Additional Hydroxy Or Nitrogen, Other Than As Nitro, Nitroso Or Azo, Bonded Directly To The Bicyclo Ring System Patents (Class 534/836)
  • Publication number: 20150141629
    Abstract: The present invention relates to a water-resistant organic thin film obtained by crosslinking, with organic nitrogen compounds, an organic thin film comprising an organic dye having an anionic group, wherein the organic nitrogen compounds are first, second, and third acyclic organic nitrogen compounds each having two or more nitrogen atoms per molecule, wherein the nitrogen atoms of each of the first, second, and third organic nitrogen compounds are each in a cationic group, and the relation A?0.4 nm<B<C is satisfied, wherein A represents a distance (nm) between adjacent nitrogen atoms in the first organic nitrogen compound, B represents a distance (nm) between adjacent nitrogen atoms in the second organic nitrogen compound, and C represents a distance (nm) between adjacent nitrogen atoms in the third organic nitrogen compound.
    Type: Application
    Filed: June 10, 2013
    Publication date: May 21, 2015
    Applicant: NITTO DENKO CORPORATION
    Inventors: Hiroshi Tomohisa, Toru Umemoto, Shoichi Matsuda, Tadayuki Kameyama
  • Publication number: 20150126717
    Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
    Type: Application
    Filed: January 8, 2015
    Publication date: May 7, 2015
    Inventors: Robert L. Mahaffey, JR., Xiaoyong Michael Hong, Eduardo Torres, Dominick J. Valenti, Gregory Scot Miracle
  • Patent number: 8962815
    Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
    Type: Grant
    Filed: January 24, 2013
    Date of Patent: February 24, 2015
    Assignee: Milliken & Company
    Inventors: Robert L Mahaffey, Jr., Xiaoyong Michael Hong, Eduardo Torres, Dominick J Valenti, Gregory Scot Miracle
  • Patent number: 8785607
    Abstract: The present invention relates to a method for manufacturing a water resistant optically anisotropic film comprising: a water resistant treatment step of bringing an optically anisotropic film containing an organic dye having an anionic group into contact with a water resistant treatment liquid containing a multivalent metal salt or a compound having two or more nitrogen atoms in a molecule thereof; and a cleaning step of cleaning the optically anisotropic film after the water resistant treatment, using a cleaning liquid containing a hydrophilic organic compound.
    Type: Grant
    Filed: August 12, 2011
    Date of Patent: July 22, 2014
    Assignee: Nitto Denko Corporation
    Inventors: Toru Umemoto, Tadayuki Kameyama
  • Publication number: 20130227797
    Abstract: The invention relates to the dyeing of human keratinous fibres, in particular the hair, using anionic direct dyes or acid dyes having a tetraalkylammonium counterion of formula (I) with Col(?)m. R1, R2, R3, R4, m, and n as defined in the description. A subject-matter of the invention is a dyeing composition comprising an anionic dye of formula (I) and a method for dyeing keratinous fibres, such as the hair, employing the said composition. A subject-matter of the invention is likewise novel dyes of formula (I) and their uses for the colouring of keratinous fibres. This composition makes it possible to obtain a chromatic, powerful and particularly persistent colouring on keratinous fibres.
    Type: Application
    Filed: November 16, 2011
    Publication date: September 5, 2013
    Applicant: L'OREAL
    Inventor: Andrew Greaves
  • Publication number: 20130211058
    Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
    Type: Application
    Filed: January 24, 2013
    Publication date: August 15, 2013
    Applicant: MILLIKEN & COMPANY
    Inventor: Milliken & Company
  • Patent number: 8477268
    Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.
    Type: Grant
    Filed: May 19, 2009
    Date of Patent: July 2, 2013
    Assignees: Nippon Kayaku Kabushiki Kaisha, Polatechno Co., Ltd.
    Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
  • Publication number: 20120101265
    Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
    Type: Application
    Filed: October 22, 2010
    Publication date: April 26, 2012
    Inventors: Robert L. Mahaffey, JR., Xiaoyong Michael Hong, Eduardo Torres, Dominick J. Valenti, Gregory S. Miracle
  • Publication number: 20120059157
    Abstract: The present invention relates to a method for manufacturing a water resistant optically anisotropic film comprising: a water resistant treatment step of bringing an optically anisotropic film containing an organic dye having an anionic group into contact with a water resistant treatment liquid containing a multivalent metal salt or a compound having two or more nitrogen atoms in a molecule thereof; and a cleaning step of cleaning the optically anisotropic film after the water resistant treatment, using a cleaning liquid containing a hydrophilic organic compound.
    Type: Application
    Filed: August 12, 2011
    Publication date: March 8, 2012
    Applicant: NITTO DENKO CORPORATION
    Inventors: Toru Umemoto, Tadayuki Kameyama
  • Publication number: 20110164208
    Abstract: Azo compounds represented by formula (1) (In the formula, R1 represents a lower alkoxy group with a sulfone group. R2-R5 each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.
    Type: Application
    Filed: May 19, 2009
    Publication date: July 7, 2011
    Applicants: NIPPON KAYAKU KABUSHIKI KAISHA, POLATECHNO CO., LTD.
    Inventors: Takuto Nishiguchi, Hiroaki Ohno, Takahiro Higeta, Yuichi Sadamitsu
  • Publication number: 20100257678
    Abstract: Disclosed is an azo compound represented by the formula (1) below, a salt thereof, or a copper complex salt compound thereof. (In the formula, R1 and R2 independently represent a hydrogen atom, a sulfonic acid group, a lower alkyl group or a lower alkoxyl group; R3-R6 independently represent a hydrogen atom, a lower alkyl group or a lower alkoxyl group; R7 represents a lower alkyl group or a lower alkoxyl group; and n represents 0 or 1.
    Type: Application
    Filed: June 21, 2007
    Publication date: October 14, 2010
    Inventors: Yuichi Sadamitsu, Takahiro Higeta
  • Publication number: 20100233443
    Abstract: Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.
    Type: Application
    Filed: June 21, 2007
    Publication date: September 16, 2010
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventor: Rainer Nusser
  • Patent number: 7638611
    Abstract: A polarizer of the present invention comprises an azo compound which is represented by the following general formula (I). In the general formula (I), Q1 represents an optionally substituted aryl group, Q2 represents an optionally substituted arylene group, M represents a counter ion, l represents an integer of from 1 to 6, and m represents an integer of from 0 to 5 (l+m?6).
    Type: Grant
    Filed: January 9, 2009
    Date of Patent: December 29, 2009
    Assignee: Nitto Denko Corporation
    Inventors: Shoichi Matsuda, Kyoko Nishiguchi, Tadayuki Kameyama
  • Publication number: 20090083913
    Abstract: The invention relates to novel dyes of the formula (1) in which D represents a phenyl or naphthalene residue which is substituted by one or two sulphonic Acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4alkyl, hydroxyl and nitro, each R1 and R2, independently, represent hydrogen or, a C1-C4alkyl group, R?1 represents hydrogen, hydroxyl, C1-C4alkyl or C1-C4hydroxyalkyl, R3 represents hydrogen, C1-C4alkyl or phenyl, which is unsubstituted or substituted by one or two groups selected from C1-C4alkyl, C1-C4alkoxy, halogen, hydroxyl, —NH2, nitro, —SO3M and —CO2M and M represents hydrogen, an alkaline or alkaline earth metal, ammonium or ammonium that is mono-, di-, tri- or tetrasubstituted by C1-C4alkyl or C2-C4hydroxyalkyl or a polyglycolammonium cation and also known dyes of formula (5), in which D? represents a phenyl or naphthalene residue which is substituted by one or two sulphonic acid or carboxylic acid groups and, optionally, by one or two groups selected from C1-C4a
    Type: Application
    Filed: June 26, 2006
    Publication date: April 2, 2009
    Inventors: Adolf Kaser, Wolfgang Schlenker
  • Patent number: 6712893
    Abstract: A compound of Formula (1) and salts thereof: In the formula, m is 1, 2 or 3; X is H or SO3H; R1 and R2 are each independently selected from optionally substituted alkyl and optionally substituted alkoxy; and R4 and R5 are each independently H, optionally substituted alkyl or optionally substituted aryl. When (i) at least one of R1 and R2 carries an —OH group; and (ii) when X is H at least one of R1 and R2 is optionally substituted alkyl. The compounds are useful as dyes for ink jet printing inks.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: March 30, 2004
    Assignee: Avecia Limited
    Inventors: Prahalad Manibhai Mistry, Roy Bradbury
  • Patent number: 6695899
    Abstract: A compound of Formula (1) and salts thereof: wherein: A is a substituted phenyl group carrying a group of the formula —NR3R4 and an ortho carboxy group; n is 0 or 1; L1 and L2 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or L1 and L2 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring; R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R3 and R4 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R3 and R4 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring; or R3 is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl; and R4 is an acyl group.
    Type: Grant
    Filed: March 26, 2002
    Date of Patent: February 24, 2004
    Assignee: Avecia Limited
    Inventor: Prahalad Manibhai Mistry
  • Patent number: 6689201
    Abstract: A compound of Formula (1) and salts thereof are useful as dyes for ink jet printing inks. In the formula (1), A is optionally substituted phenyl (other than carboxyl substituted); R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R4 and R5 are each independently H, alkyl or optionally substituted aryl. In formula (1) at least one of R1 and R2 carries an —OH group.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: February 10, 2004
    Assignee: Avecia Limited
    Inventors: Prahalad Manibhai Mistry, Roy Bradbury
  • Patent number: 6559292
    Abstract: Compounds of Formula (1) and salts thereof: wherein: A is optionally substituted phenyl; R1 and R2 are each independently optionally substituted alkyl or optionally substituted alkoxy; and R4 and R5 are each independently H, optionally substituted alkyl or optionally substituted aryl; provided that (i) at least one of R1 and R2 carries an —OH group; and (ii) A is not of the formula:  wherein m is 1, 2 or 3. The compounds are useful as dyes for ink jet printing inks.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: May 6, 2003
    Assignee: Avecia Limited
    Inventors: Prahalad Manibhai Mistry, Roy Bradbury
  • Patent number: 6451989
    Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: September 17, 2002
    Assignee: Lexmark International, Inc.
    Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
  • Patent number: 6288217
    Abstract: Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: September 11, 2001
    Assignee: Lexmark International, Inc.
    Inventors: Bradley Leonard Beach, Ann P Holloway, James F Feeman
  • Patent number: 6084078
    Abstract: The novel disazo dyestuffs of the formula (I) in which the substituents and indices have the meanings given in the description, are outstandingly suitable for dyeing cellulosic materials in red-violet to blue brilliant color shades.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: July 4, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Winfried Mennicke
  • Patent number: 5969115
    Abstract: Bisazo dyes of formula (IX) ##STR1## and of formula (X) ##STR2## wherein A, R.sub.4, M and n are as defined in the specification, are excellent dyes for dyeing and printing of cellulose containing materials and especially for the preparation of inks for ink jet printing.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: October 19, 1999
    Assignee: Ilford Imaging Switzerland GMBH
    Inventor: Heinz Peter
  • Patent number: 5891230
    Abstract: A bisazo dye of Formula (1) and salts thereof: ##STR1## in which R is H;R.sub.1 and R.sub.2 each independently is H, optionally substituted C.sub.1-4 -alkyl or optionally substituted aryl;R.sub.3 and R.sub.4 are each independently --OC.sub.1-4 -alkyl;R.sub.5 is H;R.sub.6 is COOH; andn is 1, 2 or 3.The dyes are useful for ink jet printing.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: April 6, 1999
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
  • Patent number: 5888286
    Abstract: A bisazo dye of Formula (1) and salts thereof: ##STR1## wherein: R.sub.1 and R.sub.2 each independently is H, optionally substituted C.sub.1-4 -alkyl or optionally substituted aryl;R.sub.3 is --NH.sub.2 ;R.sub.4 is OC.sub.1-4 -alkyl;each R.sub.5 independently is --COOH or --SO.sub.3 H; andn is 1,2, or 3.Also claimed are inks containing the dye, a process of ink jet printing using the inks and substrates coloured by the inks.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: March 30, 1999
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Prahalad Manibhai Mistry, Roy Bradbury, Paul Wight
  • Patent number: 5795970
    Abstract: A disazo dye composition comprising at least a disazo dye represented by the formula (I) and a disazo dye represented by the formula (II): ##STR1## (wherein X and Y indicate an alkoxy group having 1 to 4 carbon atoms, and M indicates hydrogen or a cation selected from the group consisting of, alkaline metal, NH.sub.4, alkyl-substituted ammonium, alkanolammonium, morpholinium and piperidinium), wherein, when the disazo dye composition is analyzed by liquid chromatography, the area ratio of the peak area (Sp) of the disazo dye represented by the formula (I) to the peak area (Sc) of the disazo dye represented by the formula (II), that is Sp:Sc is from 1:0.4 to 1:2.4. This disazo dye composition provides a high quality image, rapid ink fixing and the like even on the plain paper.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: August 18, 1998
    Assignees: Orient Chemical Industries, Ltd., Seiko Epson Corporation
    Inventors: Takashi Ono, Tatsuya Yagyu, Yoshihiro Sawatari, Masaki Sasaki, Miharu Kanaya, Hiroko Hayashi, Akio Owatari, Yasuhiro Ouki
  • Patent number: 5744591
    Abstract: A dyestuff of the general formula (1), ##STR1## wherein R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is a phenyl or naphthyl group, which is unsubstituted or substituted by --Cl, --Br, --I, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, --OH, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --NHCOCH.sub.3 or --COOH. The dyestuff of the present invention is suitable for dyeing and printing of materials containing hydroxyl group or amide group, in particular animal fibrous material, synthetic polyamide and polyurethane fibers.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: April 28, 1998
    Assignee: Everlight USA, Inc.
    Inventor: Min-Mey Yei
  • Patent number: 5663309
    Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted phenylamino,R.sub.2 is hydrogen, amino or N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino,R.sub.3 is hydrogen or hydroxyl,R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido or halogen andK is as defined in claim 1,the azo dyes of the formula (1) comprising at least one and not more than two sulfo groups,are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high dyeing yield, and give dyeings and prints with good fastness properties.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: September 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 5647897
    Abstract: An ink composition for ink jet recording is provided which can satisfy property requirements of quality of print, drying property of print, clogging resistance, water resistance, storage stability, and nonattacking on members constituting an ink passage, such as a printing head. The ink composition for ink jet recording comprises a dye represented by the following formula (I), glycerin, pyrrolidone, a monohydric lower alcohol, a tri(hydroxyalkyl)amine, and water: ##STR1## wherein R.sup.1 represents phenyl or naphthyl substituted by a group selected from hydroxyl, --NH.sub.2, --SO.sub.3 M and --COOM, R.sup.2 represents carboxyalkyl, alkoxyalkyl, phenyl, or alkanoyl, R.sup.3, R.sup.4, and R.sup.5 represent hydrogen or --SO.sub.3 M.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: July 15, 1997
    Assignee: Seiko Epson Corporation
    Inventors: Yasuhiro Ouki, Miharu Kanaya, Hiroko Hayashi, Kiyohiko Takemoto, Masaaki Itano
  • Patent number: 5510468
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridges,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxy-ethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, and X.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Reichelt, Ortwin Schaffer
  • Patent number: 5380859
    Abstract: There are described benzophenoneazo dyes of the formula ##STR1## where the ring A can be benzofused and a benzofused ring A can be overbridged,m is 1 or 2,K is the radical of a coupling component,Y is hydrogen or arylazo,one of the two radicals X.sup.1 and X.sup.2 is hydrogen and the other is hydroxysulfonyl,R.sup.1, R.sup.2 and R.sup.3 are independently of the others hydrogen, halogen, C.sub.1 -C.sub.12 -alkyl, cyclohexyl, phenyl, 2-hydroxyethylsulfonyl or C.sub.1 -C.sub.4 -alkoxy or, when m is 1 and Y is hydrogen, one of these substituents can also be the radical of the formula ##STR2## where L.sup.1 is a chemical bond or a bridge member, andX.sup.1, X.sup.2, R.sup.4, K and the ring A are each as defined above, andR.sup.4 is hydrogen, halogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Gunther Lamm, Helmut Beichelt, Ortwin Schaffer
  • Patent number: 5366543
    Abstract: The present invention provides a disazo salt-forming dye having excellent solubility with organic solvents, especially alcohols and glycols.The present invention thus provides a disazo salt-forming dye represented by the Formula (I): ##STR1## or the Formula (II): ##STR2## wherein Ka.sup.+ represents a cation of an amine which is substituted with at least one linear or cyclic alkyl group or aralkyl group having 6-12 carbon atoms which may be branched or interrupted by oxygen.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: November 22, 1994
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Takashi Ono, Tatsuya Yagyu, Tetsui Akase
  • Patent number: 5332806
    Abstract: Azo dyes of the formula ##STR1## where A and B are each independently of the other substituted or unsubstituted phenyl or naphthyl and X is --N(R.sub.1)--SO.sub.2 --, --O--SO.sub.2 -- or --SO.sub.2 --N(R.sub.1)--, where R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, produce very fast dyeings on nitrogen-containing or hydroxyl-containing fibre materials, paper or leather.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: July 26, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 5281263
    Abstract: According to the present invention there is provided a compound which, in the free acid form, is of the Formula (1): ##STR1## wherein A is an optionally substituted phenyl or naphthyl group;Z is H, CO.sub.2 H, SO.sub.3 H or SO.sub.2 NH.sub.2 ;T is H or SO.sub.3 H;R.sup.1 is H or optionally substituted alkyl;V is H, CO.sub.2 H, SO.sub.3 H, CH.sub.3 or Cl; provided that the compound of Formula (1) has at least as many CO.sub.2 H groups as SO.sub.3 H groups.The compound is useful as a colorant for inks used in ink jet printing.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: January 25, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Prahalad M. Mistry
  • Patent number: 5250107
    Abstract: A water-fast ink composition and method for making the same. A selected chemical dye having at least one functional group with an extractable hydrogen atom thereon (e.g. --COOH, --NH.sub.2, or --OH) is combined with an ammonium zirconium polymer salt (e.g. ammonium zirconium carbonate, ammonium zirconium acetate, ammonium zirconium sulfate, ammonium zirconium phosphate, and ammonium zirconium oxalate). The resulting mixture preferably contains about 0.01-5.0% by weight ammonium zirconium polymer salt and about 0.5-5.0% by weight chemical dye. Upon dehydration of the mixture, the ammonium zirconium polymer salt and chemical dye form a cross-linked dye complex which is stable and water-fast. The mixture may be dispensed onto a variety of substrates (e.g. paper) using thermal inkjet or other printing systems.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: October 5, 1993
    Assignee: Hewlett-Packard Company
    Inventor: Steven J. Bares
  • Patent number: 5203912
    Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: April 20, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • Patent number: 5198022
    Abstract: A alkali-soluble dye for a waterfast ink having structural formula as follows: ##STR1## and an ink containing the dye dissolved in water. Printing from the ink is insoluble below pH 6.0; is an intense black at low concentration; and remains black on acid papers. The aqueous inks are stable and exhibit good printhead nozzle maintenance.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: March 30, 1993
    Assignee: Lexmark International, Inc.
    Inventors: Rodney O. Aulick, Bradley L. Beach, Donald L. Elbert, Terence E. Franey, James F. Feeman, John M. Olson, Allen C. Sanders, Robert L. Vollmer
  • Patent number: 5175260
    Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroeder, Udo Mayer
  • Patent number: 5149366
    Abstract: A disazo compound of the formula (I) in the free acid form, ##STR1## and an ink jet recording ink composition containing the same are provided, and the composition is superior in stability during storage or use, heat resistance, image clearness, water resistance and light fastness, and has a desirable tint as a red color.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: September 22, 1992
    Assignees: Sumitomo Chemical Company, Limited, Taoka Chemical Company
    Inventors: Hideo Kawashita, Mituhiro Ohta, Kazuya Ogino
  • Patent number: 5118737
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: June 2, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 5075428
    Abstract: A dyestuff of the formula ##STR1## in which R is H or Ch.sub.3 ##STR2## in which R.sub.1 is H, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or --X--YX is a divalent aliphatic, cycloaliphatic, aliphaticcycloaliphatic radical or an araliphatic radicalY is COOH, SO.sub.3 H, OSO.sub.3 H or SO.sub.2 G, in whichG is CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, in which Z denotes a group which can be eliminated under alkaline conditions,R.sub.2 is H or C.sub.1 -C.sub.4 -alkyl, and the benzene radical D and the benzene or naphthalene radical L can contain customary substituents,is suitable for the dyeing and printing of OH- and NH-containing materials. They produce lightfast and wetfast brilliant dyeings and prints.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: December 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5062893
    Abstract: Inks are provided comprising (a) at least two dyes corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5. Also preferably, a phosphate is added to reduce kogation and a metal chelating agent is added to further reduce nozzle clogging.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: November 5, 1991
    Assignee: Hewlett-Packard Company
    Inventors: Raymond J. Adamic, Palitha Wickramanayake, Suraj L. Hindagolla, Garold E. Radke, David J. Halko
  • Patent number: 5055566
    Abstract: A compound of the Formula (1): ##STR1## wherein R is H, SO.sub.3 A, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, NO.sub.2, OH or halogen;W, X, Y and Z are independently H or SO.sub.3 A; andA is NQ.sub.4 wherein at least one Q is a branched chain fatty C.sub.6-20 -aliph atic group.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon
  • Patent number: 5053495
    Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: October 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
  • Patent number: 4963189
    Abstract: Inks are provided comprising (a) a dye corresponding to the formula ##STR1## wherein W is COOH,X is H, or COOH,Y is H, COOH, or SO.sub.3 H,Z is H, COOH, or SO.sub.3 H, andR is H, CH.sub.2 COOH, or CH.sub.2 CH.sub.2 COOH;with the proviso that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 groups, and (b) a solvent which may be water or a mixture of water and a water-soluble organic solvent provide excellent waterfast prints on paper. The inks preferably have a pH from about 7 to about 9.5.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: October 16, 1990
    Assignee: Hewlett-Packard Company
    Inventor: Suraj L. Hindagolla
  • Patent number: 4918169
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4867789
    Abstract: A method for purifying a dye solution is provided. The method comprises the steps of dissolving an impure dye in a solvent. A flocculant is then added to the dye solution in order to flocculate the imprity so that the impurity may then be removed from the solution. A method for producing on ink utilizing the purification procedure is also provided.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Makoto Shioya, Masatsune Kobayashi
  • Patent number: 4703113
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 & R.sup.2 together with the nitrogen atom form a morpholine ringa & b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: October 27, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 4594410
    Abstract: Azo dyes of the formula ##STR1## and external salts thereof, wherein F is the residue of a monoazo or disazo compound in 1:1 metal complex form or of a trisazo, disazoazoxy or tetrakisazo compound in metal-free or 1:1 metal complex form,each X is independently --NR.sub.2 --Q--NR.sub.3 R.sub.4 or --NR.sub.2 --Q--N.sup..sym. R.sub.5 R.sub.6 R.sub.7,whereinQ is linear or branched C.sub.2-6 alkylene or --NH--CO--CH.sub.2 --,R.sub.2 is hydrogen or C.sub.1-4 alkyl,each of R.sub.3 and R.sub.4 is independently hydrogen; C.sub.1-6 alkyl; C.sub.2-6 alkyl monosubstituted by cyano or hydroxy in the 2-, 3-, 4-, 5- or 6-position; phenyl(C.sub.1-3 alkyl); phenyl(C.sub.1-3 alkyl) having, on the phenyl ring, 1, 2 or 3 substituents selected from chloro, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1, 2 or 3 C.sub.1-4 alkyl groups or --NR.sub.3 R.sub.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: June 10, 1986
    Assignee: Sandoz Ltd.
    Inventor: Reinhard Pedrazzi
  • Patent number: 4544739
    Abstract: Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine or naphthylazo or phenylazo, wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, A is naphthyl or phenyl containing the oxygen atom in o-position to the azomethine and wherein naphthyl or phenyl is unsubstituted or substituted by C.sub.1-5 -alkyl, halogen or naphthylazo or phenylazo wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, D is sulfophenyl which is unsubstituted or substituted by nitro or chlorine, or sulfonaphthyl which is unsubstituted or substituted by nitro, and is bonded to the azo group in the ortho-position to the oxygen atom and R is chloroacetyl, bromoacetyl, .alpha.-chloroacryloyl, .alpha.-bromoacryloyl, .alpha.,.beta.-dichloropropionyl, .alpha.,.beta.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: October 1, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans U. Schutz, Arthur Buhler