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).

  • Patent number: 4217272
    Abstract: 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: Grant
    Filed: October 10, 1978
    Date of Patent: August 12, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4209618
    Abstract: 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: Grant
    Filed: April 10, 1978
    Date of Patent: June 24, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4206144
    Abstract: 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: Grant
    Filed: November 22, 1978
    Date of Patent: June 3, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Patrick J. Jefferies, Nathan N. Crounse
  • Patent number: 4189171
    Abstract: 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: Grant
    Filed: January 11, 1978
    Date of Patent: February 19, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4153598
    Abstract: 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: Grant
    Filed: August 4, 1977
    Date of Patent: May 8, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4146558
    Abstract: 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: Grant
    Filed: October 6, 1977
    Date of Patent: March 27, 1979
    Assignee: Sterling Drug Inc.
    Inventors: Patrick J. Jefferies, Nathan N. Crounse
  • Patent number: 4122261
    Abstract: 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: Grant
    Filed: July 5, 1977
    Date of Patent: October 24, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
  • Patent number: 4111962
    Abstract: 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: Grant
    Filed: September 19, 1973
    Date of Patent: September 5, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Kantilal B. Desai
  • Patent number: 4103092
    Abstract: 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: Grant
    Filed: July 14, 1975
    Date of Patent: July 25, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Patrick J. Jefferies, Nathan N. Crounse
  • Patent number: 4096176
    Abstract: 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: Grant
    Filed: December 12, 1972
    Date of Patent: June 20, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4094877
    Abstract: 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: Grant
    Filed: November 10, 1976
    Date of Patent: June 13, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4066653
    Abstract: 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: Grant
    Filed: June 1, 1976
    Date of Patent: January 3, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
  • Patent number: 4065500
    Abstract: 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: Grant
    Filed: March 31, 1976
    Date of Patent: December 27, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Patrick J. Jefferies, Nathan N. Crounse
  • Patent number: 4032527
    Abstract: 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: Grant
    Filed: November 27, 1974
    Date of Patent: June 28, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4028372
    Abstract: 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: Grant
    Filed: November 19, 1975
    Date of Patent: June 7, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
  • Patent number: 4005026
    Abstract: 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: Grant
    Filed: September 5, 1975
    Date of Patent: January 25, 1977
    Assignee: Sterling Drug Inc.
    Inventors: James C. Heath, Raymond E. Werner, John W. Delaney, Nathan N. Crounse
  • Patent number: 3996282
    Abstract: 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: Grant
    Filed: July 5, 1974
    Date of Patent: December 7, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Patrick J. Jefferies, Nathan N. Crounse
  • Patent number: 3993645
    Abstract: 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: Grant
    Filed: April 30, 1975
    Date of Patent: November 23, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Kantilal B. Desai
  • Patent number: 3993658
    Abstract: 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: Grant
    Filed: April 3, 1975
    Date of Patent: November 23, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
  • Patent number: 3974144
    Abstract: 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: Grant
    Filed: November 19, 1973
    Date of Patent: August 10, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Kantilal B. Desai