Amine Salt Patents (Class 534/728)
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Patent number: 7470780Abstract: The present invention relates to dyes of formula (1) that are soluble in organic solvents, wherein Cat+ is an organic cation, to a process for their preparation and to their use in the production of colored plastics or polymeric color particles, printing colorants, printing pastes and printing inks.Type: GrantFiled: December 19, 2005Date of Patent: December 30, 2008Assignee: Ciba Specialty Chemicals CorporationInventors: Thomas Ruch, Ursula Luterbacher
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Patent number: 6632932Abstract: The objective of the present invention is to provide a high-purity trisazo compound with excellent light resistance that is useful as a coloring matter for a black aqueous ink for ink jet recording and the like. Thus, the present invention provides a trisazo compound represented by the formula: wherein A1 is a group represented by the formula —COOM or —SO3M, A2 is a hydrogen atom or a group represented by the formula —COOM or —SO3M, M is each independently a hydrogen atom, or onium, R is each independently a hydrogen atom, an alkyl group, an alkoxy group and the like, B is a residue of K acid, Nps is a residue of &ggr; acid, J acid, or RR acid.Type: GrantFiled: October 25, 2002Date of Patent: October 14, 2003Assignee: Orient Chemical Industries, Ltd.Inventors: Yoshihiro Sawatari, Makiko Matsui, Shuji Sugawara
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Patent number: 6451989Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.Type: GrantFiled: June 18, 2001Date of Patent: September 17, 2002Assignee: Lexmark International, Inc.Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
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Patent number: 6320031Abstract: Monoazo dyes of formula (3) wherein A, R1, R2, M and n are as defined in the specification, are excellent dyes for dyeing and printing of cellulose containing materials and especially for the preparation of inks for ink jet printing.Type: GrantFiled: February 23, 2000Date of Patent: November 20, 2001Assignee: Ilford Imaging Switzerland GmbHInventors: Kurt Baettig, GĂ©rald Jan
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Patent number: 6288217Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.Type: GrantFiled: August 18, 2000Date of Patent: September 11, 2001Assignee: Lexmark International, Inc.Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
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Patent number: 6160169Abstract: A process for preparing amine salts of 4-nitrotoluene-2-sulfonic acid by sulfonation of nitrotoluene with oleum, subsequent dilution of the reaction mixture with water and extraction with lipophilic amines, wherein the acidic aqueous solution of the sulfonation product is partially neutralized with mineral bases. The compounds prepared according to the invention are particularly suitable for preparing dyes.Type: GrantFiled: December 7, 1998Date of Patent: December 12, 2000Assignee: BASF AktiengesellschaftInventors: Rudolf Bermes, Armin Haag, Hellmut Kast, Peter Krotzsch
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Patent number: 6130319Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.Type: GrantFiled: April 3, 1998Date of Patent: October 10, 2000Assignee: Lexmark International, Inc.Inventors: James F. Feeman, Jing X. Sun
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Patent number: 6084078Abstract: The novel disazo dyestuffs of the formula (I) in which the substituents and indices have the meanings given in the description, are outstandingly suitable for dyeing cellulosic materials in red-violet to blue brilliant color shades.Type: GrantFiled: December 17, 1997Date of Patent: July 4, 2000Assignee: Bayer AktiengesellschaftInventor: Winfried Mennicke
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Patent number: 6031083Abstract: The new disazo dyestuffs of the formula (I) ##STR1## wherein the substituents and the indices have the meanings given in the description,wherein more than 25 equivalent % of all the M cations in the molecule are alcohol ammonium radicals of the formula .sup..sym. NR.sub.1 R.sub.2 R.sub.3 R.sub.4 whereinR.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another represent hydrogen, C.sub.1 -C.sub.4 -alkyl and C.sub.2 -C.sub.4 -hydroxyalkyl, with the proviso that at least one of the radicals R.sub.1 -R.sub.4 denotes C.sub.2 -C.sub.4 -hydroxyalkyl,are excellently suitable for dyeing cellulose-containing materials, and in particular paper, and are distinguished by high degrees of fastness.Type: GrantFiled: March 19, 1999Date of Patent: February 29, 2000Assignee: Bayer AktiengesellschaftInventors: Klaus Kunde, Wolfgang Zarges
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Patent number: 5997628Abstract: Disclosed are red shade yellow compositions characterized by the formula: ##STR1## wherein X is a lower alkyl or a --COOR.sub.1 group; wherein R.sub.1 is a hydrogen or lower alkyl group; each Y is independently a lower alkyl, lower alkyloxy or halogen group; a is 0, 1, or 2; and M is a divalent metal. Also disclosed is a process for preparing red shade yellow pigment compositions prepared by initially a diazonium component comprised of one or more aromatic amines wherein at least one of said amines is a 1-sulfo-2-naphthylamine; and thereafter coupling the diazonium component with a coupling component comprised of a pyrazolone coupler to form a dye, and metallizing said dye with at least one divalent metal.Type: GrantFiled: June 8, 1998Date of Patent: December 7, 1999Assignee: Engelhard CorporationInventor: Amrit Pal Bindra
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Patent number: 5986075Abstract: The present invention relates to a process for desalting aqueous suspensions containing an organic diazonium compound and electrolytes containing Na ions, in which the aqueous suspension is passed through a semipermeable membrane.Type: GrantFiled: January 20, 1999Date of Patent: November 16, 1999Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: John C. DuBose, Andrew D. Johnson, Samuel Shaun Murphree, Edzard Tholema, Helmut Hoffmann, Wolfgang Zarges, Wolfgang Frank, Bettina Burkhardt
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Patent number: 5965716Abstract: A salt of formula IF.sub.n.A (I)in which F is the residue of a metal free anionic dyestuff having 1 to 4 acids groups,n is 1 to 2; andA is a group containing 1 to 4 sterically hindered amine groups and at least n ammonium or immonium groups.Type: GrantFiled: April 25, 1997Date of Patent: October 12, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Bansi Lal Kaul, Angelos-Elie Vougioukas
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Patent number: 5919915Abstract: An azo pyrazolone compound of the formula: ##STR1## wherein Z represents a substituent selected from Cl, Br, F, NO.sub.2, SO.sub.2 R, CO.sub.2 R, NHSO.sub.2 R.sup.1 and NHCOR.sup.1 in which R and R.sup.1 are hydrocarbyl groups and the sulphonic acid group in ring A is in the 3- or 4-position relative to the pyrazolyl group, said compound being in the form of a salt, and its use as a pigment.Type: GrantFiled: July 17, 1997Date of Patent: July 6, 1999Assignee: Zeneca LimitedInventors: Alan Patrick Chorlton, James Mason
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Patent number: 5892105Abstract: A process for preparing amine salts of 4-nitrotoluene-2-sulfonic acid by sulfonation of nitrotoluene with oleum, subsequent dilution of the reaction mixture with water and extraction with lipophilic amines, wherein the acidic aqueous solution of the sulfonation product is partially neutralized with mineral bases.The compounds prepared according to the invention are particularly suitable for preparing dyes.Type: GrantFiled: December 9, 1997Date of Patent: April 6, 1999Assignee: BASF AktiengesellschaftInventors: Rudolf Bermes, Armin Haag, Hellmut Kast, Peter Krotzsch
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Patent number: 5834600Abstract: Disclosed are diazahemicyanine hydrophobic cationic dyes represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups having not more than 5 carbon atoms, R.sup.5 is a lower alkyl group having not more than 5 carbon atoms or a lower alkoxy lower alkyl group having not more than 6 carbon atoms, and Z.sup.- is a counter ion having a hydrophobic organic group,and a thermal transfer ink ribbon having a substrate and and ink layer laminated thereon containing said cationic dye.Type: GrantFiled: June 28, 1996Date of Patent: November 10, 1998Assignees: Sony Corporation, Hodogaya Chemical Co., Ltd.Inventors: Masanobu Hida, Kengo Ito, Yoshio Fujiwara, Nobuo Suzuki, Hiroyoshi Yamaga, Junichi Hagiwara
