The Hetero Ring Is Six-membered And Contains At Least Two Nitrogens Patents (Class 534/803)
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Publication number: 20150073132Abstract: Disclosed is a method for continuously preparing a water-soluble azo dye by coupling a nebulizer with a pipeline. According to the method, the nebulizer is coupled with a pipeline with an interception tower plate, atomized and mixed reaction liquid flow flows through the pipeline with the interception tower plate, and mixing and reacting are further enhanced through turbulent mixing on the tower plate, so that instant separation of reaction heat generated in an atomizing contact reaction from a reactant is achieved, and normal-temperature rapid continuous production of the water-soluble azo dye is achieved. Fog drops which are atomized by using the nebulizer have small particle diameter and large specific surface area, so that a diazo salt and a coupling component are sprayed separately, move face to face and can be fully contacted, and mixing and reacting speeds are increased.Type: ApplicationFiled: November 30, 2012Publication date: March 12, 2015Inventors: Shufen Zhang, Bingtao Tang, Rongwen Lv, Dong Liang
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Patent number: 8585784Abstract: The present invention relates to new compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups and to a process for their preparation. Further aspects are shading compositions using these compounds.Type: GrantFiled: November 25, 2008Date of Patent: November 19, 2013Assignee: BASF SEInventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Käser, Roger Wolfgang Basler
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Publication number: 20100319142Abstract: The present invention relates to new compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups and to a process for their preparation. Further aspects are shading compositions using these compounds.Type: ApplicationFiled: November 25, 2008Publication date: December 23, 2010Applicant: BASF SEInventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaser, Roger Wolfgang Basler
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Publication number: 20090018317Abstract: The present invention provides a reactive dyestuff with an alkylthio group and a ?-sulfatoethylsulfone group, which is represented by formula (I), wherein D, R, R1, R2, R3, R4, Q, x, and y are defined the same as the specification. The reactive dyestuffs of the present invention not only have characteristics of high solubility, high alkali solubility, and easily being washed off for dyeing cellulose fiber, but also are suitably applied in cold-pad-batch dyeing, continuous-dyeing, printing, and digital printing.Type: ApplicationFiled: July 10, 2007Publication date: January 15, 2009Applicant: Everlight USA, Inc.Inventors: Wen-Jang Chen, Hong-Chang Huang, Duncan A. S. Phillips, John A. Taylor
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Publication number: 20080280053Abstract: The present invention refers to dyestuffs of the formula (I) wherein R1, R2 are independently H, optionally substituted alkyl or optionally substituted aryl, R3 is optionally substituted alkyl or optionally substituted aryl, an organic acyl group (i.e. acetyl, propionyl, benzoyl etc.) or an organic thioacyl group (i.e. 10 thioacetyl, thiopropionyl, thiobenzoyl etc.), all of which may or may not bear a reactive group able to form a dye-fibre bond, R4 is any coloured organic group, which may or may not bear a reactive group able to form a dye-fibre bond, L is any carbon containing linking group that is aliphatic, aromatic, or a combined alkyl-aryl group such as benzyl or phenethyl, X is halogen or tertiary ammonium or an optionally substitute aryl amine, processes for the preparation of said dyestuffs and their use for dyeing and printing hydroxy- and/or carboxamido-containing fiber materials.Type: ApplicationFiled: November 15, 2005Publication date: November 13, 2008Applicant: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KGInventors: Anthony Lawrence, Werner Hubert Russ, Warren J. Ebenezer
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Patent number: 7427319Abstract: The present invention relates to an azo compound represented by the following formula (1): (wherein, in the formula (1), R1 represents a hydrogen atom; a hydroxyl group; a carboxyl group; a (C1-C4)alkyl group which may be substituted by a hydroxyl group or a (C1-C4)alkoxy group; or the like, and A represents an aliphatic amine residue having a carboxyl group or a sulfo group, respectively;) or a salt thereof; an ink composition containing the same; and an inkjet recording method and a colored object using the same. Said azo compound has a high color value and has a hue between yellow and red or a brown hue. The ink containing said azo compound has satisfactory storage stability, and exhibits, when printed therewith, a stable ejection property even on a thermal type inkjet printer, and gives a print of high quality (superior in light fastness, ozone gas fastness and moisture fastness).Type: GrantFiled: June 21, 2005Date of Patent: September 23, 2008Assignee: Nippon Kayaku Kabushiki KaishaInventors: Takashi Yoneda, Hiroaki Ohno, Yasuo Shirasaki
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Patent number: 7351808Abstract: Anionic monoazo dyes of the formula (1) in which A represents 1- or 2-naphthyl residue, which is substituted by a total of one or two sulphonic and/or carboxylic acid groups.Type: GrantFiled: July 17, 2003Date of Patent: April 1, 2008Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Lennartz, Sandra Weiss
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Patent number: 7183409Abstract: The invention relates to basic mono- and bisazo compounds according to formula (I) wherein all substituents are defined as in Claim 1, their production, their use as dyestuffs as well as material dyed with these dyestuffs.Type: GrantFiled: May 29, 2002Date of Patent: February 27, 2007Assignee: Clariant Finance (BVI) LimitedInventors: Friedrich Lehr, Reinhard Pedrazzi, Heidrun Schene
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Patent number: 6974497Abstract: Claimed are compounds of formula (I) where the substituents are each as defined in the claims, their preparation, their use as dyes and as a ingredients of an ink-jet printing ink and also substrates dyed with such compounds.Type: GrantFiled: September 27, 2001Date of Patent: December 13, 2005Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 6929688Abstract: Monoazo dyes of general formula (IV) wherein R1, R2, R3, X, M and n are as described in the specification, are excellent dyes for dyeing and printing of cellulose containing materials and textile materials and especially for the preparation of inks for ink jet printing.Type: GrantFiled: May 23, 2003Date of Patent: August 16, 2005Assignee: Ilford Imaging Switzerland GmbHInventors: Kurt Baettig, Thomas Stauner
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Patent number: 6867286Abstract: Provided are novel yellow azo dyes which are useful in ink compositions, especially ink jet compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fashion and exhibit improved water solubility, thus rendering the ink compositions to be especially suitable for printheads having small nozzle openings.Type: GrantFiled: March 11, 2004Date of Patent: March 15, 2005Assignee: Lexmark International, Inc.Inventors: Ann P. Holloway, James Frederic Feeman
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Publication number: 20030221588Abstract: Monoazo dyes of general formula (IV) 1Type: ApplicationFiled: May 23, 2003Publication date: December 4, 2003Applicant: ILFORD IMAGING SWITZERLAND GmbH.Inventors: Kurt Baettig, Thomas Stauner
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Patent number: 6635747Abstract: A compound of the Formula (1) and salts thereof: wherein: D is the residue of a mono-azo chromophore; Z is an optionally substituted nitrogen containing heterocyclic group; R1 is H or optionally substituted alkyl; the dyes of Formula (1) being free from fibre reactive groups; provided that the compound of Formula (1) is other than the compound of Formula (A): Also claimed are compositions and inks containing a compound of Formula (1), a process for ink jet printing using the inks and to an ink jet printer cartridge containing the ink.Type: GrantFiled: July 24, 2002Date of Patent: October 21, 2003Assignee: Avecia LimitedInventors: Paul Wight, Prakash Patel
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Patent number: 6610132Abstract: A composition comprising: (a) a liquid medium comprising (i), (ii) or (iii): (i) a mixture of water and an organic solvent; (ii) an organic solvent free from water; or (iii) a low melting point solid; and (b) a dye of the Formula (1) or a salt thereof: wherein A, B, Z, L, R1 and n are as defined in the description. Also claimed are certain dyes of Formula (1), inks, an ink jet printing process using the inks, a substrate printed with the inks, an ink jet printer cartridge containing the inks and an ink jet printer containing the ink jet printer cartridge.Type: GrantFiled: March 1, 2001Date of Patent: August 26, 2003Assignee: Avecia LimitedInventor: Paul Wight
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Patent number: 6506241Abstract: Compounds of the Formula (1) and salts thereof: wherein: each A independently is N, C—Cl, C—CN or C—NO2; each Ar independently is a substituted aryl group carrying a —COOH group ortho to the azo (—N═N—) group; L is an aliphatic group carrying a —COOH, —SO3H or —PO3H2 group; each Z independently is —SR2, —OR3, —NR4R5 or a labile atom or group; each X independently is —S—, —O— or —NR1—; each R1 independently is H or optionally substituted alkyl; and R2, R3, R4 and R5 are independently H, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl; or R4 and R5 together with the nitrogen to which they are attached form an optionally substituted five or six membered ring, and their use in compositions and inks for ink jet printing processes and ink jet printer cartridges.Type: GrantFiled: July 10, 2000Date of Patent: January 14, 2003Assignee: Avecia LimitedInventors: Julie Ann Stocks, Paul Wight
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Patent number: 6432185Abstract: The present invention provides water-soluble acid dyes of the formula (1) in which R1 is A—X—COOM, A—X—SO3M, OR4 or NR5R6, A is NR7 or S, X is a (C1-C16)-alkylene or arylene radical optionally substituted with hydroxyl-, carboxyl- or amino-groups; R4, R5 and R6 independently of one another are hydrogen or (C1-C4)-alkyl or substituted (C1-C4)-alkyl R7 is hydrogen, methyl or ethyl; M is a cation and n is 0 or 1. which are suitable for printing natural and synthetic fiber materials for recording liquids, especially for the inkjet process, and for pulp-dyeing paper.Type: GrantFiled: March 15, 2000Date of Patent: August 13, 2002Assignee: Clariant GmbHInventors: Wolfgang Bauer, Josef Geisenberger, Heidemarie Menzel, Reinhard Pedrazzi
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Patent number: 6406527Abstract: The present invention provides water-soluble acid dyes of the formula (I) in which R1, R2 and R3 independently of one another are A—X—COOM, A—X—SO3M, OR4 or NR5R6, A is NR7or S, X is a straight-chain or branched (C1-C16)-alkylene radical, a straight-chain or branched, hydroxyl-, carboxyl- or amino-substituted (C1-C16)-alkylene radical, an arylene radical or a hydroxyl-, carboxyl- or sulfo-substituted arylene radical; R4, R5, and R6 independently of one another are hydrogen or (C1-C4)-alkyl or are (C1-C4)-alkyl substituted by one or more hydroxyl, 2-hydroxyethoxy, (C1-C4)-alkoxy or amino groups, R7 is hydrogen, methyl or ethyl; M is a monovalent cation or one equivalent of a polyvalent cation, and which are suitable for printing natural and synthetic fiber materials for recording liquids, especially for the inkjet process, and for pulp-dyeing paper.Type: GrantFiled: March 13, 2000Date of Patent: June 18, 2002Assignee: Clariant GmbHInventors: Wolfgang Bauer, Josef Geisenberger, Heidemarie Menzel, Reinhard Pedrazzi
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Patent number: 6344076Abstract: The invention relates to a compound of Formula (1) and to an ink jet printing process using inks; a substrate printed with the inks and cartridges all which comprise the compound of Formula (1) wherein A is N, C—CI, C—CN or C—NO2; L1 Is —OR3, Z is —O—, —S— or —NR2—; R1 and R2 are each independently H or optionally substituted alkyl; R3 is H or alkyl; each W independently is —CO2Q or —SO3Q; each X independently is an optionally substituted amino group or a group which is substituted by an optionally substituted amino group; each Y independently is halo, hydroxy, nitro, cyano, optionally substituted alkyl optionally substituted alkoxy, optionally substituted aryl, optionally substituted aralkyl, —SRa—CORa, —COORa, —SO3Ra or —SORa; Ra is C1-4-alkyl optionally substituted by carboxy, sulpho, hydroxy, nitro, cyano or halo: each Q independently is ammonium or substituted ammonium; m, n and p each independently haveType: GrantFiled: December 30, 1999Date of Patent: February 5, 2002Assignee: Avecia LimitedInventor: Mark Kenworthy
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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, Gérald Jan
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Patent number: 6290763Abstract: Azo dyes of Formula (1) have utility as dyes for ink-jet printing, where Formula (1) represents: which comprises any suitable form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: n represents from 1 to 5 inclusive; R1, R1B, R4 and R4B each independently comprises at least one of the following substituents, optionally substituted: H, C1-8alkyl; C1-8,alkoxy; —NHCOH, C1-8alkylcarbonylamino; and —NHCONR5R6 where R5 and R6 each independently comprises at least one of the following substituents: H, C1-8alkyl and aryl; and R2 and R3 each independently comprises at least one of the following substituents, optionally substituted: H; C1-8alkoxy; -NHC1-8alkyleneOH, —SC1-8-alkyleneSO3H; -NHC1-8alkyleneN(C1-8alkyl)2; where X comprises one of the following: —NHC1-8alkylene; —NHphenylSO2NHC1-8alkylene; and a direct link,Type: GrantFiled: March 18, 1999Date of Patent: September 18, 2001Assignee: Zeneca LimitedInventors: Christine Millard, Peter Gregory, Roy Bradbury
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Patent number: 6277185Abstract: Azo dyes of Formula (1) have utility as dyes for ink-jet printing where Formula (1) represents: which comprises any suitable form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: p represents from 1 to 7 inclusive; the napthyl moiety may be optionally substituted; R1 comprises at least one of the following substituents, optionally substituted: H, C1-4-alkyl, NHCOC1-4 alkyl, C1-4 alkoxy, NHCOaryl, NHSO2C1-4 alkyl, NHSO2aryl, NHCONR3R4 where R3 and R4 each independently comprises H, C1-4alkyl or aryl; R2 comprises H, C1-4 alkyl or C1-4 alkoxy; L1 and L2 each independently comprises at least one of the following substituents, optionally substituted: —NH2, —NHC1-4 alkyleneOH, —SC1-4alkylene —SO3H, —NHC1-4alkyleneN(C1-4alkyl)2, —N(C1-4alkyleneOH)2, —NHC1-4alkyleneSO3H, —NHC1-4alkylene(CO2H)n where n is 1, 2 or 3, —SC1-4alkylType: GrantFiled: May 26, 1999Date of Patent: August 21, 2001Assignee: Zeneca LimitedInventors: Anthony Alanzo Watson, Kathryn Carr
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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: 6127531Abstract: A dyestuff according to formula (I) ##STR1## or a salt thereof wherein the substituents have the definitions as defined in claim 1.The dyestuffs are useful for dyeing or printing nitrogen-containing or hydroxy-group-containing organic substrates and for the production of printing inks.Type: GrantFiled: May 26, 1999Date of Patent: October 3, 2000Assignee: Clariant Finance (BVI) LimitedInventor: Rainer Nusser
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Patent number: 6068687Abstract: Azo dyes of formula (4) ##STR1## wherein A, R.sub.4, M and m 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: November 19, 1998Date of Patent: May 30, 2000Assignee: Ilford Imaging Switzerland GmbHInventors: Kurt Baettig, Gerald Jan
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Patent number: 5993525Abstract: A recording liquid is disclosed comprising an aqueous medium and at least one dye selected from the dyes of which free acid form is represented by the following formula (I): ##STR1##Type: GrantFiled: March 12, 1998Date of Patent: November 30, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hideo Sano, Masahiro Yamada
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Patent number: 5929215Abstract: Compounds of Formula I ##STR1## wherein the substituents are as defined in the description, a process of manufacture thereof and a process of dyeing employing said compounds.Type: GrantFiled: July 7, 1998Date of Patent: July 27, 1999Assignee: Clariant Finance (BVI) LimitedInventor: Reinhard Pedrazzi
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Patent number: 5844100Abstract: There is described novel azo dyes of formula (4) with high water solubility for use in aqueous inks, particularly for ink jet recording, which provide images having high water, smudge and light resistance ##STR1## wherein n, m are each independently 2 to 6;R is hydrogen or an aliphatic radical having from 1 to 6 atoms;M is hydrogen, a metal atom, preferentially an alkali metal, an ammonium or ammonium substituted with alkyl, alkoxyalkyl or hydroxyalkyl each having 1 to 12 C atomsandF represents a mono-azo or a poly-azo dye residue.Type: GrantFiled: September 11, 1997Date of Patent: December 1, 1998Assignee: Ilford Imaging Switzerland GmbHInventor: Kurt Baettig
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Patent number: 5824785Abstract: 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: October 20, 1998Assignee: Ilford Imaging Switzerland GmbHInventors: Kurt Baettig, Gerald Jan
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Patent number: 5792222Abstract: Process for dyeing natural or synthetic polyamide fiber materials, which comprises dyeing these fiber materials with at least one anionic acid dye of the formula ##STR1## and treating the fiber material mentioned, during or after the dyeing process, with a colorless fixing agent which contains sulfo or sulfato groups and contains at least two fiber-reactive groups, whereR.sub.1 and R.sub.2 independently of one another are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,X.sub.1 is substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, or the radical of the formula --N(R.sub.2)--X.sub.1 is a ring, which may contain further heteroatoms,Y.sub.1 is a radical of the formula ##STR2## in which B.sub.1 is a colorless organic bridge member,R.sub.3 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl andR.sub.4 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, andA.sub.Type: GrantFiled: March 3, 1997Date of Patent: August 11, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Marie Adam, Jean-Pierre Bacher, Francine Casi
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Patent number: 5786459Abstract: Compounds of the formula (I) ##STR1## have been found which are suitable for dyeing and printing hydroxyl- and/or amido-containing substrates, in particular for printing paper by the ink-jet method.Type: GrantFiled: July 5, 1996Date of Patent: July 28, 1998Assignee: Bayer AktiengesellschaftInventors: Frank-Michael Stohr, Peter Wild
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Patent number: 5772745Abstract: A monoazo compound of the Formula (1) and salts thereof: ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3, independently, represents H, halogen, alkyl, alkoxy or acylamino, or R.sup.1 and R.sup.2 together form an optionally substituted benzo ring; L.sup.1 represents --OR.sup.4 , --SR.sub.4 or --NR.sup.5 R.sup.6 wherein each of R.sup.4, R.sup.5 and R.sup.6, independently, represents H or optionally substituted hydrocarbyl or R.sup.5 and R.sup.6 together with the attached nitrogen atom form a 5- or 6-membered ring; and L.sup.2 represents a substituted amino group selected from; ##STR2## in which either R.sup.7 is H and R.sup.8 and R.sup.9 together represent --CH.sub.2 CH.sub.2 --or R.sup.9 is H and R.sup.7 and R.sup.8 together represent --CH.sub.2 --CH.sub.2 --, ##STR3## in which X represents an optionally substituted alkylene group containing 2 or more carbon atoms and each of R.sup.10 and R.sup.Type: GrantFiled: June 12, 1997Date of Patent: June 30, 1998Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald Wynford Kenyon, Paul Wight
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Patent number: 5762653Abstract: Dye mixtures which comprise at least one dye of the formula ##STR1## and at least one dye of the formula ##STR2## in which Y.sub.1 is a radical of the formula ##STR3## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, X.sub.1, X.sub.2, X.sub.3, L, W.sub.1, B.sub.1, A.sub.1, and A.sub.3 are as defined in claim 1.The dye mixtures according to the invention are particularly suitable for dyeing or printing natural or synthetic polyamide fibre materials.Type: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Marie Adam, Jean-Pierre Bacher
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Patent number: 5759248Abstract: A monoazo compound of the Formula (1) and salts thereof: ##STR1## wherein each of R.sup.1 and R.sup.2, independently, represents H, halogen, alkyl, alkoxy or acylamino; each of R.sup.3, R.sup.4 and R.sup.5, independently, represents H or optionally substituted hydrocarbyl other than groups comprising the residue --A'NR.sup.7 R.sup.8 wherein A represents an optionally substituted alkylene group containing 2 or more carbon atoms and each of R.sup.7 and R.sup.8, independently, represents H or optionally substituted hydrocarbyl or R.sup.7 and R.sup.8 together with the attached nitrogen atom form a 5- or 6-membered ring and R.sup.6 represents an optionally substituted hydrocarbyl group not comprising the residue --A--NR.sup.7 R.sup.8 wherein A, R.sup.7 and R.sup.8 are as defined above; or R.sup.3 and R.sup.4 together with the attached nitrogen atom and/or R.sup.5 and R.sup.Type: GrantFiled: June 12, 1997Date of Patent: June 2, 1998Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald Wynford Kenyon, Paul Wight
