Specified Crystalline Form Patents (Class 534/575)
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Publication number: 20140046042Abstract: A liquid-crystalline coating fluid which comprises: an azo compound represented by the following general formula (1); and a solvent to dissolve the azo compound: wherein R is an amino group, a cyano group, a hydroxyl group, a nitro group, a halogen group or a hydrogen atom; and M is a counterion.Type: ApplicationFiled: October 22, 2013Publication date: February 13, 2014Applicant: NITTO DENKO CORPORATIONInventors: Hisanari ONOUCHI, Shoichi MATSUDA, Sadahiro NAKANISHI, Tadayuki KAMEYAMA
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Patent number: 8168764Abstract: Provided is a polyfunctional compound which can be used as an optical recording material in which a large quantity of information data can be recorded optically at a high density, which can be used as an optical waveguide material using a refractive index difference occurring between a light-irradiated part and a part not irradiated with light, and which is capable of forming a film and can be used as a photo-alignment film material having excellent photosensitivity.Type: GrantFiled: July 3, 2007Date of Patent: May 1, 2012Assignee: Nitto Denko CorporationInventors: Sadahiro Nakanishi, Mitsuru Ueda
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Patent number: 7999086Abstract: The invention provides a method of conditioning azo pigments containing carboxylic ester groups, using glycol monoalkyl ethers or mixtures of glycols and glycol dialkyl ether.Type: GrantFiled: January 30, 2009Date of Patent: August 16, 2011Assignee: Clariant Finance (BVI) LimitedInventors: Jens Paetzold, Carsten Plueg, Frank Alfter
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Patent number: 7923540Abstract: The present invention is directed to 2-[[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxo-propyl]azo]-benzoic acid (C.I. Pigment Yellow 151): (I), characterized by a ?E* (black/white) in masstone below 22.0±0.7, a process for its preparation and its use for pigmenting macromolecular organic materials of natural or synthetic origin. The pigment has high opacity and high color strength.Type: GrantFiled: January 8, 2007Date of Patent: April 12, 2011Assignee: BASF SEInventors: Hans Reichert, Max Hügin, Ulrich Veith, Sibylle Soder, Thomas Eichenberger
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Patent number: 7709614Abstract: Novel crystalline modifications (eta, theta, iota, kappa) of the C.I. Pigment Yellow 181, obtained when one of the known phases or another inventive phase of said pigment is treated with specific solvents. The novel crystalline phases are characterized by yellow shades and excellent coloring properties.Type: GrantFiled: June 15, 2005Date of Patent: May 4, 2010Assignee: Clariant Produkte (Deutschland) GmbHInventors: Martin U. Schmidt, Gerald Mehltretter
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Publication number: 20090290214Abstract: Disclosed are a new dichroic dye having liquid crystal properties and dichroic properties and capable of being used for forming a polarization film with excellent heat resistance, durability, and polarizing properties, a composition including the same for a polarization film, a method for forming a polarization plate with excellent durability using the composition, and a polarization plate prepared thereby. The new dichroic dye has a structure of R1-L1-(M,L,D) (where, D is a dichroic structure, M is a structure with liquid crystal properties, R1 is a reactive end functional group, and L and L1 are linking structures). The composition for a polarization film includes the dichroic dye. In the method for forming the polarization plate, the composition for a polarization film is applied to a substrate and cured to prepare the polarization plate. The polarization plate has excellent dichroic ratio, heat resistance, durability, and polarizing properties.Type: ApplicationFiled: September 4, 2007Publication date: November 26, 2009Inventors: Yong-Il Cho, Jeong-Su Yu, Eun-Kyung Kim, Sin-Young Kim
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Patent number: 7407517Abstract: The present disclosure relates to the use of cationic azo compounds with julolidine units as direct dyes, for the dyeing of keratin fibers, including human keratin fibers, such as the hair. The present disclosure also relates to a dyeing composition for the dyeing of keratin fibers, including human keratin fibers such as the hair, containing at least one cationic direct azo dye with julolidine units, in a suitable dyeing medium. The present disclosure also relates to a method of dyeing of keratin fibers, including human keratin fibers such as the hair, employing the dyeing composition according to the disclosure. The present disclosure also relates to cationic azo compounds with julolidine units.Type: GrantFiled: August 23, 2006Date of Patent: August 5, 2008Assignee: L'Oreal S.A.Inventors: Nicolas Daubresse, Andrew Greaves
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Patent number: 7262284Abstract: A method for the production of a diazo pigment, or a mixture of diazo pigments, according to formula (I) of the specification by azo coupling, wherein the azo coupling product is subjected to a finish in an organic solvent or in an agueous organic solvent with a neutral or alkaline pH.Type: GrantFiled: May 27, 2003Date of Patent: August 28, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Olaf Schupp, Felix W. Grimm, Manfred Opravil, Joachim Weber
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Patent number: 6784286Abstract: The invention relates to pyrazolone pigments of general formula (I), wherein the radicals R1, R2, R3 and R4 independently represent hydrogen, chlorine, methyl or ethyl, whereby at least one of the radicals R1-R4 is different from hydrogen. The inventive pigments are characterised by a CIELAB colour angle of 80-85°, a chroma of 58-62 and a luminosity ≧87 (measuring angle 45°, standard illuminant D65).Type: GrantFiled: June 13, 2003Date of Patent: August 31, 2004Assignee: BASF AktiengesellschaftInventors: Peter Blaschka, Günter Smeyts, Paul Günthert
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Patent number: 6673906Abstract: The present invention relates to the &bgr; modification of the dye of the formula IType: GrantFiled: January 11, 1996Date of Patent: January 6, 2004Assignee: DyStar Textifarben GmbH & Co. Deutschland KGInventor: Ulrich Bühler
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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: 6388057Abstract: A water-insoluble monoazo dye represented by the following structural formula [I] having a crystal modification characterized by an X-ray diffraction pattern (CuK&agr;) showing one strong peak at a diffraction angle (2&thgr;) of 11.1±0.1° and also four intermediate peaks at 8.1±0.1°, 21.8±0.1°, 23.1±0.1° and 25.2±0.1°.Type: GrantFiled: August 31, 2001Date of Patent: May 14, 2002Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Toshio Hihara, Hiroshi Inoue, Yousuke Takahashi
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Patent number: 6365718Abstract: The invention provides a dye composition for dyeing fibers comprising (a) an azo dye of formula (II) or a salt thereof, and (b) an azo dye of formula (III) or a salt thereof. The invention provides navy and black dye compositions, especially suitable for dyeing secondary cellulose acetate fibers, with superior fastness properties than known navy/black dyes. Preferably, the &agr;-crystal form of dye (III) is used, which has greater solubility and achieves quicker dyeing than the commonly-used &bgr; and &ggr; forms of (III) when dyeing cellulose acetate at 60-95° C. A new method of making the &agr; form is disclosed.Type: GrantFiled: September 22, 2000Date of Patent: April 2, 2002Assignee: Yorkshire Chemicals PLCInventors: Christopher Whitham, Alan John Buckley, Rebecca Jane Crowson
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Publication number: 20020032318Abstract: A method of printing cellulosic fiber materials in which the fiber material is brought into contact with reactive dyes of formula 1Type: ApplicationFiled: July 5, 2001Publication date: March 14, 2002Inventors: Athanassios Tzikas, Hans Reichert, Herbert Klier
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Patent number: 6303762Abstract: Disclosed is a method of producing a disazo pigment, which a coupling reaction is carried out while feeding, into an acidic aqueous solution, a tetrazo aqueous solution containing a tetrazo component of benzidines and a coupler aqueous solution containing a coupling component, wherein the coupling component is a mixture comprising a main component represented by the formula (1): CH3COCH2CONH—X, wherein X represents a phenyl group optionally having one or the same or different plural substituents selected from the group consisting of a methyl group, methoxy group and chlorine atom; a first additional component represented by the formula (2): CH3COCH2CONH—Y, wherein Y represents a phenyl group having a substituent selected from the group consisting of —CONR2 group, —SO2NR2 group and —NHCOR group, and the phenyl group may further have a substituent selected from the group consisting of a methyl group, methoxy group, chlorine atom, —CONR2 group, —SO2NR2 group and —NType: GrantFiled: April 6, 2001Date of Patent: October 16, 2001Assignee: TOYO INK Mfg. Co., Ltd.Inventors: Hitoshi Maki, Hideto Noguchi, Kenji Kitamura, Masami Shirao
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Patent number: 6228162Abstract: C.I. Pigment Red 53:2 is obtained in new crystal modifications (epsilon, zeta, eta, theta, iota, kappa, lambda, nu, xi, omicron, pi and rho phases) by heating any other phase of this pigment in certain organic solvents and reprecipitating the pigment. The new crystal phases differ from one another in rheology and coloristics.Type: GrantFiled: December 17, 1999Date of Patent: May 8, 2001Assignee: Clariant GmbHInventor: Martin U. Schmidt
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Patent number: 6197467Abstract: Charge control agent comprising a metal complex salt compound having a monoazo compound as a ligand, wherein the metal complex salt compound is amorphous, and which is excellent in charge control properties, heat resistance and light fastness, good in dispersibility in, and wettability with, toner resins, hardly damages the photoreceptor when used in a toner, and is unlikely to drop from toner particles during charging; process for manufacturing the charge control agent, comprising subjecting a crystalline metal complex salt compound having a monoazo compound as a ligand to wet milling in an organic solvent, or dissolving the crystalline metal complex salt compound in an organic solvent, and subsequently re-dispersing it in water; and toner for developing electrostatic images comprising said charge control agent, a toner resin, and a coloring agent, and method of use thereof.Type: GrantFiled: April 22, 1998Date of Patent: March 6, 2001Assignee: Orient Chemical IndustriesInventors: Shun-ichiro Yamanaka, Kazuaki Sukata, Masashi Yasumatsu
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Patent number: 6191263Abstract: The invention relates to a novel crystal modification (&ggr;-modification ) of C.I. Pigment Red 53:2 of the formula (1) having the following characteristic reflections in the X-ray powder diffraction pattern: 2&THgr; d Relative intensity in % 4.4 20.2 49 5.8 15.4 100 8.8 10.0 23 10.3 8.6 25 10.9 8.1 33 12.2 7.3 15 13.9 6.4 16 15.4 5.8 15 16.7 5.3 28 17.6 5.0 16 18.4 4.8 18 18.6 4.8 18 19.7 4.5 20 20.8 4.3 18 23.2 3.8 48 24.0 3.7 21 24.8 3.6 37 25.2 3.5 34 26.6 3.3 19 27.3 3.3 19 27.9 3.2 12 29.3 3.Type: GrantFiled: June 21, 1999Date of Patent: February 20, 2001Assignee: Clariant GmbHInventors: Martin Ulrich Schmidt, Hans Joachim Metz
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Patent number: 6146455Abstract: The invention relates to a novel crystal modification (.delta.-modification) of C.I. Pigment Red 53:2 of the formula (1) ##STR1## having the following characteristic reflections in the X-ray powder diffraction pattern:______________________________________ 2.THETA. d relative intensity (in %) ______________________________________ 3.3 26.6 32 4.7 18.7 100 7.5 11.9 14 9.4 9.3 19 10.5 8.4 13 13.8 6.4 10 14.2 6.2 9 14.9 5.9 10 16.7 5.3 11 17.6 5.0 9 18.1 4.9 16 18.9 4.7 10 20.4 4.3 7 21.1 4.2 9 22.1 4.0 9 22.7 3.9 12 23.1 3.8 9 23.6 3.8 13 24.1 3.7 9 24.9 3.6 10 25.5 3.5 23 26.3 3.4 9 27.7 3.2 9 28.1 3.2 6 28.9 3.1 6 30.4 2.Type: GrantFiled: June 21, 1999Date of Patent: November 14, 2000Assignee: Clariant GmbHInventors: Martin Ulrich Schmidt, Hans Joachim Metz
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Patent number: 6028178Abstract: Azo pigment of the formula (1) ##STR1## which has a specific surface area of the pigment powder of more than 45 m.sup.2 /g.The azo pigment is particularly suitable as colorant in electrophotographic toners and developers, and in powder coatings and electret materials.Type: GrantFiled: July 26, 1999Date of Patent: February 22, 2000Assignee: Clariant GmbHInventors: Hans Joachim Metz, Rudiger Baur, Hans-Tobias Macholdt
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Patent number: 6022957Abstract: Azothiophene disperse dyes of Formula (1) ##STR1## in which R, R.sup.1, R.sup.2 and R.sup.3 each independently is alkyl or alkenyl and mixtures thereof with other dyes are useful for dyeing synthetic textile material or a fiber blend thereof such as secondary cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile and aromatic polyester.Type: GrantFiled: April 17, 1998Date of Patent: February 8, 2000Assignee: BASF AktiengesellschaftInventor: Alan T. Leaver
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Patent number: 5958128Abstract: In the method of manufacturing a disazo pigment according to the present invention, a superior coupling reaction rate during the coupling reaction process makes it possible to manufacture a disazo pigment having superior transparency, brightness, color strength and gloss for the case in which a color strength agent is used. In this method, a coupling reaction is carried out while continuously feeding a coupler aqueous solution comprising a coupler component having the general formula (I) shown below and a tetrazo aqueous solution comprising a benzidine derivative tetrazo component at a molar ratio of 2:0.8.about.0.99 into an acidic aqueous solution held in a batch type mixing vessel. ##STR1## (where each of X, Y, Z independently represents H, CH.sub.3, OCH.sub.Type: GrantFiled: October 24, 1997Date of Patent: September 28, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yoshimi Kikuchi, Hitoshi Sugamo
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Patent number: 5942603Abstract: This invention related to a novel .beta.-crystal of the compound represented by the following formula (1), ##STR1## which is useful as a dyestuff. The .beta.-crystal of this invention is characterized by being stable in high temperature and having sharp peaks in the powder X-ray diffractometory.This invention is related to a process for producing a said .beta.-crystal, said process comprising heating a known thermally unstable .alpha.-crystal at a temperature higher than 15.degree. C., preferably higher than 40.degree. C. in water, a water-soluble organic solvent, or a solvent comprising water containing an anionic or nonionic surface active agent.Furthermore, this invention is related to a dyestuff composition containing of the said .beta.-crystal, and a process for dyeing comprising employing the said .beta.-crystal.Type: GrantFiled: December 11, 1997Date of Patent: August 24, 1999Assignee: Nippon Kayaku Co., Ltd.Inventors: Yasuo Murakami, Yoshiki Akatani
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Patent number: 5917121Abstract: The present invention relates to the .beta. and .gamma. modifications of the dye of the formula (I) ##STR1## as well as to a process for their preparation and their use for dyeing and printing textile materials of polyester and/or cellulose esters or blended fabrics of these materials and wool or cellulose.Type: GrantFiled: September 5, 1997Date of Patent: June 29, 1999Assignees: Dystar Textilfarben GmbH & Co. Deutschland KG, Dystar Japan Ltd.Inventors: Ulrich Buhler, Hubert Kruse, Heinz G. Zorn, Klaus-Wilfried Wanken
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Patent number: 5910577Abstract: Compounds of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are Cl, COO(C.sub.1 -C.sub.4)-alkyl, CONH.sub.2, CONCH.sub.3, CON(CH.sub.3).sub.2 or SO.sub.2 NRR', where R and R' are identical or different and are hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl, it being possible for phenyl to be substituted by methyl, ethyl, methoxy, ethoxy or halogen,R.sup.3 is hydrogen, methyl, methoxy, ethoxy, chloro or bromo, andR.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, chloro or bromo,are useful yellow pigments with high light fastness and weather fastness properties.Type: GrantFiled: July 31, 1998Date of Patent: June 8, 1999Assignee: Clariant GmbHInventors: Hans Joachim Metz, Joachim Weber
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Patent number: 5852179Abstract: The use of alkoxylated acetylenic diol surfactants in the aqueous synthesis of disperse azo dyes provides a simple process for improving filtration properties of dyestuff. The surfactants may be added prior to the coupling step of the synthesis or prior to heat treatment of the dye slurry. Advantages that are realized by incorporation of the surfactants into the synthesis include decreased filtration time, increased solid content in filter cake, improved washing properties of filter cake, and increased dye yield. In addition, for azo dyes that are synthesized as non-heat-stable crystal modifications, the presence of alkoxylated acetylenic diol surfactants in the dye slurry is effective in promoting the conversion of the dye to the desired thermally stable crystal modification.Type: GrantFiled: May 27, 1998Date of Patent: December 22, 1998Assignee: Air Products and Chemicals, Inc.Inventor: Gregory Paul Dado
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Patent number: 5837761Abstract: A plastics composition comprising a high molecular weight material and an effective coloring amount of an azo pigment of formula ##STR1## where M is Mg, Ca, Sr, Ba or Mn or a mixture of two or more thereof, R.sup.1 and R.sup.2 are chlorine or methyl, x is zero or 1, y is zero or 1 and the sum of x and y is 1, with the proviso that when the high molecular weight material is polyvinyl chloride y is zero.Type: GrantFiled: September 30, 1996Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ian Alexander MacPherson, Iain Frank Fraser, Alison MacLennan
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Patent number: 5824117Abstract: The present invention relates to the dyestuff of the formula I ##STR1## modifications of this dyestuff which are stable during dyeing, processes for the preparation thereof and their use for dyeing and printing synthetic fiber materials.Type: GrantFiled: June 28, 1996Date of Patent: October 20, 1998Assignee: Dystar Japan Ltd.Inventors: Ulrich Buhler, Jurgen Kuhlwein, Hubert Kruse
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Patent number: 5532344Abstract: A process for producing a monoazodye of the following formula (III): ##STR1## wherein X.sup.1 is nitro or halogen, X.sup.2 is halogen, R.sup.1 is lower alkoxy, R.sup.2 is lower alkyl, each of R.sup.3 and R.sup.4, which are independent of each other, is alkyl, cyanoalkyl or alkylcarbonyloxyalkyl, and each of m and n, which are independent of each other, is 0 or 1, which comprises diazotizing an aniline derivative of the following formula (I): ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, followed by coupling with an aniline derivative of the following formula (II): ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined above, wherein a reaction mixture obtained by the coupling reaction is heat-treated in the presence of a polyoxyethylene higher fatty acid ester type nonionic surfactant, followed by filtration to obtain said monoazo compound in the form of a cake.Type: GrantFiled: March 29, 1993Date of Patent: July 2, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yoshiharu Hamano, Shinji Kubo
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Patent number: 5502170Abstract: Azo dyes of the formula ##STR1## where L.sup.1, L.sup.2, L.sup.3, L.sup.4, X and K are as defined in the specification, and crystal forms of thienylazobenzene dyes are useful for dyeing or printing textile materials such as polyesters, fibers or fabrics made of cellulose esters or polyamides or blend fabrics from polyester and cellulose fibers with high color strength, good fastness properties and brilliant hues.Type: GrantFiled: May 17, 1995Date of Patent: March 26, 1996Assignee: BASF AktiengesellschaftInventors: Sabine Gruettner-Merten, Helmut Reichelt, Arno Lange, Helmut Degen
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Patent number: 5493011Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.Type: GrantFiled: November 6, 1992Date of Patent: February 20, 1996Assignee: Hoechst AGInventors: Rudiger Jung, Reinhold Deubel
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Patent number: 5489672Abstract: A process for the production of a dis-azo pigment which is excellent in sanitary condition and almost free of a residual coupler component and decomposition products derived from the residual coupler component, and has a reduced aromatic amine content, and a dis-azo pigment produced by the said process, the process comprising the steps of (a) coupling-reacting a solution of a tetrazonium salt of benzidine with a slurry of acetoacetanilide of which the amount is stoichiometrically excess relative to an amount of said tetrazonium salt, to prepare a dis-azo pigment slurry, and (b) adding a halogen to the dis-azo pigment slurry to treat the acetoacetanilide in said slurry.Type: GrantFiled: October 26, 1994Date of Patent: February 6, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Osamu Shiromaru, Hitoshi Sugamo
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Patent number: 5466790Abstract: Azo dyes of the formula ##STR1## where L.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl or phenyl,L.sup.2 and L.sup.3 are each substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, or together a radical of the formula ##STR2## where n is 0, 1 or 2, Y.sup.1 and Y.sup.4 are hydrogen, hydroxymethyl, 1,2-dihydroxyethyl or a radical of the formula COO.sym.M.sup..crclbar. or SO.sub.3.sup..crclbar. M.sup..sym., Y.sup.2 and Y.sup.3 are halogen or hydroxymethyl, and M.sup..sym. is the equivalent of a cation,L.sup.4 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, substituted or unsubstituted phenyl, halogen, C.sub.1 -C.sub.8 -alkoxy, substituted or unsubstituted phenoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylsulfonyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl or phenoxycarbonyl,X is nitrogen or the radical C--L.sup.5, where L.sup.Type: GrantFiled: September 30, 1994Date of Patent: November 14, 1995Assignee: BASF AktiengesellschaftInventors: Sabine Gruettner-Merten, Helmut Reichelt, Arno Lange, Helmut Degen
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Patent number: 5428136Abstract: Disazo compounds of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are a hydrogen or halogen atom or a C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyl, nitro, cyano or trifluoromethyl group and the rings A, B, C and D independently of one another are unsubstituted or contain one or more substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.5 -carbalkoxy, C.sub.2 -C.sub.5 -alkanoyl, benzoyl, acyloxy, acylamino, unsubstituted or N-mono- or N,N-disubstituted carbamoyl or unsubstituted or N-mono- or N,N-disubstituted sulfamoyl, possible substituents being C.sub.1 -C.sub.4 -alkyl or mono- to trisubstituted phenyl; C.sub.1 -C.sub.4 -alkylamino or phenylamino; C.sub.1 -C.sub.Type: GrantFiled: July 29, 1993Date of Patent: June 27, 1995Assignee: Hoechst AGInventors: Rudiger 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: 5175258Abstract: A process for the preparation of photogenerating pigments which comprises the reaction of a diaminofluorenone with an alkali nitrite, an acid, and a tetrafluoroborate; thereafter reacting the resulting product with an anilide coupler; and subsequently annealing the product obtained.Type: GrantFiled: December 14, 1990Date of Patent: December 29, 1992Assignee: Xerox CorporationInventors: Kock-Yee Law, Ihor W. Tarnawskyj
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Patent number: 5128454Abstract: The invention relates to a novel crystallographic modification (.beta.-modification) of the pigment of the formula I ##STR1## The .beta.-modification shows reflections in the Cu-K.sub..alpha. radiation X-ray diffraction spectrum at the following diffraction angles 2.theta. (accuracy .+-.0.2.degree.): at 21.95.degree. a maximum of high intensity, at 5.40.degree., 7.30.degree., 10.85.degree., 14.50.degree. and 27.60.degree. maxima of medium intensity and at 10.05.degree., 12.80.degree., 16.40.degree., 17.95.degree., 24.65.degree. and 25.80.degree. maxima of low intensity.The .beta.Type: GrantFiled: February 21, 1990Date of Patent: July 7, 1992Assignee: Hoechst AktiengesellschaftInventor: Heinrich Frolich
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Patent number: 5102466Abstract: The present invention provides a process for the production of a metallized azo pigment having the formula ##STR1## in which R and R.sub.1, independently, are hydrogen, halogen or alkyl; X.sub.1 is SO.sub.3.sup..crclbar. or CO.sub.2.sup..crclbar. ; and M is Ca, Sr, Mn or Ba; comprising coupling, at a pH value below 7.0, a diazotized amine of formula ##STR2## in which R, R.sub.1 and X.sub.1 have their previous significance, with a coupling component of formula ##STR3## to produce an azo dyestuff having the formula ##STR4## in which R, R.sub.1 and X.sub.1 have their previous significance, and Y is an alkaline earth metal or ammonium ion; and laking the dyestuff of formula IV during or after its production with one or more salts of a metal M wherein M has its previous significance.Also disclosed is a new modification of a pigment of formula I.Type: GrantFiled: February 21, 1991Date of Patent: April 7, 1992Assignee: Ciba-Geigy CorporationInventors: Michael Mordente, Alistair B. Boyd
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Patent number: 5101021Abstract: Compounds of the formula ##STR1## and mixtures of such compounds, wherein each R.sub.1 is independently halo,R.sub.3 is hydrogen or methyl, with the proviso that when R.sub.5 is ethoxy, R.sub.3 must be methyl,R.sub.4 is hydrogen or methyl, andR.sub.5 is hydrogen: C.sub.1-2 alkyl; C.sub.1-2 alkyl monosubstituted by halo; phenoxymethyl; vinyl; C.sub.1-4 alkoxy; C.sub.2-5 alkoxy monosubstituted by C.sub.1-2 alkoxy or halo; allyloxy; phenoxy or benzyloxy,useful as disperse dyes for the dyeing of substrates such as polyester by, for example, the rapid dyeing method and substrates dyed therewith.Type: GrantFiled: May 25, 1990Date of Patent: March 31, 1992Assignee: Sandoz Ltd.Inventor: Ruedi Altermatt
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Patent number: 5095122Abstract: Organic pigments selected from the diketopyrrolopyrrole, azo, isoindolinone and isoindoline series, which pigments consist of 50% by weight of platelets which are from 5 to 50 .mu.m long, 2 to 50 .mu.m wide and 0.01 to 5 .mu.m thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3.The pigments in platelet form are excellently suited to producing effect colorations in high molecular weight organic material and in cosmetic products.Type: GrantFiled: July 13, 1990Date of Patent: March 10, 1992Assignee: Ciba-Geigy CorporationInventors: Philippe Bugnon, Fritz Herren, Bernhard Medinger
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Patent number: 5069682Abstract: The present invention relates to the .beta.-modification of the dye of the formula I ##STR1## to a process for its preparation, to its use, and to a dye preparation containing it.Type: GrantFiled: December 21, 1990Date of Patent: December 3, 1991Assignee: Cassella AktiengesellschaftInventors: Rudolf Binder, Friedrich Schophoff, Klaus Hofmann
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Patent number: 5055564Abstract: A monoazo lake pigment for use in inks and paints of the formula (I): ##STR1## whose X-ray diffraction pattern shows a high diffraction intensity at a diffraction angle (2.theta..+-.0.2.degree.; Cu-K.sub..alpha.) of 5.0.degree., moderate diffraction intensity at 25.0.degree. and relatively low diffraction intensities at 14.8.degree., 19.5.degree..Type: GrantFiled: September 15, 1988Date of Patent: October 8, 1991Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Nagatoshi Koyayashi, Hirohito Ando
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Patent number: 5037962Abstract: The .beta.-modification, which is stable under dyeing conditions, of the dyestuff of the formula ##STR1## is prepared by heating the .alpha.-modification, which is unstable under dyeing conditions, at temperatures of 60.degree. to 180.degree. C. and the .beta.-modification is useful in printing and dyeing fiber materials of cellulose esters, synthetic linear polyesters or mixed fabrics of the polyester fiber material with wool or viscose staple.Type: GrantFiled: August 21, 1989Date of Patent: August 6, 1991Assignee: Cassella AGInventors: Hubert Kruse, Ulrich Buhler, Konrad Opitz, Willi Steckelberg
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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: 4985045Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety, has improved dyeing properties compared with the individual dyestuffs when used to dye or print hydrophobic fiber materials.Type: GrantFiled: October 30, 1989Date of Patent: January 15, 1991Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Klaus Hofmann
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Patent number: 4985043Abstract: Mixtures of monoazo dyes suitable for dyeing and printing hydrophobic fiber materials and mixtures thereof with natural fibers contain one or more dyes of the formula I ##STR1## and one or more dyes of the formula II ##STR2## in which Hal denotes bromo or chloro; R.sup.1 and R.sup.2, independently of one another, denote methyl or ethyl; R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently of one another, denote linear alkyl having 1 to 4 carbon atoms or alkenyl having 3 or 4 carbon atoms; and R denotes methyl, acetylamino, propionylamino, i-butyrylamino, or n-butyrylamino.Type: GrantFiled: March 15, 1989Date of Patent: January 15, 1991Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Manfred Hahnke, Reinhard Kuhn, Margarete Boos
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Patent number: 4981489Abstract: Disazo compounds based on 4,4'-diaminodiphenyl compounds contain not less than 50% by weight of a disazo compound of the general formulaA--N.dbd.N--Z--N.dbd.N--B (I)where Z is a radical of an unsubstituted or symmetrically substituted diphenylene, A is a radical of a coupling component of a 1-phenylpyrazolone or of an acetoacetarylide, where the phenyl and the aryl radical is subtsituted by sulfo or carboxyl groups, and B is a radical of a coupling component based on 1-phenylpyrazolone or acetoacetarylide, which are free of sulfo and/or carboxyl groups.The disazo compounds can be obtained by coupling the tetrazotized diamine H.sub.2 N--Z--NH.sub.2 to the coupling component AH containing an acidic group in a medium containing a mineral acid, and then coupling the product to BH in a buffered medium (pH about 4).The novel disazo compounds are suitable as additives to pigments, in particular azo and disazo pigments, for improving the transparency and heat stability of the pigment particles, and the flow behavior.Type: GrantFiled: October 23, 1989Date of Patent: January 1, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Wolfgang Ruff, Egon Liedek, Gerhard Berger, Hans W. Sonneborn
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Patent number: 4980458Abstract: Mixed crystals of at least two different compounds of formula I ##STR1## wherein R is --CH.sub.3, phenyl, --COOCH.sub.3, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, M.sup.+ and M.sub.1.sup.+ are each independently of the other an alkali metal cation, an alkaline earth metal cation or a heavy metal cation or NH.sub.4.sup.+ ; wherein X, Y, X' and Y' are each independently hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, wherein at least two of the cations M.sup.+ and M.sub.1.sup.+ in the compounds forming the mixed crystals of formula I are different and the X-ray diffraction patterns of the mixed crystals differ from the X-ray diffraction patterns of the individual components and of their sum.Type: GrantFiled: May 8, 1989Date of Patent: December 25, 1990Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Arnold Grubenmann, Andreas Burkhard
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Patent number: 4960435Abstract: A crystalline form of the dye represented by the following formula (1): ##STR1## characterized by an X-ray diffraction pattern having a strong peak at the angle of diffraction (2.theta.) of 23.2.degree. and relatively strong peaks respectively at the angles of diffraction (2.theta.) of 8.3.degree., 12.3.degree., 20.8.degree., 21.9.degree., 25.0.degree., 27.1.degree., 29.2.degree. and 30.8.degree. according to X-ray powder diffractometry through the use of a Cu-K.alpha. line and a process for preparing the same by heat-treating a heat-instable crystalline form of the dye represented by the formula (1) in water, water containing a water-soluble organic solvent, or water containing an anionic or nonionic surfactant at a temperature of 40.degree. C. or above.It withstands dyeing at high temperature, e.g. 130.degree. C. or higher, to provide dyed fibers having excellent fastness properties.Type: GrantFiled: December 5, 1989Date of Patent: October 2, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Mituaki Tunoda, Nobuharu Suzuki
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Patent number: RE35009Abstract: Organic pigments selected from the diketopyrrolopyrrole, azo, isoindolinone and isoindoline series, which pigments consist of .Iadd.at least .Iaddend.50% by weight of platelets which are from 5 to 50 .mu.m long, 2 to 50 .mu.m wide and 0.01 to 5 .mu.m thick, with the proviso that the ratios of length:thickness and width:thickness must be at least 3.The pigments in platelet form are excellently suited to producing effect colorations in high molecular weight organic material and in cosmetic products.Type: GrantFiled: October 28, 1993Date of Patent: August 1, 1995Assignee: Ciba-Geigy CorporationInventors: Philippe Bugnon, Fritz Herren, Bernhard Medinger