Patents Represented by Attorney John Kekich
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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
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Patent number: 4156065Abstract: 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: GrantFiled: January 21, 1977Date of Patent: May 22, 1979Assignee: The Upjohn CompanyInventors: Kemal B. Onder, Curtis P. Smith
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Patent number: 4152349Abstract: 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: GrantFiled: February 22, 1978Date of Patent: May 1, 1979Assignee: The Upjohn CompanyInventor: Warren J. Rabourn
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Patent number: 4152348Abstract: 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: GrantFiled: February 22, 1978Date of Patent: May 1, 1979Assignee: The Upjohn CompanyInventor: Warren J. Rabourn
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Patent number: 4143063Abstract: 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: GrantFiled: April 10, 1978Date of Patent: March 6, 1979Assignee: The Upjohn CompanyInventors: Louis M. Alberino, Curtis P. Smith
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Patent number: 4143014Abstract: 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: GrantFiled: November 9, 1977Date of Patent: March 6, 1979Assignee: The Upjohn CompanyInventors: Alexander McLaughlin, Harold E. Reymore, Jr., Reinhard H. Richter
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Patent number: 4137386Abstract: 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: GrantFiled: May 3, 1978Date of Patent: January 30, 1979Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: 4129715Abstract: 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: GrantFiled: January 16, 1978Date of Patent: December 12, 1978Assignee: The Upjohn CompanyInventors: Augustin T. Chen, William J. Farrissey, Jr., Robert G. Nelb, II
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Patent number: 4128611Abstract: 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: GrantFiled: April 7, 1977Date of Patent: December 5, 1978Assignee: The Upjohn CompanyInventors: Richard A. Kolakowski, Richard M. Stroud
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Patent number: 4123466Abstract: 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: GrantFiled: December 12, 1977Date of Patent: October 31, 1978Assignee: The Upjohn CompanyInventors: Chung-Yuan Lin, Fred A. Stuber, Henri Ulrich
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Patent number: 4112014Abstract: 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: April 11, 1977Date of Patent: September 5, 1978Assignee: The Upjohn CompanyInventors: Curtis P. Smith, Henri Ulrich
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Patent number: 4108843Abstract: 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: GrantFiled: July 5, 1977Date of Patent: August 22, 1978Assignee: The Upjohn CompanyInventors: Augustin T. Chen, Kemal B. Onder
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Patent number: 4105643Abstract: 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: GrantFiled: November 1, 1977Date of Patent: August 8, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: 4105642Abstract: 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: GrantFiled: October 31, 1977Date of Patent: August 8, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: 4104346Abstract: 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: July 29, 1976Date of Patent: August 1, 1978Assignee: The Upjohn CompanyInventors: John N. Curtiss, Charles E. Koehler, Pat L. Murray
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Patent number: 4098973Abstract: 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: GrantFiled: January 31, 1977Date of Patent: July 4, 1978Assignee: The Upjohn CompanyInventor: Curtis P. Smith
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Patent number: 4098772Abstract: 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: GrantFiled: March 11, 1976Date of Patent: July 4, 1978Assignee: The Upjohn CompanyInventors: Henry W. Bonk, Benjamin S. Ehrlich, Joseph Pleckaitis
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Patent number: 4092752Abstract: 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: GrantFiled: November 29, 1976Date of Patent: June 6, 1978Assignee: The Upjohn CompanyInventor: Thomas P. Dougan
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Patent number: 4093604Abstract: 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: GrantFiled: July 5, 1977Date of Patent: June 6, 1978Assignee: The Upjohn CompanyInventors: Augustin T. Chen, Kemal B. Onder
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Patent number: 4092343Abstract: 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: GrantFiled: May 16, 1977Date of Patent: May 30, 1978Assignee: The Upjohn CompanyInventors: Floro F. Frulla, Adnan A. R. Sayigh, Henri Ulrich, Peter J. Whitman