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: 4732991Abstract: 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: GrantFiled: February 18, 1986Date of Patent: March 22, 1988Assignee: Hilton Davis Chemical Co.Inventors: Paul J. Schmidt, Nathan N. Crounse
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Patent number: 4647578Abstract: 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: GrantFiled: February 29, 1984Date of Patent: March 3, 1987Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, James R. Heitz
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Patent number: 4595768Abstract: 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: GrantFiled: April 23, 1984Date of Patent: June 17, 1986Assignee: The Hilton-Davis Chemical Co.Inventors: Paul J. Schmidt, Nathan N. Crounse
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Patent number: 4536570Abstract: 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: GrantFiled: October 25, 1982Date of Patent: August 20, 1985Assignee: The Hilton-Davis Chemical Co.Inventor: Nathan N. Crounse
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Patent number: 4477676Abstract: 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: GrantFiled: July 6, 1982Date of Patent: October 16, 1984Assignee: The Hilton-Davis Chemical Co.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4451657Abstract: 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: GrantFiled: November 16, 1979Date of Patent: May 29, 1984Assignee: The Hilton-Davis Chemical Co.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4448722Abstract: 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: GrantFiled: September 27, 1982Date of Patent: May 15, 1984Assignee: The Hilton-Davis Chemical Co.Inventor: Nathan N. Crounse
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Patent number: 4412950Abstract: 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: GrantFiled: March 24, 1982Date of Patent: November 1, 1983Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4379710Abstract: 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: GrantFiled: February 19, 1981Date of Patent: April 12, 1983Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4379089Abstract: 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: GrantFiled: October 8, 1980Date of Patent: April 5, 1983Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4379088Abstract: 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: GrantFiled: August 17, 1981Date of Patent: April 5, 1983Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4377698Abstract: 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: GrantFiled: July 7, 1980Date of Patent: March 22, 1983Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4376729Abstract: 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: GrantFiled: October 8, 1980Date of Patent: March 15, 1983Assignee: Sterling Drug Inc.Inventor: Nathan N. Crounse
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Patent number: 4351768Abstract: 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: March 14, 1980Date of Patent: September 28, 1982Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4322352Abstract: 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: March 14, 1980Date of Patent: March 30, 1982Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4320140Abstract: 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: GrantFiled: October 9, 1980Date of Patent: March 16, 1982Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, James R. Heitz
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Patent number: 4307018Abstract: 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: March 14, 1980Date of Patent: December 22, 1981Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4275121Abstract: 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: GrantFiled: July 19, 1979Date of Patent: June 23, 1981Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4251446Abstract: 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: April 4, 1979Date of Patent: February 17, 1981Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt
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Patent number: 4220357Abstract: 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: March 28, 1979Date of Patent: September 2, 1980Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Paul J. Schmidt