Nitrogen Bonded Directly To The Sulfonyl Group Patents (Class 540/133)
  • 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: 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: 8778073
    Abstract: A phthalocyanine dye with extended conjugation includes one or both of a phthalocyanine component and a naphthalocyanine component and at least one water soluble substituent on an aryl group of the phthalocyanine dye. The extended conjugation of the phthalocyanine dye includes at least one benzene moiety of the component being one of (a) joined to an aryl group either indirectly using an alkylene linkage or directly, (b) joined to a benzene moiety of another of the components to form an oligomer of the components, and (c) a combination of (a) and (b). The extended conjugation shifts absorption of the phthalocyanine dye to greater than 800 nm.
    Type: Grant
    Filed: October 30, 2008
    Date of Patent: July 15, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Sivapackia Ganapathiappan, Zhang-Lin Zhou, Jayprakash C. Bhatt
  • Patent number: 8741264
    Abstract: Self-sterilising products, and in particular novel products comprising phthalocyanine derivatives bound to polymers, a process for the preparation of said products and their use for preparing self-sterilising industrial and medical articles or devices, are described.
    Type: Grant
    Filed: June 29, 2006
    Date of Patent: June 3, 2014
    Assignee: Molteni Therapeutics S.R.L.
    Inventors: Gabrio Roncucci, Lia Fantetti, Giacomo Chiti, Donata Dei, Carmela Alongi, Annalisa Cocchi, Valentina Paschetta
  • Patent number: 8702854
    Abstract: Azaphthalocyanine compounds of Formula (1) and salts thereof: wherein: MAzPc represents a azaphthalocyanine nucleus of formula (A): M is 2H, Cu or Ni; each P is independently CH or N; R1, R2 are independently H or optionally substituted alkyl; R3 is optionally substituted hydrocarbyl; y is greater than 0 and less than 4; z is greater than 0 and less than 4; and the sum of y+z is in the range of from 1 to 4; 15 provided that at least one P is N in any one of the four component rings of the azaphthalocyanine nucleus. Also compositions, inks, printing processes, printed materials and ink-jet cartridges.
    Type: Grant
    Filed: November 26, 2009
    Date of Patent: April 22, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Prakash Patel, Toshiki Fujiwara
  • Patent number: 8647425
    Abstract: A process for preparing azaphthalocyanine or metallo-azaphthalocyanine dyes Also novel compounds, inks, printing processes, printed materials (including color filters) and ink-jet cartridges.
    Type: Grant
    Filed: October 6, 2010
    Date of Patent: February 11, 2014
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 8591641
    Abstract: The invention is related to a weather-resistant dye and use thereof, which contains in molecules thereof not only chromophoric parent D, but also electron-accepting group Q which is linked with dye parent D through non-conjugated carbon link L to constitute D-L-Q dye molecule; the electron-accepting group Q has such a HOMO energy level that is lower than the HOMO energy level of the dye chromophoric parent D. The dye has sun-resistance and anti-ozone performances, which can be used as colorant in the ink, dope, lacquer, toner powder for laser printing, marker, paper, fabric, glass, porcelain or polymer.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: November 26, 2013
    Assignees: Dalian University of Technology, Ninestar Management Co., Ltd.
    Inventors: Xiaojun Peng, Jianzhou Zhang, Fan Jiangli, Shiguo Sun, Rong Zhang
  • Patent number: 8282722
    Abstract: A sulfonated dye salt of formula (II): wherein M is Ga(A1); A1 is an axial ligand selected from the group consisting of: —OH and halogen; and Z1+, Z2+, Z3+ and Z4+ are independently selected from the group consisting of: H and an ammonium cation including 3 or more hydroxyl groups. At least one of Z1+, Z2+, Z3+ and Z4+ is the ammonium cation. Such salts exhibit reduced kogation in thermal bubble-forming inkjet printheads.
    Type: Grant
    Filed: September 5, 2011
    Date of Patent: October 9, 2012
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Simone Charlotte Vonwiller, Sutharsiny Indusegaram, Graciel Gonzaga, Damon Donald Ridley, Kia Silverbrook
  • Publication number: 20120104335
    Abstract: The present invention provides phthalocyanine nanowires having a minor diameter of 100 nm or less and a ratio (length/minor diameter) of length to minor diameter of 10 or more, an ink composition characterized by containing, as essential components, the phthalocyanine nanowires and an organic solvent, a film including the phthalocyanine nanowires, and an electronic element including a film. Since by using an ink composition containing the phthalocyanine nanowires of the present invention a phthalocyanine film can be formed by a wet process such as coating or printing, a break-proof, lightweight, low-cost electronic element can be provided on a flexible plastic substrate.
    Type: Application
    Filed: April 13, 2010
    Publication date: May 3, 2012
    Applicant: DIC CORPORATION
    Inventors: Hideki Etori, Hideyuki Murata, Norimasa Fukazawa, Shou Inagaki, Hiroshi Isozumi, Masanori Kasai
  • Patent number: 8029611
    Abstract: A salt of a sulfonated dye comprising an ammonium cation as a counterion. The ammonium cation comprises at least 3 hydroxyl groups. The salt is useful in reducing kogation in thermal inkjet printheads. One example of these salts is the compound of formula (II): wherein M is Ga(OH); and each of Z1+, Z2+, Z3+ and Z4+ is protonated 2,2-bis(hydroxymethyl)-2,2?,2?-nitrilotriethanol.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: October 4, 2011
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Simone Charlotte Vonwiller, Sutharsiny Indusegaram, Graciel Gonzaga, Damon Donald Ridley, Kia Silverbrook
  • 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
  • Publication number: 20100104985
    Abstract: The present invention relates to a compound for photoresist, selected from the group consisting of a compound comprising an oxonol dye skeleton, a cyanine dye, a styryl dye, a compound comprising a merocyanine dye skeleton, a compound comprising a phthalocyanine dye skeleton, an azo compound, and a complex compound of an azo compound and a metal ion. The present invention further provides a photoresist liquid comprising at least one of the compound for photoresist and a method of etching a surface being processed using the photoresist liquid.
    Type: Application
    Filed: March 5, 2008
    Publication date: April 29, 2010
    Inventor: 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
  • Publication number: 20090130049
    Abstract: Self-sterilising products, and in particular novel products comprising phthalocyanine derivatives bound to polymers, a process for the preparation of said products and their use for preparing self-sterilising industrial and medical articles or devices, are described.
    Type: Application
    Filed: June 29, 2006
    Publication date: May 21, 2009
    Applicant: L. Molteni & C. Dei Fratelli Alitti Societa' Di Esercizio S.P.A.
    Inventors: Gabrio Roncucci, Lia Fantetti, Giacomo Chiti, Donata Dei, Carmela Alongi, Annalisa Cocchi, Valentina Paschetta
  • Patent number: 7485180
    Abstract: Compounds of Formula (1) and salts thereof: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus; R1 and R3 are H or optionally substituted C1-4 alkyl; R2 and R4 are H or optionally substituted hydrocarbyl; x is 0.0 to 3.9; y is 0.1 to 4.0; z is 0 to 3.9. Compositions, inks, ink-jet printing processes and cartridges, printed materials and ink jet printing cartridges are also disclosed.
    Type: Grant
    Filed: March 13, 2006
    Date of Patent: February 3, 2009
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • 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
  • Patent number: 7449058
    Abstract: A composition comprising: (a) a major dye component which is a mixture of phthalocyanine dyes of Formula (1) and salts thereof: wherein: Pc represents a phthalocyanine nucleus of formula; x is 0.1 to 3.8; y is 0.1 to 3.8; z is 0.1 to 3.8; the sum of x+y+z is 3 to 4; and the substituents, represented by x, y and z, are attached only to a ?-position on the phthalocyanine ring; and (b) a liquid medium. Also ink-jet inks and cartridges, printing processes, printed material and dye mixtures.
    Type: Grant
    Filed: January 6, 2006
    Date of Patent: November 11, 2008
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Publication number: 20080134933
    Abstract: Compounds of Formula (1) and salts thereof: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of formula; R1 is H or optionally substituted C1-4alkyl; R2 is H or optionally substituted hydrocarbyl; R3 is H or optionally substituted C1-4alkyl; R4 is H or optionally substituted hydrocarbyl; x is 0. to 3.9; y is 0.1 to 4.0; z is 0 to 3.9. Also compositions, inks, ink-jet printing processes and cartridges, printed materials and ink jet printing cartridges.
    Type: Application
    Filed: March 13, 2006
    Publication date: June 12, 2008
    Inventor: Prakash Patel
  • 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
  • Patent number: 7326287
    Abstract: A composition comprising: (a) a major dye component which is a mixture of copper phthalocyanine dyes of Formula (1): CuPc?-(SO3M)x?-(SO2NH2)y??Formula (1) wherein: Pc represents a phthalocyanine nucleus of formula; M is a cation; x and y each independently have an average value of from 0.5 to 3.5; (x+y)=4; and the sulfo and sulfonamide substituents are attached to a ?-position on the phthalocyanine ring; and (b) a liquid medium which comprises water and an organic solvent or an organic solvent free from water. Also ink-jet printing processes, printed images, ink-jet printers and ink-jet cartridges.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: February 5, 2008
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7156908
    Abstract: A process for forming an image on a substrate comprising applying a composition comprising: (a) a compound of Formula (1) and salts thereof, wherein: M is Cu or Ni; Pc represents a phthalocyanine nucleus of Formula (2); R1, R2 and R3 independently are H or optionally substituted C1-4alkyl; R4 is optionally substituted C1-4-hydroxyalkyl; x is greater than 0 and less than 1.8; y and z are both greater than 0; and the sum of (x+y+z) is 2.4 to 4.5: and (b) a liquid medium: thereto by means of an ink jet printer.
    Type: Grant
    Filed: September 19, 2003
    Date of Patent: January 2, 2007
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • 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: 6790943
    Abstract: A reactive dye compound comprising: (a) at least one chromophore moiety; (b) at least one SO2C2H4 group which is attached to the chromophore moiety either directly via the sulphur atom of the SO2C2H4 group or via a linking group L; characterized in that at least one SO2C2H4 group is substituted on its terminal carbon atom with at least one Y group wherein Y is derived from a hydrated aldehyde, a hydrated ketone, a hydrated alpha-hydroxy ketone or the hydrated form of formic acid, and linked via one of its oxygen atoms to the terminal carbon of the SO2C2H4 group thereby forming a hemiacetal.
    Type: Grant
    Filed: March 27, 2002
    Date of Patent: September 14, 2004
    Assignee: North Carolina State University
    Inventors: Peter Jeffrey Broadbent, David Malcolm Lewis, Gilles Yves Marie Fernand Genain, Wei Dong He, Taher Iqbal Yousaf
  • Publication number: 20040138436
    Abstract: The present invention relates to colorant of the general formula, wherein A, B and B′, m and m′ and n and n′ are as defined in the description. The colorants can be used for the pigmenting of porous materials and in injekt printing and, in the case of pigmenting, are converted to the insoluble pigment form. In the pigmenting of porous materials, for example in the pigmenting of wood or anodised aluminium in the pores, the colorants yield very good penetration and fastness to light and, in injekt printing, yield very good water-resistance.
    Type: Application
    Filed: October 16, 2003
    Publication date: July 15, 2004
    Inventors: Hans-Thomas Schacht, Gilbert Moegle
  • Publication number: 20030164114
    Abstract: The present invention relates to a cyan dye mixture, an ink composition containing the mixture and a method of ink-jet recording with the ink composition. The print obtained by the method is characterized by discoloring or fading little even when allowed to stand in a well ventilated shade or in an ozone gas. The cyan dye mixture comprises compounds which are obtained by chlorosulfonating, as a starting material, copper phthalocyanine or a sulfonated copper phthalocyanine and then aminating the chlorosulfonation product with an aminating agent used in an amount of at least 2.
    Type: Application
    Filed: January 17, 2003
    Publication date: September 4, 2003
    Inventors: Hirokazu Kitayama, Shinichi Namba, Takafumi Fujii, Junji Otani, Junko Yoshioka, Yasuo Shirasaki
  • Patent number: 6569212
    Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: and all IJP-effective forms of such compounds; and in which M represents a metal or H; Pc represents a phthalocyanine nucleus of Formula (2) x+y+z represents an average from 3 to 4; and z may be zero. A represents C1-4-alkylene; R1, R3 each independently represent H or C1-4-alkyl; R4 represents H; or C1-4-alkyl optionally substituted with hydroxy; R5 represents a carboxylic acid substituted aryl group; and R2 represents H, C1-4-alkyl or a group of formula BD where: B represents C1-4-alkylene; and D represents NR6R7;or SC1-4alkyleneSO3H; where: R6 represents H; or C1-4alkyl, optionally subsititued by hydroxy; R7 represents H; C1-4alkyl, optionally subsititued by hydroxy or morphlino; or R6 and R7 together with the N atom to which they are attached form a morpholino or piperazino ring.
    Type: Grant
    Filed: February 27, 2001
    Date of Patent: May 27, 2003
    Assignee: Avecia Limited
    Inventor: Kathryn Carr
  • Patent number: 6454845
    Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: MvPc(SO2NHAr)x  Formula (1) in which: M represents a metal or H; Pc represents a phthalocyanine nucleus; Ar represents an aromatic moiety optionally substituted by one or more groups selected from an optional substituent or optionally substituted C1-30carbyl; v is the valence of Pc divided by the valence of M; and x is from 2.5 to 4.5.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: September 24, 2002
    Assignee: Avecia Limited
    Inventors: Andrew Paul Shawcross, Gavin Wright, Roy Bradbury
  • 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: 6332918
    Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: which comprises any form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: M represents H, metal, halometal, oxymetal and/or hydroxymetal; k is the inverse of half of the valency of M; Pc represents a phthalocyanine nucleus of Formula (2): L represents a linking group comprising an optionally substituted C1-30carbyl; A represents —O—, —S— or —NR3—, where R3 independently comprises H or optionally substituted C1-30carbyl; R1 comprises at least one group independently selected from: an optional substituent and optionally substituted C1-15carbyl; R2 comprises optionally substituted C1-30carbyl that comprises at least one alkyl group substituted by at least one of: hydroxy, carboxy and sulpho; z repres
    Type: Grant
    Filed: February 16, 1999
    Date of Patent: December 25, 2001
    Assignee: Avecia Limited
    Inventor: Mark Kenworthy
  • Patent number: 6235097
    Abstract: Suitable phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: which comprises any form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: M represents a metal or H; Pc represents a phthalocyanine nucleus of Formula (2): L represents a linking group comprising an optionally substituted C1-30hydrocarbyl; A represents a group comprising at least one of: amino and optionally substituted C1-30hydrocarbyl comprising at least one protonable nitrogen atom; but where A comprises other than an alkyl group substituted by at least one of: hydroxy, carboxy and sulpho; R1 represents a group independently comprising at least one of: an optional substituent and optionally substituted C1-5hydrocarbyl; z represents an integer from 0 to 4; w represents an integer from 1 to 5; and the sum of w+z is from
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: May 22, 2001
    Assignee: Avecia Limited
    Inventors: Mark Kenworthy, Peter Gregory
  • Patent number: 6221114
    Abstract: Dye salts which are free from fiber-reactive radicals and have the formula where Chr is an (m+n)-valent radical of a chromophore from the series of the metal-free or metal-containing phthalocyanines, of the quinacridones, of the mono-, dis- or polyazo dyes, of the anthraquinones or copper formazans, Ar is phenyl or naphthyl each of which is unsubstituted or substituted, x⊕ is a metal cation or ammonium ion, y⊕ is a proton, metal cation or ammonium ion, m is 1 to 6 and n is 1 to 6, the sum of m and n being not more than 7, are used in methods of dyeing or printing polymeric material and in dye preparations.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: April 24, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Würthner, Rüdiger Sens, Günther Seybold, Karl-Heinz Etzbach
  • Patent number: 6190422
    Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: which includes all IJP-effective forms of such compounds; and in which: M represents a metal or H; A represents C1 4alkylene; Pc represents a phthalocyanine nucleus of Formula (2): D represents NR4R5 or SC1-4alkyleneSO3H; R1, R2 and R3each independently represents H or C1-4-alkyl; R4 represents H,; or C1-4-alkyl optionally substituted by hydroxy; R5 represents C1-4alkyl optionally substituted by hydroxy and/or morpholino; or R4 and R5 together with the N atom to which they are attached form a morpholino ring; and x+y+z represents an average of from 3 to 4.
    Type: Grant
    Filed: January 24, 2000
    Date of Patent: February 20, 2001
    Assignee: Avecia Limited
    Inventor: Kathryn Carr
  • Patent number: 6149722
    Abstract: Phthalocyanine compounds of Formula (1) have utility as colorants in inks for ink-jet printing, where Formula (1) represents: ##STR1## in which: M represents a metal or H;Pc represents a phthalocyanine nucleus; andR.sup.1 represents H or --(CH.sub.2).sub.n R.sup.3 ; R.sup.2 represents(CH.sub.2).sub.n R.sup.3 ; or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached represent a 5 or 6-membered ring; where:n is independently an integer from 1 to 30; andR.sup.3 is independently a group selected from hydroxy, sulpho, cyano, --SR.sup.4, --CO.sub.2 R.sup.5, --PO.sub.3 H.sub.2 and --NR.sup.6 R.sup.7 ; where:R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent H, C.sub.1-30 alkyl optionally substituted by one or more groups selected from hydroxy, mercapto, sulpho, carboxy, cyano and --PO.sub.3 H.sub.2 ;v is the valence of Pc divided by the valence of M;x is from 1.2 to 3.8;y is from 0.1 to 2.7;z is from 0.1 to 2.7; andx, y and z satisfy 2.ltoreq.x+y+z.ltoreq.4.
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: November 21, 2000
    Assignee: Zeneca Limited
    Inventors: Colin Dick Robertson, Mark Kenworthy
  • Patent number: 6025486
    Abstract: A compound of formula (1) and salts thereof, wherein: M is a metal or hydrogen; Pc is a phthalocyanine nucleus; each R.sup.1 independently is H or optionally substituted alkyl aryl or aralkyl; each L.sup.1 independently is a divalent organic linking group; Z is an optionally substituted piperazinyl group; q is 1 or 2; x and y each independently have a value of 0.5 to 3.5; and (x+y) is from 2 to 5. A process for making the compounds of formula (1). The compounds of formula (1) are useful as colorants for inks which are used in for example ink jet printing of substrates such as paper, plastics, textile materials, metal or glass.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: February 15, 2000
    Assignee: Zeneca Limited
    Inventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
  • Patent number: 6015896
    Abstract: A compound of formula (1) and salts thereof, wherein: M is a metal or hydrogen; Pc is phthalocyanine nucleus; R.sup.1, R.sup.2, W.sup.1 and W.sup.2 are each independently H or optionally substituted alkyl, aryl or aralkyl; R.sup.3 is an aminoalkyl group; L is a divalent organic linking group; x, y and t are each independently 0.5 to 2.5; and (x+y+t) is from 3 to 4. A process for making the compounds of formula (1). The compounds of formula (1) are useful as colorants for inks which are used in for example ink jet printing of substrates such as paper, plastics, textile materials, metal or glass.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: January 18, 2000
    Assignee: Zeneca Limited
    Inventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
  • Patent number: 5965598
    Abstract: The present invention refers to zinc-phthalocyanines of general formula (I) ##STR1## to processes for their preparation and to their use as phototherapeutic and photodiagnostic agents as free molecules and as conjugates with macromolecular carrier molecules.
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: October 12, 1999
    Assignee: Molteni L. & C. dei Fratelli Alitti Societa di esercizio S.p.A.
    Inventors: Gabrio Roncucci, Donata Dei, Maria Paola De Filippis, Lia Fantetti, Ilaria Masini, Barbara Cosimelli, Giulio Jori
  • Patent number: 5882360
    Abstract: The present application relates to water-soluble copper phthalocyanine dyestuffs of the formula I ##STR1## in which CuPc is a copper phthalocyanine radical;X is a straight-chain or branched alkylene having 2 to 6 carbon atoms;Y is a straight-chain or branched alkylene having 2 to 6 carbon atoms or a straight-chain or branched alkylene having 1 to 6 carbon atoms which is substituted by hydroxyl, carboxyl or amino;R.sup.1 and R.sup.2 independently of one another are hydrogen or alkyl having 1 to 4 carbon atoms;R.sup.3 represents hydrogen, alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms or aminoalkyl having 1 to 4 carbon atoms;R.sup.
    Type: Grant
    Filed: August 24, 1997
    Date of Patent: March 16, 1999
    Assignee: Clariant GmbH
    Inventors: Wolfgang Bauer, Dieter Baumgart, Walter Zoller, Klaus-Peter Kreutzer
  • Patent number: 5859237
    Abstract: A process for the production of a phthalocyanine pigment having a clear color tone, a high tinting strength and a finely milled structure by an efficient and economical process, in which the pigmentation from a phthalocyanine crude can be carried out without removing an aromatic hydrocarbon solvent used in the synthesis of the phthalocyanine crude, the process comprising thes steps of(a) reacting phthalic anhydride or its derivative, urea or its derivative and a catalyst in an organic solvent to synthesize a phthalocyanine crude,(b) wet-milling a slurry of the synthesized phthalocyanine crude in the presence of a milling medium without removing the aromatic hydrocarbon solvent, and(c) removing the organic solvent from the slurry of the milled product, purifying the milled product and drying the milled product with a spray type dryer.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: January 12, 1999
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Hideko Noguchi, Mikio Hayashi, Masatoshi Momose
  • Patent number: 5646274
    Abstract: A phthalocyanine monoazo compound which is represented by the following formula (I): ##STR1## wherein the variable radicals have the meaning given in the description, and the phthalocyanine monoazo compound has green color.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: July 8, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiyuki Araki, Takemi Tokieda, Shin-ichi Yabushita, Yasuyoshi Ueda, Bunzi Tsukise
  • Patent number: 5563260
    Abstract: The compounds of general formula I ##STR1## wherein R represents chlorine or hydroxylPc represents a phthalocyanine radicalR.sub.1 may be alkyl and R.sub.2 may be alkyl ammoniumare excellently suitable for dyeing of plastic materials, paper and inks for ball point pens.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: October 8, 1996
    Assignee: Sandoz Ltd.
    Inventors: Bansi L. Kaul, Dominique Pflieger
  • 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: 5516901
    Abstract: Reactive phthalocyanine dyes are prepared by reacting phthalocyaninesulfonyl chlorides with amines containing a reactive group and subjecting the resulting reaction mixture to a membrane treatment.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: May 14, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Dornhagen, Manfred Patsch
  • Patent number: 5501710
    Abstract: The novel copper phthalocyanine dyestuffs of the formula (I) ##STR1## in which CuPc represents a copper phthalocyanine radical,W represents branched or straight-chain C.sub.9-16 -alkylene,a represents 2 to 4,b represents 0 to 2, andthe sum of a and b is 3 to 4,are suitable for dyeing and printing cellulose-coating materials and for producing printing inks, in particular for ink-jet printing systems.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Wunderlich
  • Patent number: 5444163
    Abstract: There is described a process for preparing reactive phthalocyanine dyes with .beta.-substituted ethylsulfonyl or vinylsulfonyl groups by reacting a phthalocyaninesulfonyl chloride with amines with .beta.-substituted ethylsulfonyl or vinylsulfonyl groups with or without further amines in the presence of a heterocyclic catalyst.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: August 22, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Dornhagen, Manfred Patsch
  • Patent number: 5359056
    Abstract: A novel fluorine-containing phthalocyanine compound represented by the following formula (I): ##STR1## wherein Y is ##STR2## wherein R.sub.1 and R.sub.2 are independently a hydrogen atom or a C1-C8 alkyl group; R.sub.3 and R.sub.4 are independently a C1-C8 alkyl group; X is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a halogen atom; Z is a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group, a C1-C4 alkoxycarbonyl group or a halogen atom; W is a C1-C4 alkoxyl group; e, f, g, h and j are independently an integer of 1 or 2; n is an integer of 1 to 8; and p and q are independently an integer of 1 to 6; a to d are an integer of 0 to 2 with the proviso that the sum of a to d is 1 to 8; and M is a non-metal, a metal, a metal oxide, a metal carbonyl or a metal halide, and further, a method of producing a fluorine-containing phthalocyanine compound represented by the above formula (I).
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: October 25, 1994
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Osamu Kaieda, Takashi Yodoshi, Hideki Itoh, Miho Onozaki
  • 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: 5296023
    Abstract: A colorant of Formula (1): ##STR1## wherein: L is a metal cation or hydrogen;Pc is a phthalocyanine radical having a valency from 3 to 4;R.sup.1 is H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aralkyl or substituted aralkyl;R.sup.2 is H, alkyl, alkoxy, halo or an optionally substituted amino group;M.sup.+ is NH.sub.4.sup.+ or a substituted annonium cation; and(t+q) is from 3 to 4 inclusive;with the proviso that the group CO.sub.2 -M.sup.+ is at the 2-, 3-, 5- or 6-position in Formula (1).
    Type: Grant
    Filed: January 4, 1993
    Date of Patent: March 22, 1994
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald W. Kenyon