Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component At A Specified Ph Range Patents (Class 534/582)
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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: 4916215Abstract: Water-soluble disazo compounds of the general formula ##STR1## in which D.sub.1 and D.sub.2 are each a phenylene or naphthylene radical which can be substituted by 1 or 2 substituents from the group consisting of 1 chlorine, 1 bromine, 2 sulfo, 2 carboxyl, 2 alkyl of 1 to 4 carbon atoms and 2 alkoxy of 1 to 4 carbon atoms, R' and R" each denote an amino or hydroxyl group, R.sup.+ and R* each represent methyl, carboxyl or lower carbalkoxy, R.sup.1 and R.sup.3 are each hydrogen, lower alkyl, lower alkoxy, chlorine or bromine, R.sup.2 and R.sup.4 each denote hydrogen, lower alkyl, lower alkoxy or chlorine, X denotes a vinyl, .beta.-sulfatoethyl,.beta.-thiosulfatoethyl or .beta.-chloroethyl group and Y is a chlorine, fluorine or bromine atom or a sulfo, hydroxyl, aliphatic or aromatic ether group or thioether group or a primary, secondary or tertiary amino group.Type: GrantFiled: March 29, 1988Date of Patent: April 10, 1990Assignee: Hoechst AktiengesellschaftInventors: Ernst Hoyer, Rudolf Fass
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Patent number: 4910298Abstract: A monoazo compound of the following formula, ##STR1## wherein D is sulfonaphthyl, sulfophenyl or carboxyphenyl, any one of A.sub.1 and A.sub.2 is sulfo and the other is hydrogen, methoxy or ethoxy, R.sub.1 and R.sub.2 are independently hydrogen or alkyl, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, and Y.sub.1 and Y.sub.2 are independently vinyl, .beta.-sulfatoethyl or the like, which is useful for dyeing or printing fiber materials to give dyed or printed products of a deep color excellent in fastness properties.Type: GrantFiled: November 3, 1987Date of Patent: March 20, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Kazufumi Yokogawa, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
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Patent number: 4891424Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.Type: GrantFiled: April 1, 1988Date of Patent: January 2, 1990Assignee: Ciba-Geigy CorporationInventors: Raymond Seltzer, Roland A. E. Winter
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Patent number: 4875903Abstract: Compounds of the formula ##STR1## wherein each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano or C.sub.1-4 alkoxy,each of X.sub.1 and X.sub.3 is independently halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, phenoxy, amino or an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group,each of X.sub.2 and X.sub.4 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group containing at least one protonatable nitrogen atom or quaternary ammonium group,m is 0 or 1, andeach of n.sub.1 and n.sub.2 is independently 0 or 1, with the proviso that n.sub.1 +n.sub.2 is 1 or 2,wherein each halo is independently fluoro, chloro or bromo, with the provisos that (1) the total number of basic and cationic groups present as X.sub.1 -X.sub.Type: GrantFiled: June 5, 1987Date of Patent: October 24, 1989Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4873319Abstract: Disazo dyes which are suitable for dyeing and printing, especially of paper of all kinds. The dyes correspond to the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each an alkyl radical, A is an alkylene radical, n is 1 or 2, V, X, Y and Z are nonionic substituents customarily in azo dyes, K is a pyrimidine coupling and An is an anion.Type: GrantFiled: September 25, 1987Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Willy Stingelin
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Patent number: 4873320Abstract: Water-soluble dyes which contain one or two fiber-reactive groups of the formula ##STR1## in which each R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, it being possible for both R to have a meaning which is identical to or different from one another, Y is the vinyl group or a group of the general formula --CH.sub.2 --CH.sub.2 --X in which X represents a substituent which can be eliminated as an anion, and m represents the number 2 or 3. These novel dyes can be used to dye hydroxy and/or carboxamide group-containing materials in particular fiber-materials, such as, in particular, cellulose fiber materials, in fast shades.Type: GrantFiled: December 15, 1987Date of Patent: October 10, 1989Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Manfred Kuhn, Holger M. Buch
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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: 4855411Abstract: This invention is directed to new water-soluble, monoazo dyes having the following general formula: ##STR1## in which: X and Y are independently selected from the group consisting of: ##STR2## R, R.sub.1, R.sub.2 are independently selected from H, lower alkyl of one to four carbons and sulfonated lower alkyl;A is a phenyl or napthyl radical optionally substituted with halogen, hydroxy, lower alkyl, lower alkoxy, carboxylic acid or sulfonic acid;W is a phenyl or naphthyl radical optionally substituted by carboxylic acid, sulfonic acid, amino, amido, lower alkyl, lower alkoxy, hydroxy or halogen groups;Z is a phenyl radical optionally substituted with halogen, lower alkoxy or lower alkyl groups; andcopper, chromium, cobalt and nickel metallized complexes of said dyestuffs.The dyes of this invention on cellulose textiles have high tinctorial strength, purity of shade, light and wash fastness particularly chlorine wash fastness.Type: GrantFiled: March 17, 1988Date of Patent: August 8, 1989Assignees: Hugh C. Crall, Hoechst Celanese Corp.Inventors: Glenn A. Thompson, Anthony J. Corso, Hans H. Steuernagel
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Patent number: 4851516Abstract: This invention relates to novel disazo dyes and processes for their production having the structure: ##STR1## wherein: R.sub.1 is H, lower alkyl, chloro, lower alkoxy, --CO.sub.2 M;R.sub.2 is H, lower alkyl, lower alkoxy, chloro;R.sub.3 is lower alkylene;R.sub.4 is H or lower alkyl;R.sub.5 is H, lower alkyl, lower alkoxy, chloro, nitro, --NHCO-- lower alkyl; CF.sub.3 ;R.sub.6 is H, lower alkyl, lower alkoxy, chloro, --SO.sub.3 M;R.sub.7 is --SO.sub.3 M, --CO.sub.2 MM is H, Na, Li, K, N.sub.Type: GrantFiled: November 20, 1987Date of Patent: July 25, 1989Assignee: Crompton & Knowles CorporationInventor: James F. Feeman
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Patent number: 4843151Abstract: The monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the aminobenzene, alkoxybenzene, hydroxybenzene, pyrazolone, aminopyrazole, pyrimmidine, indole, diphenylamine or acetoacetamide series, R is a substituted or unsubstituted C.sub.1-12 alkyl, cycloalkyl, aralkyl or aryl radical, X is a --CO-- or --SO.sub.2 -- group, a --COO-- group, R being attached to the oxygen atoms, or an --SO.sub.2 NH-- or ##STR2## group, R being attached to the nitrogen atom and Y being hydrogen or C.sub.1-4 alkyl, and Z is hydrogen or C.sub.1-4 alkyl, produce dyeings having good fastness to light and wet processing on polyamide material.Type: GrantFiled: April 9, 1987Date of Patent: June 27, 1989Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
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Patent number: 4841037Abstract: A naphthalene trisazo compound represented by the general formula (I) or (II): ##STR1## wherein A and B each represents a substituted or unsubstituted benzene or naphthalene ring; m represents zero or 1; and M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); or ##STR2## wherein X represents a hydrogen atom, a lower alkyl group, a phenyl group or a phenyl group substituted by --SO.sub.3 M; m represents zero or 1; M represents an alkali metal atom, ammonium or H.Am (wherein Am represents an amine); A, B and C each represents a substituted or an unsubstituted benzene or naphthalene ring, provided that B and C do not represent a naphthalene ring at the same time. A recording liquid containing these compounds is suitable for use in an ink-jet recording system.Type: GrantFiled: June 10, 1986Date of Patent: June 20, 1989Assignees: Canon Kabushiki Kaisha, Mitsubishi Chemical Industries LimitedInventors: Tokuya Ohta, Masatsune Kobayashi, Yuko Suga, Konoe Miura, Hiroshi Takimoto, Tomio Yoneyama
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Patent number: 4841027Abstract: Improvement in a process for producing an arylazo-aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR1## wherein A is a phenyl or naphthyl group unsubstituted or substituted by one to four members selected from alkyl, alkoxy, phenoxy, sulfonic acid, carboxylic acid, arylamino, amino, nitro and hydroxyl groups and halogen atoms, and m is 0 or 1, which comprises reacting an aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR2## wherein m is as defined above, with a dibasic acid anhydride to obtain an acylaminonaphtholsulfonic acid, coupling a diazonium compound of amine of the formula,A'--NH.sub.Type: GrantFiled: February 11, 1985Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Takashi Omura, Yasuo Tezuka, Hideharu Sone
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Patent number: 4824942Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthylene unsubstituted or substituted with sulfo, R.sub.1 and R.sub.2 are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R.sub.1 and R.sub.2 are hydrogen, and X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Y in which Y is a splittable group by the action of an alkali, which is useful for dyeing or printing fiber materials in a deep red color, and an aqueous liquid product of which is stable chemically and physically, even when stored for a long period of time.Type: GrantFiled: January 21, 1988Date of Patent: April 25, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazufumi Yokogawa, Noriaki Yamauchi, Takashi Omura
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Patent number: 4818814Abstract: Water-soluble disazo compounds of the formula ##STR1## in which D is a benzene ring or a naphthalene ring which can both be substituted by substituents from the group consisting of chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy and sulfo, X is the vinyl group or a .beta.-sulfatoethyl group, R is a .beta.-sulfatoethylsulfonyl, 3-(.beta.-chloroethylsulfonyl)-benzoyl, 4-(.beta.-chloroethylsulfonyl)-benzoyl, 3-(.beta.-chloroethylsulfonylmethyl)-benzoyl, 4-(.beta.-chloroethylsulfonylmethyl)-benzoyl,4-(.beta.-chloroethylsulfonyl )-cinnamoyl, 3-(N-methyl-N-.beta.chloroethylsulfonyl)-aminobenzoyl or 4-(N-methyl-N-.beta.-chloroethylsulfonyl)-aminobenzoyl group, m is the number 1 or 2 and M denotes a hydrogen atom or an alkali metal.The disazo compounds are suitable for use as dyes having fiber-reactive properties for dyeing hydroxy- and/or carboxamido-containing fiber material, such as in particular cellulose fiber materials and polyamide fiber materials.Type: GrantFiled: October 14, 1986Date of Patent: April 4, 1989Assignee: Hoechst AktiengesellschaftInventor: Ludwig Schlafer
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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: 4791211Abstract: An improved process for the production of 2-stilbylnaphthotriazole optical bleaches which involves diazotizing aminostilbene 2-sulfonic acids, coupling the thus formed diazonium salt with naphthylamino-sulfonic acid to form the stilbylnaphthyl monoazo salt by adding the naphthylamino-sulfonic acid to the diazonium salt from the diazotization, neutralized to a pH in the range of 6-8, in the presence of 2-butoxyethanol, oxidizing said monoazo salt to form the 2-stilbylnaphthotriazole compounds with air in an aqueous alkaline medium containing butoxyethanol and isolating and recovering said 2-stilbylnaphotriazole optical bleaches as their sodium salts.Type: GrantFiled: January 20, 1987Date of Patent: December 13, 1988Assignee: Ciba-Geigy CorporationInventors: Richard B. Lund, Larry W. Bass
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Patent number: 4786721Abstract: The reactive dyes are useful, in particular, for dyeing or printing cellulose-containing fiber materials by the cold pad-batch method and produce, with a high dyeing yield, dyeings and prints having good fastness properties.Type: GrantFiled: August 13, 1986Date of Patent: November 22, 1988Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann, Paul Herzig
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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: 4780533Abstract: A disazo pigment is prepared by coupling the tetrazo compound of 3,3'-dichlorobenzidine with an acetoacetanilide compound which is other than those represented by the below-described general formula (I) and is free of water-soluble groups. In the present invention, about 0.5-50 mole % of the acetoacetanilide compound is replaced by a compound represented by the following general formula (I): ##STR1## wherein R means a methyl, ethyl, propyl or butyl group or a substituted or unsubstituted phenyl group.Type: GrantFiled: February 9, 1987Date of Patent: October 25, 1988Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Naonori Takami, Tetsuo Fukuda, Takeshi Uehara
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Patent number: 4775746Abstract: Water-soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.Type: GrantFiled: September 30, 1986Date of Patent: October 4, 1988Assignee: Hoechst AktiengesellshaftInventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
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Patent number: 4772687Abstract: Metal complex dyestuffs which in the form of the free acid correspond to the formula ##STR1## in which the substituents have the meaning given in the description are, depending on the meanings of the substituents, suitable for use as reactive dyestuffs for cotton, wool or polyamide, as direct dyestuffs for cotton or as pigment dyestuffs. Dyeings are obtained which have good fastness properties, in particular good wet-, light- and chlorine fastness.Type: GrantFiled: May 1, 1986Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventor: Hermann Henk
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Patent number: 4771129Abstract: An azo compound of the formula: ##STR1## wherein M.sub.1, M.sub.2 and M.sub.3 are, the same or different, each a hydrogen atom, an alkali metal atom, an ammonium group or an organic ammonium group; R.sub.1 and R.sub.2 are, the same or different, each a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group, a halogen atom or a hydrogen atom; m is 1 or 2; and X and Y are, the same or different, each a C.sub.6 -C.sub.18 alkylamine, alkoxyalkylamine, arylamine, aralkylamine, alkanolamine or alkarylamine residue, which is useful as a magenta color dyestuff for an aqueous ink composition, particularly for ink jet recording.Type: GrantFiled: March 13, 1986Date of Patent: September 13, 1988Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, LimitedInventors: Hideo Kawashita, Mitsuhiro Ota
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Patent number: 4769447Abstract: The present invention provides gamma-glutamyl-4-azoanilides, processes for their preparation and their use as substrates for gamma-glutamyl transferase determination, of the formula ##STR1## wherein X is alkyl, --(CH.sub.2).sub.m --COOH or --O--(CH.sub.2).sub.n --COOH wherein m is 0-4 and n is 1-4; R is optionally substituted p-nitrophenyl; an optionally substituted thiophene residue; an optionally substituted thiazole residue; an optionally substituted benzothiazole residue; an optionally substituted benzoisothiazole residue; an N-alkylthiazole residue; or an optionally substituted 1,3,5-thiodiazole residue; as well as the alkali metal, alkaline earth metal and ammonium salts thereof.Type: GrantFiled: January 27, 1987Date of Patent: September 6, 1988Assignee: Boehringer Mannheim GmbHInventors: Elli Rauscher, John Griffiths, Leonard F. Dixon
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Patent number: 4762916Abstract: Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;B is chlorine or fluorine;R is hydrogen, chlorine, an alkyl of 1 to 4 carbon atoms or an alkoxy of 1 to 4 carbon atoms;M is hydrogen or an alkali metal;n stands for the number zero, 1 or 2,K is a radical of the formula ##STR3## in which D is phenylene which can be substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy or sulfo, or is naphthalene with optionally 1 or 2 sulfo groups,R.sup.1 denotes hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,R.sup.Type: GrantFiled: December 23, 1986Date of Patent: August 9, 1988Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Hartmut Springer, Michael Kunze
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Patent number: 4758659Abstract: A hexakisazo dye suitable for dyeing cellulose, natural or synthetic polyamide meterials, leather, represented by the formula ##STR1## wherein X is --CH.dbd.CH--, --CONH--, --CRH-- (wherein R is phenyl which is unsubstituted or substituted by H or a sulfonic acid group), -SO.sub.2 -- or --O--; Y is H, CH.sub.3 OCH.sub.3, Cl or SO.sub.3 M; A.sub.1 and A.sub.2 are each ##STR2## (wherein Z.sub.1 is H, Cl, CH.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or SO.sub.3 M, and Z.sub.2 is H, CH.sub.3, NO.sub.2 or COOM); B.sub.1 and B.sub.2 are each ##STR3## (wherein Z.sub.3 is H, OH, NH.sub.2 Cl or COOM, Z.sub.4 is H, Cl, CH.sub.3, OH OCH.sub.3, NH.sub.2, COOM or SO.sub.3 M, and Z.sub.5 is H, C.sub.1 -C.sub.4 alkyl or OH); M is H, Na, K, Li or NH.sub.4 ; f is 0 or 1; m is 0, 1 or 2; and n is 0, 1 or 2.Type: GrantFiled: July 29, 1986Date of Patent: July 19, 1988Assignee: Orient Chemical Industries, Ltd.Inventors: Hisashi Senshu, Sadahiko Matsubara, Tamotsu Naito
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Patent number: 4757136Abstract: Water-soluble azo compounds having fiber-reactive dye properties conforming to the formula ##STR1## in which D denotes a benzene or naphthalene ring;R.sup.1 denotes hydrogen, alkyl, alkoxy, sulfo or carboxy;R.sup.Type: GrantFiled: September 30, 1986Date of Patent: July 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
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Patent number: 4754020Abstract: A new method of diazotization consists in using as the diazotizing agent in an aqueous, aqueous organic or organic medium the system comprising salt of nitrous acid+acid insoluble in the reaction medium, in particular organic or inorganic cation exchangers having acid groups. The diazonium salt solutions thus prepared are immediately reacted with coupling components to give azo dyestuffs, the insoluble acid and/or its salt being separated off before or after the coupling.Type: GrantFiled: March 7, 1986Date of Patent: June 28, 1988Assignee: Bayer AktiengesellschaftInventors: Joachim Wolff, Karlheinz Wolf, Reinhold M. Klipper, Peter M. Lange
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Patent number: 4754023Abstract: A reactive dye of the formula ##STR1## in which: F is a radical selected from the group consisting of metal-free or metal-containing monoazo or disazo dyes containing at least one --SO.sub.3 H group, anthraquinone dyes, sulfophthalocyanine dyes, formazan dyes, phenazine dyes, oxazine dyes and nitroaryl dyes,R is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with --COOH or --SO.sub.3 H, cyanoethyl, or hydroxyethyl,X is fluorine, chlorine, bromine, --SO.sub.3 H, phenylsulfonyl or C.sub.1 -C.sub.4 -alkylsulfonyl,p is 1 or 2 andA is a radical of the formula ##STR2## in which: Y is chlorine, bromine, fluorine, --OH, --OSO.sub.3 H, --O-acyl, --CN, --COOH, --COO--C.sub.1 -C.sub.4 -alkyl, --CONH.sub.2 or --SO.sub.2 --Z,the group designated "alk" is a straight or branched polymethylene radical having 2 to 6 carbon atoms,V is ##STR3## hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.2 -alkoxy, carboxyl, sulfo, halogen or hydroxy,Z is .beta.Type: GrantFiled: January 23, 1986Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Herbert Seiler, Peter Scheibli
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Patent number: 4749813Abstract: 4-Alkyl-2-trifluoromethylanilines, in particular the 4-isopropyl derivative, are starting materials for preparing valuable azo dyestuffs. While the nonionic dyestuff types can preferably be used in transfer printing synthetic hydrophobic fibre materials, the sulpho-containing dyestuffs--in particular those based on "gamma acid"--are suitable for dyeing polyamides.Type: GrantFiled: December 30, 1982Date of Patent: June 7, 1988Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Gerhard Wolfrum
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Patent number: 4749784Abstract: The specification describes a new group of alkanol substituted disazo compounds that are useful in dyeing polyamide textile fibers in orange hues. The new compounds are compatible with several acid blue dyes and several acid red dyes that are commercially important as dyes for nylon. The new compounds are particularly well suited for use as the "yellow" component in trichromatic systems for dying polyamide carpeting and other textiles. The new compounds are relatively inexpensive to make and have outstanding application and fastness properties. Other aspects of the specification are concerned with a method of making the new compounds and with a method of dyeing polyamides with said compounds and to the novel dyed polyamides resulting from the use of the new group of compounds as dyes.Type: GrantFiled: February 10, 1987Date of Patent: June 7, 1988Assignee: Crompton & Knowles CorporationInventors: James F. Feeman, Jay E. Rowe
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Patent number: 4743683Abstract: A photographic recording material which contains at least one dye of the formula ##STR1## wherein D is the group of atoms necessary to complete a 5-membered ring that contains at least one nitrogen atom, A is hydrogen, alkyl, alkoxy, phenyl, alkylthio, cyano, nitro or halogen, n is 0 to 3, R.sub.1 is hydrogen, alkyl, hydroxyl, acylamino, R.sub.6 is hydrogen or unsubstituted or substituted amino, and R.sub.4 is hydrogen or alkoxy. The material is distinguished by good color reproduction, brilliant colors and excellent lightfastness.Type: GrantFiled: December 3, 1986Date of Patent: May 10, 1988Assignee: Ciba-Geigy AGInventor: Paul Tschopp
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Patent number: 4742160Abstract: Metal-free compounds of the formula ##STR1## and 1:1 and 1:2 metal complexes thereof, and salts of the metal-free compounds and 1:1 and 1:2 metal complexes, whereR is hydrogen, --SO.sub.3 H or --NR.sub.5 R.sub.6 ;R.sub.a is hydrogen or --NR.sub.5 R.sub.6 ;R.sub.1 is hydrogen, halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or --SO.sub.3 H;R.sub.3 is hydrogen or C.sub.1-4 alkyl;R.sub.4 is halogen, --OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, --NH.sub.2, an aliphatic, cycloaliphatic or aromatic amino group, a heterocyclic amino group containing 1 to 3 hereto atoms or a hydrazino group,R.sub.5 is hydrogen or C.sub.1-4 alkyl; andR.sub.6 is an organic radical, are useful as cationic dyes for dyeing and printing fibers, threads and textile materials comprising, for example, a natural or regenerated cellulosic material such as cotton, a modified synthetic polyamide or polyester, and a homo- or co-polymer of acrylonitrile or 1,1-dicyanoethylene, bast fibers such as hemp and particularly paper and leather.Type: GrantFiled: February 28, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4737240Abstract: Black trisazo dyes for cellulosic textiles, leather and especially paper having the structure ##STR1## where A is ##STR2## one of B.sub.1 and B.sub.2 is hydrogen and the other is --SO.sub.3 M or a mixture thereof, and M is hydrogen, sodium, potassium, lithium or --HNR.sub.1 R.sub.2 R.sub.3 wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different substituents selected from hydrogen, lower alkyl and lower hydroxyalkyl, and stable liquid concentrates of these dyes are described.Type: GrantFiled: June 27, 1986Date of Patent: April 12, 1988Assignee: Ciba-Geigy CorporationInventors: Herbert S. Davis, Roy E. Smith, Mortimer Weiser
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Patent number: 4734489Abstract: An azo compound of the formula: ##STR1## wherein R is of the formula: ##STR2## R.sub.1 is hydrogen, methyl or --SO.sub.3 M; R.sub.2 is hydrogen or --SO.sub.3 M; R.sub.2 is hydrogen or --SO.sub.3 M; R.sub.3 is C.sub.4 -C.sub.18 alkyl and M is hydrogen, an alkali metal, ammonium or organic ammonium, provided that when R includes --SO.sub.3 M, R.sub.1 l and R.sub.2 are not --SO.sub.3 M, and when R does not include --SO.sub.3 M, either one of R.sub.1 and R.sub.2 is --SO.sub.3 M, which is useful as a black dyestuff for a solvent type ink composition, particularly for ink jet recording.Type: GrantFiled: March 27, 1986Date of Patent: March 29, 1988Assignees: Taoka Chemical Company, Limited, Sumitomo Chemical Company, LimitedInventors: Shinjiro Kawasaki, Hideo Kitagawa, Yutaka Nishii, Hideo Kawashita, Minoru Akagi
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Patent number: 4730037Abstract: The invention relates to a method of determining and controlling the diazonium ion concentration in diazotization solutions and/or in azo coupling reactions, which comprises determining said diazonium ion concentration by means of IR spectroscopy from the intensity of the N.tbd.N stretching frequency.The method is extremely selective and virtually trouble-free and permits the simultaneous determination of the concentration of different diazonium salts in mixtures.Type: GrantFiled: August 22, 1986Date of Patent: March 8, 1988Assignee: Ciba-Geigy CorporationInventors: Ferenc Rakoczi, Rudiger Oxenius
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Patent number: 4725675Abstract: Water-soluble azo compounds of the formula (1) ##STR1## in which R is hydrogen or alkyl of 1 to 4 carbon atoms, X is alkyl of 1 to 6 carbon atoms substituted by carboxy or sulfo, or is phenyl substituted by 1 or 2 sulfo or carboxy or both, and Z is vinyl, .beta.-thiosulfatoethyl or .beta.-sulfatoethyl and M is hydrogen or the equivalent of a metal, and in which the second sulfo group in the naphthalene is bonded in the m-position or p-position relative to the acylated amino group. The new azo compounds are very valuable dyestuffs having fiber-reactive properties, and give color-fast and deep dyeings and prints on fiber materials made of cellulose or synthetic or natural polyamide fibers.Type: GrantFiled: December 5, 1983Date of Patent: February 16, 1988Assignee: Hoechst AktiengesellschaftInventors: Fritz Meininger, Joachim Otten
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Patent number: 4724259Abstract: Compounds of the general formula I ##STR1## where R.sup.1 and R.sup.2 independently of one another are each C.sub.6 -C.sub.24 -alkyl or are each benzyl which is unsubstituted or substituted by alkyl or by cycloalkyl, and one of the radicals may furthermore be hydrogen, and the rings A, B, C and D can be further substituted by chlorine, methyl or methoxy, with the exception of the compound of the formula ##STR2## are useful as dyes in electrooptical liquid crystal displays or for the production of polarization films.Type: GrantFiled: November 21, 1984Date of Patent: February 9, 1988Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Werner Juenemann, Johannes Dehnert
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Patent number: 4711954Abstract: Azo dyestuffs which contain at least one water-solubilizing group and have the formula ##STR1## wherein K stands for the radical of a coupling component,R.sub.1 stands for CN, COOX, CONXY or COZ,R.sub.2 stands for hydrogen, halogen, CN, alkyl or aryl,R.sub.3 stands for alkyl or aryl,X stands for H, alkyl, alkenyl, cycloalkyl, aryl or aralkyl andY stands for H or alkyl andZ stands for alkyl or aryl,are highly suitable for dyeing polyamide fibres. The resulting dyeings are distinguished by good all-round fastness properties.Type: GrantFiled: March 4, 1986Date of Patent: December 8, 1987Assignee: Bayer AktiengesellschaftInventors: Holger Heidenreich, Gerhard Wolfrum
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Patent number: 4703111Abstract: Water-soluble monoazo and disazo compounds having fiber-reactive dye properties which are suitable for dyeing carboxamido and/or hydroxy-containing materials, in particular cellulose fiber materials, and contain as coupling component that of a naphthol, aminonaphthalene or aminobenzene and as diazo component an optionally chlorine-, alkyl-, alkoxy- and/or sulfo-substituted phenyl radical or an optionally substituted phenylazophenyl or phenylazonaphthyl radical having the fiber-reactive group of the general formula ##STR1## in which the two R.sup.1, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom or a sulfo group and Y represents the vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, as substituent, and a further such fiber-reactive grouping can be bonded to the radical of the coupling component.Type: GrantFiled: April 7, 1986Date of Patent: October 27, 1987Inventors: Marcos Segal, Michael Kunze
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Patent number: 4703112Abstract: Water-soluble azo compounds, having fiber-reactive properties and yielding (for instance, on cellulose fiber materials) deep and fast dyeings and prints, of the formula ##STR1## in which D is phenylene which can be substituted by one or two subtituents from the group consisting of lower alkyl, lower alkoxy, hydroxy, lower alkanoylamino, benzoylamino, benzoylamino substituted by lower alkyl, lower alkoxy, chlorine and/or sulfo, chlorine, bromine, fluorine and carboxy and/or by a nitro group and/or by a further group of the formula Y--SO.sub.2 --(CH.sub.2).sub.Type: GrantFiled: October 30, 1986Date of Patent: October 27, 1987Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Ludwig Schlafer
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Patent number: 4701523Abstract: Water-soluble disazo compounds which have fiber-reactive dye properties, which are suitable for dyeing carboxamido- and/or hydroxy- containing materials, in particular cellulose fiber materials, and which contain as bivalent coupling component 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid and as diazo components an optionally substituted phenyl radical or naphthyl radical, one or both of the diazo components possessing a fiber-reactive group of the general formula ##STR1## in which the two R.sup.1, identical to or different from each other, denote a hydrogen atom or an optionally substituted alkyl group of 1 to 4 carbon atoms, R is a hydrogen atom of a sulfo group and Y represents the vinyl group or a .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl or .beta.-sulfatoethyl group, and it being possible for one of these diazo components also to contain, as substituent in place of this fiber-reactive grouping, a fiber-reactive group of the formula --SO.sub.Type: GrantFiled: May 13, 1986Date of Patent: October 20, 1987Inventors: Marcos Segal, Michael Kunze
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Patent number: 4701524Abstract: A monoazo compound, or a salt thereof, of the formula, ##STR1## wherein W is a hydrogen atom or a carbamoyl group, R.sub.1 is a lower alkyl group, R.sub.2 and R.sub.3 are independently a hydrogen atom or a lower alkyl group, A is an unsubstituted or substituted phenylene or naphthylene group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali, and X is an aromatic or aliphatic group substituted with one or two members selected from sulfonic acid group and carboxylic acid group, which is useful for dyeing fiber materials to give dyed products of a characteristic yellow color excellent in various fastness properties.Type: GrantFiled: November 5, 1985Date of Patent: October 20, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
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Patent number: 4698421Abstract: A compound, or a salt thereof, represented by the following formula, ##STR1## wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is ##STR2## in which R.sub.3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R.sub.4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R.sub.1 and R.sub.3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.Type: GrantFiled: June 7, 1985Date of Patent: October 6, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada
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Patent number: 4686285Abstract: (i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii),(iv) salts of (i), (ii), and (iii), and(v) mixtures of (i), (ii), (iii), and (iv),wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.Type: GrantFiled: February 8, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventor: Reinhard Pedrazzi
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Patent number: 4663440Abstract: A brown reactive dye represented by a free acid of the formula, ##STR1## wherein R is a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group, X is --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H or --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H.sub.2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1.This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.Type: GrantFiled: May 26, 1981Date of Patent: May 5, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Masaki Sunami, Yasuo Tezuka
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Patent number: 4652631Abstract: 1:2 chromium complex dyes suitable for dyeing nitrogen-containing materials and materials which contain hydroxyl groups, are disclosed which, in the form of the free acid, have the formula ##STR1## wherein each of the symbols independently has the following meanings: Z is nitrogen or a --CH,A is a benzene or naphthalene radical which carries the hydroxyl or carboxy ortho to the azo or azomethine group, or, if n is 1 and Z is a --CH, is the radical of an aliphatic, cycloaliphatic or aromatic aminocarboxylic acid,B and D are each independently of the other the radical of a coupling component which couples in the alpha- or o-position relative to X if Z is nitrogen, or the radical of an o-hydroxyaldehyde if Z is --CH,X is oxygen or --NR, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl, with the proviso that X must be oxygen if Z is --CH,Y is a bridge member of the formula --SO.sub.2 or --SO.sub.2 --NR--SO.sub.2 --, wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl,n is 0 or 1, andp is an integer from 0 to 6.Type: GrantFiled: March 28, 1985Date of Patent: March 24, 1987Assignee: Ciba-Geigy CorporationInventors: Fabio Beffa, Ulrich Schlesinger
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Patent number: 4652633Abstract: Compounds useful for dyeing nylon, wool, and leather, having the formula: ##STR1## wherein X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, Y.sup.3 is chlorine or bromine, and K.sup.1 is a radical of the formula ##STR2## where R.sup.3 is C.sub.2 to C.sub.4 hydroxyalkyl, methoxyethyl or methoxypropyl.Type: GrantFiled: February 15, 1985Date of Patent: March 24, 1987Assignee: BASF AktiengesellschaftInventor: Gunther Lamm
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Patent number: 4649194Abstract: 1:2 Metal complexes of the formula ##STR1## wherein X.sub.1 is --O-- or ##STR2## and X.sub.2 is --O-- or ##STR3## the starred atom being attached A.sub.1 or A.sub.2, respectively, A.sub.1 is a diazo component radical of the benzene series,A.sub.2 is a diazo component radical of the benzene or naphthalene series,W is --CH.sub.3 or --COOH,R is hydrogen or --SO.sub.3 H,each of B.sub.1 and B.sub.2 is independently a coupling component radical or a phenolic hydroxy group-containing coupling component radical at least one phenolic hydroxy group of which is etherified or acylated,M is iron, cobalt or chromium, andn is 1 or 2,which complexes are useful as anionic dyestuffs having olive to brown colors for substrates such as natural and regenerated cellulose, natural and synthetic polyamides, polyurethane and anodized aluminum, especially leather.Type: GrantFiled: July 27, 1983Date of Patent: March 10, 1987Assignee: Sandoz Ltd.Inventor: Heinz Wicki
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Patent number: 4644058Abstract: A monoazo compound represented by a free acid of the formula: ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom, or an alkyl, aralkyl or cyclohexyl group; R.sub.3 represents a hydrogen atom or a methyl or sulfonic acid group; R.sub.4 represents a hydrogen atom or an alkyl group; A represents an oxygen atom or --NH--; X.sub.1 and X.sub.2 independently represent a hydrogen or chlorine atom, or a methyl, methoxy, carboxyl or sulfonic acid group; and Y represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 Z in which Z represents a halogen atom, --OSO.sub.3 H or --OPO.sub.3 H.sub.2. This compound is used for dyeing cellulose fibers to give dyed products of yellow to reddish yellow having excellent fastnesses, particularly chlorine fastness.Type: GrantFiled: November 18, 1982Date of Patent: February 17, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yasutaka Shimidzu, Naoki Harada, Yasuo Tezuka