Patents by Inventor Reinhard H. Richter
Reinhard H. Richter has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4565835Abstract: A novel aliphatic diisocyanate, namely 1,4-bis(2-isocyanatoethyl)cyclohexane, is disclosed. Polyurethanes derived from this diisocyanate exhibit advantageous properties. Illustratively, polyurethane elastomers prepared from the above diisocyanate, a polymeric diol and a low molecular weight diol extender, possess significantly improved resilience properties and are useful in the preparation of automobile bumpers, fenders and the like.Type: GrantFiled: March 25, 1985Date of Patent: January 21, 1986Assignee: The Upjohn CompanyInventors: Richard W. Oertel, III, Benjamin W. Tucker, Reinhard H. Richter
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Patent number: 4522762Abstract: A novel aliphatic diisocyanate, namely 1,4-bis(2-isocyanatoethyl)cyclohexane, is disclosed. Polyurethanes derived from this diisocyanate exhibit advantageous properties. Illustratively, polyurethane elastomers prepared from the above diisocyanate, a polymeric diol and a low molecular weight diol extender, possess significantly improved resilience properties and are useful in the preparation of automobile bumpers, fenders and the like.Type: GrantFiled: November 10, 1982Date of Patent: June 11, 1985Assignee: The Upjohn CompanyInventors: Richard W. Oertel, III, Reinhard H. Richter, Benjamin W. Tucker
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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: 4257996Abstract: 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: GrantFiled: April 14, 1980Date of Patent: March 24, 1981Assignee: The Upjohn CompanyInventors: William J. Farrissey, Jr., Alexander McLaughlin, Reinhard H. Richter, Curtis P. Smith, Benjamin W. Tucker
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Patent number: 4257995Abstract: 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: GrantFiled: March 26, 1980Date of Patent: March 24, 1981Assignee: The Upjohn CompanyInventors: Alexander McLaughlin, Reinhard H. Richter, Harold E. Reymore, Jr.
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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: 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: 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: 4154931Abstract: A novel process is disclosed for the preparation of cyclic ureas having the formula ##STR1## wherein A is a straight chain alkylene radical of 2 to 4 carbon atoms, inclusive, wherein said alkylene radical can be substituted by at least one member selected from the group consisting of halogen, lower alkyl, lower alkoxy, aryl, aryloxy, aralkyl, and cycloaklyl. An alkylene diamine having the formula NH.sub.2 ANH.sub.2, wherein A is defined as above, is reacted in a solvent with carbonyl sulfide to form the corresponding N-(.omega.-aminoalkyl)thiocarbamic acid (NH.sub.2 ANHCOSH) or zwitterion thereof. The thiocarbamic acid is then heated to form the cyclic urea.The cyclic ureas are useful as cross-linkers and extenders in polyurethane formulations, and those ureas having 4 carbons in the alkylene chain find particular utility in the production of bis cyclic ureas which serve as masked isocyanate compounds in one-component polyurethane elastomer formulations.Type: GrantFiled: February 6, 1978Date of Patent: May 15, 1979Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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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: 4138398Abstract: 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: February 1, 1978Date of Patent: February 6, 1979Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4058563Abstract: A process is described for isomerizing the cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer. The starting isomer, or mixture of isomers, is converted to the corresponding bis-benzaldimine by reaction with benzaldehyde (or benzaldehyde containing 1 to 3 inert substituents), the bis-benzaldimine is isomerized in the presence of a basic catalyst (potassium t-butoxide, potassium hydroxide preferred) to give predominantly the trans,trans-isomer of the bis-benzaldimine, and the latter is subjected to acid hydrolysis to yield the trans,trans-isomer of the free diamine. The process can be applied to the individual cis,cis- and cis,trans-isomers of the diamine as well as to admixtures of these isomers with the trans,trans-isomer, such as the mixtures of these stereo-isomers obtained by catalytic hydrogenation of di-(p-aminophenyl)methane.Type: GrantFiled: March 28, 1977Date of Patent: November 15, 1977Assignee: The Upjohn CompanyInventor: Reinhard H. Richter
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Patent number: 4051166Abstract: Novel araliphatic diisocyanates having the formulaOCN(CH.sub.2).sub.3 OArX(CH.sub.2).sub.3 NCOare disclosed wherein X is oxygen or a single bond and Ar is an arylene radical. The araliphatic diisocyanates are prepared from well known and readily obtainable starting materials. When X represents a single bond, the starting material is a monohydric phenol wherein a C-alkylation reaction followed by an O-alkylation reaction with acrylonitrile provides an intermediate dipropionitrile which is converted to the diisocyanate via phosgenation of the corresponding diamine. When X represents oxygen, the starting material is a dihydric phenol wherein O-alkylation with acrylonitrile provides the dipropionitrile which in turn is converted to the diisocyanate via the phosgenation of the corresponding diamine. The diisocyanates find particular utility in the preparation of color and light stable polyurethane products.Type: GrantFiled: June 8, 1976Date of Patent: September 27, 1977Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Benjamin W. Tucker, Henri Ulrich
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Patent number: 4026943Abstract: The trans-trans-isomer content of a mixture of stereoisomers of di-(p-aminocyclohexyl)methane is enriched by treating the latter mixture, optionally in solution in an organic solvent, with the trans,trans-isomer of a bisbenzaldimine of di-(p-aminocyclohexyl)methane.Type: GrantFiled: September 20, 1976Date of Patent: May 31, 1977Assignee: The Upjohn CompanyInventor: Reinhard H. Richter
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Patent number: 4020104Abstract: A process is described for isomerizing the cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer. The starting isomer, or mixture of isomers, is converted to the corresponding bis-benzaldimine by reaction with benzaldehyde (or benzaldehyde containing 1 to 3 inert substituents), the bis-benzaldimine is isomerized in the presence of a basic catalyst (potassium t-butoxide, potassium hydroxide preferred) to give predominantly the trans,trans-isomer of the bis-benzaldimine, and the latter is subjected to acid hydrolysis to yield the trans,trans-isomer of the free diamine. The process can be applied to the individual cis,cis- and cis,trans-isomers of the diamine as well as to admixtures of these isomers with the trans,trans-isomer, such as the mixtures of these stereoisomers obtained by catalytic hydrogenation of di-(p-aminophenyl)methane.Type: GrantFiled: September 20, 1976Date of Patent: April 26, 1977Assignee: The Upjohn CompanyInventor: Reinhard H. Richter
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Patent number: 3951922Abstract: The compounds 4-azidocarbonylphthalic anhydride, 4-isocyanatophthalic anhydride, and the lower-alkyl carbamates obtained by reacting the latter isocyanate with a lower-aliphatic alcohol, are described. A process for the preparation of a polyimide by heating these compounds alone or in admixture with other polyisocyanates is also described. The 4-azidocarbonylphthalic anhydride is an intermediate for the 4-isocyanatophthalic anhydride.Type: GrantFiled: June 10, 1974Date of Patent: April 20, 1976Assignee: The Upjohn CompanyInventors: Reinhard H. Richter, Henri Ulrich