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Patent number: 5770708Abstract: A process for preparing aqueous preparations of azo dyes of the formula ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl andKat.sym. is the equivalent of a cation which derives from a tertiary amine of the ethanolamine or propanolamine series,by diazotization of an aniline of the formula ##STR2## with neopentylglycol dinitrite in an aqueous medium and coupling of the resulting reaction mixture with .beta.-naphthol in the presence of a water-miscible diluent and of an amine comprises using an amine comprising a tertiary amine of the ethanolamine or propanolamine series.Type: GrantFiled: May 27, 1997Date of Patent: June 23, 1998Assignee: BASF AktiengesellschaftInventor: Rudolf Bermes
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Patent number: 5744590Abstract: An azo pyrazolone compound of the formula: ##STR1## in the form of a salt, and its use as a pigment.Type: GrantFiled: July 17, 1997Date of Patent: April 28, 1998Assignee: Zeneca LimitedInventors: Alan Patrick Chorlton, James Mason
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Patent number: 5684140Abstract: There is described a new magenta azo dye which can be used in an aqueous composition in an ink-jet printing process.Type: GrantFiled: December 16, 1996Date of Patent: November 4, 1997Assignee: Ilford A.G.Inventors: Kurt Baettig, Gerald Jan
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Patent number: 5616694Abstract: A compound of Formula (1) and salts thereof wherein the variables are as defined in the specification:Ar.sup.1 N.dbd.N-J-X-L-X-J-N.dbd.NAr.sup.2 (1)A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness. It is especially suitable for use in the printing of paper by non-impact printing techniques, such as ink jet printing, especially thermal ink jet printing.Type: GrantFiled: July 12, 1995Date of Patent: April 1, 1997Assignee: Zeneca LimitedInventors: Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5597387Abstract: The present invention relates to water-soluble polyazo dyestuffs of the general formula I ##STR1## wherein Y, Z, m and M.sup..sym.1 to M.sup..sym.4 are as defined in claim 1, processes for dyeing leather and paper with the polyazo dyestuffs, and recording liquids and inks containing the polyazo dyestuffs.Type: GrantFiled: November 9, 1995Date of Patent: January 28, 1997Assignee: Hoechst AGInventors: Wolfgang Bauer, Dieter Baumgart, Walter Zoller
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Patent number: 5571899Abstract: Salts of the formulaF.sub.n.A,wherein F is an anion of a metal-free anionic dye having m acid groupswherein m is 1 to 4, inclusive,A is a cation of an amine containing 1 to 6 sterically hindered amine groups, andn is 1 or 2,with the proviso that the salt contains 1 to n.times.m groups selected from ammonium and immonium groups, useful as pigments, particularly for the coloring of solvent-free and solvent-containing plastic materials, lacquers and printing inks.Type: GrantFiled: June 6, 1995Date of Patent: November 5, 1996Assignee: Sandoz, Ltd.Inventors: Bansi L. Kaul, Angelos-Elie Vougioukas
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Patent number: 5556885Abstract: There are provided N-arylthiohydrazone derivatives of formula I ##STR1## the use thereof for the control of insect and acarid pests and methods and compositions for the protection of crops from the damage and loss caused by said pests.Type: GrantFiled: October 27, 1994Date of Patent: September 17, 1996Assignee: American Cyanamid CompanyInventors: Susan Trotto, Joseph A. Furch, III, David G. Kuhn, David A. Hunt
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Patent number: 5554735Abstract: Azo oxime ethers of formula (I), in which X is CH or N, R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or cylclopopy and R.sub.2 is aryl or heteroaryl, have an activity against phytopathogenic fungi. They can be used in the form of formulaions as crop protection products, seed-dressing products and wood preservatives.Type: GrantFiled: August 26, 1994Date of Patent: September 10, 1996Assignee: Ciba-Geigy CorporationInventors: Hugo Ziegler, Stephan Trah
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Patent number: 5523387Abstract: This invention relates to dyes in salt form which are useful for mass dyeing of synthetic polymers. In particular, this invention relates to ammonium or immonium salt-containing dyes that display good polymer affinity, and the methods for using those dyes to color polymeric substrates.Type: GrantFiled: June 14, 1994Date of Patent: June 4, 1996Assignee: Sandoz Ltd.Inventors: Jurgen Goldmann, Bansi L. Kaul
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Patent number: 5519121Abstract: Novel dyestuffs of the formula (I) ##STR1## in which DK denotes a radical of the formula ##STR2## where m is 1 or 2 and DK' denotes a radical of the formula ##STR3## where n is 1 or 2 R.sub.1 represents hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl,R.sub.2 represents hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sub.3 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acylamino andR.sub.4 represents substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl.have now been found.The invention also relates to a process for their preparation and to their use for dyeing/coloring and printing textiles and paper, in particular in printing inks containing these dyestuffs.Type: GrantFiled: February 24, 1995Date of Patent: May 21, 1996Assignee: Bayer AktiengesellschaftInventors: Gerd-Friedrich Renner, Peter Wild, Karin Hassenruck
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Patent number: 5510467Abstract: Salts of the formulaF.sub.n .multidot.A,wherein F is an anion of a metal-free anionic dye having m acid groupswherein m is 1 to 4, inclusive,A is a cation of an amine containing 1 to 4 sterically hindered amine groups, andn is 1 or 2,with the proviso that the salt contains 1 to n.times.m groups selected from ammonium and immonium groups, useful as pigments, particularly for the coloring of solvent-free and solvent-containing plastic materials, lacquers and printing inks.Type: GrantFiled: December 13, 1993Date of Patent: April 23, 1996Assignee: Sandoz Ltd.Inventors: Bansi L. Kaul, Angelos-Elie Vougioukas
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Patent number: 5486601Abstract: Disclosed is a trisazo dye represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent a substituted amino group which is substituted with hydrogen, a hydroxyl group, a carboxyl group, an amino group, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group or an acyl group, or an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R.sup.3 is hydrogen, an alkyl or alkoxy group having 1 to 6 carbon atoms; provided that R.sup.1 and R.sup.2 are not amino groups or substituted amino groups simultaneously.A process for producing the trisazo dye and an aqueous ink composition containing the trisazo dye are also disclosed.Type: GrantFiled: September 28, 1994Date of Patent: January 23, 1996Assignee: Orient Chemical Industries, Ltd.Inventors: Tatsuya Yagyu, Takashi Ono
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Patent number: 5473053Abstract: A compound of Formula (1) and salts thereof:Ar.sup.1 N.dbd.N--J--X--L--X--J--N.dbd.NAr.sup.2 (1)wherein: ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl containing at least two carboxy groups; andL is a group of the Formula (3a) or (3b): ##STR2## in which T.sup.1 and T.sup.2 each independently is C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl;T.sup.3 and T.sup.4 each independently is H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl provided that T.sup.3 and T.sup.4 are not both H;each X independently is a group of the Formula (4), (5) or (6): ##STR3## each Z independently is H, halogen, alkyl, NR.sup.1 R.sup.2, SR.sup.3 or 0R.sup.3 ;each Y independently is Z, SR.sup.4 or OR.sup.4 ;each E independently is Cl or CN; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as defined in the specification.A compound of Formula (1) is suitable for use in the coloration of cellulosic substrates, such as paper, to give bright prints with good light and water fastness.Type: GrantFiled: January 7, 1994Date of Patent: December 5, 1995Assignee: Zeneca LimitedInventors: Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5453495Abstract: A compound of Formula (1) and salts thereof: ##STR1## wherein: L is optionally substituted piperazinyl;D is optionally substituted phenylene or naphthylene;E is optionally substituted phenylene, naphthylene or quinoline;R is H or C.sub.1-4 -alkyl;Z is optionally substituted carboxyaryl; andn has a value of 0 or 1.A compound of Formula (1) is useful as a colorant for black inks suitable for ink jet printing.Type: GrantFiled: December 22, 1994Date of Patent: September 26, 1995Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5446134Abstract: Bis(perfluorosulphonyl)methanes, process for preparing same and uses thereof. The compounds of the invention are based on the formula (1/nM)+[(R.sub.F SO.sub.2).sub.2 CY].sup.- in which Y denotes an electron-attracting group chosen from --C.dbd.N and RZ groupings in which Z denotes a carbonyl grouping, sulphonyl grouping or a phosphonyl grouping and R denotes an organic monovalent grouping, M denotes a metal having valency n or an organic group capable of existing in the cationic form, R.sub.F denotes a perfluoroalkyl or perfluoroaryl grouping. Said compounds are especially useful in the production of electrochemical devices.Type: GrantFiled: July 8, 1993Date of Patent: August 29, 1995Assignees: Centre National de la Recherche Scientifique, Hydro QuebecInventors: Michel Armand, Djamila Benrabah, Jean-Yves Sanchez
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Patent number: 5378269Abstract: A recording liquid for ink-jet recording comprising coloring matter, which is an image-forming component, and a liquid medium for dissolving the coloring matter therein. The liquid medium is ethanol and the coloring matter is a dye represented by the following general formula (A): ##STR1## or the following general formula (B): ##STR2## as an image-forming component.Type: GrantFiled: December 29, 1993Date of Patent: January 3, 1995Assignee: Scitex Digital Printing, Inc.Inventors: Louis J. Rossi, Sunita P. Chavan
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Patent number: 5366543Abstract: The present invention provides a disazo salt-forming dye having excellent solubility with organic solvents, especially alcohols and glycols.The present invention thus provides a disazo salt-forming dye represented by the Formula (I): ##STR1## or the Formula (II): ##STR2## wherein Ka.sup.+ represents a cation of an amine which is substituted with at least one linear or cyclic alkyl group or aralkyl group having 6-12 carbon atoms which may be branched or interrupted by oxygen.Type: GrantFiled: June 9, 1993Date of Patent: November 22, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Tetsui Akase
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Patent number: 5359064Abstract: This invention relates to salts of triazine derivatives with oxygenated as of phoshporus, having general formula (I): ##STR1## obtained by salification, with an acid containing phosphorus, of polycondensates of 2,4,6-triamino-1,3,5-triazine. The compounds having the general formula (I) are particularly used as flame-resistant additives.Type: GrantFiled: July 10, 1991Date of Patent: October 25, 1994Assignee: Ministero Dell `Universita` e Della Ricerca Scientifica e TecnologicaInventors: Roberto Cipolli, Enrico Masarati, Gilberto Nucida, Roberto Oriani, Mario Pirozzi
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Patent number: 5340929Abstract: The present invention provides a trisazo dye represented by the formula: ##STR1## wherein B is a substituted or non-substituted phenyl group, A is a phenyl group substituted with at least one substituent selected from the group consisting of an amino group, a substituted amino and a hydroxyl group, R is a substituted or non-substituted phenyl group or an alkyl group having 1 to 8 carbon atoms, and M is hydrogen, alkali metal, aliphatic alkyl ammonium or alkanol ammonium. An aqueous ink composition and a process for the producing a concentrated solution containing the trisazo dye are also disclosed.Type: GrantFiled: February 12, 1993Date of Patent: August 23, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
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Patent number: 5336763Abstract: The present invention provides a trisazo dye represented by the formula: ##STR1## [wherein A is a phenyl group substituted with at least one substituent selected from the group consisting of an amino group, a substituted amino group and a hydroxyl group, B is a substituted or non-substituted phenyl group, X is a group of the formula: ##STR2## Q is a group of the formula: ##STR3## (wherein n is 1 or 2), and M is hydrogen, alkali metal, aliphatic alkyl ammonium or alkanol ammonium]. An aqueous ink composition and a process for the producing a concentrated solution containing the trisazo dye are also disclosed.Type: GrantFiled: February 12, 1993Date of Patent: August 9, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Yonezawa
