Chalcogen Bonded Directly To The Sulfonyl Group Patents (Class 540/132)
  • Publication number: 20140366285
    Abstract: 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: Application
    Filed: August 29, 2014
    Publication date: December 18, 2014
    Inventors: Hiromi KOBAYASHI, Yoshiaki KONDOU, Yoshiharu YABUKI, Kazunari YAGI
  • Patent number: 8808439
    Abstract: 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: Grant
    Filed: July 31, 2009
    Date of Patent: August 19, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8795422
    Abstract: 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: Grant
    Filed: August 31, 2009
    Date of Patent: August 5, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
  • Patent number: 8784548
    Abstract: 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: Grant
    Filed: July 31, 2009
    Date of Patent: July 22, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8206496
    Abstract: 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: Grant
    Filed: September 22, 2009
    Date of Patent: June 26, 2012
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Patent number: 8202358
    Abstract: 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: Grant
    Filed: October 2, 2009
    Date of Patent: June 19, 2012
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
  • Publication number: 20120137928
    Abstract: 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: Application
    Filed: July 31, 2009
    Publication date: June 7, 2012
    Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
  • Publication number: 20120139994
    Abstract: 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: Application
    Filed: August 31, 2009
    Publication date: June 7, 2012
    Inventors: Sivapackia Ganapathiappan, Jayprakash C. Bhatt
  • Publication number: 20120121868
    Abstract: 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: Application
    Filed: May 26, 2010
    Publication date: May 17, 2012
    Applicant: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7964719
    Abstract: 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: Grant
    Filed: October 20, 2006
    Date of Patent: June 21, 2011
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Sutharsiny Indusegaram, Kia Silverbrook, Paul Lapstun
  • Publication number: 20100193777
    Abstract: 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: Application
    Filed: September 9, 2008
    Publication date: August 5, 2010
    Inventors: Keita Takahashi, Tetsu Kitamura, Tetsuya Watanabe
  • Patent number: 7658792
    Abstract: 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: Grant
    Filed: July 10, 2006
    Date of Patent: February 9, 2010
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
  • Patent number: 7544236
    Abstract: 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: Grant
    Filed: October 21, 2005
    Date of Patent: June 9, 2009
    Assignee: Fujifilm Imaging Colorants Limited
    Inventors: John Mayall, Prakash Patel
  • Patent number: 7541457
    Abstract: 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: Grant
    Filed: May 14, 2004
    Date of Patent: June 2, 2009
    Assignee: Universite de Sherbrooke
    Inventors: Johannes E. Van Lier, Haroutioun Minas Hasséssian, Hongjian Tian, Nicole Cauchon, Hasrat Ali
  • Patent number: 7459016
    Abstract: 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: Grant
    Filed: November 27, 2003
    Date of Patent: December 2, 2008
    Assignee: Clariant Produkte (Deutschland) GmbH
    Inventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
  • Publication number: 20080110369
    Abstract: 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: Application
    Filed: October 21, 2005
    Publication date: May 15, 2008
    Inventors: John Mayall, Prakash Patel
  • Publication number: 20080108593
    Abstract: 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: Application
    Filed: March 29, 2004
    Publication date: May 8, 2008
    Applicants: Shinshu TLO Co., Ltd, Daiwabo Co., Ltd.
    Inventors: Hirofusa Shirai, Seigo Higaki, Hisanaga Tsuiki, Yasuji Sugihara
  • Patent number: 7022171
    Abstract: 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: Grant
    Filed: February 27, 2003
    Date of Patent: April 4, 2006
    Assignee: Avecia Limited
    Inventors: Prakash Patel, Tina Margaret Horrobin
  • Patent number: 6444807
    Abstract: 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: Grant
    Filed: March 12, 2001
    Date of Patent: September 3, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Annemarie Wolleb, Heinz Wolleb, Gerardus De Keyzer, Barbara Wagner
  • Patent number: 6087492
    Abstract: 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: Grant
    Filed: February 9, 1999
    Date of Patent: July 11, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Heinz Wolleb
  • Patent number: 5739318
    Abstract: 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: Grant
    Filed: July 12, 1993
    Date of Patent: April 14, 1998
    Assignee: Axis Research AS
    Inventors: Frank Frantzen, Erling Sundrehagen
  • Patent number: 5534055
    Abstract: 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: Grant
    Filed: August 24, 1994
    Date of Patent: July 9, 1996
    Assignee: Bayer Corporation
    Inventors: Herman Gerson, Abdul Sattar
  • Patent number: 5438135
    Abstract: Water-soluble tetraazaporphins with novel structure is suitable as a fluorochrome for labeling and provides a reagent usable for fluorescence analysis process.
    Type: Grant
    Filed: March 5, 1992
    Date of Patent: August 1, 1995
    Assignee: Hitachi Chemical Company
    Inventors: Seiji Tai, Mitsuo Katayose, Hiroo Watanabe
  • Patent number: 5346670
    Abstract: 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: Grant
    Filed: June 8, 1992
    Date of Patent: September 13, 1994
    Assignee: 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
  • Patent number: 5319074
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: June 7, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
  • Patent number: 5302708
    Abstract: 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: Grant
    Filed: August 6, 1992
    Date of Patent: April 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
  • Patent number: 5278292
    Abstract: 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: Grant
    Filed: July 17, 1992
    Date of Patent: January 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Rolf Gleissner, Gunther Schwaiger
  • Patent number: 5231171
    Abstract: 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: Grant
    Filed: December 13, 1991
    Date of Patent: July 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
  • Patent number: 5210187
    Abstract: 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: Grant
    Filed: April 9, 1992
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
  • Patent number: 5135972
    Abstract: 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: Grant
    Filed: July 15, 1991
    Date of Patent: August 4, 1992
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, John W. Rekers, Max A. Weaver
  • Patent number: 5084068
    Abstract: 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: Grant
    Filed: February 23, 1990
    Date of Patent: January 28, 1992
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 5023325
    Abstract: 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: Grant
    Filed: May 11, 1988
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 5015735
    Abstract: 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: Grant
    Filed: December 4, 1989
    Date of Patent: May 14, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato
  • Patent number: 4968782
    Abstract: 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: Grant
    Filed: October 13, 1989
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4952688
    Abstract: 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: Grant
    Filed: August 17, 1988
    Date of Patent: August 28, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hartmut Springer
  • Patent number: 4845209
    Abstract: 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: Grant
    Filed: August 4, 1988
    Date of Patent: July 4, 1989
    Inventor: Jean-Marie Adam
  • Patent number: 4824948
    Abstract: 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: Grant
    Filed: March 1, 1988
    Date of Patent: April 25, 1989
    Assignee: Imperial Chemical Industries plc
    Inventors: William Stark, Nigel Hughes, Donald M. Gunn
  • Patent number: 4801694
    Abstract: 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: Grant
    Filed: July 13, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Scheibli, Karl Seitz, Herbert Seiler, Athanassios Tzikas
  • Patent number: 4745187
    Abstract: 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: Grant
    Filed: January 29, 1987
    Date of Patent: May 17, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hartmut Springer
  • Patent number: 4668774
    Abstract: 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: Grant
    Filed: April 23, 1985
    Date of Patent: May 26, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Rainer Dyllick-Brenzinger
  • Patent number: 4652635
    Abstract: 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: Grant
    Filed: June 15, 1984
    Date of Patent: March 24, 1987
    Assignee: Polaroid Corporation
    Inventor: Patrick F. King
  • Patent number: 4648992
    Abstract: 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: Grant
    Filed: February 11, 1985
    Date of Patent: March 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Gregor Graf, Gerd Holzle, Gerhard Reinert
  • Patent number: RE35145
    Abstract: 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: Grant
    Filed: October 25, 1993
    Date of Patent: January 9, 1996
    Assignee: Zeneca Limited
    Inventors: William Stark, Nigel Hughes, Donald M. Gunn