Plural Amino Nitrogens Bonded Directly To A Benzene Ring Which Is Between The Azo Groups Patents (Class 534/748)
  • Patent number: 8815485
    Abstract: A compound that can improve azo pigment dispersibility in a non-water-soluble solvent. The compound is represented by formula (1): wherein R1 to R4 represent hydrogen or halogen; R5 to R9 represent hydrogen, COOR17 or CONR18R19, and at least one of R5 to R9 represents COOR17 or CONR18R19, where R17 to R19 represent hydrogen or an alkyl group having 1 to 3 carbons; R10 represents an alkyl group having 1 to 6 carbons or a phenyl group; R11 to R15 represent a hydrogen, L1R20 or L2R21R22, and at least one of R11 to R15 represents L1R20 or L2R21R22, where L1 represents a divalent linking group, L2 represents a trivalent linking group, and R20 to R22 represent an alkyl group having 8 or more carbons or an alkenyl group having 8 or more carbons; and R16 represents an alkyl group having 1 to 6 carbons or a phenyl group.
    Type: Grant
    Filed: August 11, 2011
    Date of Patent: August 26, 2014
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masatake Tanaka, Masashi Kawamura, Yuki Hasegawa, Takayuki Toyoda, Yasuaki Murai, Masashi Hirose, Takeshi Miyazaki
  • Patent number: 6756486
    Abstract: Disclosed are green shade yellow pigments represented by the Formula I: wherein R1 and R2 are independently selected from hydrogen, hydroxy, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, a halo-alkyl group containing 1 to about 4 carbon atoms, an alkoxy carbonyl group having 1 to about 5 carbon atoms; R3 and R4 are independently selected from hydrogen, hydroxy, halogen, an alkyl group containing from 1 to about 4 carbon atoms, an alkoxy group containing from 1 to about 4 carbon atoms, and halo-alkyl groups containing from 1 to about 4 carbon atoms; and M is at least one divalent metal. Also disclosed are methods of making the green shade yellow pigments, methods of using the green shade yellow pigments, and coating compositions, ink compositions, electrostatic toner compositions, paint compositions, paper compositions, and plastic compositions containing the green shade yellow pigments.
    Type: Grant
    Filed: September 18, 2003
    Date of Patent: June 29, 2004
    Assignee: Engelhard Corporation
    Inventors: Amrit P. Bindra, Steven A. Zamborsky
  • Patent number: 6504045
    Abstract: The invention relates to six new crystal polymorphs, &agr; (alpha), &bgr; (beta), &ggr; (gamma), &dgr; (delta), &zgr; (zeta), and &eegr; (eta), of the disazo colorant of the formula I, having characteristic reflections in the X-ray diffraction spectrum. The novel crystal polymorphs are prepared by treatment in organic solvents.
    Type: Grant
    Filed: September 13, 2001
    Date of Patent: January 7, 2003
    Assignee: Clariant GmbH
    Inventors: Ruediger Jung, Hans-Joachim Metz, Joachim Weber, Martin U. Schmidt, Olaf Schupp, Andreas Wacker
  • Patent number: 6437104
    Abstract: A process for preparing disazo condensation pigments by diazotization of an aromatic amine, azo coupling with a coupling component to form an azocarboxylic acid or azodicarboxylic acid, formation of an azocarbonyl chloride or azodicarbonyl dichloride and condensation of the azocarbonyl chloride with an aromatic diamine or of the azodicarbonyl dichloride with an aromatic amine comprises effecting the acyl chloride formation and/or the condensation and optionally the diazotization and optionally the azo coupling in a microreactor.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: August 20, 2002
    Assignee: Clariant GmbH
    Inventors: Uwe Nickel, Klaus Kund, Frank Alfter
  • Patent number: 5889162
    Abstract: In one embodiment, the present invention relates to a green shade yellow pigment composition comprising a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, an alkyl group having 1 to about 4 carbon atoms, an alkoxy group having 1 to about 4 carbon atoms, an alkoxycarbonyl group having 1 to about 6 carbon atoms, nitro, cyano, phenoxy or trifluoromethyl. The green shade yellow pigment composition is suitable for use in plastics, paints and inks.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: March 30, 1999
    Assignee: Engelhard Corporation
    Inventor: Byron G. Hays
  • Patent number: 5559216
    Abstract: An ecologically and economically advantageous process for preparing a disazo pigment of the formula (I) or a mixture of said disazo pigments ##STR1## where D.sup.1 and D.sup.2 are identical or different and each is unsubstituted phenyl, phenyl with from 1 to 5 substituents, unsubstituted naphthyl, naphthyl with from 1 to 3 substituents, unsubstituted anthraquinonyl, anthraquinonyl with from 1 to 3 substituents, or a radical of a fused aromatic heterocycle which contains from 1 to 3 identical or different heteroatoms from nitrogen or oxygen and sulfur and is unsubstituted or has from 1 to 3 substituents,R.sup.1 and R.sup.2 are identical or different and each is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: September 24, 1996
    Assignee: Hoechst AG
    Inventors: Ruediger Jung, Joachim Weide, Hans J. Metz
  • Patent number: 5298609
    Abstract: Compounds of formula I ##STR1## wherein R is a radical of formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III ##STR2## and B is a radical of formula ##STR3## wherein n is 1 or 2,R.sub.1 is --H or --Cl,R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl, --CONH--phenyl, --NHCO-phenyl or phenoxy, each unsubstituted or substituted in the phenyl nucleus by one or two chlorine atoms or by one or two methyl, methoxy or ethoxy groups,R.sub.3 is C.sub.5 -C.sub.12 cycloalkyl, which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.5 -C.sub.6 cycloalkyl groups,R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3, andX is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2,are suitable for use as pigments, especially for colouring polyolefins.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: March 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Stefan Hari
  • Patent number: 5266110
    Abstract: The invention relates to three new crystal modifications (.gamma., .delta., .epsilon. modification) of C.I. Pigment Yellow 16 ##STR1## having their characteristic reflections in the X-ray diffraction spectrum. The new crystal modifications are prepared by heat treatment of the known .alpha. or .beta. modification in selected organic solvents.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: November 30, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Rieper, Edwin Baier
  • Patent number: 5185435
    Abstract: The present invention relates to the preparation of bisazo pigments by reaction (a) of 2 mol of an azocarbonyl chloride of the formula ##STR1## with 1 mol of a diamine of the formula ##STR2## by reaction (b) of one mole of a bis(azocarbonyl chloride) of the formula ##STR3## with 2 mol of an amine of the formula ##STR4## which comprises carrying out the reactions (a) or (b) in the presence of 1,2,3-trimethylbenzene or anisole as the solvent.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: February 9, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Klaus Ruf, Bilge Gulec, Michael Reisinger, Werner Surber
  • Patent number: 5062894
    Abstract: Diarylide pigment compositions useful for preparing storage stable printing inks (especially of the publication gravure type) are prepared using a poly (alkylene oxide) substituted acetoacetanilide together with a typical acetoacetanilide and coupling the mixture of acetoacetanilides with tetrazotized dichlorobenzidine.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: November 5, 1991
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
  • Patent number: 5030247
    Abstract: Mixtures of azo pigments of the formulae ##STR1## wherein each R.sub.1 is independently C.sub.1-4 alkyl, andeach R.sub.2 is independently 1,4-phenylene; 1,4-phenylene substituted by 1 or 2 substituents independently selected from chloro, bromo, methyl, methoxy, trifluoromethyl (maximum of one) and nitro (maximum of one); 4,4'-diphenylene substituted by 1 or 2 substituents independently selected from chloro, bromo, methyl and methoxy, each substituent being in the 3- or 3'-position; 1,4-naphthylene or 1,5-naphthylene, the mixture containing from 8 to 20% mole of benzoic acid ester residues and from 92 to 80% mole of terephthalic acid ester residues, useful for pigmenting in the mass synthetic polymers, for example, polyethylene, polypropylene, polystyrene, polyvinyl chloride, synthetic leather and rubber latices.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: July 9, 1991
    Assignee: Sandoz Ltd.
    Inventor: Jurgen Goldmann
  • Patent number: 4946508
    Abstract: Disazo pyrazolone pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment is prepared by reacting a primary amine terminated alkylene oxide polymer and acetoacetanilide or substituted acetoacetanilide to form an azomethine coupler, and subsequently co-reacting the azomethine coupler and a pyrazolone coupler with tetrazotized 3,3'-dichlorobenzidine or tetrazotized o-dianisidine. The pigment is useful in printing ink, plastics and paints.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: August 7, 1990
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio
  • Patent number: 4946948
    Abstract: Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Fridolin Babler
  • Patent number: 4946509
    Abstract: Diarylide pigments modified with alkylene oxide polymers. The modified pigments are useful in both water-based and solvent-based coating and ink compositions.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: August 7, 1990
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio, Anthony C. Zwirgzdas
  • Patent number: 4544736
    Abstract: The compound of the formula ##STR1## exists in an .alpha.-modification and a .beta.-modification, the latter being obtained by treatment of the .alpha.-form with a boiling organic solvent, each of which, but especially the .beta.-modification, is useful as a pigment for the mass pigmentation of synthetic plastics and resins, free from or containing a solvent (e.g., viscose, cellulose acetate, polyethylene, polystyrene, polyvinyl chloride, synthetic leathers and synthetic rubbers), surface coatings (e.g., oil- and water-based paints), lacquers and inks and for pigment printing, textile coating and pigmenting paper in the mass.
    Type: Grant
    Filed: May 26, 1983
    Date of Patent: October 1, 1985
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4540775
    Abstract: The compound of the formula, ##STR1## a pigment existing in a yellow (.alpha.) modification and an orange (.beta.) modification, the latter being obtained by treatment of the .alpha. form with boiling organic solvents, is useful for the mass pigmenting of synthetic plastics and resins, free from or containing solvents, such as viscose, cellulose acetate, polyethylene, polystyrene, polyvinyl chloride and synthetic leathers and rubbers, of surface coatings such as paints and lacquers and of inks and for pigment printing, textile coating and pigmenting paper in the mass.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: September 10, 1985
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul