Phthalocyanine Dye Patents (Class 8/661)
  • Patent number: 8876915
    Abstract: There is provided a coloring composition and an ink for inkjet recording which have an excellent ozone fastness and a high print density and is excellent in storage stability over time, and one example of the coloring composition is a coloring composition contains a compound (1A) and a compound (2B):
    Type: Grant
    Filed: May 7, 2014
    Date of Patent: November 4, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Yoshihiko Fujie, Prakash Patel, Clive Edwin Foster, Keiichi Tateishi
  • Patent number: 8715369
    Abstract: The present invention provides a treatment composition comprising a hydrophobic dye.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: May 6, 2014
    Assignee: The Sun Products Corporation
    Inventors: Stephen Norman Batchelor, Jayne Michelle Bird
  • Patent number: 8685116
    Abstract: The present invention relates to a shading process characterized by using a composition comprising a phthalocyanine to which at least one dyestuff is attached through a covalent bonding, to shading compositions, to new compounds used in these shading compositions as well as to the production of these new compounds.
    Type: Grant
    Filed: July 21, 2010
    Date of Patent: April 1, 2014
    Assignee: BASF SE
    Inventors: Alfred Hohener, Frank Bachmann, Adolf Kaser, Chandrasekhar Dayal Mudaliar, Dinesh Narendra Rele, Sneha Shankar Rane, Georg Roentgen
  • Patent number: 8652219
    Abstract: The invention herein provides for an improved dye material composed of a dry particulate mixture of azo and phthalocyanine dyes for concrete surface applications.
    Type: Grant
    Filed: February 22, 2007
    Date of Patent: February 18, 2014
    Assignee: Ameripolish, Inc.
    Inventor: Clint Howle
  • 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: 8585784
    Abstract: The present invention relates to new compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups and to a process for their preparation. Further aspects are shading compositions using these compounds.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: November 19, 2013
    Assignee: BASF SE
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Käser, Roger Wolfgang Basler
  • Patent number: 8414661
    Abstract: The present invention relates to new compositions comprising compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups. Further aspects are an improved shading process for textile materials and also use of these shading compositions for shading textiles.
    Type: Grant
    Filed: January 24, 2012
    Date of Patent: April 9, 2013
    Assignee: The Procter & Gamble Company
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaeser, Roger Wolfgang Basler, Neil Joseph Lant, Gregory Scot Miracle
  • Patent number: 8293695
    Abstract: The present invention relates to a composition comprising at one photocatalyst and at least one azo dyestuff and/or at least one triphenylmethane dyestuff, which produces in the CIElab color coordinate system a relative hue angle of 220-320°, to a detergent composition, a fabric softener composition as well as to a shading.
    Type: Grant
    Filed: July 28, 2004
    Date of Patent: October 23, 2012
    Assignee: BASF SE
    Inventor: Alfred Höhener
  • Patent number: 8292995
    Abstract: A salt of a sulfonated dye modulates a stability of the dye, particularly its ozonefastness. The salt comprises an organic cation selected from the group consisting of: a first organic cation having a positive charge delocalized between a nitrogen atom and at least one other heteroatom; a second organic cation having a positive charge delocalized between a nitrogen atom and at least two other atoms; and a third organic cation of formula (A): wherein: Rp, Rq and Rr are each independently selected from a C1-6 alkyl group; s is 0, 1, 2 or 3; and Ar is a C6-12 aryl group or C3-12 heteroaryl group.
    Type: Grant
    Filed: February 10, 2009
    Date of Patent: October 23, 2012
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
  • 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
  • Publication number: 20120081482
    Abstract: A process for preparing a mixture of phthalocyanine or metallo-phthalocyanine dyes and salts thereof which comprises cyclisation of a compound of Formula (1) with a compound of Formula (2) and/or Formula (3): wherein: R1 is a hydrocarbyl group; R2 is H or a hydrocarbyl group; R3 is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted heterocyclyl; R4 and R5 are cyano, carboxy carboxamide or together form a group of formula X is an electron withdrawing group; and n is 1 to 4: wherein the cyclisation process is carried out in the presence of a suitable nitrogen source (if required) and a metal salt (if required). Also novel compounds, inks, printing processes, printed materials (including color filters) and ink jet cartridges.
    Type: Application
    Filed: May 26, 2010
    Publication date: April 5, 2012
    Applicant: Fujifilm Imaging Colorants Limited
    Inventors: Patricia Mary Dunwoody, Prakash Patel
  • Patent number: 8128713
    Abstract: The present invention relates to new compositions comprising compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups. Further aspects are an improved shading process for textile materials and also use of these shading compositions for shading textiles.
    Type: Grant
    Filed: February 14, 2011
    Date of Patent: March 6, 2012
    Assignee: The Procter & Gamble Company
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaeser, Roger Wolfgang Basler, Neil Joseph Lant, Gregory Scot Miracle
  • Patent number: 8038737
    Abstract: A method of modulating a stability of a sulfonated dye, particularly its ozonefastness is provided. The method comprises providing a salt of the dye, wherein the salt comprises at least one organic cation selected from the group consisting of: a first organic cation having a positive charge delocalized between a nitrogen atom and at least one other heteroatom; a second organic cation having a positive charge delocalized between a nitrogen atom and at least two other atoms; and a third organic cation of formula (A): wherein: Rp, Rq and Rr are each independently selected from a C1-6 alkyl group; s is 0, 1, 2 or 3; and Ar is a C6-12 aryl group or C3-12 heteroaryl group.
    Type: Grant
    Filed: February 10, 2009
    Date of Patent: October 18, 2011
    Assignee: Silverbrook Research Pty Ltd
    Inventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
  • Publication number: 20110204234
    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: Application
    Filed: October 30, 2008
    Publication date: August 25, 2011
    Inventors: Sivapackia Ganapathiappan, Zhang-Lin Zhou, Jayprakash C. Bhatt
  • Publication number: 20110131738
    Abstract: The present invention relates to new compositions comprising compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups. Further aspects are an improved shading process for textile materials and also use of these shading compositions for shading textiles.
    Type: Application
    Filed: February 14, 2011
    Publication date: June 9, 2011
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaeser, Roger Wolfgang Basler, Neil Joseph Lant, Gregory Scot Miracle
  • Patent number: 7942938
    Abstract: The present invention relates to dyes of formula (1), wherein Pc is a phthalocyanine of formula (2), Me is a metal, [MePc] is a phthalocyanine-metal complex of formula (3), M+ is an inorganic or organic cation, R1 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and R2 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and n and m are each independently of the other 0, 1, 2, 3, 4, 5, 6, 7 or 8, the sum of (n+m) being a number 5, 6, 7 or 8, and also to mixtures thereof, to processes for the preparation thereof and to the use thereof in dyeing or printing natural, semi-synthetic or synthetic material.
    Type: Grant
    Filed: June 28, 2006
    Date of Patent: May 17, 2011
    Assignee: BASF SE
    Inventor: Urs Lehmann
  • Patent number: 7927410
    Abstract: A near infrared dye composition includes a microcapsule that includes an inner core region and an outer shell. The inner core region includes a cross-linked polymer-near infrared dye aggregate. The outer shell includes nanoparticles.
    Type: Grant
    Filed: January 23, 2009
    Date of Patent: April 19, 2011
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Zhang-Lin Zhou, Sivapackia Ganapathiappan
  • Patent number: 7909890
    Abstract: The present invention relates to new compositions comprising compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups. Further aspects are an improved shading process for textile materials and also use of these shading compositions for shading textiles.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: March 22, 2011
    Assignee: The Procter & Gamble Company
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaeser, Roger Wolfgang Basler, Neil Joseph Lant, Gregory Scot Miracle
  • Publication number: 20100319142
    Abstract: The present invention relates to new compounds, which are molecular combinations of a phthalocyanine and a mono-azo dyestuff linked via specific linking groups and to a process for their preparation. Further aspects are shading compositions using these compounds.
    Type: Application
    Filed: November 25, 2008
    Publication date: December 23, 2010
    Applicant: BASF SE
    Inventors: Hans Kramer, Frank Bachmann, Christof Dosenbach, Mini Jeevanath, Georg Roentgen, Adolf Kaser, Roger Wolfgang Basler
  • Publication number: 20100299849
    Abstract: The present invention relates to a shading process characterized by using a composition comprising a phthalocyanine to which at least one dyestuff is attached through a covalent bonding, to shading compositions, to new compounds used in these shading compositions as well as to the production of these new compounds.
    Type: Application
    Filed: July 21, 2010
    Publication date: December 2, 2010
    Inventors: Alfred HÖHENER, Frank BACHMANN, Adolf KÄSER, Chandrasekhar Dayal MUDALIAR, Dinesh Narendra RELE, Sneha Shankar RANE, Georg ROENTGEN
  • Patent number: 7799098
    Abstract: The present invention relates to a shading process characterized by using a composition comprising a phthalocyanine to which at least one dyestuff is attached through a covalent bonding, to shading compositions, to new compounds used in these shading compositions as well as to the production of these new compounds.
    Type: Grant
    Filed: August 22, 2005
    Date of Patent: September 21, 2010
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Alfred Höhener, Frank Bachmann, Adolf Käser, Chandrasekhar Dayal Mudaliar, Dinesh Narendra Rele, Sneha Shankar Rane, Georg Roentgen
  • Patent number: 7641725
    Abstract: A mixture of 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 is H or optionally substituted C1-4alkyl; R2 is optionally substituted alkyl or optionally substituted heterocyclyl; R3 is H or optionally substituted C1-4alkyl; R4 is optionally substituted hydrocarbyl; w is 0.1 to 3.7 x is 0.1 to 3.7; y is 0.1 to 3.7; z is 0.1 to 3.7: and provided that the groups represented by y and z are different. Also compositions and inks, printing processes, printed material and ink-jet printer cartridges.
    Type: Grant
    Filed: April 11, 2006
    Date of Patent: January 5, 2010
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7641726
    Abstract: A mixture of 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 optionally substituted alkyl; R3 is H or optionally substituted C1-4alkyl; R4 is optionally substituted heterocycyl; L is a direct covalent bond or a divalent linking group; w, x, y and z are each independently greater than zero. Also compositions and inks, printing processes, printed material and ink-jet printer cartridges.
    Type: Grant
    Filed: March 30, 2007
    Date of Patent: January 5, 2010
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7575627
    Abstract: A mixture of dyes 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 (2); R1 is methyl; R2 is H or methyl; R3 and R4 independently are H or optionally substituted C1-4alkyl; L is a divalent linking group; A and B are independently H or a substituent. 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 2 to 4; and the substituents, represented by x, y and z, are only attached to a ? position on the phthalocyanine ring and the dyes are free from fiber reactive groups. Also compositions, inks, printed material and in-jet processes and cartridges.
    Type: Grant
    Filed: December 2, 2005
    Date of Patent: August 18, 2009
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7575626
    Abstract: A mixture of dyes 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 and R2 independently are H or optionally substituted C1-4alkyl; L is a divalent linking group; B is a substituent. 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 2 to 4; and the substituents, represented by x, y and z, are only attached to a ? position on the phthalocyanine ring and the dyes are free from fiber reactive groups. Also novel compositions and ink-jet printer inks, processes and cartridges.
    Type: Grant
    Filed: December 2, 2005
    Date of Patent: August 18, 2009
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Publication number: 20090202930
    Abstract: An infrared dye composition including at least: a compound (I) whose spectral absorption maximum wavelength is in a range of from 750 nm to 1,050 nm; and a compound (II) whose spectral absorption maximum wavelength is in a range of from 400 nm to 700 nm, wherein, when an absorbance of the infrared dye composition at a spectral absorption maximum wavelength in the range of from 750 nm to 1,050 urn is designated as 1, a maximum absorbance (Dmax) of the infrared dye composition in the range of from 400 nm to 700 nm is 0.5 or lower, and a ratio (Dmax/Dmin) is 10 or lower, and an infrared dye composition excellent in gray balance in the visible light region, and an infrared ray absorbing ink and an electrophotographic toner using the same are provided.
    Type: Application
    Filed: February 13, 2009
    Publication date: August 13, 2009
    Inventors: Kazushi FURUKAWA, Nobuyoshi KASHIWAGI, Keizo KIMURA, Katsuyoshi YAMAKAWA
  • Patent number: 7527657
    Abstract: A liquid preparation of a paper dye comprising a) 15 to 50% by weight of the dye of the formula CuPc[SO2NH(CH2)3N(CH3)2]2 to 3[SO3H]1 to 2 (1), in which CuPc represents copper phthalocyanine, or the alkali metal salt of (1), b) 5 to 15% by weight of ?-caprolactam, c) 1 to 8% by weight of formic acid, d) 1 to 7% by weight of benzyl alcohol, e) 0 to 3% by weight of a lower aliphatic organic acid, f) 0 to 5% by weight of an inorganic salt and g) water, to complete to 100% by weight, a process for the production of said preparation and the use thereof for dyeing, in particular dyeing of paper.
    Type: Grant
    Filed: January 20, 2004
    Date of Patent: May 5, 2009
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Adolf Käser, Charles Hunger
  • Publication number: 20090083912
    Abstract: The present invention relates to dyes of formula (1), wherein Pc is a phthalocyanine of formula (2), Me is a metal, [MePc] is a phthalocyanine-metal complex of formula (3), M+ is an inorganic or organic cation, R1 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and R2 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aralkyl or unsubstituted or substituted aryl, and n and m are each independently of the other 0, 1, 2, 3, 4, 5, 6, 7 or 8, the sum of (n +m) being a number 5, 6, 7 or 8, and also to mixtures thereof, to processes for the preparation thereof and to the use thereof in dyeing or printing natural, semi-synthetic or synthetic material.
    Type: Application
    Filed: June 28, 2006
    Publication date: April 2, 2009
    Inventor: Urs Lehmann
  • 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
  • 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: 7300503
    Abstract: A phthalocyanine dye mixture having a specific structure, an ink using the dye mixture, an inkjet recording ink, an inkjet recording method and a method for improving preservability of image formed are provided.
    Type: Grant
    Filed: July 20, 2005
    Date of Patent: November 27, 2007
    Assignee: Fujifilm Corporation
    Inventors: Keiichi Tateishi, Yoshiharu Yabuki, Shigeaki Tanaka
  • Patent number: 7247195
    Abstract: The present invention is drawn to dye sets for formulating ink-jet inks, including ink sets having six ink-jet inks. In one embodiment, the dye set can comprise a yellow dye for formulating a yellow ink, a pair of magenta dyes for formulating a magenta ink and a pale magenta ink, a pair of cyan dyes for formulating a cyan ink and a pale cyan ink, and a black dye for formulating a black ink-jet ink. The pair of magenta dyes can be a transition metal-containing azo dye and a non-metallized dye. The pair of cyan dyes can be a first copper phthalocyanine dye and a second copper phthalocyanine dye that is different than the first copper phthalocyanine dye.
    Type: Grant
    Filed: March 9, 2005
    Date of Patent: July 24, 2007
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Tye Dodge, Linda C. Uhlir-Tsang, Hiang P Lauw, Matthew Thornberry
  • Patent number: 7235110
    Abstract: A method for surface dyeing a range of textile materials, in the form of yarn, fabric, or garments, includes: a) preparing a dyebath including dye particles and an additive, such as an anionic acrylic copolymer, causing the particles to become charged; b) preparing the textile material by applying an additive, such as a cationic polyamide, forming a substrate with a charge attracting the particles, c) immersing the textile material in the dyebath; d) chemically reducing the dye particles retained on the textile material to a leuco form; and e) oxidizing the dye material.
    Type: Grant
    Filed: November 14, 2005
    Date of Patent: June 26, 2007
    Inventor: Melvin Alpert
  • Patent number: 7211134
    Abstract: A novel compound having sufficiently high fastness to light, heat, humidity and active gas in the environment and a coloring composition using the compound, particularly, an ink for ink jet recording, an ink jet recording method and a method for improving the preservability of formed image, which can form an image having high fastness to light and ozone gas in the environment. A phthalocyanine dye mixture having a specific structure and an ink, an ink for ink jet recording, an ink jet recording method and a method for improving the preservability of formed image, using the phthalocyanine dye mixture.
    Type: Grant
    Filed: January 17, 2003
    Date of Patent: May 1, 2007
    Assignee: Fujifilm Corporation
    Inventors: Keiichi Tateishi, Shigeaki Tanaka, Yoshiharu Yabuki
  • Patent number: 7189283
    Abstract: A composition comprising: (a) a major dye component which is a mixture of phthalocyanine dyes of Formula (1) and salts thereof: wherein: M is Cu or Ni; Pc represents a phthalocyanine nucleus of formula R1, R2 and R3 independently are H or optionally substituted C1-4alkyl; R4 is optionally substituted C1-4-hydroxyalkyl; 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 4; and the substituents, represented by x, y and z, are attached to a ? position on the phthalocyanine ring; and (b) a liquid medium which comprises water, water and an organic solvent or an organic solvent free from water. Also novel dyes, ink-jet printing processes, printed images, printers and cartridges.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: March 13, 2007
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 7182806
    Abstract: A composition comprising: (a) a major dye component which is a mixture of phthalocyanine dyes of Formula (1) and salts thereof: wherein: M is Cu or Ni; Pc represents a phthalocyanine nucleus of formula; R1 and R2 independently are H or optionally substituted C1-4alkyl; R3 is H or optionally substituted hydrocarbyl; and R4 is optionally substituted hydrocarbyl; or R3 and R4 together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system; 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 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 which comprises water and an organic solvent or an organic solvent free from water. Also novel dyes, ink-jet printing processes, printed images, and cartridges.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: February 27, 2007
    Assignee: Fujifilm Imaging Colorants Limited
    Inventor: Prakash Patel
  • Patent number: 6997962
    Abstract: A method for dyeing a cellulosic material, such as cotton or a blend including cotton, in the form of yarn, fabric, or garments, includes: a) preparing a dyebath including particles of indigo and an additive, such as an anionic acrylic copolymer, causing the particles to become charged; b) preparing the cellulosic material by applying an additive, such as a cationic polyamide, forming a substrate with a charge attracting the particles, c) immersing the cellulosic material in the dyebath; d) chemically reducing the particles retained on the cellulosic material to a leuco form; and e) oxidizing the dye material.
    Type: Grant
    Filed: February 18, 2004
    Date of Patent: February 14, 2006
    Inventor: Melvin Alpert
  • Patent number: 6991676
    Abstract: The present invention is drawn to dye sets for formulating ink-jet ink sets, and to specific ink sets. The dye set can comprise cyan colorant including a phthalocyanine dye; magenta colorant including a copper- or nickel-containing azo dye; and yellow colorant including at least one of Yellow 1189 dye and Yellow 104 dye yellow colorant having the structure Formula 1: wherein R1 is H, SO3M, COOM, or SO2NH2; and wherein R2 is H, SO3M, COOM, or SO2NH2; and wherein R3 is H or CH3; and wherein n and m are 2, 3, 4, 5 or 6; and wherein M is H, Na, Li, K, ammonium, ammonium substituted with alkyl or combinations thereof. Optionally, a cyan triarylmethine dye such as Acid Blue 9, or another similar cyan dye, can be blended with the phthalocyanine dye; a rhodamine dye can be blended with the copper- or nickel-containing azo dye; and/or Acid Yellow 17 or Acid Yellow 23 can be blended with Formula 1.
    Type: Grant
    Filed: July 18, 2003
    Date of Patent: January 31, 2006
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Alexey S Kabalnov, Charles G. Dupuy, Luanne J. Rolly, Naomi Oak, Patricia A Wang
  • Patent number: 6916348
    Abstract: Tanned leather is (a) pretreated in an aqueous and alkaline medium either with ammonia, primary amines or a mixture of ammonia and primary amines and then with a polyfunctional organic compound containing at least one aldehyde group as a functional group, or (b) in an aqueous and acidic medium with a polyfunctional organic compound and then ammonia, primary amines or a mixture of ammonia and primary amines, and (c) then dyed in an aqueous and alkaline medium with a water-soluble dye containing at least one functional group which is capable of reacting with one of the functional groups of the organic compound, forming a covalent bond. A tanned and dyed leather is obtainable with a high color intensity, outstanding wet fastness and excellent grain tightness, wherein the dye is permanently and covalently bonded to the leather via a bridging group, preferably in the region of the surface, and the bridging group is essentially bonded to the leather via —N?CH— groups.
    Type: Grant
    Filed: August 27, 2001
    Date of Patent: July 12, 2005
    Assignee: TFL Ledertechnik GmbH
    Inventors: Jens Fennen, Campbell Thomas Page, Jon Louis McHugh
  • Patent number: 6641655
    Abstract: A fluidizing agent which is a diamine and/or diquaternary ammonium salt of a coloured acid of the phthalocyanine or disazo series of dyestuffs wherein the diamine or diquaternary ammonium cation is of formula (1) wherein R is optionally substituted C6-30-alkyl or optionally substituted C6-30-alkenyl; R1 is hydrogen, optionally substituted C1-30-alkyl or C2-30-alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl; R2, R3 and R5 are each, individually, optionally substituted C1-6-alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl; R4 is hydrogen, optionally substituted C1-6-alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl; X is C1-12-alkylene or C2-14-alkenylene; or R1 and R3 together with the two nitrogen atoms to which they are attached and X form a ring; and/or R4 and R5 together with the nitrogen atom to which they are attached form a ring.
    Type: Grant
    Filed: February 26, 2002
    Date of Patent: November 4, 2003
    Assignee: Avecia Limited
    Inventors: John Joseph McElhinney, Kristen Susan Low, Laura Janette Murphy
  • 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
  • Publication number: 20030131756
    Abstract: Disclosed is a process which comprises (a) preparing a first solution comprising water and an anionic dye; (b) preparing a second solution comprising water and a polyquaternary amine compound; (c) admixing the first solution and the second solution, thereby causing formation of a complex of the anionic dye and the polyquaternary amine compound and precipitation of the complex from the solution; and (d) isolating the complex thus formed.
    Type: Application
    Filed: November 7, 2001
    Publication date: July 17, 2003
    Applicant: Xerox Corporation
    Inventors: Thomas W. Smith, Richard L. Colt, Kathleen M. McGrane
  • Publication number: 20030127018
    Abstract: A cyan dye set and ink-jet ink composition with high water-fastness. The cyan dye set is suitable for use in ink-jet printing and includes Acid Blue 90 dye and at least one copper phthalocyanine type blue dye. The cyan dye set has good water-fastness and exhibits improved printing quality when applied in ink-jet printing.
    Type: Application
    Filed: December 17, 2002
    Publication date: July 10, 2003
    Applicant: BENO CORPORATION
    Inventors: Yu-Chang Shen, In-Shan Sir, Chia-Hsin Chien
  • 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: 6511535
    Abstract: The invention relates to a method for printing fibrous textile materials using the ink-jet printing technique, wherein the fibrous materials are printed with an aqueous ink that comprises at least one acid dye according to claim 1 and that has a viscosity of from 1 to 40 mPa·s.
    Type: Grant
    Filed: January 3, 2001
    Date of Patent: January 28, 2003
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Roger Lacroix, Peter Scheibli, Mickael Mheidle
  • Patent number: 6451071
    Abstract: This invention relates to colorants comprising organic chromophores, in particular reactive dyes, which comprise electrophilic reactive groups, and which are also covalently bonded to fatty amine moieties through amino linking groups. Such colorants provide excellent colorability and long-term stability, both within (or on) colored substrates and upon long-term storage. Such colorants exhibit particularly good coloring and stability within hydrocarbon compositions, such as fuels, mineral oil, and the like, and wax compositions, including candles, crayons, and the like. Methods of making such colorants as well as methods of coloring hydrocarbon and wax compositions are also contemplated within this invention.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: September 17, 2002
    Assignee: Milliken & Company
    Inventor: John D. Bruhnke
  • Publication number: 20020083532
    Abstract: Anionic coloring agents comprising at least one spacer arm bounded to their chemical structure. These anionic coloring agents have the following general formula: CA-BE, wherein, CA is an anionic coloring agent comprising at least a cromophore group; and BE is the spacer arm, which has the following chemical structure: —(X—R—Z)r, wherein X is a direct link or a group having the formula —S(O)s, wherein s is 0, 1 or 2; or —NR1—, wherein, R1 is hydrogen or a C1-C10 alkyl group; R is a C1-C10 straight or branched alkylene group: Z is a polar group; and r is an integer equal or higher than 1.
    Type: Application
    Filed: December 18, 2001
    Publication date: July 4, 2002
    Inventor: Jorge Mazza
  • Patent number: 6287348
    Abstract: This invention relates to colorants comprising organic chromophores, in particular reactive dyes, which comprise electrophilic reactive groups, and which are also covalently bonded to fatty amine moieties through amino linking groups. Such colorants provide excellent colorability and long-term stability, both within (or on) colored substrates and upon long-term storage. Such colorants exhibit particularly good coloring and stability within hydrocarbon compositions, such as fuels, mineral oil, and the like, and wax compositions, including candles, crayons, and the like. Methods of making such colorants as well as methods of coloring hydrocarbon and wax compositions are also contemplated within this invention.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: September 11, 2001
    Assignee: Milliken & Company
    Inventor: John D. Bruhnke
  • Patent number: 6251177
    Abstract: Solid preparations of metal-containing or metal-free phthalocyanine dyes, a) which have an average particle size of greater than 100 &mgr;m, and b) which have a pH of greater than or equal to 10 when dissolved in 10 times the amount of water, are particularly suitable for the dyeing and printing of paper, after dissolution in water.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: June 26, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventor: Josef-Walter Stawitz
  • 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