Patents Represented by Attorney John Kekich
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Patent number: 4446247Abstract: The photopolymerization of ethylenically unsaturated compounds is effected using a combination of an aromatic ketone photosensitizer and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) or N,N-disubstituted acid amide. Storage stable liquid photoinitiator compositions comprising an aromatic ketone sensitizer (e.g. benzophenone) and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) are also disclosed. The use of the tetrasubstituted urea or N,N-disubstituted amide possesses advantages (storage stability, lack of discoloration on curing) over photosensitizers such as Michler's ketone which have been used previously in combination with aromatic ketone photosensitizers.Type: GrantFiled: October 11, 1983Date of Patent: May 1, 1984Assignee: The Upjohn CompanyInventor: Anthony F. Jacobine
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Patent number: 4431667Abstract: Phenylcarbamoylbenzimidates of the formula ##STR1## wherein X.sub.1 and X.sub.2 are the same or different and are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, methoxy and trifluoromethyl; R is alkyl of from 1 to 5 carbon atoms; Y is selected from oxygen or sulfur; and R.sub.1 is selected from a halo(C.sub.1 -C.sub.3)alkyl. These compounds are useful for controlling susceptible insect and arachnoid pests.Type: GrantFiled: December 4, 1981Date of Patent: February 14, 1984Assignee: The Upjohn CompanyInventor: Stephen J. Nelson
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Patent number: 4428897Abstract: Particle boards are currently prepared by treating the particles (e.g. wood chips) with a binder comprising an organic polyisocyanate and, optionally, a release agent and then subjecting the treated particles to a molding process involving heat and pressure. The resulting particle board will generally release well from the caul plates of the press after forming. However, it has been found that the ease of release is enhanced, particularly where the wood particles in the board are derived from hardwood, by utilizing a metal selected from magnesium and zinc in the metallic surfaces of the caul plates or platens which come into contact with the particle board during the application of heat and pressure.Type: GrantFiled: December 23, 1982Date of Patent: January 31, 1984Assignee: The Upjohn CompanyInventors: Steven B. Lowenkron, Richard A. Prather, Howard R. Steele
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Patent number: 4425208Abstract: The photopolymerization of ethylenically unsaturated compounds is effected using a combination of an aromatic ketone photosensitizer and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) or N,N-disubstituted acid amide. Storage stable liquid photoinitiator compositions comprising an aromatic ketone sensitizer (e.g. benzophenone) and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) are also disclosed. The use of the tetrasubstituted urea or N,N-disubstituted amide possesses advantages (storage stability, lack of discoloration on curing) over photosensitizers such as Michler's ketone which have been used previously in combination with aromatic ketone photosensitizers.Type: GrantFiled: August 6, 1981Date of Patent: January 10, 1984Assignee: The Upjohn CompanyInventor: Anthony F. Jacobine
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Patent number: 4420602Abstract: A melt-polymerization process is described for the preparation of thermoplastic polyamides and polyesteramides by reaction of the appropriate organic diisocyanate and dicarboxylic acid or difunctional carboxylic acid-terminated polyol. The process, which can be conducted in a batch or continuous manner, comprises the steps of admixing the reactants (preferably in the liquid state), heating the mixed reactants at reaction temperature in a manner such that eliminated carbon dioxide can be vented freely, allowing the reaction to proceed until approximately 25-95 percent (preferably at least 50 percent) of the theoretical carbon dioxide has been eliminated and reducing the resulting intermediate to a powder before completing the reaction by melting, homogenizing, and devolatilizing.Type: GrantFiled: September 27, 1982Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventors: Henry W. Bonk, Robert G. Nelb, II, Richard W. Oertel, III
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Patent number: 4420603Abstract: A continuous, solvent-free process is described for the preparation of thermoplastic polyamides and polyester-amides by the reaction of the appropriate organic diisocyanate and dicarboxylic acid or difunctional carboxylic acid-terminated polyester.Type: GrantFiled: September 27, 1982Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventors: Robert G. Nelb, II, Richard W. Oertel, III
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Patent number: 4410689Abstract: Bis(cyclic ureas) are disclosed which have the formula ##STR1## wherein R is ##STR2## and C.sub.n H.sub.2n is ethylene or 1,3-propylene each of which can be substituted by one or more inert substituents.These compounds are useful as masked diisocyanates which, on heating in the presence of a polyol and, optionally, a polyurethane catalyst, give rise to polyurethane resins. Accordingly, they are useful as a component of storage stable compositions which are convertible to polyurethanes upon heating. Such compositions are particularly useful as solvent-less coating compositions. The properties of the above compounds are distinguished in a number of respects from the known bis(cyclic ureas) in which C.sub.n H.sub.2n has 4 or more carbon atoms in the chain between the valencies. Illustratively, the above compounds are more stable on exposure to heat in the absence of catalysts but, in the presence of polyurethane catalysts, react with polyols at a significantly faster rate than the prior art compounds.Type: GrantFiled: June 16, 1982Date of Patent: October 18, 1983Assignee: The Upjohn CompanyInventors: Edward A. Barsa, Chung-Yuan Lin, Fred A. Stuber
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Patent number: 4391751Abstract: Compounds are described which are characterized by the formula ##STR1## C.sub.n H.sub.2n =alkylene with 2 to 6 C atoms in the chain. R=inert substituent and m=0-3.The compounds contain an anhydride group and a hetero ring capable of opening to yield an isocyanate group on heating. Accordingly, they can undergo self-condensation on heating to yield polyamide-imides. The compounds can also be polymerized by heating in the presence of difunctional monomers such as diols, diamines, alkanolamines and the like.Type: GrantFiled: March 8, 1982Date of Patent: July 5, 1983Assignee: The Upjohn CompanyInventor: Chung-Yuan Lin
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Patent number: 4385133Abstract: Polyurethanes having a two phase morphology and characterized by high impact strength and, optionally, high modulus are obtained by reaction of 4,4'-methylenebis(phenyl isocyanate) and modified forms thereof with an aliphatic glycol extender and a blend of at least two polyoxypropylene-polyoxyethylene polyols both of which have average functionalities in the range of 2 to 4, one of which has a molecular weight in the range of about 3000 to 10,000 and contains at least 23 percent by weight of ethylene oxide residues and the other has a molecular weight in the range of about 750 to about 2000 and contains at least 45 percent by weight of ethylene oxide. The two or more such polyols are employed in proportions such that the aliphatic glycol extender is completely miscible with said polyols if blended together.Type: GrantFiled: June 7, 1982Date of Patent: May 24, 1983Assignee: The Upjohn CompanyInventors: Louis M. Alberino, Robert J. Lockwood
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Patent number: 4382108Abstract: Composite panels are disclosed which comprise outer layers derived from cellulosic and like material conventionally employed in particle boards and an inner layer which is comminuted scrap plastic material, the various layers and the particles in them being bonded together using an organic polyisocyanate binder. Optionally the binder contains an internal release agent. The composites, in addition to representing a valuable way in which to utilize scrap plastic, also possess improved properties compared with the corresponding panels which lack the inner core. In a particular embodiment the scrap plastic used is derived from junked automobiles.Type: GrantFiled: December 21, 1981Date of Patent: May 3, 1983Assignee: The Upjohn CompanyInventors: Woodrow Carroll, Thomas R. McClellan
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Patent number: 4376834Abstract: Polyurethane resins are described having high impact strength and other structural strength properties, and significantly improved resistance to deformation by heat. The properties of these materials are such as to make them comparable to engineering thermoplastics such as nylon and like materials commonly used to fabricate structural components such as automotive parts, equipment housing, sporting goods, furniture, toys, household and like consumer goods.The resins are prepared from organic polyisocyanates, an isocyanate-reactive material (polyol, polyamine, etc.) having an average functionality of at least 1.9, a Tg less than 20.degree. C. and molecular weight of 500-20,000, and one or more low molecular weight extenders the major distinguishing feature being the markedly lower proportion by weight (2 to 25 percent) in which the isocyanate-reactive material is employed as compared with polyurethane resins conventionally prepared in the art.Type: GrantFiled: October 14, 1981Date of Patent: March 15, 1983Assignee: The Upjohn CompanyInventors: David J. Goldwasser, Kemal Onder
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Patent number: 4376088Abstract: 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 organic sulfonic acids, hydrogen sulfates, salts and derivatives thereof, into the polyisocyanate to be used as binder. The polyisocyanates and the sulfonic acids, hydrogen sulfates, salts and derivatives 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 of in the form of an emulsion or emulsions.Type: GrantFiled: March 18, 1981Date of Patent: March 8, 1983Assignee: The Upjohn CompanyInventor: Richard A. Prather
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Patent number: 4374791Abstract: Particle boards are currently prepared by treating the particles (e.g. wood chips) with a binder comprising an organic polyisocyanate and an internal release agent and then subjecting the treated particles to a forming process involving heat and pressure. While the resulting particle board will generally release well from the caul plates of the press after forming, due to the effect of the internal release agent, it has been found that the ease of release is enhanced by precoating the surfaces of the caul plates or platens which come into contact with the particle board with a layer of polytetrafluoroethylene which layer optionally contains an internal release agent.Type: GrantFiled: September 28, 1981Date of Patent: February 22, 1983Assignee: The Upjohn CompanyInventors: William J. Farrissey, Alexander McLaughlin, Douglas P. Waszeciak
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Patent number: 4374210Abstract: The use of certain prepolymers of 4,4'-methylenebis(phenyl isocyanate), in place of the latter diisocyanate itself in the preparation of polyurethane-polyureas using aromatic diamine extenders, has a number of advantages particularly when the compositions are prepared by reaction injection molding techniques using two streams of reactants. The principal advantages are (i) a useful increase in gel time and (ii) a ratio of amounts of the two reactant streams which more nearly approaches 1:1.This latter factor not only improves the efficiency of mixing of the components in the mixing head but, together with the longer gel time, significantly increases the output of mixed reactants per unit of time. The prepolymers of 4,4'-methylenebis(phenyl isocyanate) employed to achieve the above results are those derived from polyoxyethylene polyoxypropylene polyether diols and triols (MW=1000-10,000), polytetramethylene glycols (MW=600-5,000) and polyester diols and triols (MW=500-8,000).Type: GrantFiled: September 18, 1981Date of Patent: February 15, 1983Assignee: The Upjohn CompanyInventors: James H. Ewen, Thomas R. McClellan, Michael H. McMillin, Pat L. Murray
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Patent number: 4352696Abstract: 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 certain phosphinic and or phosphonic acids or derivatives thereof or phosphites into the polyisocyanate to be used as binder. The polyisocyanates and the phosphorus compounds 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: GrantFiled: March 30, 1981Date of Patent: October 5, 1982Assignee: The Upjohn CompanyInventor: Richard A. Prather
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Patent number: 4351957Abstract: A process is described for the preparation of bis(aminophenyl)alkanes and bis(aminophenyl)cycloalkanes which comprises condensing a m-alkylphenol with an alkanone or cycloalkanone and heating the resulting condensation product with an at least stoichiometric amount of an acid addition salt of aniline or a substituted aniline or a mixture of such amines.Type: GrantFiled: June 29, 1979Date of Patent: September 28, 1982Assignee: The Upjohn CompanyInventor: Kwok K. Sun
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Patent number: 4349663Abstract: Bis(cyclic ureas) are disclosed which have the formula ##STR1## wherein R is ##STR2## and C.sub.n H.sub.2n is ethylene or 1,3-propylene each of which can be substituted by one or more inert substituents.These compounds are useful as masked diisocyanates which, on heating in the presence of a polyol and, optionally, a polyurethane catalyst, give rise to polyurethane resins. Accordingly, they are useful as a component of storage stable compositions which are convertible to polyurethanes upon heating. Such compositions are particularly useful as solvent-less coating compositions. The properties of the above compounds are distinguished in a number of respects from the known bis(cyclic ureas) in which C.sub.n H.sub.2n has 4 or more carbon atoms in the chain between the valencies. Illustratively, the above compounds are more stable on exposure to heat in the absence of catalysts but, in the presence of polyurethane catalysts, react with polyols at a significantly faster rate than the prior art compounds.Type: GrantFiled: November 10, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventors: Edward A. Barsa, Chung-Yuan Lin, Fred A. Stuber
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Patent number: 4339381Abstract: 1,3-alkylene-diazetidinediones-2,4, wherein alkylene contains at least 8 carbon atoms, are described. These compounds, which can be regarded as intramolecular dimers of alkylene diisocyanates, give rise to the latter on heating. Accordingly, these compounds are useful in a variety of situations in which it is desirable to have a compound which is stable on storage in admixture with other compounds such as polyols, polyamines and the like (which latter would react with a compound containing free isocyanate groups) but which can, at any desired moment, be converted by heating to the free diisocyanate. The latter then reacts with the other component(s) of the mixture to form a polymer.The above compounds are derived by cyclization of the appropriate cyclic allophanoyl halide.Type: GrantFiled: February 5, 1981Date of Patent: July 13, 1982Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4335218Abstract: Improved adhesion between the skin and core of laminates having rigid polyisocyanurate foam cores is obtained by incorporating a dipolar aprotic organic solvent, in minor amount, into the reaction mixture employed to prepare the polyisocyanurate foam core.Type: GrantFiled: October 27, 1980Date of Patent: June 15, 1982Assignee: The Upjohn CompanyInventor: David T. DeGuiseppi
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Patent number: RE31703Abstract: 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: GrantFiled: August 2, 1982Date of Patent: October 9, 1984Assignee: The Upjohn CompanyInventors: Richard A. Prather, David L. Williams, Robert M. Partin, Warren J. Rabourn, deceased