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Patent number: 5721344Abstract: There is described novel azo dyes of formula (4) with high water solubility for use in aqueous inks, particularly for ink jet recording, which provide images having high water, smudge and light resistance ##STR1## wherein n, m are each independently 2 to 6;R is hydrogen or an aliphatic radical having from 1 to 6 atoms;M is hydrogen, a metal atom, preferentially an alkali metal, an ammonium or ammonium substituted with alkyl, alkoxyalkyl or hydroxyalkyl each having 1 to 12 C atomsandF represents a mono-azo or a poly-azo dye residue.Type: GrantFiled: July 19, 1996Date of Patent: February 24, 1998Assignee: Ilford A.G.Inventor: Kurt Baettig
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Patent number: 5713992Abstract: The present invention relates to a recording liquid characterized by comprising an aqueous medium and at least one monoazo dye selected from dyes, the free acid forms of which are represented by general formula {I}: ##STR1## (wherein R.sub.1, R.sub.2, and R.sub.3 each independently represents a substituted or unsubstituted alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, a halogen atom, a hydrogen atom, a hydroxyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted sulfamoyl group, a substituted or unsubstituted amino group, a nitro group, a sulfonic ester group, a sulfonyl group, a COOH group, or a carboxylic ester group;m represents a number of 0, 1, or 2; andR.sub.4, R.sub.5, R.sub.6, and R.sub.Type: GrantFiled: January 13, 1997Date of Patent: February 3, 1998Assignee: Mitsubishi Chemical CorporationInventors: Nobuyoshi Satoh, Takashi Hirasa, Yukichi Murata
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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: 5684139Abstract: Dyestuffs of the formula (I) ##STR1## wherein R.sup.1 and R.sup.4 independently of one another represent an acyl radical,R.sup.2 and R.sup.3 independently of one another represent hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl,X represents a bridge member which is not fibre-reactive andn and m independently of one another represent 1 or 2,are outstandingly suitable for dyeing and printing substrates containing hydroxyl and/or amide groups, in particular for printing paper by the ink-jet method.Type: GrantFiled: July 5, 1996Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Peter Wild, Karin Hassenruck, Frank-Michael Stohr
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Patent number: 5466282Abstract: Disclosed herein is a monoazo dye compound having a structural unit represented by the following formula in its molecule:--X--Y--(R.sub.1)(R.sub.2)(R.sub.3).sub.k [I]wherein Y is a 6-membered ring containing 2 or 3 nitrogen atoms, X is a linking group for bonding a main body of the dye molecule to Y, R.sub.1 is the first amino acid residue, R.sub.2 is an atomic group selected from the following group A, R.sub.3 is another atomic group selected from the following group BB, and k is a number of 0 or 1:Group A: H, OH, NH.sub.2, CN, .dbd.O and the second amino acid residue;Group BB: H, OH, NH.sub.2, CN and .dbd.O,the first and second amino acid residues being identical with or different from each other.Type: GrantFiled: May 12, 1994Date of Patent: November 14, 1995Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Osamu Nishiwaki, Takao Yamamoto, Kumiko Mafune
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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: 4968784Abstract: Disazo compounds represented by the following formula (I): ##STR1## in which R.sub.1 and R.sub.2 are hydrogen, C.sub.1-3 alkyl, C.sub.1-4 alkoxy C.sub.1-3 alkyl, phenyl C.sub.1-3 alkyl, phenoxy C.sub.1-3 alkyl, hydroxy C.sub.1-3 alkyl, cyano C.sub.1-3 alkyl, C.sub.1-4 alkoxyhydroxy C.sub.1-3 alkyl or hydroxyphenoxy C.sub.1-3 alkyl,R.sub.3 is C.sub.1-4 alkyl,R.sub.4 is methyl or ethyl,R.sub.5 is hydrogen, chlorine, methyl or methoxy,n is 2 or 3 respectivelyin the form of the free acid is disclosed and these present compounds are used for dyeing of various fibre materials, leather, wood, pulp and paper etc. in black shade and preparing of black ink for ink-jet, felt-pen and signpen etc. The present compounds have high color value, high affinity and high dyeing velocity on paper and excellent fastnesses.Type: GrantFiled: May 31, 1989Date of Patent: November 6, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hidenori Imai, Masahiro Hiraki, Yoshiaki Shimizu
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Patent number: 4931067Abstract: Method is set forth of dyeing a material comprising forming a solution having a basic salt of a water soluble dye of the formula: ##STR1## wherein n is 0 or 1;m is 0 or 1;m=1 when n=0;p=0 when m=1;p=1 when m=0;the subscripts 1 and 0 indicating, respectively, the presence and absence of the substituent subscripted;Y is CR.sub.2 COO, CR.sub.2 CR.sub.2 COO or CR.sub.2 CR.sub.2 CR.sub.2 COO;each R is independently hydrogen, methyl, ethyl, phenyl or phenyl substituted with methyl, ethyl, halo, cyano, ethynyl or nitro;G is CR, CR.sub.2 CR, CRCR.sub.2, CR.sub.2 CR.sub.2 CR, CR.sub.2 CRCR.sub.2 or CRCR.sub.2 CR.sub.2 ;E is OH, SH or NH.sub.Type: GrantFiled: March 27, 1987Date of Patent: June 5, 1990Assignee: SRI InternationalInventor: Ronald Swidler
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Patent number: 4875903Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano or C.sub.1-4 alkoxy,each of X.sub.1 and X.sub.3 is independently halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, phenoxy, amino or an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group,each of X.sub.2 and X.sub.4 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group containing at least one protonatable nitrogen atom or quaternary ammonium group,m is 0 or 1, andeach of n.sub.1 and n.sub.2 is independently 0 or 1, with the proviso that n.sub.1 +n.sub.2 is 1 or 2,wherein each halo is independently fluoro, chloro or bromo, with the provisos that (1) the total number of basic and cationic groups present as X.sub.1 -X.sub.Type: GrantFiled: June 5, 1987Date of Patent: October 24, 1989Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4840642Abstract: Compounds of the formula ##STR1## and salts thereof, useful for dyeing and printing hydroxy group - or nitrogen-containing organic substrates, for example, leather and fibrous materials containing or consisting of natural or synthetic polyamides or natural or regenerated cellulose; preferably textile material containing or consisting of cotton which is preferably dyed using the exhaust dyeing method.Type: GrantFiled: September 4, 1987Date of Patent: June 20, 1989Assignee: Sandoz Ltd.Inventors: Gunther Auerbach, Helmut A. Moser
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Patent number: 4839468Abstract: Triazine compounds which in their betaine form correspond to the formula ##STR1## wherein Y denotes hydrogen or the radical of an azo dye-stuff,R denotes hydrogen or alkyl,Ar denotes arylene,Z denotes halogen, hydroxyl, alkoxy, alkyl, aryl or an amino group which may be monosubstituted or disubstituted,m denotes 0 or 1 andX.sup.(+) denotes an ammonium groupamd whereimthe cyclic and acyclic radicals can carry further substituents,are used for dyeing/coloring natural and synthetic substrates and compositions, in particular paper.Type: GrantFiled: November 13, 1984Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
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Patent number: 4777248Abstract: 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;X is the residue of a diazotisable amineY is NR.sup.1 R.sup.2 or non-chromophoric groups OR.sup.3 or NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are independently selected from H, alkyl and aryl, andZ is: ##STR2## wherein M is a monovalent cation, and an ink containing the dye suitable for use in an ink jet printing process.Type: GrantFiled: December 27, 1985Date of Patent: October 11, 1988Assignee: Imperial Chemical Industries PLCInventor: Greenwood, David
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Patent number: 4771129Abstract: An azo compound of the formula: ##STR1## wherein M.sub.1, M.sub.2 and M.sub.3 are, the same or different, each a hydrogen atom, an alkali metal atom, an ammonium group or an organic ammonium group; R.sub.1 and R.sub.2 are, the same or different, each a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group, a halogen atom or a hydrogen atom; m is 1 or 2; and X and Y are, the same or different, each a C.sub.6 -C.sub.18 alkylamine, alkoxyalkylamine, arylamine, aralkylamine, alkanolamine or alkarylamine residue, which is useful as a magenta color dyestuff for an aqueous ink composition, particularly for ink jet recording.Type: GrantFiled: March 13, 1986Date of Patent: September 13, 1988Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, LimitedInventors: Hideo Kawashita, Mitsuhiro Ota
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Patent number: 4764175Abstract: Metal-free compounds of the formula, ##STR1## and 1:1 copper complexes of metallizable metal-free compounds of said formula and internal and external salts of metal-free compounds of said formula and of 1:1 copper complexes of metallizable metal-free compounds of said formula, whereineach Q is independently linear or branched C.sub.2-6 alkylene; linear or branched C.sub.2-6 alkylene interrupted by --O--, --S-- or --NR.sub.4 --; linear or branched C.sub.3-6 alkylene monosubstituted or disubstituted by hydroxy or --*NHCO--CH.sub.2 --, wherein the * denotes the atom attached to the --NR.sub.4 -- radical,each R.sub.1 is independently hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, --SO.sub.2 NR.sub.3 R.sub.4, --CONR.sub.4 --C.sub.6 H.sub.5 or benzamido,R.sub.2 is hydrogen, hydroxy, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NHCONR.sub.3 R.sub.4,X is --NR.sub.5 R.sub.6 or --N.sup..sym. R.sub.7 R.sub.8 R.sub.9 An.sup..crclbar.Type: GrantFiled: August 15, 1986Date of Patent: August 16, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4757137Abstract: Azo dyestuffs of the formula ##STR1## wherein R.sub.1 denotes acyl,R.sub.2 denotes hydrogen, fluorine, chlorine or trifluoromethyl,R.sub.3 denotes hydrogen, optionally substituted C.sub.1 -C.sub.4 -alkyl, cyclohexyl or optionally substituted phenyl andR.sub.4 denotes hydrogen or C.sub.1 -C.sub.4 -alkyl groupare suitable for dyeing natural and synthetic fibre materials, for example for dyeing wool or polyamide fibres, in level read to violet shades with very good fastnesses to light, wet processing and perspiration, the color yield being good.Type: GrantFiled: September 22, 1983Date of Patent: July 12, 1988Assignee: Bayer AktiengesellschaftInventors: Gerhard Wolfrum, Erich Klauke, Hans-Gunter Otten
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Patent number: 4742160Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof, and salts of the metal-free compounds and 1:1 and 1:2 metal complexes, whereR is hydrogen, --SO.sub.3 H or --NR.sub.5 R.sub.6 ;R.sub.a is hydrogen or --NR.sub.5 R.sub.6 ;R.sub.1 is hydrogen, halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --SO.sub.3 H;R.sub.3 is hydrogen or C.sub.1-4 alkyl;R.sub.4 is halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, --NH.sub.2, an aliphatic, cycloaliphatic or aromatic amino group, a heterocyclic amino group containing 1 to 3 hereto atoms or a hydrazino group,R.sub.5 is hydrogen or C.sub.1-4 alkyl; andR.sub.6 is an organic radical, are useful as cationic dyes for dyeing and printing fibers, threads and textile materials comprising, for example, a natural or regenerated cellulosic material such as cotton, a modified synthetic polyamide or polyester, and a homo- or co-polymer of acrylonitrile or 1,1-dicyanoethylene, bast fibers such as hemp and particularly paper and leather.Type: GrantFiled: February 28, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4705528Abstract: 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 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;q is 1/2 or 1p is 1 or 2L is a transition metal capable of complexing with a dyeM is H, ammonium, or a monovalent metal;Q is H or SO.sub.3 MT is H or C.sub.1-4 -alkyl;D is a substituted azo group;B, E & F are H or substituents;X is NR.sup.1 R.sup.2, NR.sup.3 R.sup.4, --NR.sup.3 --Z--NR.sup.4 --, Or.sup.3, or the residue of a mono- or bis-azo chromophore comprising benzene, naphthalene or mono- or bi- cyclic heteroaryl diazo and coupling components, linked to the triazine nucleus through a primary or secondary amine linking group, wherein R.sup.3 & R.sup.Type: GrantFiled: August 12, 1985Date of Patent: November 10, 1987Assignee: Imperial Chemical Industries PLCInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood