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: 4732991
    Abstract: Process comprises the combination of the three steps of condensing 3-N(R).sub.2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R).sub.2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R).sub.2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R).sub.2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl, 9-R.sup.7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R.sup.8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl or 1-R.sup.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: March 22, 1988
    Assignee: Hilton Davis Chemical Co.
    Inventors: Paul J. Schmidt, Nathan N. Crounse
  • Patent number: 4647578
    Abstract: Water insoluble, photodynamic insecticidal compositions comprising the free acids of erythrosin B, phloxin B, rose bengal, octabromofluorescein or fluorescein or the aluminum lakes thereof, optionally including a dispersant, aqueous dispersions of the same and a method of combatting adult insects and insect larvae by use of the same.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: March 3, 1987
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, James R. Heitz
  • Patent number: 4595768
    Abstract: Process comprises the combination of the three steps of condensing 3-N(R).sub.2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R).sub.2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(.alpha.-Y-.alpha.-Z)methyl-4-X-5-N(R).sub.2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R).sub.2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl, 9-R.sup.7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R.sup.8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R.sup.1 -3-R.sup.2 -2-R.sup.1 -phenyl, 1-R.sup.5 -2-R.sup.6 -5/6-R.sup.4 -3-indolyl or 1-R.sup.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: June 17, 1986
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Paul J. Schmidt, Nathan N. Crounse
  • Patent number: 4536570
    Abstract: This invention relates to novel mixtures consisting essentially of benzanilide bridged disazo compounds which are randomly substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said disazo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted disazo compounds.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: August 20, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventor: Nathan N. Crounse
  • Patent number: 4477676
    Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: October 16, 1984
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4451657
    Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: May 29, 1984
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4448722
    Abstract: Storage-stable aqueous compositions containing dissolved water-soluble novel acid addition salts of poly(N-substituted sulfonamido) phthalocyanines which are prepared by the interaction of a single acid or a mixture of acids and poly(N-substituted sulfonamido) phthalocyanines, are useful for direct dyeing, particularly the dyeing of cellulose.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: May 15, 1984
    Assignee: The Hilton-Davis Chemical Co.
    Inventor: Nathan N. Crounse
  • Patent number: 4412950
    Abstract: This invention relates to novel (N-substituted sulfonamido) monoazo and disazo compounds, to acid-addition salts of said azo compounds which are useful as direct dyes particularly in the dyeing of cellulose, to novel (N-substituted sulfonamido) substituted nitrobenzene, aniline and acetanilide intermediates to said azo compounds and to methods of preparation of said azo compounds and said intermediates to said azo compounds.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: November 1, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4379710
    Abstract: Storage-stable aqueous compositions containing dissolved water-soluble novel acid addition salts of poly(N-substituted sulfonamido) phthalocyanines which are prepared by the interaction of a single acid or a mixture of acids and poly(N-substituted sulfonamido) phthalocyanines, are useful for direct dyeing, particularly the dyeing of cellulose.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: April 12, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4379089
    Abstract: This invention relates to novel mixtures consisting essentially of monoazo compounds and disazo compounds which are substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said azo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted monoazo and disazo compounds.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: April 5, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4379088
    Abstract: This invention relates to novel mixtures consisting essentially of monoazo compounds and disazo compounds which are substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said azo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted monoazo and disazo compounds.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: April 5, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4377698
    Abstract: Mono-. bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(inodlyl)-substituted furanone.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: March 22, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4376729
    Abstract: This invention relates to novel (N-substituted sulfonamido) monoazo and disazo compounds, to acid-addition salts of said azo compounds which are useful as direct dyes particularly in the dyeing of cellulose, to novel (N-substituted sulfonamido) substituted nitrobenzene, aniline and acetanilide intermediates to said azo compounds and to methods of preparation of said azo compounds and said intermediates to said azo compounds.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: March 15, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4351768
    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: March 14, 1980
    Date of Patent: September 28, 1982
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4322352
    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: March 14, 1980
    Date of Patent: March 30, 1982
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4320140
    Abstract: Synergistic insecticidal compositions are mixtures of at least one insecticidally active water-soluble xanthene dye chosen from amongst erythrosine and Rose Bengal in admixture with the essentially non-insecticidally active and synergistically-effective fluorescein sodium.
    Type: Grant
    Filed: October 9, 1980
    Date of Patent: March 16, 1982
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, James R. Heitz
  • Patent number: 4307018
    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: March 14, 1980
    Date of Patent: December 22, 1981
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4275121
    Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: June 23, 1981
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4251446
    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: April 4, 1979
    Date of Patent: February 17, 1981
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4220357
    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: March 28, 1979
    Date of Patent: September 2, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt