Nitrogen Bonded Directly To The Sulfonyl Group Patents (Class 540/133)
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Patent number: 8808439Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and a metal atom complexed thereto and having a valency of at least three, with two valencies complexed to the phthalocynanine ring or the naphthalocyanine ring, each unit joined to another through a fused ring, at least one valency attached to water-soluble axial ligands. The dyes to may be employed in inkjet inks in conjunction with colorants.Type: GrantFiled: July 31, 2009Date of Patent: August 19, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8784548Abstract: A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and, optionally, a metal atom complexed thereto and, if present, having a valency of from 1 to 5, with two valencies complexed to the phthalocyanine ring or the naphthalocyanine ring. Each unit has two linker moieties on opposite sides or adjacent sides of the unit, wherein water-soluble groups are present on at least one of the linkers, on the metal atom, and optionally on the phthalocyanine or naphthalocyanine moiety.Type: GrantFiled: July 31, 2009Date of Patent: July 22, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Jayprakash Bhatt
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Patent number: 8778073Abstract: 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: GrantFiled: October 30, 2008Date of Patent: July 15, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Zhang-Lin Zhou, Jayprakash C. Bhatt
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Patent number: 8741264Abstract: 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: GrantFiled: June 29, 2006Date of Patent: June 3, 2014Assignee: Molteni Therapeutics S.R.L.Inventors: Gabrio Roncucci, Lia Fantetti, Giacomo Chiti, Donata Dei, Carmela Alongi, Annalisa Cocchi, Valentina Paschetta
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Patent number: 8702854Abstract: 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: GrantFiled: November 26, 2009Date of Patent: April 22, 2014Assignee: FUJIFILM CorporationInventors: Prakash Patel, Toshiki Fujiwara
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Patent number: 8647425Abstract: 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: GrantFiled: October 6, 2010Date of Patent: February 11, 2014Assignee: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel
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Patent number: 8591641Abstract: 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: GrantFiled: April 30, 2009Date of Patent: November 26, 2013Assignees: Dalian University of Technology, Ninestar Management Co., Ltd.Inventors: Xiaojun Peng, Jianzhou Zhang, Fan Jiangli, Shiguo Sun, Rong Zhang
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Patent number: 8282722Abstract: 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: GrantFiled: September 5, 2011Date of Patent: October 9, 2012Assignee: Silverbrook Research Pty LtdInventors: Simone Charlotte Vonwiller, Sutharsiny Indusegaram, Graciel Gonzaga, Damon Donald Ridley, Kia Silverbrook
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Publication number: 20120104335Abstract: 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: ApplicationFiled: April 13, 2010Publication date: May 3, 2012Applicant: DIC CORPORATIONInventors: Hideki Etori, Hideyuki Murata, Norimasa Fukazawa, Shou Inagaki, Hiroshi Isozumi, Masanori Kasai
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Patent number: 8029611Abstract: 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: GrantFiled: May 14, 2009Date of Patent: October 4, 2011Assignee: Silverbrook Research Pty LtdInventors: Simone Charlotte Vonwiller, Sutharsiny Indusegaram, Graciel Gonzaga, Damon Donald Ridley, Kia Silverbrook
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Patent number: 7964719Abstract: An inkjet ink for use in netpage, Hyperlabel and other applications. The ink includes an IR-absorbing dye of formula (I): wherein M is Ga(A1); A1 is an axial ligand selected from —OH, halogen, —OR3, —OC(O)R4, a hydrophilic ligand and/or a ligand suitable for reducing cofacial interactions; R1 and R2 may be the same or different and are selected from hydrogen or C1-12 alkoxy; R3 is selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); R4 is selected from C1-12 alkyl, C5-12 aryl or C5-12 arylalkyl; Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy; W is a hydrophilic group, each W group being independently selected from a substituent including a sulfonic acid group (including salts thereof), or a substituent comprising a sulfonamide group; n1 is 0, 1, 2 or 3; n2 is 0, 1, 2 or 3; n3 is 0, 1, 2 or 3; n4 is 0, 1, 2 or 3; and at least one of n1, n2, n3 or n4 is greater than 0.Type: GrantFiled: October 20, 2006Date of Patent: June 21, 2011Assignee: Silverbrook Research Pty LtdInventors: Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Sutharsiny Indusegaram, Kia Silverbrook, Paul Lapstun
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Publication number: 20100193777Abstract: A method of producing a desubstituted compound, including: applying an external stimulation to a compound A-(B)m having a solvent-soluble group B (wherein A represents a residue of a solvent-insoluble compound, B represents a specific solvent-soluble group, and m represents a natural number, and the solvent-soluble group B bonds to a carbon atom of the residue A of a solvent-insoluble compound), to cause desubstitution of the solvent-soluble group B, and converting the compound to a solvent-insoluble compound to which a hydrogen atom bonds in place of the solvent-soluble group B; a method of producing an organic semiconductor film, including: forming a film of a ?-conjugated compound having a substituent represented by formula (2-I), on a substrate; and causing desubstitution of the substituent from the compound; and an organic semiconductor film and an organic electronic device each obtained by these methods: wherein R11 represents a substituent other than a hydrogen atom.Type: ApplicationFiled: September 9, 2008Publication date: August 5, 2010Inventors: Keita Takahashi, Tetsu Kitamura, Tetsuya Watanabe
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Publication number: 20100104985Abstract: 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: ApplicationFiled: March 5, 2008Publication date: April 29, 2010Inventor: Tetsuya Watanabe
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Patent number: 7658792Abstract: There is provided an IR-absorbing naphthalocyanine dye of formula (I): wherein M is Ga(A1); A1 is an axial ligand selected from —OH, halogen, —OR3, —OC(O)R4 or —O(CH2CH2O)eRe wherein e is an integer from 2 to 10 and Re is H, C1-8 alkyl or C(O)C1-8 alkyl; R1 and R2 may be the same or different and are selected from hydrogen or C1-12 alkoxy; R3 is selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); R4 is selected from C1-12 alkyl, C5-12 aryl or C5-12 arylalkyl; Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy; and each B is independently selected from a base, wherein BH+ has a pKa of between 4 and 9. The dye is suitable for use in IR-absorbing inkjet inks, providing compatibility with known CMYK inks together with an optimally red-shifted ?max.Type: GrantFiled: July 10, 2006Date of Patent: February 9, 2010Assignee: Silverbrook Research Pty LtdInventors: Sutharsiny Indusegaram, Graciel Gonzaga, Simone Charlotte Vonwiller, Scott Matthew Starling, Lachlan Everett Hall, Damon Donald Ridley, Kia Silverbrook
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Patent number: 7544236Abstract: A compound of Formula (1) in the free acid or salt form: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of formula; each R1 and R2 independently is H, optionally substituted alkyl or optionally substituted aryl; each R3 independently is optionally substituted alkyl or optionally substituted aryl; each n independently is 1 or 2; x is 0 to 2; y is 0.1 to 2.5; x is 0.1 to 2.5; and the sum (x+y+z) is 2.2 to 4. Also compositions, ink jet printer inks, cartridges and processes and printed materials.Type: GrantFiled: October 21, 2005Date of Patent: June 9, 2009Assignee: Fujifilm Imaging Colorants LimitedInventors: John Mayall, Prakash Patel
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Publication number: 20090130049Abstract: 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: ApplicationFiled: June 29, 2006Publication date: May 21, 2009Applicant: 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
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Patent number: 7485180Abstract: 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: GrantFiled: March 13, 2006Date of Patent: February 3, 2009Assignee: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel
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Patent number: 7459016Abstract: A method for the production of a phthalocyanine pigment preparation includes finely distributing a crude phthalocyanine pigment by dry milling, wet milling, salt kneading, acid pasting or acid swelling to give a pre-pigment, the pre-pigment is subjected to a finishing treatment in a mixture of water and an organic solvent at alkaline pH, increased temperature and in the presence of at least one pigment dispersant from the group of phthalocyanine sulphonic acids, phthalocyanine carboxylic acids, phthalocyanine sulphonate salts, phthalocyanine carboxylate salts and phthalocyanine suiphonamides.Type: GrantFiled: November 27, 2003Date of Patent: December 2, 2008Assignee: Clariant Produkte (Deutschland) GmbHInventors: Klaus Brychcy, Joachim Weber, Heidrun Mehler
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Patent number: 7449058Abstract: 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: GrantFiled: January 6, 2006Date of Patent: November 11, 2008Assignee: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel
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Publication number: 20080134933Abstract: 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: ApplicationFiled: March 13, 2006Publication date: June 12, 2008Inventor: Prakash Patel
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Publication number: 20080110369Abstract: A compound of Formula (1) in the free acid or salt form: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc represents a phthalocyanine nucleus of formula; each R1 and R2 independently is H, optionally substituted alkyl or optionally substituted aryl; each R3 independently is optionally substituted alkyl or optionally substituted aryl; each n independently is 1 or 2; x is 0 to 2; y is 0.1 to 2.5; x is 0.1 to 2.5; and the sum (x+y+z) is 2.2 to 4. Also compositions, ink jet printer inks, cartridges and processes and printed materials.Type: ApplicationFiled: October 21, 2005Publication date: May 15, 2008Inventors: John Mayall, Prakash Patel
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Patent number: 7326287Abstract: 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: GrantFiled: July 2, 2004Date of Patent: February 5, 2008Assignee: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel
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Phthalocyanine compounds, ink compositions comprising said compounds, and printing process therewith
Patent number: 7156908Abstract: 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: GrantFiled: September 19, 2003Date of Patent: January 2, 2007Assignee: Fujifilm Imaging Colorants LimitedInventor: Prakash Patel -
Patent number: 7022171Abstract: A process for coloration of a substrate comprising applying thereto by means of an ink-jet printer an ink composition comprising a compound of Formula (1) or salt thereof: wherein: M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; Pc is a phthalocyanine nucleus of Formula (2); each R1 and R2 independetly are H, C1-4alkyl or C1-4hydroxyalkyl; R3 is phenyl carrying 1 or 2 sulpho substituents or phenyl carrying at least 1 carboxy or 1 phosphato substituent and having further optional substituents; x, y and z are all greater than 0 and the sum of (x+y+z) is 2 to 5.Type: GrantFiled: February 27, 2003Date of Patent: April 4, 2006Assignee: Avecia LimitedInventors: Prakash Patel, Tina Margaret Horrobin
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Patent number: 6790943Abstract: 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: GrantFiled: March 27, 2002Date of Patent: September 14, 2004Assignee: North Carolina State UniversityInventors: Peter Jeffrey Broadbent, David Malcolm Lewis, Gilles Yves Marie Fernand Genain, Wei Dong He, Taher Iqbal Yousaf
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Publication number: 20040138436Abstract: 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: ApplicationFiled: October 16, 2003Publication date: July 15, 2004Inventors: Hans-Thomas Schacht, Gilbert Moegle
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Publication number: 20030164114Abstract: 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: ApplicationFiled: January 17, 2003Publication date: September 4, 2003Inventors: Hirokazu Kitayama, Shinichi Namba, Takafumi Fujii, Junji Otani, Junko Yoshioka, Yasuo Shirasaki
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Patent number: 6569212Abstract: 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: GrantFiled: February 27, 2001Date of Patent: May 27, 2003Assignee: Avecia LimitedInventor: Kathryn Carr
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Patent number: 6454845Abstract: 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: GrantFiled: January 31, 2001Date of Patent: September 24, 2002Assignee: Avecia LimitedInventors: Andrew Paul Shawcross, Gavin Wright, Roy Bradbury
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Patent number: 6444807Abstract: The invention relates to phthalocyanine compounds and are represented by the formula: The compounds are used as a colorant and a pigment precursor, especially in light-sensitive compositions for color filters.Type: GrantFiled: March 12, 2001Date of Patent: September 3, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Annemarie Wolleb, Heinz Wolleb, Gerardus De Keyzer, Barbara Wagner
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Patent number: 6332918Abstract: 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 represType: GrantFiled: February 16, 1999Date of Patent: December 25, 2001Assignee: Avecia LimitedInventor: Mark Kenworthy
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Patent number: 6235097Abstract: 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 fromType: GrantFiled: March 2, 2000Date of Patent: May 22, 2001Assignee: Avecia LimitedInventors: Mark Kenworthy, Peter Gregory
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Patent number: 6221114Abstract: 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: GrantFiled: September 17, 1999Date of Patent: April 24, 2001Assignee: BASF AktiengesellschaftInventors: Frank Würthner, Rüdiger Sens, Günther Seybold, Karl-Heinz Etzbach
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Patent number: 6190422Abstract: 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: GrantFiled: January 24, 2000Date of Patent: February 20, 2001Assignee: Avecia LimitedInventor: Kathryn Carr
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Patent number: 6149722Abstract: 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: GrantFiled: February 1, 1999Date of Patent: November 21, 2000Assignee: Zeneca LimitedInventors: Colin Dick Robertson, Mark Kenworthy
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Patent number: 6025486Abstract: 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: GrantFiled: April 7, 1998Date of Patent: February 15, 2000Assignee: Zeneca LimitedInventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
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Patent number: 6015896Abstract: 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: GrantFiled: April 7, 1998Date of Patent: January 18, 2000Assignee: Zeneca LimitedInventors: Prahalad Manibhai Mistry, Ronald Wynford Kenyon
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Patent number: 5965598Abstract: 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: GrantFiled: August 13, 1998Date of Patent: October 12, 1999Assignee: 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
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Patent number: 5882360Abstract: 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: GrantFiled: August 24, 1997Date of Patent: March 16, 1999Assignee: Clariant GmbHInventors: Wolfgang Bauer, Dieter Baumgart, Walter Zoller, Klaus-Peter Kreutzer
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Patent number: 5859237Abstract: 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: GrantFiled: October 8, 1997Date of Patent: January 12, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hideko Noguchi, Mikio Hayashi, Masatoshi Momose
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Patent number: 5646274Abstract: 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: GrantFiled: October 30, 1995Date of Patent: July 8, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiyuki Araki, Takemi Tokieda, Shin-ichi Yabushita, Yasuyoshi Ueda, Bunzi Tsukise
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Patent number: 5563260Abstract: 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: GrantFiled: February 9, 1995Date of Patent: October 8, 1996Assignee: Sandoz Ltd.Inventors: Bansi L. Kaul, Dominique Pflieger
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Patent number: 5534055Abstract: This invention relates to a process for preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments comprising(a) acid pasting or acid swelling a crude metal phthalocyanine pigment;(b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment in the presence of 5 to 50 parts by weight of a stabilizer per 100 parts by weight of the crude metal phthalocyanine pigment until the average particle size is reduced to less than about 0.5 .mu.m;(c) finishing the milled metal phthalocyanine pigment by thoroughly mixing said milled metal phthalocyanine pigment with a finishing solvent mixture comprising 3 to 6 parts by weight, relative to the crude metal phthalocyanine pigment, of water and 0.4 to 1.Type: GrantFiled: August 24, 1994Date of Patent: July 9, 1996Assignee: Bayer CorporationInventors: Herman Gerson, Abdul Sattar
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Patent number: 5516901Abstract: 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: GrantFiled: December 10, 1993Date of Patent: May 14, 1996Assignee: BASF AktiengesellschaftInventors: Juergen Dornhagen, Manfred Patsch
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Patent number: 5501710Abstract: 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: GrantFiled: October 14, 1994Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventor: Klaus Wunderlich
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Patent number: 5444163Abstract: 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: GrantFiled: November 12, 1993Date of Patent: August 22, 1995Assignee: BASF AktiengesellschaftInventors: Juergen Dornhagen, Manfred Patsch
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Patent number: 5359056Abstract: 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: GrantFiled: July 14, 1992Date of Patent: October 25, 1994Assignee: Nippon Shokubai Co., Ltd.Inventors: Osamu Kaieda, Takashi Yodoshi, Hideki Itoh, Miho Onozaki
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Patent number: 5319074Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.Type: GrantFiled: January 24, 1992Date of Patent: June 7, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
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Patent number: 5302708Abstract: Phthalocyanine dyes, in particular copper phthalocyanine and nickel phthalocyanine dyes which contain one or more groups of the formula given and defined below ##STR1## or one or more carboxy groups or both groups and which furthermore can contain one or more sulfo groups, customary sulfonamide groups and/or groups of the formula given and defined below ##STR2## dye hydroxy- and/or carboxamide-containing materials, in particular fiber materials, such as cellulose fiber materials, wool and polyamide fibers, in fast, predominantly green hues of high color strength.Type: GrantFiled: August 6, 1992Date of Patent: April 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
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Patent number: 5296023Abstract: 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: GrantFiled: January 4, 1993Date of Patent: March 22, 1994Assignee: Zeneca LimitedInventors: Peter Gregory, Ronald W. Kenyon