Patents by Inventor Nathan N. Crounse
Nathan N. Crounse 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: 4217272Abstract: Water-insoluble azo dyestuffs of the formula ##STR1## and water-soluble acid addition salts thereof useful for coloring natural fibers, synthetic fiber-forming material and cellulosic materials as well as in the manufacture of paper, varnishes, inks, coatings and plastics in which A represents an azoic coupling radical derived from a coupling component selected from the group consisting of arylides of hydroxy-substituted carbocyclic aromatic carboxylic acids, 1-aryl-5-hydroxy-pyrazoles, 6-amino-1-naphthol-3-sulfonic acid, and compounds having an enolizable ketomethylene group of the formula ##STR2## R is hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.2 is hydrogen, lower-alkyl, lower-alkoxy, halogen, aminomethyl or 2-aminoethyl with the proviso that A is other than .beta.-naphthol when R.sup.2 is aminomethyl or 2-aminoethyl; R.sup.1 and R.sup.3 are the same or different and are each hydrogen, lower-alkyl, lower-alkoxy, halogen or aminomethyl with the proviso that at least one of R.sup.1 and R.sup.Type: GrantFiled: October 10, 1978Date of Patent: August 12, 1980Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4209618Abstract: Substituted 3,3-diphenylphthalides, useful as color precursors, particularly in the art of pressure-sensitive duplicating systems and heat-sensitive marking systems, are prepared by condensing substituted 2-benzoylbenzoic acids with substituted anilines.Type: GrantFiled: April 10, 1978Date of Patent: June 24, 1980Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4206144Abstract: N,N-Dialkyl-N-aminoalkyl-N-aminophenylalkyl quaternary ammonium salts and N-methyl-N-(3-aminophenoxy-2-hydroxy-1-propyl)-N,N-bis(3-aminopropyl) quaternary ammonium salts and their N-nitrophenylalkyl and N-(3-nitrophenoxy) precussor quaternary ammonium salts, respectively are intermediates to water-soluble azo-dyestuffs useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials. These dyes dye cotton and paper various shades of yellows, reds, and oranges with less prone to bleed and with a high degree of discharge when bleached with hypochlorite or chlorine bleaches.Type: GrantFiled: November 22, 1978Date of Patent: June 3, 1980Assignee: Sterling Drug Inc.Inventors: Patrick J. Jefferies, Nathan N. Crounse
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Patent number: 4189171Abstract: 3-Aryl-3-indolylphthalides, 3-aryl-3-pyrrolylphthalides and 3-aryl-3-carbazolylphthalides prepared by interaction of the appropriate 2-(heteroaryl)carbonylbenzoic acid and the appropriate phenylamine, and 3,3-bis(indolyl)phthalides prepared by the interaction of the appropriate 2-(indolyl)carbonylbenzoic acid and the appropriate indole are useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems.Type: GrantFiled: January 11, 1978Date of Patent: February 19, 1980Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4153598Abstract: Water-insoluble azo dyestuffs of the formula ##STR1## AND WATER-SOLUBLE ACID ADDITION SALTS THEREOF USEFUL FOR COLORING NATURAL FIBERS, SYNTHETIC FIBER-FORMING MATERIAL AND CELLULOSIC MATERIALS AS WELL AS IN THE MANUFACTURE OF PAPER, VARNISHES, INKS, COATINGS AND PLASTICS IN WHICH A represents an azoic coupling radical derived from a coupling component selected from the group consisting of arylides of hydroxysubstituted carbocyclic aromatic carboxylic acids, 1-aryl-5-hydroxypyrazoles, 6-amino-1-naphthol-3-sulfonic acid, and compounds having an enolizable ketomethylene group of the formula ##STR2## R is hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.2 is hydrogen, lower-alkyl, lower-alkoxy, halogen, aminomethyl or 2-aminoethyl with the proviso that A is other than .beta.-naphthol when R.sup.2 is aminomethyl or 2-aminoethyl; R.sup.1 and R.sup.3 are the same or different and are each hydrogen, lower-alkyl, lower-alkoxy, halogen or aminomethyl with the proviso that at least one of R.sup.1 and R.sup.Type: GrantFiled: August 4, 1977Date of Patent: May 8, 1979Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4146558Abstract: Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl;R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino;Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl;A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge.K is a small integer whose value is dependent on the nature of A such that it has a range from one to two;R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ;R.sup.10 is lower-alkyl or lower-alkenyl;A.sup.Type: GrantFiled: October 6, 1977Date of Patent: March 27, 1979Assignee: Sterling Drug Inc.Inventors: Patrick J. Jefferies, Nathan N. Crounse
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Patent number: 4122261Abstract: This invention relates to novel compounds of the isoindolenine series. More particularly, the present invention relates to certain novel 1-imino-3-(4-imino-5-thiazolidinylidene)isoindolines, 1-imino-3-(4-imino-2-thiazolin-5-ylidene)isoindolines, water-insoluble pigments prepared therefrom, and to methods for their preparation.Type: GrantFiled: July 5, 1977Date of Patent: October 24, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
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Patent number: 4111962Abstract: 2-Phenylnaphtho[1,2-b]furan, 2-phenylnaphtho[2,1-b]-furan and derivatives thereof substituted in the phenyl ring by alkyl, halo or cyano are useful as antifertility agents, and are prepared by cyclization of a naphthyloxyacetophenone with a strong acid.Type: GrantFiled: September 19, 1973Date of Patent: September 5, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Kantilal B. Desai
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Patent number: 4103092Abstract: Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl;R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino;Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl;A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge.k is a small integer whose value is dependent on the nature or A such that it has a range from one to two;R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ;R.sup.10 is lower-alkyl or lower-alkenyl;A.sup.Type: GrantFiled: July 14, 1975Date of Patent: July 25, 1978Assignee: Sterling Drug Inc.Inventors: Patrick J. Jefferies, Nathan N. Crounse
