Chalcogen Bonded Directly To The Sulfonyl Group Patents (Class 540/132)
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Publication number: 20140366285Abstract: A coloring composition for textile printing including a dye represented by Formula (X) and water are provided [in Formula (X), each of X21 to X24 independently represents an oxygen atom or a sulfur atom; each of R21 to R24 represents an alkyl group, an aryl group, or a heteroaryl group; M represents a hydrogen atom, a metal element, a metal oxide, a metal hydroxide, or a metal halide; each of P1 to P4 independently represents an aromatic ring, and the aromatic ring may have a particular substituent; each of n21 to n24 independently represents from 0 to 4, and the sum of n21 to n24 is at least 1; provided that, the structure of Formula (X) contains at least two ionic hydrophilic groups].Type: ApplicationFiled: August 29, 2014Publication date: December 18, 2014Inventors: Hiromi KOBAYASHI, Yoshiaki KONDOU, Yoshiharu YABUKI, Kazunari YAGI
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Patent number: 8808439Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.Type: GrantFiled: July 31, 2009Date of Patent: August 19, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8795422Abstract: The present disclosure includes naphthalocyanine dyes or fused naphthalocyanine dyes represented by one of the general structures I to XV; inkjet ink formulations including the naphthalocyanine dyes; and a detection system (300) including the dyes.Type: GrantFiled: August 31, 2009Date of Patent: August 5, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
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Patent number: 8784548Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and, optionally, a metal atom complexed thereto and, if present, having a valency of from 1 to 5, with two valencies complexed to the phthalocyanine ring or the naphthalocyanine ring. Each unit has two linker moieties on opposite sides or adjacent sides of the unit, wherein water-soluble groups are present on at least one of the linkers, on the metal atom, and optionally on the phthalocyanine or naphthalocyanine moiety.Type: GrantFiled: July 31, 2009Date of Patent: July 22, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8206496Abstract: Mixed phthalocyanine and naphthalocyanine water-soluble dyes with near-infrared absorption comprise four isoindole units linked together in a large ring to form a phthalocyanine macrocycle. At least one benzene ring is linked to an isoindole unit and at least one naphthalene ring is linked to another isoindole unit. The remaining two isoindole units each have a benzene ring or a naphthalene ring linked thereto, in any combination. A metal atom is optionally complexed to the phthalocyanine macrocycle.Type: GrantFiled: September 22, 2009Date of Patent: June 26, 2012Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8202358Abstract: Phthalocyanine dyes, naphthalocyanine dyes, and/or bridged phthalocyanine/naphthalocyanine dyes represented by one of the general structures I to XVII, inkjet ink formulation comprising said dyes, and detection systems using said dyes are disclosed and described.Type: GrantFiled: October 2, 2009Date of Patent: June 19, 2012Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
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Publication number: 20120137928Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.Type: ApplicationFiled: July 31, 2009Publication date: June 7, 2012Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Publication number: 20120139994Abstract: The present disclosure includes naphthalocyanine dyes or fused naphthalocyanine dyes represented by one of the general structures I to XV; inkjet ink formulations including the naphthalocyanine dyes; and a detection system (300) including the dyes.Type: ApplicationFiled: August 31, 2009Publication date: June 7, 2012Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
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Publication number: 20120121868Abstract: A process for preparing phthalocyanine, azaphthalocyanine, metallo-phthalocyanine or metallo-azaphthalocyanine dyes and salts thereof. Also novel compounds, inks, printing processes, printed materials and ink jet cartridges.Type: ApplicationFiled: May 26, 2010Publication date: May 17, 2012Applicant: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel
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Patent number: 7964719Abstract: An inkjet ink for use in netpage, Hyperlabel and other applications. The ink includes an IR-absorbing dye of formula (I): wherein M is Ga(A1); A1 is an axial ligand selected from —OH, halogen, —OR3, —OC(O)R4, a hydrophilic ligand and/or a ligand suitable for reducing cofacial interactions; R1 and R2 may be the same or different and are selected from hydrogen or C1-12 alkoxy; R3 is selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); R4 is selected from C1-12 alkyl, C5-12 aryl or C5-12 arylalkyl; Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy; W is a hydrophilic group, each W group being independently selected from a substituent including a sulfonic acid group (including salts thereof), or a substituent comprising a sulfonamide group; n1 is 0, 1, 2 or 3; n2 is 0, 1, 2 or 3; n3 is 0, 1, 2 or 3; n4 is 0, 1, 2 or 3; and at least one of n1, n2, n3 or n4 is greater than 0.Type: GrantFiled: October 20, 2006Date of Patent: June 21, 2011Assignee: Silverbrook Research Pty LtdInventors: Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Sutharsiny Indusegaram, Kia Silverbrook, Paul Lapstun
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Publication number: 20100193777Abstract: A method of producing a desubstituted compound, including: applying an external stimulation to a compound A-(B)m having a solvent-soluble group B (wherein A represents a residue of a solvent-insoluble compound, B represents a specific solvent-soluble group, and m represents a natural number, and the solvent-soluble group B bonds to a carbon atom of the residue A of a solvent-insoluble compound), to cause desubstitution of the solvent-soluble group B, and converting the compound to a solvent-insoluble compound to which a hydrogen atom bonds in place of the solvent-soluble group B; a method of producing an organic semiconductor film, including: forming a film of a ?-conjugated compound having a substituent represented by formula (2-I), on a substrate; and causing desubstitution of the substituent from the compound; and an organic semiconductor film and an organic electronic device each obtained by these methods: wherein R11 represents a substituent other than a hydrogen atom.Type: ApplicationFiled: September 9, 2008Publication date: August 5, 2010Inventors: Keita Takahashi, Tetsu Kitamura, Tetsuya Watanabe
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Patent number: 7658792Abstract: There is provided an IR-absorbing naphthalocyanine dye of formula (I): wherein M is Ga(A1); A1 is an axial ligand selected from —OH, halogen, —OR3, —OC(O)R4 or —O(CH2CH2O)eRe wherein e is an integer from 2 to 10 and Re is H, C1-8 alkyl or C(O)C1-8 alkyl; R1 and R2 may be the same or different and are selected from hydrogen or C1-12 alkoxy; R3 is selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); R4 is selected from C1-12 alkyl, C5-12 aryl or C5-12 arylalkyl; Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy; and each B is independently selected from a base, wherein BH+ has a pKa of between 4 and 9. The dye is suitable for use in IR-absorbing inkjet inks, providing compatibility with known CMYK inks together with an optimally red-shifted ?max.Type: GrantFiled: July 10, 2006Date of Patent: February 9, 2010Assignee: Silverbrook Research Pty LtdInventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
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Patent number: 7544236Abstract: A compound of Formula (1) in the free acid or salt form: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of formula; each R1 and R2 independently is H, optionally substituted alkyl or optionally substituted aryl; each R3 independently is optionally substituted alkyl or optionally substituted aryl; each n independently is 1 or 2; x is 0 to 2; y is 0.1 to 2.5; x is 0.1 to 2.5; and the sum (x+y+z) is 2.2 to 4. Also compositions, ink jet printer inks, cartridges and processes and printed materials.Type: GrantFiled: October 21, 2005Date of Patent: June 9, 2009Assignee: Fujifilm Imaging Colorants LimitedInventors: John Mayall, Prakash Patel
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Patent number: 7541457Abstract: Disclosed herein are novel trisulfonated tribenzo-mononahptho-porphyrazines, processes for making them and their application as improved photosensitizing drugs for the treatment of various medical conditions by photodynamic therapy (PDT). These water-soluble amphiphilic porphyrazines are substituted with different alkylyl, aryl, aminoalkyl and aminoaryl groups, with or without carboxyl moeity.Type: GrantFiled: May 14, 2004Date of Patent: June 2, 2009Assignee: Universite de SherbrookeInventors: Johannes E. Van Lier, Haroutioun Minas Hasséssian, Hongjian Tian, Nicole Cauchon, Hasrat Ali
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Patent number: 7459016Abstract: A method for the production of a phthalocyanine pigment preparation includes finely distributing a crude phthalocyanine pigment by dry milling, wet milling, salt kneading, acid pasting or acid swelling to give a pre-pigment, the pre-pigment is subjected to a finishing treatment in a mixture of water and an organic solvent at alkaline pH, increased temperature and in the presence of at least one pigment dispersant from the group of phthalocyanine sulphonic acids, phthalocyanine carboxylic acids, phthalocyanine sulphonate salts, phthalocyanine carboxylate salts and phthalocyanine suiphonamides.Type: GrantFiled: November 27, 2003Date of Patent: December 2, 2008Assignee: Clariant Produkte (Deutschland) GmbHInventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
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Publication number: 20080110369Abstract: A compound of Formula (1) in the free acid or salt form: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of formula; each R1 and R2 independently is H, optionally substituted alkyl or optionally substituted aryl; each R3 independently is optionally substituted alkyl or optionally substituted aryl; each n independently is 1 or 2; x is 0 to 2; y is 0.1 to 2.5; x is 0.1 to 2.5; and the sum (x+y+z) is 2.2 to 4. Also compositions, ink jet printer inks, cartridges and processes and printed materials.Type: ApplicationFiled: October 21, 2005Publication date: May 15, 2008Inventors: John Mayall, Prakash Patel
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Publication number: 20080108593Abstract: An allergen decomposer which contains as an active ingredient a derivative of metal phthalocyanine represented by the following formula (I) (M is a metal selected among iron, cobalt, manganese, titanium, vanadium, nickel, copper, zinc, molybdenum, tungsten, and osmium).Type: ApplicationFiled: March 29, 2004Publication date: May 8, 2008Applicants: Shinshu TLO Co., Ltd, Daiwabo Co., Ltd.Inventors: Hirofusa Shirai, Seigo Higaki, Hisanaga Tsuiki, Yasuji Sugihara
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Patent number: 7022171Abstract: A process for coloration of a substrate comprising applying thereto by means of an ink-jet printer an ink composition comprising a compound of Formula (1) or salt thereof: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc is a phthalocyanine nucleus of Formula (2); each R1 and R2 independetly are H, C1-4alkyl or C1-4hydroxyalkyl; R3 is phenyl carrying 1 or 2 sulpho substituents or phenyl carrying at least 1 carboxy or 1 phosphato substituent and having further optional substituents; x, y and z are all greater than 0 and the sum of (x+y+z) is 2 to 5.Type: GrantFiled: February 27, 2003Date of Patent: April 4, 2006Assignee: Avecia LimitedInventors: Prakash Patel, Tina Margaret Horrobin
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Patent number: 6444807Abstract: The invention relates to phthalocyanine compounds and are represented by the formula: The compounds are used as a colorant and a pigment precursor, especially in light-sensitive compositions for color filters.Type: GrantFiled: March 12, 2001Date of Patent: September 3, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Annemarie Wolleb, Heinz Wolleb, Gerardus De Keyzer, Barbara Wagner
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Patent number: 6087492Abstract: This invention relates to a phthalocyanine or its metal complex of a divalent metal, oxometal, halogenometal or hydroxymetal, which comprises at least one unsubstituted or substituted formyl, carbonyl, hydroxymethyl or carboxyl group which as attached at the peripheral carbon skeleton.These phthalocyanines or their derivatives are used in recording layers of optical recording media.There is also claimed a novel process for the preparation of some of these compounds corresponding to formula III ##STR1## wherein M is a divalent metal, oxometal, halogenometal or hydroxymetal, or 2 hydrogen atoms,X is halogen, or 2 X in vicinal position on a phenyl ring form together a --C.dbd.C--C.dbd.C-- bridge so that an additional phenyl ring is obtained,Y is --OR.sub.1, --OOC--R.sub.2, --NHR.sub.1, --N(R.sub.1)R.sub.2 or --SR.sub.Type: GrantFiled: February 9, 1999Date of Patent: July 11, 2000Assignee: Ciba Specialty Chemicals CorporationInventor: Heinz Wolleb
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Patent number: 5739318Abstract: The present invention relates to labelling agents comprising non-proteinaceous boronic acid conjugates having absorption maxima at not less than 600 nm, said label being provided by e.g., an azine, triphenylmethane, cyanine or phthalocyanine dye. The labelling agents are useful in the estimation and quantification of cisdiols such as glycosylated haemoglobin, by virtue of the substantially total absence of overlap with the absorption spectrum of haemoglobin. Oxazine and thiazine dyes exhibiting similar absorption characteristics and containing other activated moieties are similarly useful labelling agents, especially in the presence of haemoglobin.Type: GrantFiled: July 12, 1993Date of Patent: April 14, 1998Assignee: Axis Research ASInventors: Frank Frantzen, Erling Sundrehagen
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Patent number: 5534055Abstract: This invention relates to a process for preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments comprising(a) acid pasting or acid swelling a crude metal phthalocyanine pigment;(b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment in the presence of 5 to 50 parts by weight of a stabilizer per 100 parts by weight of the crude metal phthalocyanine pigment until the average particle size is reduced to less than about 0.5 .mu.m;(c) finishing the milled metal phthalocyanine pigment by thoroughly mixing said milled metal phthalocyanine pigment with a finishing solvent mixture comprising 3 to 6 parts by weight, relative to the crude metal phthalocyanine pigment, of water and 0.4 to 1.Type: GrantFiled: August 24, 1994Date of Patent: July 9, 1996Assignee: Bayer CorporationInventors: Herman Gerson, Abdul Sattar
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Patent number: 5438135Abstract: Water-soluble tetraazaporphins with novel structure is suitable as a fluorochrome for labeling and provides a reagent usable for fluorescence analysis process.Type: GrantFiled: March 5, 1992Date of Patent: August 1, 1995Assignee: Hitachi Chemical CompanyInventors: Seiji Tai, Mitsuo Katayose, Hiroo Watanabe
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Patent number: 5346670Abstract: Red-shifted, water-soluble, fluorescent, monomerically-tetherable derivatives having the formula: ##STR1##wherein, M represents either H.sub.2 or is selected from among the following metals: aluminum, silicon, phosphorus, gallium, germanium, cadmium, scandium, magnesium, tin, and zinc. Each R.sub.1 is independently selected from --XYW, --YW, and --W. X represents either a carbon, or heteroatom selected from among oxygen, nitrogen, sulfur, phosphorus, silicon, and selenium; Y represents a linking group; and W represents a water solubilizing group. The substituent R.sub.2 is selected from among --A, --Y'A, --XA, and --XY'A, where A denotes a biological entity such as an antibody, antibody fragment, nucleotide, nucleic acid probe, antigen, oligonucleotide, deoxynucleotide, dideoxynucleotide, avidin, streptavidin or membrane probe, or R.sub.2 is a reactive or activatable group suitable for conjugating to a biological entity.Type: GrantFiled: June 8, 1992Date of Patent: September 13, 1994Assignee: British Technology Group U.S.A. Inc.Inventors: George E. Renzoni, Deborah C. Schindele, Louis J. Theodore, Clifford C. Leznoff, Karen L. Fearon, Barry V. Pepich
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Patent number: 5319074Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.Type: GrantFiled: January 24, 1992Date of Patent: June 7, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
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Patent number: 5302708Abstract: Phthalocyanine dyes, in particular copper phthalocyanine and nickel phthalocyanine dyes which contain one or more groups of the formula given and defined below ##STR1## or one or more carboxy groups or both groups and which furthermore can contain one or more sulfo groups, customary sulfonamide groups and/or groups of the formula given and defined below ##STR2## dye hydroxy- and/or carboxamide-containing materials, in particular fiber materials, such as cellulose fiber materials, wool and polyamide fibers, in fast, predominantly green hues of high color strength.Type: GrantFiled: August 6, 1992Date of Patent: April 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
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Patent number: 5278292Abstract: Water-soluble fiber-reactive dyes are described conforming to the below-indicated formula (1) which are capable of dyeing hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fiber materials, in strong, fast shades. ##STR1## in which F is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, triphenoldioxazine, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, formazan, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye;R.sup.x is hydrogen or alkyl of 1 to 4 carbon atoms;R is hydrogen, sulfo, carboxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or chlorine;w is 1, 2, 3 or 4;Y is vinyl or an ethyl group which contains in the .beta.-position a substituent which is eliminable by alkali to form a vinyl group;n is 1 or 2.Type: GrantFiled: July 17, 1992Date of Patent: January 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Rolf Gleissner, Gunther Schwaiger
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Patent number: 5231171Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where Rg is a radical of the formula ##STR2## Ar is the radical of a benzene or naphthalene ring, Z.sup.1 and Z.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,Z.sup.3, Z.sup.4 and Z.sup.5 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl,U is a group which is detachable under alkaline reaction conditions,X is in case a) the radical of a chromophore or in case b) the radical of a coupling component to which may additionally be attached, via an azo bridge, the radical of a diazo component and which may have additional reactive groups, andL is in case a) a bridge member or in case b) an azo bridge.Type: GrantFiled: December 13, 1991Date of Patent: July 27, 1993Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
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Patent number: 5210187Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.Type: GrantFiled: April 9, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
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Patent number: 5135972Abstract: Colorants and compositions containing the same, including polymeric substrates, especially polyurethane foams which are tinted or deeper colored with the colorants which have the general formula: ##STR1## wherein R.sub.2 is selected from hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted or unsubstituted; Z is an arylene moiety; each D or D' is selected from a covalent bond or a linking group consisting of or containing at least one of --O--, --S--, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloaliphatic or aryl, and R.sub.3 is R.sub.Type: GrantFiled: July 15, 1991Date of Patent: August 4, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, Max A. Weaver
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Patent number: 5084068Abstract: Compounds of the formula ##STR1## and mixtures thereof, whereineach Mt is independently copper, nickel or cobalt,each Pc is the phthalocyanine radical,each R.sub.4 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy,each R.sub.5 and R.sub.6 is independently C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by halo, cyano, hydroxy or phenyl; or C.sub.5-6 cycloalkyl,each W.sub.1 is independently --A--.sup..sym. NR.sub.1 R.sub.2 R.sub.3 An.sup..crclbar. or --A--NR.sub.2 R.sub.3, wherein R.sub.1 is hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by halo, cyano, hydroxy or phenyl; or C.sub.5-6 cycloalkyl, andeach of R.sub.2 and R.sub.3 is independently C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by halo, cyano, hydroxy or phenyl; or C.sub.Type: GrantFiled: February 23, 1990Date of Patent: January 28, 1992Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5023325Abstract: A reactive dye of the formulaD--U--R).sub.nin which D is the radical of an anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is a polymethylene radical having 1 to 6 C atoms or its branched isomers; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl;or a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: May 11, 1988Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
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Patent number: 5015735Abstract: A process for the preparation of a copper phthalocyanine pigment which comprises adding a dry ground mixture of crude copper phthalocyanine containing 0.1 to 20% by weight of a crystal growth inhibitor to a 50 to 90% by weight aqueous solution of sulfuric acid to obtain a sulfuric acid slurry of the dry ground mixture, adding water to the slurry to form a precipitate and recovering it to obtain pigment grade copper phthalocyanine. The copper phthalocyanine pigment prepared according to the present invention is usable in coating materials, inks or plastics.Type: GrantFiled: December 4, 1989Date of Patent: May 14, 1991Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato
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Patent number: 4968782Abstract: Reactive dyes of the formula ##STR1## in which D is the radial of an anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; Q is hydrogen or alkyl which has 1 to 4 carbon atoms and can be substituted by carboxyl, sulfo, cyano, hydroxyl, C.sub.1- C.sub.4 alkoxy or halogen; B is a radical --CH.sub.2n, --O--CH.sub.2n or --NH --CH.sub.2n and n is 1 to 6; R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl; alk is an alkylene radical having 1 to 6 C atoms or branched isomers thereof; Y is hydrogen, chlorine, bromine, flourine, hydroxyl, sulfato, acyloxy having 1 to 4 C atoms, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.Type: GrantFiled: October 13, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
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Patent number: 4952688Abstract: Phthalocyanine compounds having fiber-reactive dye properties which dye hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as cellulose fibers, wool and synthetic polyamide fibers, in fast and deep shades and which conform to the general formula (1) ##STR1## where Pc is the radical of copper- or nickel-phthalocyanine whose benzene nuclei can be substituted by chlorine or phenyl,R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms which can be substituted by a hydroxy, sulfato, cyano or sulfo group,M is a hydrogen atom or one equivalent of a salt-forming metal, preferably a hydrogen atom or an alkali metal,Y is a vinyl group or preferably a .beta.-sulfatoethyl group,R.sup.1 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms which can be substituted, andR.sup.2 has one of the meanings of R.sup.1 and is identical to R.sup.1 or different from R.sup.1 or --NR.sup.1 R.sup.Type: GrantFiled: August 17, 1988Date of Patent: August 28, 1990Assignee: Hoechst AktiengesellschaftInventor: Hartmut Springer
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Patent number: 4845209Abstract: The invention relates to phthalocyanine compounds of the formula ##STR1## wherein MePc is a copper, cobalt or nickel phthalocyanine radical,R.sub.1 is hydrogen or alkyl,X is alkylene, andR.sub.2, R.sub.3 and R.sub.4, are each independently alkyl which is unsubstituted or substituted by hydroxy, alkoxy, phenyl or amino, or R.sub.1 and R.sub.2, when taken together, are methylene, ethylene or propylene if X is methylene or ethylene, or two or three of R.sub.2, R.sub.3 and R.sub.3, together with the nitrogen atom, form a 5- to 7-membered unsubstituted or substituted heterocyclic ring which may contain one or two additional hetero atoms selected from the group consisting of O, N and S as ring members,An.sup..crclbar. is a cation and M is a cation, and x is greater than y and y is greater than 0, and the sum of x+y is 4 or less than 4.These compounds can be used as dyes, in particular for dyeing and printing cellulosic materials and polyacrylonitrile materials, especially paper.Type: GrantFiled: August 4, 1988Date of Patent: July 4, 1989Inventor: Jean-Marie Adam
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Patent number: 4824948Abstract: A phthalocyanine compound of the formula:(R--X--).sub.m Pc (--Y--R.sup.1 --Z--).sub.n (--SO.sub.3 M).sub.p IwhereinPc is a phthalocyanine nucleus (Pc);eachR independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X;X selected from S, Se and Te;m is 4 to 16;eachR.sup.1 independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z;Y is selected from S, NT, Se and Te;Z is selected from S, Se, Te, NT and O;T is selected from H, alkyl and aryl;n is 0 to 7;M is H, a metal or optionally-substituted ammonium;andP is from 1 to 16.The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media.Type: GrantFiled: March 1, 1988Date of Patent: April 25, 1989Assignee: Imperial Chemical Industries plcInventors: William Stark, Nigel Hughes, Donald M. Gunn
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Patent number: 4801694Abstract: Reactive dyes of the formula ##STR1## in which D is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthrone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, X is a substituent which is detachable as an anion, B is a radical of the formula ##STR2## R.sub.1 and R.sub.2, independently of each other, are hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl or phenyl, A is a substituted or unsubstituted aliphatic or aromatic bridge member, Y is a --CO--Z or --SO.sub.2 --Z radical, Z is an aliphatic, aromatic or heterocyclic reactive radical, and n is 1 or 2, are suitable for dyeing or printing cellulose-containing and nitrogen-containing materials and in high dyeing yield produce dyeings and prints having good fastness properties.Type: GrantFiled: July 13, 1987Date of Patent: January 31, 1989Assignee: Ciba-Geigy CorporationInventors: Peter Scheibli, Karl Seitz, Herbert Seiler, Athanassios Tzikas
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Patent number: 4745187Abstract: Water-soluble phthalocyanine dyestuffs having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups are prepared by reaction of phthalocyanine sulfonyl chlorides, which may contain sulfo groups, with a primary or secondary amine having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups and, if appropriate, with a second primary or secondary amine of the aliphatic, heterocyclic or aromatic series, in the presence of a pyridinesulfonamide or pyridinecarboxamide.Type: GrantFiled: January 29, 1987Date of Patent: May 17, 1988Assignee: Hoechst AktiengesellschaftInventor: Hartmut Springer
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Patent number: 4668774Abstract: Novel dye salts of anionic dyes of the general formula I ##STR1## where F is a radical of an anionic dye, n is 1, 2, 3 or 4, and B.sup.1 and B.sup.2 independently of one another are each unsubstituted or substituted branched alkyl or alkyl-substituted cycloalkyl having a total of 10 to 36 carbon atoms, are very useful for dyeing solvents, printing inks or polymeric film-forming materials.Type: GrantFiled: April 23, 1985Date of Patent: May 26, 1987Assignee: BASF AktiengesellschaftInventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
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Patent number: 4652635Abstract: A method for converting ether groups such as alkyl or aryl ether groups including hydroquinone ether groups to hydroxyl groups and ester groups such as alkyl or aryl ester groups to carboxylic acid groups which comprises reacting a compound including at least one ether and/or ester group with a 2-halo-1,3,2-benzodioxaborole to form an intermediate and hydrolyzing the intermediate such as by quenching it into water to form the desired final product.Type: GrantFiled: June 15, 1984Date of Patent: March 24, 1987Assignee: Polaroid CorporationInventor: Patrick F. King
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Patent number: 4648992Abstract: Novel phthalocyanine compounds are described, which have the formula ##STR1## in which MePc is the Si(IV)-, P(V)-, Ti(IV)-, Ge(IV)-, Cr(IV)-, Ga(III)-, Zr(IV)-, In(III)-, Sn(IV)- or Hf(IV)- phthalocyanine or -naphthalocyanine ring system, A is an anionic, nonionic or cationic group which imparts solubility in water, Z is the counter-ion to A, if the latter is an ionic group, and is 0 if A is a nonionic group, n is any desired number from 1 to 8, Y is a neutral substituent which does not impart solubility in water and p is any desired number from 0 to 6, it being possible for the groups AZ and Y present in the molecule to be identical or different in either case, and the sum of n+p being not more than 8 and MePc not being the Sn(IV)-phthalocyanine or Sn(IV)-naphthalocyanine ring system if p is 0 and if the only groups imparting water-solubility in the molecule are sulfo groups.Type: GrantFiled: February 11, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventors: Gregor Graf, Gerd Holzle, Gerhard Reinert
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Patent number: RE35145Abstract: A phthalocyanine compound of the formula:(R--X--).sub.m Pc(--Y--R.sup.1 --Z--).sub.n (--SO.sub.3 M).sub.p IwhereinPc is a phthalocyanine nucleus (Pc);eachR independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X;X selected from S, Se and Te;m is 4 to 16;eachR.sup.1 independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z;Y is selected from S, NT, Se and Te;Z is selected from S, Se, Te, NT and O;T is selected from H, alkyl and aryl;n is 0 to 7;M is H, a metal or optionally-substituted ammonium;andP is from 1 to 16.The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media.Type: GrantFiled: October 25, 1993Date of Patent: January 9, 1996Assignee: Zeneca LimitedInventors: William Stark, Nigel Hughes, Donald M. Gunn