate, a trimerization catalyst, and a minor amount of a carbamate modifier.The use of the carbamate modifier allows for the presence of high catalyst levels without shortening the reaction initiation period. At the same time, the resulting cure is very rapid and the extent of cure much deeper than has heretofore been attainable.Type: GrantFiled: February 21, 1979Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Edward J. Thompson
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Portable, expandable mold for fabricating substantially isotropic isocyanate based polymer foam buns
Patent number: 4179094Abstract: 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: GrantFiled: May 26, 1978Date of Patent: December 18, 1979Assignee: The Upjohn CompanyInventors: John N. Curtiss, Charles E. Koehler, Pat L. Murray -
Patent number: 4178432Abstract: Novel copolyoxalamides having the recurring unit ##STR1## are disclosed wherein R is a divalent aromatic radical and R.sub.1 is a divalent radical selected from the group consisting of 2,2,4- and 2,4,4-trimethylhexylene, ##STR2## and mixtures thereof. The novel copolyoxalamides are injection-moldable, thermoplastic materials which are characterized by good high temperature resistance and excellent resistance to oxidative degradation.Type: GrantFiled: July 19, 1978Date of Patent: December 11, 1979Assignee: The Upjohn CompanyInventors: Augustin T. Chen, Kemal B. Onder
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Patent number: 4177211Abstract: 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: GrantFiled: April 21, 1978Date of Patent: December 4, 1979Assignee: The Upjohn CompanyInventor: Kwok K. Sun
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Patent number: 4173602Abstract: 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: GrantFiled: June 28, 1978Date of Patent: November 6, 1979Assignee: The Upjohn CompanyInventors: Curtis P. Smith, Henri Ulrich