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Patent number: 4096176Abstract: Substituted 3,3-diphenylphthalides, useful as color precursors, particularly in the art of pressure-sensitive duplicating systems, are prepared by condensing substituted 2-benzoylbenzoic acids with substituted anilines.Type: GrantFiled: December 12, 1972Date of Patent: June 20, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4094877Abstract: Substituted 3,3-diphenylphthalides, useful as color precursors, particularly in the art of pressure-sensitive duplicating systems and heat-sensitive marking systems, are prepared by condensing substituted 2-benzoylbenzoic acids with substituted anilines.Type: GrantFiled: November 10, 1976Date of Patent: June 13, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4066653Abstract: This invention relates to novel compounds of the isoindolenine series. More particularly, the present invention relates to certain novel 1-imono-3-(4-imino-5-thiazolidinylidene)isoindolines, 1-imino-3-(4-imino-2-thiazolin-5-ylidene)isoindolines, water-insoluble pigments prepared therefrom, and to methods for their preparation.Type: GrantFiled: June 1, 1976Date of Patent: January 3, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
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Patent number: 4065500Abstract: Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.degree. is hydrogen, lower-alkyl or hydroxy-lower-alkyl;R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.degree.Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino;Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl;A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge.k is a small integer whose value is dependent on the nature of A such that it has a range from one to two;R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ;R.sup.10 is lower-alkyl or lower-alkenyl;A.sup.Type: GrantFiled: March 31, 1976Date of Patent: December 27, 1977Assignee: Sterling Drug Inc.Inventors: Patrick J. Jefferies, Nathan N. Crounse
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Patent number: 4032527Abstract: Substituted 3,3-diphenylphthalides, useful as color precursors, particularly in the art of pressure-sensitive duplicating systems, are prepared by condensing substituted 2-benzoylbenzoic acids with substituted anilines.Type: GrantFiled: November 27, 1974Date of Patent: June 28, 1977Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4028372Abstract: This invention relates to novel compounds of the isoindoline series. More particularly, the present invention relates to certain novel 1-imino-3-(2-oxo-4-thioxo-5-thiazolidinylidene)isoindolines, 1-imino-3-(2,4-dithioxo-5-thiazolidinylidene)isoindolines, water-insoluble pigments prepared therefrom, and to methods for their preparation.Type: GrantFiled: November 19, 1975Date of Patent: June 7, 1977Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
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Patent number: 4005026Abstract: Novel crystalline needle forms of the fluorescent compounds disodium 4,4'-bis(4-anilino-6-morpholino-s-triazin-2-ylamino)-2,2'-stilbenedisulfon ate and disodium 4,4'-bis(4,6-dianilino-s-triazin-2-ylamino)-2,2'-stilbenedisulfonate, useful as optical brightening agents, particularly when incorporated into detergent compositions. The novel crystalline forms are prepared by heating the compound in an aqueous alkaline medium containing excess amine reactant.Type: GrantFiled: September 5, 1975Date of Patent: January 25, 1977Assignee: Sterling Drug Inc.Inventors: James C. Heath, Raymond E. Werner, John W. Delaney, Nathan N. Crounse
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Patent number: 3996282Abstract: Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl;R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino;Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl;A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge.K is a small integer whose value is dependent on the nature of A such that it has a range from one to two;R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl;R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ;R.sup.10 is lower-alkyl or lower-alkenyl;A.sup.Type: GrantFiled: July 5, 1974Date of Patent: December 7, 1976Assignee: Sterling Drug Inc.Inventors: Patrick J. Jefferies, Nathan N. Crounse
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Patent number: 3993658Abstract: This invention relates to novel compounds of the isoindolenine series. More particularly, the present invention relates to certain novel 1-imino-3-(4-imino-5-thiazolidinylidene)isoindolines, 1-imino-3-(4-imino-2-thiazolin-5-ylidene)isoindolines, water-insoluble pigments prepared therefrom, and to methods for their preparation.Type: GrantFiled: April 3, 1975Date of Patent: November 23, 1976Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
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Patent number: 3993645Abstract: Benzofurans, benzothiophenes, indoles, naphthofurans and benzofuranobenzofurans which are substituted by 4-vinylphenyl groups wherein the 2-position of the vinyl is substituted by a monovalent aromatic radical having one to three aromatic rings are optical brightening agents useful for whitening and brightening natural and synthetic fibers, papers, resins and the like. The compounds are conveniently prepared by interacting benzofurans, benzothiophenes, indoles, naphthofurans or benzofuranobenzofurans which are substituted by a p-tolyl group, with an aromatic aldehyde or preferably the anil derivative thereof.Type: GrantFiled: April 30, 1975Date of Patent: November 23, 1976Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Kantilal B. Desai
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Patent number: 3974144Abstract: Benzofurans, benzothiophenes, and naphthofurans which are substituted by carboxystyrylphenyl groups and their corresponding esters and amides are optical brightening agents useful for whitening and brightening natural and synthetic fibers, papers, resins and the like. The compounds are conveniently prepared by interacting benzofurans, benzothiophenes or naphthofurans, which are substituted by a p-tolyl group, with an aromatic aldehyde or preferably the anil derivative thereof.Type: GrantFiled: November 19, 1973Date of Patent: August 10, 1976Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Kantilal B. Desai