Quinacridone Pigment Or Derivative Patents (Class 106/497)
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Patent number: 5968242Abstract: A molecular sieve, which contains in all, or only in some, of its cavities colorant molecules as well as a modifier which is covalently bound to said molecular sieve and which reduces its pore diameter, a process for its preparation as well as its use as pigment for coloring high molecular weight organic materials, preferably biopolymers and plastic materials, glasses, ceramic products, for formulations of decorative cosmetics, for the preparation of paint systems, preferably automotive lacquers, printing inks, dispersion paints and color filters as well as materials comprising the novel molecular sieves.Type: GrantFiled: December 19, 1997Date of Patent: October 19, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Wolfgang Holderich, Nadja Rohrlich, Laurent Chassot
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Patent number: 5958129Abstract: Novel pigment formulations which comprise at least one organic pigment selected from the class consisting of perylene, perinone, quinacridone, azo, benzimidazolone, anthraquinone or anthanthrone pigments and at least one pigment-dispersing agent of the formula (I) ##STR1## have improved rheological and coloristic properties, in particular in aqueous and nonaqueous coating systems.Type: GrantFiled: March 9, 1998Date of Patent: September 28, 1999Assignee: Clariant GmbHInventors: Manfred Urban, Dieter Schnaitmann, Margit Haberlick
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Patent number: 5944886Abstract: Colored aluminum pigments having a color pigment adhered closely, uniformly and firmly thereto through inorganic acid radical adsorbed on the surface of the aluminum pigment are suitable for use in paints, inks and molded resins. Color fading, poor chroma and processing complications commonly encountered with conventional aluminum pigments are avoided.Type: GrantFiled: May 22, 1997Date of Patent: August 31, 1999Assignee: Toyo Aluminium Kabushiki KaishaInventor: Yoshiki Hashizume
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Patent number: 5928419Abstract: A surface-treated organic pigment excellent in initial dispersibility and long-term dispersion stability in water and an organic solvent and free from the coagulation of pigment particles, obtained by reacting a sulfonating agent with an organic pigment dispersed in a solvent in which the organic pigment is insoluble or sparingly soluble, and thereby introducing a sulfonic acid group to the surface of each particle of the organic pigment.Type: GrantFiled: October 6, 1997Date of Patent: July 27, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Toshiyuki Uemura, Tsukasa Iguchi, Sunao Satake, Hisashi Uraki, Yasuharu Iida
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Patent number: 5922122Abstract: A composition containing an organic pigment and a compound having the formula (I): ##STR1## in which R.sup.1 is a group having the formula (II): ##STR2## in which R.sup.4 and R.sup.5 represent hydrogen or alkyl, or R.sup.4 and R.sup.5 are bonded to each other to form a ring together with a nitrogen atom, X represents alkylene or alkyleneoxyalkylene, and Y represents --O--, --S-- or a group represented by --NR.sup.6 -- wherein R.sup.6 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 represent a group having the formula (II), alkyl, aralkyl, aryl, alkoxy, aralkyloxy, aryloxy, alkylamino, arylamino or a halogen atom. A photosensitive colored composition is made of the composition, a polymer having acidic group, a photopolymerizable monomer and a photopolymerization initiator.Type: GrantFiled: July 29, 1997Date of Patent: July 13, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Akihiko Takeda, Takekatsu Sugiyama
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Patent number: 5922123Abstract: This invention relates to a process for preparing pigment compositions by conditioning an organic pigment, at about 50 to about 200.degree. C., with(1) at least about 0.1% by weight, relative to the organic pigment, of one or more surfactants of formula (I) ##STR1## wherein R.sup.1 is a C.sub.8 -C.sub.30 aliphatic group optionally having one or more carbon atoms in the main chain replaced with --O--, --S--, --CONH--, --NHCO--, --CH.dbd.CH--, C.sub.5 -C.sub.7 cycloalkylene, phenylene, or --OSi(C.sub.1 -C.sub.4 alkyl).sub.2 -,R.sup.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 hydroxyalkyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 hydroxyalkyl, or R.sup.2 and R.sup.3 together are C.sub.4 -C.sub.7 alkylene, andX is a direct bond, or X and R.sup.2 form a five- to seven-membered heterocyclic ring (and R.sup.3 can form a double bond in X), or X, R.sup.2, and R.sup.Type: GrantFiled: December 17, 1997Date of Patent: July 13, 1999Assignee: Bayer CorporationInventors: Charles W. Sandefur, Charles E. Shannon, Brian L. Thompson
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Patent number: 5919299Abstract: A process for preparing transparent, pigmentary quinacridone compounds and solid solutions thereof comprises combining a premilled, sub-pigmentary powder containing at least one unsubstituted or substituted quinacridone or a derivative thereof with a sufficient amount of moderately concentrated sulfuric acid to form a slurry, then agitating this slurry in the presence of an organic liquid which is immiscible or only partially miscible with the slurry and which is effective in deagreggating and improving the crystallinity of the pigment, for an effective length of time to convert the sub-pigmentary unsubstituted or substituted quinacridone or solid solution thereof to a transparent, pigmentary form.Type: GrantFiled: December 3, 1997Date of Patent: July 6, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Lindsay Kilmurray, deceased, Edward E. Jaffe
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Patent number: 5900050Abstract: This invention relates to a process for preparing pigment compositions by conditioning an organic pigment, at about 50 to about 200.degree. C., with(1) at least about 0.1% by weight, relative to the organic pigment, of one or more surfactants of formula (I) and/or formula (II) ##STR1## and/or ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, Z, and Z' are defined herein; and (2) about 1 to about 100 parts by weight, per part by weight of the organic pigment, of a liquid in which the organic pigment is substantially insoluble.Type: GrantFiled: October 17, 1997Date of Patent: May 4, 1999Assignee: Bayer CorporationInventors: Michael D. Hayden, Charles W. Sandefur, Abdul Sattar, Charles E. Shannon, Brian L. Thompson
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Patent number: 5879444Abstract: This invention relates to pigment compositions containing an organic pigment treated with a pigment derivative having the formula (I) ##STR1## wherein Q represents an organic pigment moiety;X is O, S, or N--R.sup.1 ;Y is N--R.sup.2, O, or a direct bond;Z is --CO--, --Alk--, --Ar--, or chemically reasonable combinations thereof;Alk is C.sub.1 -C.sub.5 alkylene, C.sub.2 -C.sub.5 alkenylene, or C.sub.4 -C.sub.5 alkadienylene, or substituted derivatives thereof;Ar is arylene;R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.7 -C.sub.16 aralkyl, or --CN; andR.sup.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.16 aralkyl, or C.sub.6 -C.sub.10 aryl;with the provisos that(1) the cyclic moiety represented by the formula ##STR2## must be a four- to seven-membered ring, (2) Z can contain a C.dbd.O group adjacent to the nitrogen atom of the Q--CH.sub.2 --N moiety only if Y is N--R.sup.2 or O, and(3) X can be O only if Y is N--R.sup.2 or O.Type: GrantFiled: September 2, 1997Date of Patent: March 9, 1999Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, Daphne J. Rice
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Patent number: 5868828Abstract: This invention relates to quinacridone pigments of formula (I) ##STR1## wherein X is O, S, or NR;R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, or C.sub.7 -C.sub.16 aralkyl;Y is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, or halogen;the dashed line represents an optional double bond;R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.16 aralkyl, nitrile, or carboxyl or an ester or an amide thereof, or R.sup.1 and R.sup.2 together form a C.sub.5 -C.sub.8 cycloaliphatic ring or a fused-on aromatic or heteroaromatic ring;R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl; andm is 0, 1, or 2.This invention further relates to the preparation and use of such quinacridone pigments.Type: GrantFiled: May 20, 1998Date of Patent: February 9, 1999Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, Guenter Franke
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Patent number: 5855662Abstract: Aqueous pigment preparations comprisinga) 10 to 80% by weight, in particular 20 to 60% by weight, of a pigment,b) 0.1 to 20% by weight, in particular 0.1 to 15% by weight, of an oxyalkylation product which is obtained by addition of optionally substituted styrenes onto optionally substituted phenols and reaction with ethylene oxide and/or propylene oxide,c) 2 to 30% by weight of a polyether-polyol having a boiling point under normal pressure of greater than 150.degree. C. andd) if appropriate further additives, and water as the remainder,which are particularly suitable for pigmenting naturally occurring and synthetic materials, such as emulsion paints, emulsion coatings and emulsion printing inks, have been found.Type: GrantFiled: March 26, 1996Date of Patent: January 5, 1999Assignee: Bayer AktiengesellschaftInventors: Achim Brand, Josef Leitermann, Roger Nyssen, Klaus Schubert, Erhard Schuffenhauer, Karlheinz Wieser, Herbert Wigger
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Patent number: 5843220Abstract: The present invention relates to a process for preparing a pigment composition whereby a mixture of an organic pigment and an inorganic filler is subjected to an air jet milling step. The inventive process is an environmentally friendly process which yields pigments having outstanding dispersibility and wetting characteristics when incorporated in plastics, aqueous or solvent based coatings and inks.Type: GrantFiled: December 1, 1997Date of Patent: December 1, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Fridolin Babler
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Patent number: 5837045Abstract: A surface-modified colored pigment is disclosed which includes a colored pigment having no primary amines and at least one attached hydrophilic organic group, wherein said organic group comprises a) at least one aromatic group, and b) at least one ionic group or ionizable group, or a mixture of an ionic group or an ionizable group. The colored pigment may be blue, brown, cyan, green, violet, magenta, red, orange, yellow, mixtures thereof and the like. The surface-modified colored pigment, due to the hydrophilic groups on its surface, is readily dispersed in a liquid vehicle without the addition of a surfactant or other dispersing aid or additive. The surface-modified color pigment may be used in a variety of aqueous systems including, but not limited to, coatings, paints, papers, adhesives, latexes, inks, toners, textiles and fibers. In addition, an aqueous composition is disclosed including water-based liquid vehicle and the surface-modified colored pigment described above.Type: GrantFiled: June 17, 1996Date of Patent: November 17, 1998Assignee: Cabot CorporationInventors: Joseph E. Johnson, James A. Belmont
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Patent number: 5827364Abstract: Pigment compositions comprising a pigment and both a phthalimidomethylquinacridone and a pyrazolylmethylquinacridone as additives are disclosed. The disclosed pigment compositions are useful for coloring coating compositions. Coating composition colored with the inventive pigment compositions have excellent rheological characteristics and which yield coatings having excellent saturation.Type: GrantFiled: February 21, 1997Date of Patent: October 27, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Shivakumar Basalingappa Hendi
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Patent number: 5800607Abstract: Process for the preparation of pigment preparations, which comprises wet milling the crude pigments which are present in coarsely crystalline state, or prepigments or pigments which are present in a form in which they are difficult to disperse, in a concentration of from 20 to 60% by weight based on the total weight of the pigment preparation, in a flocculation-stable liquid medium and in a stirred ball mill which is operated with a peripheral stirrer speed of more than 12 m/s, under the action of nonmetallic grinding media with a diameter of less than or equal to 1.0 mm, until the desired degree of fine division is reached, and then isolating the pigment preparation.Type: GrantFiled: July 3, 1996Date of Patent: September 1, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Schnaitmann, Martin Bohmer, Manfred Urban
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Patent number: 5785750Abstract: Pyrrolopyrrole derivatives of the formula (I) ##STR1## wherein QA is a quinacridone radical are disclosed. The inventive pyrrolopyrrole derivatives show excellent rheology enhancing properties for pigment dispersions, especially those containing quinacridones, DPPs and their solid solution pigments.Type: GrantFiled: September 26, 1997Date of Patent: July 28, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Shivakumar B. Hendi
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Patent number: 5779783Abstract: A composition used for an ingredient of printing ink, which comprises an organic pigment and a pigment derivative represented by the formula (I) in the acid form: ##STR1## wherein D represents a residue of an organic pigment other than azo, R.sub.1 represents a hydrogen atom or an unsaturated aliphatic, saturated aliphatic or aromatic hydrocarbon group having 1 to 20 carbon atoms, R.sub.2 represents an unsaturated aliphatic, saturated aliphatic or aromatic hydrocarbon group having 1 to 20 carbon atoms, m represents a number of from 0 to 3 and n represents a number of from 1 to 4, provided that m+n is from 1 to 5.Type: GrantFiled: September 23, 1997Date of Patent: July 14, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Hideki Senba, Hiroki Inoue, Yoshiaki Hayashi, Makoto Akita, Keisuke Ito
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Patent number: 5756746Abstract: The present invention relates to a solid solution consisting of 60-90 mol-% of an asymmetric 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (I) ##STR1## in which G.sub.1 and G.sub.2 independently of one another are different substituted or unsubstituted aromatic radicals or pyridyl, but the volume of all substituents on G.sub.1 and G.sub.2 is greater than that of two methyl groups;and 40-10 mol-% of a 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (IIa) ##STR2## in which G.sub.3 and G.sub.4 independently of one another are different substituted or unsubstituted aromatic radicals or pyridyl, but the volume of all substituents on G.sub.3 and G.sub.4 is less than that of two butoxy groups;or 40-10 mol-% of a quinacridone of the formula (IIb) ##STR3## in which R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;which is a single-phase solid solution having the crystal structure of the asymmetric 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (I).Type: GrantFiled: September 23, 1996Date of Patent: May 26, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, Abul Iqbal
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Patent number: 5755873Abstract: This invention relates to a process for the preparation of quinacridone pigments by(a) heating a reaction mixture comprising(i) a 2,5-dianilinoterephthalic acid, a 2,5-dianilino-3,6-dihydroterephthalic acid, or a 2,5-dianilino-3,6-dioxo-1,4-cyclohexadiene-1,4-dicarboxylic acid;(ii) about 0.1 to about 15 percent by weight, based on component (a)(i), of one or more sulfonyl-containing derivatives of 2,5-dianilinoterephthalic acid, 2,5-dianilino-3,6-dihydroterephthalic acid, and/or 2,5-dianilino-3,6-dioxo-1,4-cyclohexadiene-1,4-dicarboxylic acid; and(iii) about 3 to about 20 parts by weight, per part of component (a)(i), of a dehydrating agent,with the proviso that if either component (a)(i) or component (a)(ii) is a 2,5-dianilino-3,6-dihydroterephthalic acid or derivative thereof, reaction step (a) additionally comprises an oxidation step;(b) drowning the reaction mixture from step (a) with a liquid in which the quinacridone pigment is substantially insoluble; and(c) isolating the quinacridone pigment.Type: GrantFiled: November 18, 1996Date of Patent: May 26, 1998Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, John F. Britanak, Daphne J. Rice
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Patent number: 5755872Abstract: A process for preparing quinacridone pigmentsA process for preparing pigments, mixed crystal pigments and pigment preparations based on linear unsubstituted or substituted quinacridones of the formula (I) ##STR1## in which the substituents R.sup.1 and R.sup.2 are identical or different and are hydrogen, chlorine, bromine or fluorine atoms or are C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or carboxamido groups which may be substituted by C.sub.1 -C.sub.6 -alkyl groups; or are phenoxy or C.sub.6 -C.sub.10 -aryl rings onto which further aromatic, aliphatic or heterocyclic rings can be fused, which process comprises hydrolyzing the reaction mixture resulting from cyclization of the respective dianilinoterephthalic acid with polyphosphoric acid or polyphosphate at a temperature of or above 110.degree. C.Type: GrantFiled: April 1, 1997Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Manfred Urban, Dieter Schnaitmann, Martin Bohmer
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Patent number: 5755874Abstract: Process for preparing linear unsubstituted .beta.-phase quinacridone pigments A process for preparing linear unsubstituted .beta.-phase quinacridone pigments or pigment preparations, which comprisesa) cyclizing 2,5-dianilinoterephthalic acid in polyphosphoric acid or polyphosphoric ester with a phosphorus pentoxide content of at least 84% by weight to form the quinacridone,b) subsequently hydrolyzing this quinacridone with water or with an aqueous mineral acid solution, preferably orthophosphoric acid solution, at a temperature of at least 40.degree. C., preferably from 60.degree. to 105.degree. C., to form the crude quinacridone pigment which is predominantly in the .alpha.-phase,c) then heating the crude .alpha.-phase quinacridone pigment to a temperature between 120.degree. and 200.degree. C. in the presence of a from 0.1 to 3% strength by weight, preferably from 0.Type: GrantFiled: April 1, 1997Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Manfred Urban, Dieter Schnaitmann
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Patent number: 5746820Abstract: The use of sulfuric monoesters of the formulae (I) and (II)R.sup.1 --O--(CH.sub.2 O).sub.n --SO.sub.3 .sup.- M.sup.+ (I)R.sup.1 --CO--NR.sup.2 --(CH.sub.2 O)(.sub.n+1)--SO.sub.3 .sup.- M.sup.+ (II)in whichR.sup.1 is a straight-chain or branched alkyl group of 10 to 24 carbon atoms,R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.6 -alkyl group,M.sup.+ is a hydrogen ion, an alkali metal ion, 1/2 an alkaline earth metal ion, or an ammonium ion of the formula N.sup.+ R.sup.3 R.sup.4 R.sup.5 R.sup.6, where the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another are each hydrogen atoms or C.sub.1 -C.sub.6 -alkyl groups, which alkyl groups can be substituted by 1 to 3 hydroxyl groups, andn is a number from 0 to 4; or of a mixture of at least two sulfuric monoesters of the formulae (I) and/or (II),for preparing surface-treated pigments from the classes of the quinacridones and dioxazines.Type: GrantFiled: April 22, 1997Date of Patent: May 5, 1998Assignee: Hoechst AktiengesellschaftInventors: Manfred Urban, Dieter Schnaitmann
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Patent number: 5725651Abstract: Mono-N-alkyl-quinacridone pigments are disclosed. They exhibit high light fastness, high temperature stability and high migration fastness. Moreover, they show hypsochromic shifts, fluorescence and high photoconductivity. These pigments are suited for coloring high molecular weight organic materials, for use as light emitting materials of organic electroluminescent elements as well as photoreceptors of electrophotography.Type: GrantFiled: March 10, 1997Date of Patent: March 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: John Zambounis, Jin Mizuguchi
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Patent number: 5718753Abstract: The instant invention relates to a process for the production of colored metallic pigments, as well as these colored metallic pigments themselves, their use to color high molecular weight organic material in the mass and compositions or masterbatches containing them.The colored metallic pigment consists essentially of multiple loose particles of 0.1-1000 .mu.m size each, said particles comprising a core of a transition metals, metalloid or alloy, preferably an aluminum flake, and a very fine, substantially continuous, uniform and homogeneous layer of organic pigment particles which is directly in contact with the metallic core. The core may be superficially oxidized.The colored metallic pigment is prepared by a vacuum deposition process, said process being performed in an apparatus constructed, modified or charged in such a way that the organic pigment gas flows toward the metallic core.Type: GrantFiled: October 15, 1996Date of Patent: February 17, 1998Assignee: Ciba Specialty Chemicals Holding, Inc.Inventors: Masakazu Suzuki, Hiroshi Nakaminami, Seiji Homma
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Patent number: 5718754Abstract: The invention provides a pigment composition comprising a pigment having adsorbed on its surface, or as a physical mixture, up to 10% by weight, based on the total weight of pigment composition of a coding compound which is a compound containing an azo, azomethine or polycyclic chromophore and which has an absorption spectrum and a Raman spectrum different from that of the pigment. The compositions are suitable for use in printing inks for security applications.Type: GrantFiled: January 24, 1997Date of Patent: February 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ian Alexander Macpherson, Iain Frank Fraser, Peter Cyril White, William Ewen Smith, Calum Hugh Munro
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Patent number: 5716435Abstract: A water-dispersed inkjet recording liquid excellent in water resistance and transparency and also excellent in the property of ejection from a nozzle, containing, as a colorant, a water-based dispersion of an organic pigment (A) having an average particle diameter of 10 to 150 nm (measured by laser scattering), the water-based dispersion of the organic pigment (A) being obtained by mechanically kneading a mixture containing at least three components, said components being, the organic pigment (A), a water-soluble inorganic salt (B) in an amount by weight at least three times as large as the amount of the organic pigment (A) and a water-soluble solvent (C) to finely mill the organic pigment (A), and then removing the water-soluble inorganic salt (B) and the water-soluble solvent (C) by washing the kneaded mixture with water, and a process for the production thereof.Type: GrantFiled: September 17, 1996Date of Patent: February 10, 1998Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Seiji Aida, Tsutomu Fujigamori, Hisashi Uraki, Ichiro Toyoda, Sunao Satake, Seiji Sawada, Yasuharu Iida
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Patent number: 5713999Abstract: This invention relates to a process for the preparation of quinacridone pigments by(a) heating, at a temperature of about 80.degree. C. to about 145.degree. C., a reaction mixture containing(i) 2,5-dianilinoterephthalic acid, a 2,5-dianilino-3,6-dihydroterephthalic acid ester, and/or a derivative thereof,(ii) about 3 to about 15 parts by weight, per part of component (a)(i), of a dehydrating agent, and(iii) about 0.Type: GrantFiled: April 29, 1996Date of Patent: February 3, 1998Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, Margot Campos, Michael J. Greene, Daphne J. Rice
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Patent number: 5711800Abstract: This invention relates to pigment compositions comprising an organic pigment treated with about 0.1 to about 20% by weight, based on the organic pigment, of an N-heteroarylamidomethyl pigment derivative having the formula (I) ##STR1## wherein, Q represents an organic pigment moiety,NHet represents a nitrogen-containing heteroaromatic group attached at a ring nitrogen atom to the carbonyl function of the amidomethyl linking group, andn is from 1 to 4.Type: GrantFiled: December 31, 1996Date of Patent: January 27, 1998Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, John F. Britanak, Margot Campos, Daphne J. Rice, Niran Nugara
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Patent number: 5698024Abstract: This invention relates to pigment compositions comprising an organic pigment treated with about 0.1 to about 20% by weight, based on the organic pigment, of a compound having the formula (I) ##STR1## wherein Q represents an organic pigment moiety,X is O or S,Het represents a heteroaromatic group attached at a ring carbon atom to the (thio)amidomethyl --CH.sub.2 --NH--CX-- linking group, andn is from 1 to 4.Type: GrantFiled: December 31, 1996Date of Patent: December 16, 1997Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, Daphne J. Rice
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Patent number: 5685901Abstract: The present invention relates to a pigment composition comprising a diketopyrrolopyrrole pigment of formula (I) ##STR1## wherein A and B are as defined in claim 1, on the particle surface of which pigment an organometallic compound or a modified diketopyrrolopyrrole is adsorbed, and an aminoalkyl acrylate, and to the use of said composition for coloring organic material of high molecular weight.Type: GrantFiled: November 29, 1994Date of Patent: November 11, 1997Assignee: Ciba-Geigy CorporationInventor: Philippe Bugnon
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Patent number: 5683502Abstract: This invention relates to a process for the preparation of quinacridone pigments by(a) heating, at a temperature of about 80.degree. C. to about 145.degree. C., a reaction mixture containing(i) 2,5-dianilinoterephthalic acid, a 2,5-dianilino-3,6-dihydroterephthalic acid ester, and/or a derivative thereof,(ii) about 3 to about 15 parts by weight, per part of component (a)(i), of a dehydrating agent, and(iii) about 0.Type: GrantFiled: April 29, 1996Date of Patent: November 4, 1997Assignee: Bayer CorporationInventors: Ibraheem T. Badejo, Daphne J. Rice
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Patent number: 5679142Abstract: The invention provides an ink jet pigment set comprising a magenta pigment, a yellow pigment, and a cyan pigment wherein the normalized spectral transmission density distribution curve of the cyan pigment has a density between 0.66 and 0.94 at 600 nm and a density between 0.83 and 1.0 at 610 nm. Such a pigment set enables an increase in the color gamut obtainable for ink jet imaging.Type: GrantFiled: August 20, 1996Date of Patent: October 21, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth McInerney, David Joseph Oldfield, Douglas Eugene Bugner, Alexandra DiLauro Bermel, Domenic Santilli
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Patent number: 5679139Abstract: The invention provides a pigment set comprising a magenta pigment, a yellow pigment, and a cyan pigment wherein the normalized spectral transmission density distribution curve of the cyan pigment has a density between 0.66 and 0.94 at 600 nm and a density between 0.83 and 1.0 at 610 nm, and the magenta pigment has a density between 0.25 and 0.93 at 520 nm, a density between 0.9 and 1.0 at 540 nm, and a density between 0.9 and 1.0 at 560 nm. Such a pigment set enables an increase in the color gamut available for imaging.Type: GrantFiled: August 20, 1996Date of Patent: October 21, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth McInerney, David Joseph Oldfield, Douglas Eugene Bugner, Alexandra DiLauro Bermel, Domenic Santilli
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Patent number: 5679141Abstract: The invention provides an ink jet pigment set comprising a magenta pigment, a yellow pigment, and a cyan pigment wherein the normalized spectral transmission density distribution curve of the magenta pigment has a density between 0.25 and 0.93 at 520 nm, a density between 0.9 and 1.0 at 540 nm, and a density between 0.9 and 1.0 at 560 nm. Such a pigment set enables an increase in the color gamut obtainable for ink jet imaging.Type: GrantFiled: August 20, 1996Date of Patent: October 21, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth McInerney, David Joseph Oldfield, Douglas Eugene Bugner, Alexandra DiLauro Bermel, Domenic Santilli
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Patent number: 5679148Abstract: A pigment composition comprisingA) a 1,4-diketopyrrolo?3,4-c!pyrrole pigment of formula ##STR1## wherein A and B are each independently of the other a group of formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, halogen or CN, andB) 0.1-20% by weight, based on the diketopyrrolopyrrole of formula I, of an acrylic resin obtainable by homopolymerisation of a monomer of formula ##STR3## wherein R.sub.3 is hydrogen or methyl and R.sub.4 and R.sub.5 are each independently of the other hydrogen, methyl or ethyl, and n is an integer from 1 to 6, or by copolymerisation of the same monomer with a monomer which is copolymerisable with said same monomer, wherein the homopolymerization or copolymerization is carded out in the absence of a nonionic active agentThese pigment compositions have excellent rheology and the colorations obtained with them have surprisisingly high gloss.Type: GrantFiled: February 7, 1996Date of Patent: October 21, 1997Assignee: Ciba-Geigy CorporationInventor: Philippe Bugnon
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Patent number: 5679140Abstract: The invention provides a dye set comprising a magenta dye, a yellow dye, and a cyan dye wherein the normalized spectral transmission density distribution curve of the magenta dye has a density between 0.25 and 0.93 at 520 nm, a density between 0.9 and 1.0 at 540 nm, and a density between 0.9 and 1.0 at 560 nm and the yellow dye has a density between 0.9 and 1.0 at 450 nm and a density between 0.8 and 1.0 at 470 nm. Such a dye set enables an increase in the color gamut obtainable for imaging.Type: GrantFiled: August 20, 1996Date of Patent: October 21, 1997Assignee: Eastman Kodak CompanyInventors: Elizabeth McInerney, David Joseph Oldfield
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Patent number: 5662739Abstract: Readily dispersible polycyclic pigments from the class of the quinacridones and dioxazines are prepared by using a fatty acid tauride of the formula (I)R.sup.1 --CO--NR.sup.2 --(CH.sub.2).sub.n --SO.sub.3.sup.- M.sup.+(I)in whichR.sup.1 is a straight-chain or branched alkyl group having from 10 to 24 carbon atoms andR.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.6 -alkyl group,M.sup.+ is a hydrogen ion, ammonium ion, alkali metal ion or alkaline earth metal ion and n is 1 or 2, or a mixture of at least two fatty acid taurides of the formula (I).Type: GrantFiled: January 5, 1995Date of Patent: September 2, 1997Assignee: Hoechst AktiengesellschaftInventors: Manfred Urban, Erwin Dietz
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Patent number: 5641351Abstract: Heat-stable, red pigment compositions comprising a physical mixture of 1,4-diketo-3,6-di(4-biphenylyl)-pyrrolo [3,4 c]-pyrrole and a 2,9-dichloroquinacridone pigments, processes for preparing the pigment compositions and the use of the compositions for pigmenting high-molecular-weight organic materials are disclosed.Type: GrantFiled: April 14, 1995Date of Patent: June 24, 1997Assignee: Ciba-Geigy CorporationInventor: Fridolin Babler
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Patent number: 5641350Abstract: Pigment compositions comprising an organic pigment whose particle surface is provided with a protective coating layer, which coating comprises(a) a metal phosphate complex in which the metal is selected from the group consisting of, zirconium, titanium and mixtures thereof in a quantity of from 0.5 to 100% by weight, preferably to 20% by weight, particularly preferably from 1 to 10% by weight, based on the pigment; and(b) an amine or ammonium salt, in a quantity of from 0.5 to 15% by weight, preferably up to 10% by weight, particularly preferably up to 5% by weight, based on the pigment. The compositions are distinguished by outstanding properties, especially by the high gloss of the colorations obtained therewith, by very good dispersibility, high dispersion stability and heat resistance and by very good rheological characteristics of the paint millbases or printing inks prepared therewith. The plastics pigmented with the compositions of the invention are likewise distinguished by good dispersibility.Type: GrantFiled: December 8, 1995Date of Patent: June 24, 1997Assignee: Ciba-Geigy CorporationInventors: Laurent Chassot, Philippe Bugnon
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Patent number: 5626662Abstract: Organic polycyclic crude pigments are finely divided in an ecologically and economically advantageous manner by first of all subjecting crude, coarsely crystalline pigments to dry milling and wet-milling the resulting finely divided prepigments in aqueous suspension in a stirred ball mill which is operated at a power density of more than 2.5 kW per liter of milling space and a peripheral stirrer speed of more than 12 m/s under the action of grinding media having a diameter of less than or equal to 1 mm. Pigments prepared in this way are particularly suitable as colorants for the pigmentation of paints, printing inks and plastics.Type: GrantFiled: April 13, 1995Date of Patent: May 6, 1997Assignee: Hoechst AktiengesellschaftInventor: Manfred Urban
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Patent number: 5618343Abstract: The present invention relates to pigment and coating compositions that are used to prepare pigmented coatings that exhibit geometric metamerism or metallic flop. The pigment compositions comprise a small particle size pigment and a flop-enhancing agent, which flop-enhancing agent is a copper phthalocyanine, an indanthrone or a carbazole dioxazine compound. A method of enhancing the flop of a pigmented polymeric coating by incorporating one or more flop-enhancing agents into the composition is also disclosed.Type: GrantFiled: December 27, 1994Date of Patent: April 8, 1997Assignee: Ciba-Geigy CorporationInventors: Shivakumar B. Hendi, Edward E. Jaffe
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Patent number: 5614014Abstract: Pigments, mixed-crystal pigments or pigment preparations based on linear, unsubstituted or substituted quinacridones are prepared advantageously by initially wet-milling the coarsely crystalline crude pigments in a liquid aqueous, aqueous-organic or organic medium in a stirred ball mill which is operated at a power density of more than 2.5 kW per liter of milling space and a peripheral stirrer speed of more than 12 m/s under the action of grinding media having a diameter of less than or equal to 0.9 mm, until the desired degree of fine division is reached, and then isolating the resulting pigment in a conventional manner, or subjecting the resulting prepigment to solvent treatment at a temperature of from 50.degree. to 200.degree. C. and then isolating the pigment in a conventional manner.Type: GrantFiled: February 1, 1995Date of Patent: March 25, 1997Assignee: Hoechst AktiengesellschaftInventor: Manfred Urban
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Patent number: 5591258Abstract: Linear, unsubstituted quinacridone pigments of the .beta.-phase can be produced in an environmentally friendly manner bya) cyclizing 2,5-dianilinoterephthalic acid in polyphosphoric acid or a polyphosphoric ester to the quinacridone,b) then hydrolyzing the quinacridone with water at a temperature of at least 40.degree. C., preferably at from 60.degree. to 100.degree. C., to obtain a finely divided quinacridone pigment crude which is predominantly in the .alpha.-phase,c) then optionally wet grinding the finely divided quinacridone pigment crude from b) (pre-pigment), andd) then heating the crude pigment from b) or the pre-pigment from c) to a temperature between 120.degree. and 200.degree. C. in the presence of from 0.1 to 1.5 times the amount of an inorganic base, based on the weight of the crude pigment, in an inert liquid medium (solvent finish).To improve the depth and hue of the color, an oxidative treatment with a peroxodisulfate can be carried out subsequently.Type: GrantFiled: November 21, 1994Date of Patent: January 7, 1997Assignee: Hoechst AktiengesellschaftInventors: Manfred Urban, Erwin Dietz
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Patent number: 5584922Abstract: Disclosed is a process for coloring high-molecular-weight coatings and ink systems which comprises uniformly dispersing an effective pigmenting amount of a stir-in pigment in the coating or ink system; wherein the stir-in pigment is an organic pigment crude consisting essentially of non-platelet-shaped particles having an average particle size of from 0.5 to 25 .mu.m and/or a pigment composition consisting essentially of an organic pigment having an average particle size of from 0.01 to 25 .mu.m and inorganic filler pigment.Type: GrantFiled: September 14, 1994Date of Patent: December 17, 1996Assignee: Ciba-Geigy CorporationInventor: Fridolin Babler
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Patent number: 5582621Abstract: Bulk dyeing of plastics using dyestuffs of the formula (I) ##STR1## wherein n denotes 1 or 2, preferably 1,R.sub.o for n=1, denotes aryl, hetaryl or heterocyclylidenemethyl, or for n=2, denotes a direct bond or arylene andthe ring A is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.10 -aryl, C.sub.1 -C.sub.4 -alkyloxy, C.sub.6 -C.sub.10 -aryloxy, C.sub.6 -C.sub.10 -aryl- or C.sub.1 -C.sub.4 -alkylsulphonyl, cyano, halogen, in particular chlorine or bromine, or a radical of the formula --COR.sub.1, wherein R.sub.1 represents C.sub.1 -C.sub.4 -alkoxy, amino, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.6 -C.sub.10 -arylamino, C.sub.1 -C.sub.4 -alkyl or C.sub.6 -C.sub.10 -aryl, or contains a fused-on aromatic or cycloaliphatic ring,the plastics used being, in particular, thermoplastics, preferably vinyl polymers, polyesters or polyamides.Type: GrantFiled: September 13, 1995Date of Patent: December 10, 1996Assignee: Bayer AktiengesellschaftInventors: Peter Roschger, Stephan Michaelis, Hauke Furstenwerth
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Patent number: 5554217Abstract: Disclosed is a process for coloring high-molecular-weight coatings and ink systems which comprises uniformly dispersing an effective pigmenting amount of a stir-in pigment in the coating or ink system; wherein the stir-in pigment is an organic pigment crude consisting essentially of non-platelet-shaped particles having an average particle size of from 0.5 to 25 .mu.m and/or a pigment composition consisting essentially of an organic pigment having an average particle size of from 0.01 to 25 .mu.m and inorganic filler pigment.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: Ciba-Geigy CorporationInventor: Fridolin B abler
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Patent number: 5529623Abstract: Binary and ternary pigmentary solid solutions are disclosed. The binary solid solutions are binary solid compounds consisting of 35-45 weight-percent unsubstituted DPP and 55-65 weight-percent dichloro DPP. The ternary solid solutions are guest-host solid solutions wherein the binary solid compound is the host and up to 30 weight-percent of a disubstituted quinacridone pigment is the guest. The binary and ternary solid solutions are useful as pigments for coloring high-molecular-weight organic materials; especially as replacements for perylene pigments in automotive finishes.Type: GrantFiled: September 28, 1994Date of Patent: June 25, 1996Assignee: Ciba-Geigy CorporationInventors: Shivakumar B. Hendi, James B. Ganci, Edward E. Jaffe
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Patent number: 5522925Abstract: Pigment compositions comprising an organic pigment, the particle surface of which is provided with a protective coating, which coating consists of a metal phosphate complex in which the metal is selected from the group consisting of zirconium, titanium and mixtures thereof, and the amount of said coating is 0.5 to 100% by weight, preferably from 0.5 to 40% by weight, most preferably from 5 to 40% by weight, based on the pigment. They are distinguished by excellent properties, in particular by the high gloss of the colorations obtained with them, by superior dispersion stability, heat resistance and by very good rheology of the mill bases or printing inks prepared with them. Plastics pigmented with the novel compositions are also distinguished by superior heat resistance and plastic parts are substantially warp-free.Type: GrantFiled: December 20, 1994Date of Patent: June 4, 1996Assignee: Ciba-Geigy CorporationInventors: Laurent Chassot, Philippe Bugnon
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Patent number: 5518539Abstract: The present invention relates to a process for the preparation of synergistic pigment mixtures by mixing solutions of at least two pigments solubilized by introducing carbamate groups, and subsequently precipitating the mixture in pigment form by subjecting said mixture to a thermal, photolytic or chemical treatment, either before or after incorporation in the substrate to be pigmented.Type: GrantFiled: November 18, 1994Date of Patent: May 21, 1996Assignee: Ciba-Geigy CorporationInventors: Zhimin Hao, Abul Igbal, John S. Zambounis, Bernhard Medinger
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Patent number: 5476544Abstract: A water-based pigment dispersion excellent in gloss of a coating, tinting strength, fluidity and storage stability, comprising a pigment, a pigment dispersing agent of the formula (1) and a solid content, of a water-based resin which is obtained by copolymerizing an .alpha., .beta.-ethylenically unsaturated carboxylic acid (a), an .alpha., .beta.-ethylenically unsaturated, nitrogen-containing monomer (b) and other .alpha., .beta.-ethylenically unsaturated monomer (c),P--[X--Y--Z--N(R.sup.1)R.sup.2 ].sub.n ( 1)wherein:P is an organic dyestuff residue or a heterocyclic ring residue,X is a divalent binding group consisting of 2 to 15 atoms selected from S, C, N, O and H atoms,Y is a direct bond, --N(R)-- in which R is H, an alkyl group having 1 to 18 carbon atoms or Q--N(R.sup.3)R.sup.4 in which Q is an alkylene group having 1 to 6 carbon atoms and each of R.sup.3 and R.sup.4 is independently an optionally substituted alkyl group having 1 to 18 carbon atoms or R.sup.3 and R.sup.Type: GrantFiled: January 6, 1995Date of Patent: December 19, 1995Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Atsushi Endo, Akimitsu Mochizuki, Michichika Hikosaka, Tsutomu Fujigamori