Plural Amino Nitrogens Bonded Directly To A Benzene Ring Which Is Between The Azo Groups Patents (Class 534/748)
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Patent number: 8815485Abstract: 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: GrantFiled: August 11, 2011Date of Patent: August 26, 2014Assignee: Canon Kabushiki KaishaInventors: Masatake Tanaka, Masashi Kawamura, Yuki Hasegawa, Takayuki Toyoda, Yasuaki Murai, Masashi Hirose, Takeshi Miyazaki
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Patent number: 6756486Abstract: 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: GrantFiled: September 18, 2003Date of Patent: June 29, 2004Assignee: Engelhard CorporationInventors: Amrit P. Bindra, Steven A. Zamborsky
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Patent number: 6504045Abstract: 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: GrantFiled: September 13, 2001Date of Patent: January 7, 2003Assignee: Clariant GmbHInventors: Ruediger Jung, Hans-Joachim Metz, Joachim Weber, Martin U. Schmidt, Olaf Schupp, Andreas Wacker
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Patent number: 6437104Abstract: 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: GrantFiled: June 28, 2001Date of Patent: August 20, 2002Assignee: Clariant GmbHInventors: Uwe Nickel, Klaus Kund, Frank Alfter
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Patent number: 5889162Abstract: 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: GrantFiled: August 10, 1998Date of Patent: March 30, 1999Assignee: Engelhard CorporationInventor: Byron G. Hays
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Patent number: 5559216Abstract: 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: GrantFiled: September 1, 1993Date of Patent: September 24, 1996Assignee: Hoechst AGInventors: Ruediger Jung, Joachim Weide, Hans J. Metz
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Patent number: 5298609Abstract: 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: GrantFiled: July 14, 1993Date of Patent: March 29, 1994Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 5266110Abstract: 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: GrantFiled: October 29, 1992Date of Patent: November 30, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Rieper, Edwin Baier
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Patent number: 5185435Abstract: 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: GrantFiled: January 30, 1992Date of Patent: February 9, 1993Assignee: Ciba-Geigy CorporationInventors: Klaus Ruf, Bilge Gulec, Michael Reisinger, Werner Surber
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Patent number: 5062894Abstract: 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: GrantFiled: June 25, 1991Date of Patent: November 5, 1991Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
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Patent number: 5030247Abstract: 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: GrantFiled: November 9, 1989Date of Patent: July 9, 1991Assignee: Sandoz Ltd.Inventor: Jurgen Goldmann
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Patent number: 4946508Abstract: 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: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio
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Patent number: 4946509Abstract: Diarylide pigments modified with alkylene oxide polymers. The modified pigments are useful in both water-based and solvent-based coating and ink compositions.Type: GrantFiled: May 23, 1989Date of Patent: August 7, 1990Assignee: Sun Chemical CorporationInventors: Russell J. Schwartz, Manuel Z. Gregorio, Anthony C. Zwirgzdas
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Patent number: 4946948Abstract: 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: GrantFiled: August 31, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Fridolin Babler
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Patent number: 4544736Abstract: 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: GrantFiled: May 26, 1983Date of Patent: October 1, 1985Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4540775Abstract: 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: GrantFiled: May 11, 1981Date of Patent: September 10, 1985Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul