Patents Represented by Attorney Terrence E. Miesle
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Patent number: 4414399Abstract: Dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'-6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans, esterified dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans and 3,3-(corresponding-substituted-diaryl)-5/6-carboxyphthalides useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted diphenylamines to produce the phthalides which are then subjected to ring closure to produce the carboxyfluorans and by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoid acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterified with alkyl halides or dialkyl sulfates.Type: GrantFiled: April 15, 1983Date of Patent: November 8, 1983Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, William M. Hung
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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: 4399291Abstract: Process comprises the combination of the two steps of condensing Y-benzaldehyde with N--R.sup.2 --N--R.sup.3 -aniline and 3--N--R--N--R.sup.1 -benzoic acid, under acidic conditions to produce 2-[(Y-phenyl) (4--N--R.sup.2 --N--R.sup.3 -aminophenyl)methyl]-5--N--R--N--R.sup.1 -aminobenzoic acid, and oxidizing said benzoic acid to produce 3-(Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide.Type: GrantFiled: December 9, 1981Date of Patent: August 16, 1983Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, Patrick J. Jefferies
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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: 4370443Abstract: Water-soluble triazine-nucleated polymeric quaternary ammonium compounds, which are prepared by the interaction of 2,4,6-trichloro-1,3,5-triazine with one molecular proportion of an aliphatic or cycloaliphatic diamine containing at least one tertiary nitrogen atom capable of being quaternized to effect polymerisation and then with a second molecular equivalent of the same diamine or a different amine, are useful as mordants for water-soluble dyestuffs on cellulosic fibers; as fixing agents for pigments on cellulosic fibers; as softening agents for fibers; and as surface active agents for effecting aqueous dispersions of pigments and of colorless dyestuff precursors for carbonless duplicating systems.Type: GrantFiled: January 11, 1982Date of Patent: January 25, 1983Assignee: Sterling Drug Inc.Inventor: Eugene P. Wesseler
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Patent number: 4363664Abstract: Stable, concentrated, free-flowing aqueous dispersion compositions containing one or more colorless dyestuff precursors and one or more surface active agents, are useful in the manufacture of paper for pressure sensitive carbonless duplicating manifold systems and thermal marking systems.Type: GrantFiled: January 25, 1980Date of Patent: December 14, 1982Assignee: Sterling Drug Inc.Inventor: John W. Delaney
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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: 4347352Abstract: Water-soluble triazine-nucleated polymeric quaternary ammonium compounds, which are prepared by the interaction of 2,4,6-trichloro-1,3,5-triazine with one molecular proportion of an aliphatic or cycloaliphatic diamine containing at least one tertiary nitrogen atom capable of being quaternized to effect polymerization and then with a second molecular equivalent of the same diamine or a different amine, are useful as mordants for water-soluble dyestuffs on cellulosic fibers; as fixing agents for pigments on cellulosic fibers; as softening agents for fibers; and as surface active agents for effecting aqueous dispersions of pigments and of colorless dyestuff precursors for carbonless duplicating systems.Type: GrantFiled: April 15, 1981Date of Patent: August 31, 1982Assignee: Sterling Drug Inc.Inventor: Eugene P. Wesseler
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Patent number: 4343493Abstract: This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.Type: GrantFiled: August 29, 1980Date of Patent: August 10, 1982Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, William M. Hung
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Patent number: 4314001Abstract: Water-soluble triazine-nucleated polymeric quaternary ammonium compounds, which are prepared by the interaction of 2,4,6-trichloro-1,3,5-triazine with one molecular proportion of an aliphatic or cycloaliphatic diamine containing at least one tertiary nitrogen atom capable of being quaternized to effect polymerization and then with a second molecular equivalent of the same diamine or a different amine, are useful as mordants for water-soluble dyestuffs on cellulosic fibers; as fixing agents for pigments on cellulosic fibers; as softening agents for fibers; and as surface active agents for effecting aqueous dispersions of pigments and of colorless dyestuff precursors for carbonless duplicating systems.Type: GrantFiled: March 3, 1980Date of Patent: February 2, 1982Assignee: Sterling Drug Inc.Inventor: Eugene P. Wesseler
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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: 4298215Abstract: Dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans, esterified dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans and 3,3-(corresponding-substituted-diaryl)-5/6-carboxyphthalides useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of 4/5-carboxy-2-(4-dialkylamino-subsituted-2-hydroxybenzoyl)benzoic acids and substituted diphenylamines to produce the phthalides which are then subjected to ring closure to produce the carboxyfluorans and by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterified with alkyl halides or dialkyl sulfates.Type: GrantFiled: March 31, 1980Date of Patent: November 3, 1981Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, William M. Hung
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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: 4257954Abstract: Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.Type: GrantFiled: June 14, 1979Date of Patent: March 24, 1981Assignee: Sterling Drug Inc.Inventors: Paul J. Schmidt, William M. Hung
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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: 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