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Patent number: 5330542Abstract: A dye-incorporated composition which comprises a cyanine type dye and an azo metal chelate compound comprising an azo type compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic ring or a hetero ring together with the two carbon atoms to which it is bonded, and X is a group having an active hydrogen), and a metal, and an optical recording medium comprising a recording layer which contains the dye-incorporated composition.Type: GrantFiled: January 24, 1992Date of Patent: July 19, 1994Assignee: Mitsubishi Kasei CorporationInventors: Shuichi Maeda, Satoru Imamura, Kazuo Mitsuhashi, Takako Tsukahara
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Patent number: 5262527Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## Ar.sup.1 and Ar.sup.2 are each independently aryl or substituted aryl providing at least one of Ar.sup.1 and Ar.sup.2 has at least one substituent selected from COOH and COSH;each R.sup.1 and R.sup.2 is independently H, alkyl, substituted alkyl, alkenyl or substituted alkenyl;L is a divalent organic linking group;n is 0 or 1;each X independently is carbonyl or a group of the formula (2), (3) or (4): ##STR2## each Z independently is NR.sup.3 R.sup.4, SR.sup.5 or OR.sup.5 ; each Y independently is H, Cl, Z, SR.sup.6 or OR.sup.6 ;each E independently is Cl or CN;R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl, substituted aralkyl or R.sup.3 and R.sup.Type: GrantFiled: June 28, 1991Date of Patent: November 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon, Prahalad M. Mistry
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Patent number: 5258505Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.Type: GrantFiled: March 27, 1992Date of Patent: November 2, 1993Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
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Patent number: 5254674Abstract: A diaminoazothiophene compound represented by the formula (I): ##STR1## salts thereof or metal complexes thereof and a method for preparing the same.Type: GrantFiled: November 6, 1992Date of Patent: October 19, 1993Assignee: Osaka Gas Company, LimitedInventors: Yasunori Yokomichi, Shinichi Tada, Hitoshi Nishino, Kenji Seki
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Patent number: 5241058Abstract: Azo dye salts corresponding to formula I are suitable as masking couplers. ##STR1## In Formula I, A denotes an optionally substituted aryl group;CC denotes a group optionally carrying a ballast group and capable of coupling under the conditions of photographic color development to produce a dye preferably a cyan dye (color coupler residue);L denotes a linking member which is attached at the coupling position of the color coupler residue by an oxygen, sulphur or nitrogen atom;Z denotes a group conferring solubility in alkalies;R denotes NH--CO--R.sup.1, NH--SO.sub.2 --R.sup.1, COOR.sup.2 or NR.sup.1 --R.sup.2 ;R.sup.1 denotes an optionally substituted alkyl or aryl group;R.sup.2 denotes H or a group such as R.sup.1 ;[M.sup..sym. ] denotes a mixture of organic and inorganic cations optionally containing protons, in which the proportion of organic cation amounts to at least 1/2 mol per mol of dye;m stands for 0, 1 or 2; andn stands for 1, 2, 3 or 4; n.gtoreq.m.Type: GrantFiled: May 15, 1991Date of Patent: August 31, 1993Assignee: Agfa-Gevaert AktiengesellschaftInventors: Gunter Renner, Hans Langen, Ulrich Klein
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Patent number: 5229503Abstract: The invention relates to azo compounds, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.Type: GrantFiled: September 11, 1991Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventor: Jui Y. Chang
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Patent number: 5210188Abstract: 1. Dyestuffs for cyclic or straight polyfluoropolyoxyalkylenes, of general formula:Q[B--(A).sub.s ].sub.t (III)or[(Q).sub.s --B].sub.2 A (IV)where:Q=an organic group containing a chromophore group, free from free or salified sulphonic and/or carboxylic groups, and/or sulphon-amidic groups;A=a perfluorooxyalkylene chain, which is monovalent in formula (II) and divalent in formula (III);B=an organic at least divalent group;s, t=1 or 2, respectively.2. Compositions comprising cyclic or straight polyfluoropolyoxyalkylenes and at least a dyestuff of formula (III) or (IV) dissolved therein.Type: GrantFiled: February 11, 1992Date of Patent: May 11, 1993Assignee: Ausimont S.p.A.Inventors: Ezio Strepparola, Piero Gavezotti, Giovanni Gavazzi
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Patent number: 5175260Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.Type: GrantFiled: August 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Udo Mayer
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Patent number: 5171848Abstract: Black compounds of Formula (1) having enhanced solubility in polar organic liquids which are useful as ink colorants in conventional and hot melt ink-jet printing and automatic identification, as black colorants for toners and thermal wax transfer sheets and as charge control agents for electrophotographic toners; ##STR1## wherein R is H, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, aryl, C.sub.4-8 cycloalkyl, --CN, --NO.sub.2, halogen, --COOR.sup.1, --OH, --SH or --SO.sub.3 A;R.sup.1 is A, C.sub.1-4 -alkyl or aryl;R.sup.2 is --NH.sub.2, --OH or --SO.sub.3 A;R.sup.3 is --NH.sub.2 or --OH;R.sup.4 is --NH.sub.2, --OH, --SO.sub.3 A or H; andA is NQ.sub.4 in which at least one Q is a branched chain fatty C.sub.6-20 -aliphatic group.Type: GrantFiled: March 30, 1992Date of Patent: December 15, 1992Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Peter Gregory, John E. Presgrave
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Patent number: 5151505Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.Type: GrantFiled: November 13, 1990Date of Patent: September 29, 1992Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh
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Patent number: 5118737Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: June 22, 1990Date of Patent: June 2, 1992Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
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Patent number: 5091517Abstract: The invention relates to novel azo dyes of the formula ##STR1## wherein R.sup.1 is an alkyl radical containing 1 to 12 carbon atoms, which is unsubstituted or substituted by hydroxy, alkoxy, cyano or phenyl, or is an aryl radical selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 2-pyridyl, 4-pyridyl, 2-pyrimidinyl and 2-thienyl, these radicals being unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, --NHR.sup.3, --NH--C.sub.2 -C.sub.6 alkanoyl,--NH--benzoyl, phenoxy, COOR.sup.3, --CONHR.sup.3, phenyl, sulfo or C.sub.1 -C.sub.4 alkylsulfone,R.sup.2 is hydrogen or a radical as defined for R.sup.1,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, which is unsubstituted or substituted by hydroxy, alkoxy, cyano or phenyl, or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, --NH--C.sub.2 -C.sub.6 alkanoyl, --NH--benzoyl, phenoxy, phenyl, sulfo or C.sub.1 -C.sub.Type: GrantFiled: November 6, 1990Date of Patent: February 25, 1992Assignee: Ciba-Geigy CorporationInventor: Rudolf Naef
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Patent number: 5071968Abstract: Azo dyes of the formula ##STR1## where D is a diazo component, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, and n is 1,2,3,4 or 5, produce dyeings of good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: March 5, 1990Date of Patent: December 10, 1991Assignee: Ciba-Geigy CorporationInventor: Harald Walter
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Patent number: 5053495Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.Type: GrantFiled: August 24, 1989Date of Patent: October 1, 1991Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
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Patent number: RE35359Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 --C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.6 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.Type: GrantFiled: September 26, 1994Date of Patent: October 22, 1996Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh