Specified Crystalline Form Patents (Class 534/575)
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Patent number: 4952680Abstract: Stable solutions of azo dyes obtained by diazotizing and coupling m-phenylenediamine or derivatives thereof are prepared after the reaction has ended by treating the resulting reaction mixture with from 0.1 to 1.2 moles of formic acid, based on 1 mole of m-phenylenediamine, at from 60.degree. C. to the boiling point of the reaction mixture.Type: GrantFiled: April 14, 1988Date of Patent: August 28, 1990Assignee: BASF AktiengesellschaftInventor: Karl Schmeidl
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Patent number: 4946948Abstract: Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.Type: GrantFiled: August 31, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Fridolin Babler
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Patent number: 4940492Abstract: Colorant mixtures for use in printing inks contain isoquinoline-azo pigments of the formula I ##STR1## where X is chlorine, bromine, C.sub.1 -C.sub.4 -alkoxy or nitro,n is 1, 2 or 3, and the ring A can be substituted, and an isoquinoline-azo dye of the formula II ##STR2## where Y is C.sub.6 -C.sub.20 -alkoxy which may be interrupted by one or more oxygen atoms, and the ring B can be substituted.Type: GrantFiled: June 22, 1988Date of Patent: July 10, 1990Assignee: BASF AktiengesellschaftInventors: Heinrich Kowarsch, Johannes P. Dix
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Patent number: 4937325Abstract: 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. The monoazo dyestuff mixtures are used for the dyeing and printing of hydrophobic fibers such as high molecular weight polyesters of their mixtures with natural fiber material.Type: GrantFiled: December 12, 1988Date of Patent: June 26, 1990Assignees: Cassella Aktiengesellschaft, Tokico Ltd.Inventors: Ulrich Buhler, Klaus Hofmann, Hiroshi Mitsuhashi, Harutsugu Ushiota, Akiharu Odagiri, Gen Kano, Susumu Sakamoto
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Patent number: 4935502Abstract: When a diamine of the formula ##STR1## in which n is 1 to 4, is bis-diazotized and the resulting bis-diazo compound is coupled with 2 moles of one or more coupling components of the formula ##STR2## in which R.sup.1 is hydrogen, chlorine, bromine, methyl or methoxy and R.sup.2 is hydrogen or, if R.sup.1 is hydrogen, also methyl or ethyl, disazo compounds are obtained which are colorants. Due to their high fastness to light and to migration and their heat stability and dispersibility, these compounds are useful for pigmenting high molecular weight materials, especially polyolefins.Type: GrantFiled: August 22, 1989Date of Patent: June 19, 1990Assignee: Hoechst AktiengesellschaftInventors: Rudolf Kuhne, Heinrich Hamal
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Patent number: 4923972Abstract: Liquid formulations of basic azo dyes are prepared from unsubstituted or C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted m-phenylenediamine by diazotizing and coupling in carboxylic acid solution, which comprises performing the reaction with 0.76 to 0.95 mole of nitrile, calculated as nitrous acid and based on 1 mole of m-phenylenediamine, and then heating the resulting reaction mixture at from 60.degree. C. to the boiling point of the reaction mixture.Type: GrantFiled: April 14, 1988Date of Patent: May 8, 1990Assignee: BASF AktiengesellschaftInventor: Karl Schmeidl
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Patent number: 4921505Abstract: In the process for the preparation of the dyestuff of the formula I ##STR1## by diazotization and coupling, the aqueous suspension present when the coupling has ended is heated to temperatures of 50.degree. C. up to the boiling point of the aqueous phase in the presence of a dispersing agent.Type: GrantFiled: December 12, 1988Date of Patent: May 1, 1990Assignee: Cassella AktiengesellschaftInventors: Gunther Effenberger, Hubert Kruse
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Patent number: 4920205Abstract: Azo pigments are made by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65.degree. C. in the aqueous/acid and aqueous/netural pH-ranges. More specifically, an aqueous/alkaline solution of the coupling component is continuously mixed in a first reaction step with an aqueous solution of acetic acid, boric acid, phosphoric acid, hydrochloric acid or sulfuric acid at a temperature lower than 65.degree. C. within a period of less than 1 minute, during which the coupling component commenences precipitating at least partially as reactive matter; next, the suspension obtained is continuously mixed, in a second reaction step immediately following the first reaction step, with an aqueous/acid solution of the diazo component at a temperature of less than 65.degree. C.Type: GrantFiled: March 28, 1989Date of Patent: April 24, 1990Assignee: Hoechst AktiengesellschaftInventors: Heinrich Rehberg, Hartmut Behringer
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Patent number: 4920206Abstract: Azo Pigments are made by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65.degree. C. in the aqueous/acid and aqueous/neutral pH-ranges. More specifically, an aqueous/acid-solution of the diazo component is continuously mixed at a temperature of less than 65.degree. C. within a period of less than 1 minute with the aqueous/alkaline solution of the coupling component and a predetermined pH between 2 and 9 is established by controlling the flow of the mass streams of diazo component and coupling component; in this way a portion of the coupling component is caused to undergo immediate reaction to the azo pigment to be made whereas the balance portion of the coupling component simultaneously commences precipitating as finely crystalline reactive matter, which is reacted in a post-reaction phase with unreacted diazo component to give the azo pigment to be made.Type: GrantFiled: March 29, 1989Date of Patent: April 24, 1990Assignee: Hoechst AktiengesellschaftInventors: Hartmut Behringer, Heinrich Rehberg
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Patent number: 4906735Abstract: An improved process for the manufacture of a monoazo acetoacetylaminobenzimidazolone pigment of the formula ##STR1## by coupling the components in an aqueous medium in the presence of an oxethylation product of an alcohol or alcohol mixture having from 8 to 14 carbon atoms and 3 to 10 mols of ethylene oxide, and heating the aqueous pigment suspension after complete coupling. The pigment thus obtained avoids an after-treatment in anhydrous organic solvents and has good tinctorial strength, high hiding power and good properties with respect to flow and dispersibility.Type: GrantFiled: June 15, 1989Date of Patent: March 6, 1990Assignee: Hoechst AktiengesellschaftInventor: Klaus Hunger
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Patent number: 4879373Abstract: each of R.sub.2 and R.sub.3 is independently hydrogen, chloro, bromo, methyl, methoxy or ethoxy,useful as pigments for, for example, the mass pigmenting of viscose and surface coatings such as oil and water base paints, lacquers and inks, pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: February 19, 1987Date of Patent: November 7, 1989Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4876333Abstract: A crystalline modification, designated ".beta.", of the dye of the structure ##STR1## The .beta.-crystalline modification of the dye is easier to isolate from water and gives filter cakes of higher solids and color content. The .beta.-form is also more suitable for making liquid formulations of the dye; the liquid formulations of the crystalline modification have lower viscosity and better dispersion stability than liquid formulations of non-modified form. The .beta.-modification of the dye is obtained by heating an aqueous slurry of the dye at about 90.degree.-95.degree. C. and pH of 8.5 to 9.5 until the modification is complete. The crystalline modification of the dye gives Debye-Scherrer X-ray diffraction patterns substantially different from the non-modified form.Type: GrantFiled: October 15, 1985Date of Patent: October 24, 1989Assignee: Ciba-Geigy CorporationInventors: Alfred Hoehener, Roy E. Smith
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Patent number: 4870164Abstract: Symmetrical and asymmetrical disazo compounds of the formula: ##STR1## wherein: the R.sup.1 's are identical or different and are hydrogen, chlorine, bromine, methyl or methoxy;the R.sup.2 's are hydrogen, or, if the R.sup.1 's are hydrogen, the R.sup.2 's are hydrogen, methyl or ethyl, the two R.sup.2 radicals being identical or different; andn is 1 to 4and mixtures of such compounds as colorants, especially for pigmenting high molecular weight organic material.Type: GrantFiled: January 28, 1985Date of Patent: September 26, 1989Assignee: Hoechst AktiengesellschaftInventors: Rudolf Kuhne, Heinrich Hamal
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Patent number: 4847365Abstract: The invention relates to novel 1:1 metal complexes of a divalent transition metal and an azo compound of the formula (1) ##STR1## wherein X is a hydrogen or a halogen atom, an alkyl, alkoxy, aryloxy, nitro, acylamino, ureido, arylureido, thioureido, thiocyano or sulfamoyl group or a phthalimido group which is unsubstituted or substituted by halogen atoms,Y is a hydrogen or halogen atom, an alkyl or alkoxy group, andR is an alkyl, alkoxycarbonyl, carbamoyl or alkylcarbamoyl group, orwherein X and Y, together with two vicinal carbon atoms of the benzene ring, form a fused benzene or imidazolone ring.These metal complexes, in particular the nickel and copper complexes, are suitable for the mass coloration of polymer fibres, especially polyolefins, polyamides or polyesters. The colored fibres have good fastness to heat, light and weather, as well as good rub- and wetfastness properties.Type: GrantFiled: February 17, 1988Date of Patent: July 11, 1989Assignee: Ciba-Geigy CorporationInventor: Paul Lienhard
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Patent number: 4795807Abstract: Azo disperse dyestuffs are prepared by diazotization and coupling in an aqueous phase, the coupling being carried out in the presence of an ester of a lower aliphatic carboxylic acid.Type: GrantFiled: March 30, 1987Date of Patent: January 3, 1989Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Friedrich Schophoff, Wolf Weidemuller
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Patent number: 4785083Abstract: Mixtures comprising at least two dyes of formula I ##STR1## where R is unsubstituted linear C.sub.3-7 alkyl, with the proviso that at least two different dyes of formula I are each present to the extent of at least 10 mole %, based on the total molar quantity of dyes present, which are useful for dyeing and printing synthetic and semi-synthetic high molecular weight, hydrophobic organic substrates, particularly for rapid dyeing.Type: GrantFiled: December 27, 1982Date of Patent: November 15, 1988Assignee: Sandoz Ltd.Inventor: Ulrich Zirngibl
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Patent number: 4773915Abstract: Azo dyestuffs of the formula ##STR1## wherein R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxyethoxy andX denotes acyl,are distinguished by good levelling properties and good allround fastness properties. They dye polyester fibres in a bright blue shade.Type: GrantFiled: January 7, 1987Date of Patent: September 27, 1988Assignee: Bayer AktiengesellschaftInventors: Winfried Kruckenberg, Klaus Leverenz, Hans-Gunter Otten
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Patent number: 4737581Abstract: Azo compounds of the formula I ##STR1## wherein X is --H, --CH.sub.3, --CF.sub.3, --NO.sub.2, --COOR.sub.1, --NHCOR.sub.2 or --COHN.sub.2, and R.sub.1 and R.sub.2 are as defined in claim 1, are suitable for pigmenting high-molecular organic material.Type: GrantFiled: April 18, 1985Date of Patent: April 12, 1988Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 4734101Abstract: A monoazo dye for polyester fiber represented by formula ##STR1## and having a crystal modification characterized by an X-ray diffraction spectrum (CuK.alpha.) showing a very strong peak at an angle of diffraction (2.theta.) of about 14.2.degree., a strong peak at about 24.5.degree., and four weak peaks at about 16.9.degree., 23.6.degree., 25.3.degree., and 26.8.degree.. The monoazo dye exhibits excellent dispersibility to effect level dyeing even under high temperature and severe conditions and provides a dyed material excellent in light fastness and rubbing fastness, as well as wet fastness after post-finish.Type: GrantFiled: December 29, 1986Date of Patent: March 29, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Kiyoshi Himeno, Junji Yoshihara, Masateru Ishida
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Patent number: 4732975Abstract: Compounds of the general formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and denote hydrogen, chlorine or bromine, methyl, ethyl, methoxy, ethoxy or nitro and K denotes identical or different radicals of enolizable ketomethylene compounds which do not contain groups imparting solubility in water, are obtained by coupling one equivalent of the bisdiazonium compound obtained by bisdiazotizing the diamine of the formula ##STR2## in which R.sup.1 and R.sup.2 have the meaning mentioned above, with 2 equivalents of one or more compounds of the formula KH in which K has the meaning mentioned above. These disazo compounds are pigments which have a high tinctorial strength and good fastness to migration, light, heat and chemicals.Type: GrantFiled: December 21, 1981Date of Patent: March 22, 1988Assignee: Hoechst AktiengesellschaftInventor: Manfred Pesenacker
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Patent number: 4722737Abstract: The azo dyestuff of the formula ##STR1## having the interplanar spacings D/.ANG. 3.13, 3.36, 4.85, 9.26 and 13.94 for the five strongest lines having the relative intensity use 98, 89, 82, 100 and 87 is distinguished, compared to known modifications by an increased dye bath stability.Type: GrantFiled: February 10, 1987Date of Patent: February 2, 1988Assignee: Bayer AktiengesellschaftInventors: Horst Brandt, Klaus Leverenz
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Patent number: 4719292Abstract: A novel crystallographic modification (.beta.-modification) of the pigment C. I. Pigment Red 53:1 is described and claimed which has characteristic reflection values in its X-ray diffraction pattern obtained by means of Cu-K.sub..alpha. radiation. This novel pigment form is obtained by reacting an aqueous solution of an alkali metal or ammonium salt of the formula 1 ##STR1## with the equivalent amount of a water-soluble barium salt in the presence of a compound of the formula 2 ##STR2## The modification is distinguished by a more yellowish-red shade as compared to the known .alpha.-modification.Type: GrantFiled: June 23, 1983Date of Patent: January 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Franz Schui, Reinhold Deubel, Norbert Wester
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Patent number: 4719293Abstract: The invention relates to disazo pigments of the formula ##STR1## wherein R is an ethyl, propyl or isopropyl radical. These pigments colour plastics, especially rigid PVC, in brown shades of excellent fastness properties.Type: GrantFiled: October 17, 1984Date of Patent: January 12, 1988Assignee: Ciba-Geigy CorporationInventor: Karl Ronco
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Patent number: 4709019Abstract: Anthraquinone-azo pyridone-containing compounds which in one of their tautomeric structures, correspond to the formula ##STR1## in which A denotes an .alpha.-anthraquinone radical which is free from sulphonic acid groups and is unsubstituted or substituted and preferably consists of at most 5 fused rings;R.sub.1 denotes hydrogen; alkyl, preferably C.sub.1 -C.sub.4 -alkyl; aryl, preferably phenyl or naphthyl; carboxyl; carboxylic acid ester, preferably carboxylic acid C.sub.1 -C.sub.4 -alkyl ester; or hydroxyl andR.sub.2 denotes hydrogen; halogen; nitro; cyano; unsubstituted or substituted carbamoyl or sulphamoyl; alkylcarbonyl, in particular (C.sub.1 -C.sub.4 -alkyl)-carbonyl; alkoxycarbonyl, in particular (C.sub.1 -C.sub.4 -alkoxy)-carbonyl; alkyl- or unsubstituted or substituted aryl-sulphone, preferably C.sub.1 -C.sub.Type: GrantFiled: April 21, 1983Date of Patent: November 24, 1987Assignee: Bayer AktiengesellschaftInventors: Meinhard Rolf, Rutger Neeff, Walter Muller
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Patent number: 4686287Abstract: Disazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A.sup.1 and A.sup.2, independently of each other, represent hydrogen, methyl or ethyl and Z.sup.1 and Z.sup.2 in the 6- or 7-position of the heteroaromatic ring system, independently of each other, represent hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro, are obtained by coupling a monodiazotized p-diaminobenzene substituted by X and Y analogously to the formula I with a 5-acetoacetylaminobenzimidazolone which carries the radicals A.sup.1 and Z.sup.2 analogously to the formula I, and reacting the resulting aminoazo compound after another diazotization with a 5-acetoacetylaminobenzimidazolone which carries the radicals A.sup.2 and Z.sup.2 analogously to the formula I, to give the disazo compound of the formula I.Type: GrantFiled: April 3, 1985Date of Patent: August 11, 1987Assignee: Hoechst AktiengesellschaftInventor: Klaus Hunger
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Patent number: 4681932Abstract: Azo dyestuffs of the formula ##STR1## wherein R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxyethoxy andX denotes acyl,are distinguished by good levelling properties and good allround fastness properties. They dye polyester fibres in a bright blue shade.Type: GrantFiled: June 27, 1985Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Winfried Kruckenberg, Klaus Leverenz, Hans-Gunter Otten
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Patent number: 4638052Abstract: An azo-pigment represented by the general formula: ##STR1## where R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, an unsubstituted phenyl group or a substituted phenyl group, R.sub.2 is a residue of a phenylenediamine, and R.sub.3 is a hydrogen atom, a methyl group, a methoxy group or a halogen atom. The azo-pigment of the present invention is useful in applications where azo-pigments are used.Type: GrantFiled: December 27, 1984Date of Patent: January 20, 1987Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Kimihide Kawamura, Shojiro Horiguchi, Hisao Okamoto
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Patent number: 4623397Abstract: Compounds of the formula I ##STR1## in which each R.sub.1, independently, is hydrogen, C.sub.1-8 alkyl, C.sub.2-3 alkyl substituted by one or two substituents selected from the group consisting of halo, hydroxy, cyano, methoxy, ethoxy and (C.sub.1-2 alkoxy)carbonyl or cyclohexyl, and each R.sub.2 and R.sub.3, independently, is hydrogen, chlorine, bromine, methyl, methoxy or ethoxy, their production and use as pigments for the mass pigmentation of, for example, viscose, surface coatings such as oil and water base paints and lacquers and inks, pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: October 10, 1984Date of Patent: November 18, 1986Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4609726Abstract: Compounds of the general formula I ##STR1## where R is hydrogen or C.sub.1 -C.sub.6 -alkyl and X is chlorine or bromine, with the proviso that X is only bromine when R is H, possess pigment properties and are distinguished by high color strength, brilliance and very good fastness properties.Type: GrantFiled: March 14, 1984Date of Patent: September 2, 1986Assignee: BASF AktiengesellschaftInventors: Reinhard Kemper, Egon Liedek
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Patent number: 4607096Abstract: Azo pigments are obtained by diazotizing a diazotizable aromatic amine without solubilizing groups in anhydrous dipolar aprotic water-miscible solvents with the stoichiometric amount or a small excess of nitrosylsulfuric acid or nitrosyl chloride, coupling the diazonium compound so obtained with a coupling component and isolating the pigment obtained in usual manner. This process is carried out in homogeneous solution and yields azo pigments the advantageous properties of which cannot be achieved by other methods, for example, the excellent purity, grain softness, narrow range of particle size distribution, excellent dispersibility in plastic materials and color lacquers, high gloss and excellent opacity in color lacquers.Type: GrantFiled: November 4, 1982Date of Patent: August 19, 1986Assignee: Hoechst AktiengesellschaftInventors: Josef Landler, Klaus Hunger, Erhard Worfel
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Patent number: 4585459Abstract: A process is described for separating sodium sulfate from aqueous solutions, containing less than 2% by weight of chloride, of certain fiber-reactive copper-formazan dyestuffs wherein this dyestuff solution is cooled down to a temperature between +5.degree. C. and -15.degree. C. In the course of the cooling the sodium sulfate precipitates in the form of the decahydrate and can be separated off in conventional manner, for example by filtration. The products obtained in this way are liquid low-salt aqueous copper-formazan dyestuff preparations which contain less than 4% by weight of sodium sulfate.Type: GrantFiled: April 4, 1985Date of Patent: April 29, 1986Assignee: Hoechst AktiengesellschaftInventors: Konrad Opitz, Gunther Schwaiger
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Patent number: 4544736Abstract: The compound of the formula ##STR1## exists in an .alpha.-modification and a .beta.-modification, the latter being obtained by treatment of the .alpha.-form with a boiling organic solvent, each of which, but especially the .beta.-modification, is useful as a pigment for the mass pigmentation of synthetic plastics and resins, free from or containing a solvent (e.g., viscose, cellulose acetate, polyethylene, polystyrene, polyvinyl chloride, synthetic leathers and synthetic rubbers), surface coatings (e.g., oil- and water-based paints), lacquers and inks and for pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: May 26, 1983Date of Patent: October 1, 1985Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4540775Abstract: The compound of the formula, ##STR1## a pigment existing in a yellow (.alpha.) modification and an orange (.beta.) modification, the latter being obtained by treatment of the .alpha. form with boiling organic solvents, is useful for the mass pigmenting of synthetic plastics and resins, free from or containing solvents, such as viscose, cellulose acetate, polyethylene, polystyrene, polyvinyl chloride and synthetic leathers and rubbers, of surface coatings such as paints and lacquers and of inks and for pigment printing, textile coating and pigmenting paper in the mass.Type: GrantFiled: May 11, 1981Date of Patent: September 10, 1985Assignee: Sandoz Ltd.Inventor: Bansi L. Kaul
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Patent number: 4536569Abstract: A compound of the formula, ##STR1## wherein R.sup.1 is methyl or ethyl, R.sup.2 and R.sup.3 are each C.sub.5 -- or C.sub.6 --alkyl, and Z is chlorine for use as a blue disperse dye of hydrophobic fibers, either alone or as a mixed dye in combination with anthraquinone; the compound combines low cost relative to anthraquinone with superior stability in the dye bath and excellent dyeability; mixed dyes retain anthraquinone-imparted brilliance of color, have good color fastness, dyeability and reproducibility characteristics, and maintain low cost.Type: GrantFiled: March 26, 1981Date of Patent: August 20, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoyasu Hashimoto, Kenji Yoshinaga, Yoshio Mori, Junzaburo Seino, Hirohito Kenmochi, Katsunobu Sato