Mixed Phthalocyanines Or Derivatives Patents (Class 106/411)
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Patent number: 5725649Abstract: The present invention provides a composition comprising copper phthalocyanine containing 0-4 chlorine atoms having a crystal size in the range of from 0.01 to 0.2 .mu.m, and from 10 to 15% by weight of an ionic complex formed from copper phthalocyanine sulphonic acid and a quaternary amine of the formula (I) ##STR1## where R.sub.1 is a C.sub.1 -C.sub.6 alkyl group; R.sub.2 is a C.sub.1 -C.sub.18 alkyl group; R.sub.3 is the same as R.sub.2 or is a hydroxyethyl or ethoxylated ethyl group having up to 5 ethyleneoxy units: R.sub.4 is a hydroxyethyl or ethoxylated ethyl group having up to 5 ethyleneoxy units; and X is a halogen atom.Type: GrantFiled: August 20, 1996Date of Patent: March 10, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Alastair McAlpine Marr
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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: 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: 5698023Abstract: This invention provides a process for producing copper phthalocyanine pigments which comprises reacting either phthalic anhydride or its derivatives with urea and a copper-containing substance, or either phthalonitrile or its derivative with a copper-containing substance in a reaction solvent by heating characterized in that an alkylxylene ingredient having a branched C4 side-chain represented by the following formula (1) is used as the reaction solvent: ##STR1##Type: GrantFiled: March 18, 1996Date of Patent: December 16, 1997Assignee: Nippon Petrochemical Co., Ltd.Inventors: Tsutomu Takashima, Kikuo Sasaki, Hideyuki Dohi
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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: 5614342Abstract: Cocrystallized titanyl phthalocyanine-titanyl fluorophthalocyanine compositions, preparation methods, and electrophotographic elements utilizing the compositions. The method has the steps of: admixing crude titanyl phthalocyanine and crude titanyl fluorophthalocyanine to provide a pigment mixture; increasing the amorphousness of the pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu K.alpha. at a wavelength of 1.541 .ANG. of the Bragg angle 2.theta. to provide an amorphous pigment mixture; contacting the amorphous pigment mixture with organic solvent having a gamma.sub.c hydrogen bonding parameter of less than 8.0; and prior to the contacting, substantially excluding the amorphous pigment mixture from contact with organic solvent having a gamma.sub.c hydrogen bonding parameter greater than 9.0.Type: GrantFiled: May 2, 1995Date of Patent: March 25, 1997Assignee: Eastman Kodak CompanyInventors: Michel F. Molaire, Jeanne E. Kaeding
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Patent number: 5534055Abstract: This invention relates to a process for preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments comprising(a) acid pasting or acid swelling a crude metal phthalocyanine pigment;(b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment in the presence of 5 to 50 parts by weight of a stabilizer per 100 parts by weight of the crude metal phthalocyanine pigment until the average particle size is reduced to less than about 0.5 .mu.m;(c) finishing the milled metal phthalocyanine pigment by thoroughly mixing said milled metal phthalocyanine pigment with a finishing solvent mixture comprising 3 to 6 parts by weight, relative to the crude metal phthalocyanine pigment, of water and 0.4 to 1.Type: GrantFiled: August 24, 1994Date of Patent: July 9, 1996Assignee: Bayer CorporationInventors: Herman Gerson, Abdul Sattar
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Patent number: 5512095Abstract: Naphthalocyanines of the general formula I ##STR1## where the variables have the following meanings: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each independently of the others hydrogen, hydroxyl or C.sub.1 -C.sub.20 -alkyl or C.sub.1 -C.sub.20 -alkoxy, whose carbon chains may each be interrupted by from 1 to 4 oxygen atoms in ether function and which may be phenyl-substituted,R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are each independently of the others hydrogen, halogen or C.sub.1 -C.sub.20 -alkyl or C.sub.1 -C.sub.20 -alkoxy, whose carbon chains may each be interrupted by from 1 to 4 oxygen atoms in ether function,Me is two hydrogen atoms, two univalent metal atoms or a bivalent metal atom with or without further substituents for valence saturation,are pigments with isometric particles and a particle size distribution from 10 to 300 nm.Type: GrantFiled: June 8, 1994Date of Patent: April 30, 1996Assignee: BASF AktiengesellschaftInventors: Benno Sens, Andres C. G. Espino, Bernhard Albert, Juergen Kipper
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Patent number: 5492563Abstract: Copper phthalocyanine pigments are finely divided in an ecologically and economically advantageous manner by first of all subjecting crude, coarsely crystalline copper phthalocyanine pigments to dry milling and then wet milling the finely divided prepigments which are obtained in the course of dry milling, in aqueous suspension and with the addition of from 0.1 to 5% by weight, based on the total millbase, of an organic solvent which is inert with respect to the process conditions, on a stirred ball mill which is operated at an energy 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. Copper phthalocyanine pigments prepared in this way are particularly suitable as colorants for pigmenting paints, printing inks and plastics.Type: GrantFiled: April 13, 1995Date of Patent: February 20, 1996Assignee: Hoechst AGInventor: Manfred Urban
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Patent number: 5489330Abstract: The new aqueous finished preparations of copper phthalocyanine dyestuffs comprising a dyestuff of the formula ##STR1## where CuPc, A, R.sup.1, R.sup.2, x and y have the meaning given in the description, are storage-stable and are outstandingly suitable for dyeing and printing cellulose-containing materials.Type: GrantFiled: October 29, 1993Date of Patent: February 6, 1996Assignee: Bayer AktiengesellschaftInventor: Klaus Wunderlich
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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
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Patent number: 5472490Abstract: A pigment composition which comprises a phthalocyanine pigment, a phthalocyanine derivative (A) of the formula (1),Pc-(SO.sub.3.sup.-+ NR.sub.1 R.sub.2 R.sub.3 R.sub.4).sub.n(1)and at least one compound (B) selected from the class consisting of a compound of the formula (2),(M.sub.1).sub.j X (2)an aliphatic compound containing carboxylic acid alkali metal salt and an aliphatic compound containing carboxylic acid ammonium salt, and which imparts a printing or a coating with excellent gloss and shows excellent fluidity and stability with time when dispersed in a vehicle for a printing ink or a coating composition.Type: GrantFiled: April 19, 1994Date of Patent: December 5, 1995Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Katsuhiko Sawamura, Shigeki Kato, Hitoshi Maki, Mikio Hayashi
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Patent number: 5427616Abstract: A process for the production of a copper phthalocyanine pigment composition from 70 to 99% by weight of a crude copper phthalocyanine and 30 to 1% by weight of a phthalocyanine derivative,the crude copper phthalocyanine being converted to a pigment without a large amount of energy and the treatment of exhaust water,the copper phthalocyanine pigment composition having excellent fluidity, tinting strength and stability with time when used in a coating composition or a printing ink,the copper phthalocyanine pigment composition showing almost no "strike-through" when used for gravure printing on low-quality paper,the process comprising dry milling the entirety of the crude copper phthalocyanine and the phthalocyanine derivative in an amount of 0.5 to 10% by weight of a final composition in the absence of a milling auxiliary until the content of an .alpha.Type: GrantFiled: June 1, 1994Date of Patent: June 27, 1995Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Kosaku Tsuji, Yoshio Muramatsu, Shigeki Kato
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Patent number: 5393339Abstract: This invention relates to an improved process for preparing metal phthalocyanine pigments comprising(a) heating at a temperature of about 150.degree. C. to about 200.degree. C. a mixture comprising(i) a phthalocyanine-forming material based on phthalic acid,(ii) at least about 25 mole percent, relative to the phthalocyanine-forming material (i), of a metal donor,(iii) at least about 100 mole percent, relative to the phthalocyanine-forming material (i), of a nitrogen donor,(iv) 1 to about 20 percent by weight, relative to the phthalocyanine-forming material (i), of a catalyst, and(v) about 250 to about 400 percent by weight, relative to the phthalocyanine-forming material (i), of a di(C.sub.1 -C.sub.3 alkyl) phthalate solvent; and(b) isolating the metal phthalocyanine pigment.Type: GrantFiled: May 11, 1994Date of Patent: February 28, 1995Assignee: Miles Inc.Inventors: Herman Gerson, Abdul Sattar
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Patent number: 5378274Abstract: Disclosed herein are a color filter wherein an organic pigment is comprised of primary particles having an average particle size of 20 to 200 nm and a particle size distribution within .+-.35 nm and said organic pigment has a color difference of 5 or less when it is subjected to exposure at an illuminance of 100,000 lux or more for 100 hours or more under the condition of a surface temperature at 50.degree. C.; a color filter wherein the film of coloring matter in green has a ratio (T.sub.485 /T.sub.610) of the transmittance of 485 nm (T.sub.485) to that of 610 nm (T.sub.610 ) of 3.5 or less, the maximum transmittance of the film of coloring matter in green is 60% or more and said maximum transmittance is assigned a wavelength of 540 to 550 nm; and a color filter using a specific organic pigment as each of red, green and blue pigments.Type: GrantFiled: October 19, 1993Date of Patent: January 3, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Seiichiro Yokoyama, Motoharu Ishikawa, Yoshio Hiroi, Nobuaki Watanabe
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Patent number: 5296034Abstract: Copper phthalocyanine pigments and pigment preparations in the .alpha. phase are prepared with phase conversion from copper phthalocyanine crude pigments of the .beta. phase in an environmentally safe and economical manner bya) first wet milling a copper phthalocyanine pigment, which is predominantly present in the .beta. phase, in an aqueous, preferably neutral to alkaline medium in a stirred ball mill which is operated at a power density of more than 2.Type: GrantFiled: June 18, 1993Date of Patent: March 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Manfred Urban
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Patent number: 5296033Abstract: Phthalocyanine pigments and phthalocyanine pigment preparations in the .alpha. phase and in the .beta. phase are prepared with phase conservation in an environmentally safe and economical manner bya) first wet milling a phthalocyanine pigment in an inert liquid medium in a stirred ball mill which is operated at a power density of more than 2.Type: GrantFiled: June 18, 1993Date of Patent: March 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Manfred Urban
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Patent number: 5284511Abstract: The present invention relates to a process for preparing a beta-phase metal phthalocyanine pigments in which(a) a crude metal phthalocyanine having an average particle size of about 10 to about 200 .mu.M is dry milled until the average particle size is reduced to about 0.01 to about 0.5 .mu.m;(b) the milled metal phthalocyanine is finished by thoroughly mixing said metal phthalocyanine with at least about 4 parts by weight, relative to the metal phthalocyanine, of a finishing solvent containing a mixture of(i) about 5 to 100 percent by weight, based on the total amount of finishing solvent, of a monocarboxylic acid monoester, dicarboxylic acid diester, diol diester, lactone, or cyclic carbonate, or a mixture thereof, and(ii) 0 to about 95 percent by weight, based on the total amount of finishing solvent, of water;(c) the ester used in step (b) is hydrolyzed; and(d) the beta-phase metal phthalocyanine pigment is collected.Type: GrantFiled: April 12, 1993Date of Patent: February 8, 1994Assignees: Miles Inc., Bayer AktiengesellschaftInventors: Meinhard Rolf, Abdul Sattar
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Patent number: 5282896Abstract: A process for producing a pigment composition containing a highly halogenated copper phthalocyanine, produced by halogenation of copper phthalocyanine in the presence of chlorosulfonic acid, titanium tetrachloride or a mixture of titanium tetrachloride with aluminum chloride, a highly halogenated copper phthalocyanine produced by halogenation of a copper phthalocyanine in a solid powder state, or a highly halogenated copper phthalocyanine produced by cyclization. The composition further contains at least one highly halogenated different-metalo-phthalocyanine selected from highly halogenated metalo-phthalocyanines each of which has Al, Mg, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge or Sn as a central metal.Type: GrantFiled: August 16, 1991Date of Patent: February 1, 1994Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Junichi Tsuchida, Masami Shirao, Michichika Hikosaka, Yoshiyuki Nonaka
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Patent number: 5281268Abstract: A process for the production of a .beta.-form copper phthalocyanine having a particle size of 0.005 to 0.2 .mu.m and an aspect ratio of 1 to 3, which comprises the following steps:a. dry-milling a crude copper phthalocyanine in a milling apparatus until the resultant dry-milled product has an .alpha.-crystal content of more than 45% by weight,wet-milling the resultant dry-milled product in the presence of a water-soluble inorganic salt and at least one organic liquid selected from the group consisting of water-soluble alkylene glycols having 2 to 3 carbon atoms and polyoxyalkylene glycols, wherein the inorganic salt is used in an amount that is 2 to 10 times, by weight, as large as that of the dry-milled copper phthalocyanine, and wherein the organic liquid is used in an amount that is 0.1 to 2 times, by weight, as large as that of the dry-milled copper phthalocyanine, andc. removing the inorganic salt and the organic liquid from the resultant wet-milled product.Type: GrantFiled: April 23, 1993Date of Patent: January 25, 1994Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yusaku Ide, Toshimitsu Ikegaya, Michichika Hikosaka
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Patent number: 5279654Abstract: A pigment composition comprising (A) a pigmentary phthalocyanine, (B) a phthalocyanine derivative of formula ##STR1## where Pc is a residue of a metal-free or metal phthalocyanine, X is --CH.sub.2 -- or --SO.sub.2 --, R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.20 alkyl optionally substituted by hydroxyl, C.sub.1 to C.sub.4 alkoxy, amino, C.sub.1 to C.sub.10 alkylamino or di(C.sub.1 to C.sub.10 alkyl)amino, C.sub.5 to C.sub.10 cycloalkyl, or phenyl optionally substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy or halogen, or R.sup.1 and R.sub.2 together with the indicated nitrogen atom denote a five-, six- or seven-membered heterocyclic ring, or R.sup.1 and R.sup.2 together denote a group of formula ##STR2## R.sup.3 is an o-phenylene group optionally substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.Type: GrantFiled: July 20, 1992Date of Patent: January 18, 1994Assignee: Ciba-Geigy CorporationInventors: David Keirs, Robert Langley, Ian A. Lambie
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Patent number: 5271759Abstract: Pigment compositions comprisinga) at least one organic pigment,b) 0.05 to 10% by weight, based on the organic pigment a), of at least one modified organic pigment of formula ##STR1## wherein A is the radical of an organic pigment, X is H, Na or K and m is an integer from 0.05 to 3, andc) 0.05 to 10% by weight, based on the organic pigment a), of at least one polymeric ammonium salt having an average molecular weight from 500 to 2 500 000 and which is soluble in water or a lower alkanol.These pigment compositions have excellent suitability for the wrap-free pigmenting of polyolefins and, when incorporated in paint systems and printing inks, exhibit excellent rheology.Type: GrantFiled: May 1, 1992Date of Patent: December 21, 1993Assignee: Ciba-Geigy CorporationInventors: Gary Wooden, Olof Wallquist
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Patent number: 5264032Abstract: Pigment preparation essentially comprisinga) at least one pigment from the class of azo, anthrapyrimidine, anthanthrone, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, flavanthrone, indanthrone, isoindolinone, isoviolanthrone, perylene, phthalocyanine, pyranthrone or thioindigo pigments or a mixture of pigments belonging to various classes, andb) at least one dispersant of the formula (I) ##STR1## in which P, independently of the pigments mentioned in a), is a radical of an anthanthrone azo, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, indanthrone, perylene, phthalocyanine or thioindigo pigment,R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.Type: GrantFiled: October 21, 1992Date of Patent: November 23, 1993Assignee: Hoechst AGInventors: Erwin Dietz, Manfred Urban
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Patent number: 5250111Abstract: A pigment composition comprising a) a pigment; and b) a phthalocyanine compound having the formula I:MPc(CH.sub.2 NHCO--A).sub.n Iin which Pc represents a phthalocyanine residue which is optionally further substituted by up to an average of one chlorine or bromine atom or by a sulphonic acid group; M is hydrogen or a metal capable of forming a metal phthalocyanine; n is a number ranging from 0.1 to 4.0; and A is C.sub.3 -C.sub.21 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, a 5- or 6-membered heterocyclic residue or a fused heterocyclic system.Type: GrantFiled: April 6, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Robert Langley, Michael D. McFarland
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Patent number: 5248336Abstract: This invention relates to solid solutions containing (a) about 90 to about 10% by weight of a chlorinated copper phthalocyanine containing about 14 to about 16 atoms of chlorine per molecule and (b) about 10 to about 90% by weight of a copper phthalocyanine containing about 3 to about 4 atoms of chlorine wherein said compositions are characterized by X-ray diffraction patterns that differ from the sum of the X-ray diffraction patterns of the individual components.Type: GrantFiled: November 5, 1991Date of Patent: September 28, 1993Assignee: Miles Inc.Inventors: Herman Gerson, Abdul Sattar
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Patent number: 5207829Abstract: Pigment preparations whose pigment portion is composed essentially of organic pigments and of pigment additives of the formula I ##STR1## in which P is a radical of an organic pigment and X in the methylene groups of the lactam ring is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, hydroxyl, NR.sup.1 R.sup.2 or COOM, m is an integer from 3 to 20 and n can have a value from 0.1 to 4, are suitable for pigmenting high-molecular-weight organic materials in solvent-borne as well as aqueous systems.The pigment preparations have high flocculation stability and good rheological properties.Type: GrantFiled: December 4, 1991Date of Patent: May 4, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Schwab, Erwin Dietz
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Patent number: 5194088Abstract: A process for converting crude pigments into pigmentary form wherein the crude pigment is premilled, then contacted with a polar solvent at temperatures below 50.degree. C., with or without the presence of particle growth inhibitors, and finally isolated.Type: GrantFiled: July 8, 1991Date of Patent: March 16, 1993Assignee: Ciba-Geigy CorporationInventors: Fridolin Babler, Edward E. Jaffe
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Patent number: 5112404Abstract: The invention relates to readily dispersible pigment formulations which are stable to flocculation and are used for pigmenting naturally occurring and synthetic materials, preferably paints and printing inks, plastics and lacquers, in particular stoving lacquers. The pigment formulations contain compounds of the general formula (I) ##STR1## in which Q.sup.1, Q.sup.2 and Q.sup.3 each denote --X--A, --OR.sup.1, --SR.sup.1, halogen, --NR.sup.2 R.sup.3 or a radical Q which is built up from up to 15 trivalent groups (Ia) such that in each case one group (Ia) is bonded via W to a free valency of the next group (Ia) or to the triazine ring of (I) and the other free valencies are bonded to --X--A, --O--R.sup.1, halogen or --NR.sup.2 R.sup.3, at least one radical --X--A being present in (I), and A stands for an aromatic system with 2 to 6 rings and at least 9 ring atoms, or stands for a group of 2 to 3 aromatic ring systems, bonded via O, S, CO, SO, SO.sub.2 or C.sub.1 -C.sub.Type: GrantFiled: April 4, 1990Date of Patent: May 12, 1992Assignee: Hoechst AktiengesellschaftInventors: Andreas Sommer, Erwin Dietz, Manfred Urban
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Patent number: 5071483Abstract: A process for the preparation of pigment preparations of the anthanthrone series, which comprises subjecting anthanthrone crude pigments to aqueous pearl milling in the presence of dispersants of the formulaeQ.sub.1 -[A.sub.1 -X].sub.n (I)and/or[Q.sub.2 -A.sub.2 ].sub.z -Y (II)in which in formula (I) Q.sub.1 is the radical of an anthanthrone, azo, isoindolinone, diketopyrrolopyrrole or perinone compound, A.sub.1 is a direct bond or --O--, --S--, --NR.sub.3, --CO--, --SO.sub.2 --, --CR.sub.4 R.sub.5 -- or arylene, X is a group ##STR1## or a heterocyclic radical having at least one nitrogen atom, and R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are hydrogen atoms or saturated or unsaturated alkyl groups and n is 1 to 4, and in formula (II) Q.sub.2 is a radical of the formula ##STR2## in which R.sub.1 is hydrogen, halogen, alkyl, alkoxy or cyano, or, in the case that m.sub.1 >1, R.sub.1 can also be a combination of these substituents, R.sub.Type: GrantFiled: September 19, 1989Date of Patent: December 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Manfred Urban, Siegfried Schiessler
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Patent number: 5071482Abstract: Pigment preparations consisting of organic pigments and basic additives of the general formula I(Q-A).sub.x Y (I)in which Q is a radical of the formula II ##STR1## in which R.sup.1 is halogen, an alkyl, alkoxy or cyano group, R.sup.2 is halogen, m and n are integers from 0 to 4, A is a chemical bond or a divalent group from the series consisting of --(CH.sub.2).sub.p --, --CR.sup.3 R.sup.4 --, arylene, --S--, --O-- and --NR.sup.5 --, in which p is an integer from 1 to 12, R.sup.3 is hydrogen or alkyl, R.sup.4 is alkyl and R.sup.5 is hydrogen or alkyl, Y is a tertiary nitrogen atom or a group ##STR2## in which R.sup.6, R.sup.7 and R.sup.8 are alkyl or alkenyl or a cycloaliphatic or araliphatic radical or an alkyleneheteroaryl radical, or Y is a saturated or unsaturated heterocyclic radical in which at least one tertiary nitrogen atom is included in the meanings mentioned for Y and x is a number from 1 to 6.Type: GrantFiled: September 20, 1989Date of Patent: December 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Siegfried Schiessler, Manfred Urban
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Patent number: 4888422Abstract: Dimethylaminomethyl copper phthalocyanine and/or its derivative represented by the general formula, ##STR1## wherein CuPc represents a copper phthalocyanine residue, X represents a hydrogen atom, a halogen atom, the group --SO.sub.3 H or the group --CH.sub.2 OH, and m and n independently represent an integer of 1 to 4,and containing only small amounts of by-products is produced by a process comprising reacting aminomethyl copper phthalocyanine and/or its derivatives represented by the general formula ##STR2## wherein CuPc, X, m and n are as defined above, with formic acid and a formaldehyde-generating substance at a temperature of 130.degree. to 150.degree. C. under a pressure of 3 to 10 kg/cm.sup.2 (gauge).Type: GrantFiled: December 5, 1988Date of Patent: December 19, 1989Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Toshio Takei, Toshio Tanaka
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Patent number: 4810297Abstract: Dimethylaminomethyl copper phthalocyanine and/or its derivative represented by the general formula, ##STR1## wherein CuPc represents a copper phthalocyanine residue, X represents a hydrogen atom, a halogen atom, the group --SO.sub.3 H or the group --CH.sub.2 OH, and m and n independently represent an integer of 1 to 4,and containing only small amounts of by-products is produced by a process comprising reacting aminomethyl copper phthalocyanine and/or its derivative represented by the general formula ##STR2## wherein CuPc, X, m and n are as defined above, with formic acid and a formaldehyde-generating substance at a temperature of 130.degree. to 150.degree. C. under a pressure of 3 to 10 kg/cm.sup.2 (gauge).Type: GrantFiled: November 30, 1987Date of Patent: March 7, 1989Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Toshio Takei, Toshio Tanaka