Formation Of Azo Group By Coupling Diazonium Compound With Coupling Component In Presence Of An Additional Organic Compound Patents (Class 534/581)
  • Patent number: 4929720
    Abstract: Isothiazole dyes of the formula ##STR1## where X is substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or substituted or unsubstituted phenyl,Y is hydrogen, cyano, chlorine or bromine,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.2 is hydrogen, cyano, carbamoyl, C.sub.1 -C.sub.4 -monoalkyl- or -dialkyl-carbamoyl, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or 2-(C.sub.1 -C.sub.4 -alkoxy)-ethoxycarbonyl andR.sup.3 is hydrogen, C.sub.1 -C.sub.8 -alkyl which may be substituted and/or interrupted by one or two oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or phenyl, are useful for dyeing synthetic fibers.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: May 29, 1990
    Assignee: Basf Aktiengesellschaft
    Inventors: Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4920208
    Abstract: Basic azo dyestuffs of the general formula ##STR1## and tautomers thereof, in which D is the radical of a diazo or tetrazocomponent free of anionic groups,X is O or NH,R.sup.1, R.sup.2 are hydrogen, alkyl or aryl,B is a bridge member andR.sup.3, R.sup.4 are hydrogen, alkyl, alkenyl or aralkyl orR.sup.2 and R.sup.3 together with B and the two nitrogen atoms to which they are bonded form a 5- or 6-membered heterocyclic and in this caseB also stands for a direct bond, orR.sup.3 and R.sup.4 together with the nitrogen atom to which they are bonded form a 5- or 6-membered heterocyclic,n is 1 or 2, and in whichthe cyclic and acyclic radicals can in turn be substituted by radicals customary in dyestuff chemistry, find utility for dyeing and coloring synthetic and natural materials.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: April 24, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Aloysius Engel
  • Patent number: 4891424
    Abstract: 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: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4889924
    Abstract: A bisazo compound having good electrophotographic properties is disclosed, which is represented by formula (I) ##STR1## wherein X represents a hydrogen atom, a chlorine atom or a nitro group. A process for producing the bisazo compound is also disclosed.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: December 26, 1989
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Yutaka Akasaki, Akihiko Tokita, Kaoru Torikoshi, Akira Imai, Touru Ishii
  • Patent number: 4889535
    Abstract: Compounds of the formula ##STR1## and mixtures thereof, wherien p1 R.sub.1 is hydrogen, chloro or bromo, p1 R.sub.2 is hydrogen, chloro, bromo or nitro, p1 R.sub.3 is hydrogen, chloro, bromo, nitro or --SCN, p1 R.sub.4 is hydrogen, chloro or bromo, p1 R.sub.5 is hydrogen or C.sub.1-4 alkyl, and p1 R.sub.5 is C.sub.8-14 alkyl,with the provisos that (i) at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than hydrogen, (ii) when R.sub.3 is nitro or --SCN, R.sub.2 is other than nitro, and (iii) when two or more of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are halo, then R.sub.3 is one of those halos, are useful as disperse dyes for dyeing substrates such as synthetic and semi-synthetic, hydrophobic, high molecular weight organic materials.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: December 26, 1989
    Assignee: Sandoz Ltd.
    Inventor: Beat Henzi
  • Patent number: 4886920
    Abstract: An improved process is disclosed for preparing aromatic fluorides by diazotization-fluorination in hydrogen fluoride wherein the diazotized reaction mixture includes an oxidizing agent such as nitrosonium ion from excess diazotization agent. The improvement includes, prior to decomposing the diazonium fluoride, adding to the diazotized reaction mixture a member selected from hydrazine, aromatic hydrazine, semi-carbazide, thio-semicarbazide, acid salts thereof, sulfur dioxide, sodium sulfate, and sodium bisulfite to remove at least a portion of the oxidizing agent. Urea was found to be ineffective.
    Type: Grant
    Filed: April 5, 1988
    Date of Patent: December 12, 1989
    Assignee: Mallinckrodt, Inc.
    Inventor: Gary L. Cantrell
  • Patent number: 4879373
    Abstract: 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: Grant
    Filed: February 19, 1987
    Date of Patent: November 7, 1989
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4870164
    Abstract: 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: Grant
    Filed: January 28, 1985
    Date of Patent: September 26, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4841027
    Abstract: 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: Grant
    Filed: February 11, 1985
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Takashi Omura, Yasuo Tezuka, Hideharu Sone
  • Patent number: 4826505
    Abstract: A monoazo pyridone compound of the following formula, ##STR1## wherein X is a member selected from hydrogen, halogeno, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or cyano, and R is alkyl, alkenyl, cycloalkyl, phenyl or anilino, with the provisos that X is a member selected from those defined above except for hydrogen, chloro, methyl and methoxy when R is ethyl, and X is a member selected from those defined above except for alkyl when R is iso-butyl, which is stable under dyeing conditions, and useful for dyeing hydrophobic fiber materials to give dyed products of a deep, fast and brilliant color of greenish yellow to orange.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
  • Patent number: 4824942
    Abstract: 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: Grant
    Filed: January 21, 1988
    Date of Patent: April 25, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Noriaki Yamauchi, Takashi Omura
  • Patent number: 4801696
    Abstract: Disazo dyes for dyeing cellulose-containing fibers represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 each represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocyanato group, a trifluoromethyl group, a formyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a sulfamoyl group, an N-lower alkylsulfamoyl group or an N,N-di-lower alkylsulfamoyl group, R.sup.3 represents a hydrogen atom, a methyl group, a chlorine atom, a lower alkoxy group or an acylamino group, R.sup.4 represents a hydrogen atom, a methyl group, a chlorine atom or a lower alkoxy group, R.sup.5 represents a hydrogen atom, a lower alkyl group or a halogen atom, --X-- represents ##STR2## --SO.sub.2 -- or --CH.sub.2 --, and n represents 0 or 1. These dyes are capable of dyeing cellulose-containing fibers, particularly fiber blends composed of cellulose fibers and polyester fibers, blue to bluish green with good fastness properties.
    Type: Grant
    Filed: June 22, 1987
    Date of Patent: January 31, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Shuichi Maeda
  • Patent number: 4791194
    Abstract: An azo compound with the following general formula (I): ##STR1## wherein X is selected from the group consisting of hydrogen atom, lower alkyl group, lower alkoxy group, halogen atom and cyano group;Y is phenylene or naphthylene group;Z.sub.1 and Z.sub.2 are independently the divalent group represented by the following formula: ##STR2## wherein A is a divalent group derived from the aromatic hydrocarbon or heterocyclic compound including one or more nitrogen atoms in the ring; andn is 1 or 2,is disclosed. Such compounds are useful in forming a photosensitive layer of an electrophotographic photoreceptor.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: December 13, 1988
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Tetsumi Suzuki, Tetsuo Murayama, Hitoshi Ono, Shinji Aramaki, Michiyo Yokoyama
  • Patent number: 4785082
    Abstract: According to the invention, addition of one or more surfactants having a cloud point in aqueous solution to an aqueous suspension of an azo disperse dye gives after the isolation of the dye at a temperature above the cloud point aqueous press cakes containing a large amount of this dye.The direct processing of press cakes as obtained for example after the synthesis and isolation of azo disperse dyes to practical dispersions for use requires a minimum dye content in the press cakes. The minimum content is frequently not obtained when conventional methods of isolation are used, so that it is necessary to proceed via the indirect route of drying to obtain powders and redispersing the powders. By using the process according to the invention it is possible to cut out the costly indirect route or, if desired, to reduce the expense of drying to obtain powders by an appreciable margin.
    Type: Grant
    Filed: November 5, 1985
    Date of Patent: November 15, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Joachim Weide, Erwin Dietz, Reinhold Deubel
  • Patent number: 4769447
    Abstract: 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: Grant
    Filed: January 27, 1987
    Date of Patent: September 6, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elli Rauscher, John Griffiths, Leonard F. Dixon
  • Patent number: 4769449
    Abstract: Azo dyes of the formula ##STR1## wherein R.sup.1 is alkyl having 1 to 4 carbon atoms; R.sup.2 is alkyl having 1 to 3 carbon atoms; R.sup.3 is alkylcarbonyloxyethyl having 1 to 3 carbon atoms in the alkyl moiety, alkoxycarbonyloxyethyl having 1 to 4 carbon atoms in the alkoxy moiety, methoxyethoxycarbonyloxyethyl or ethoxyethoxycarbonyloxyethyl; and R.sup.4 is one of the definitions of R.sup.3 or cyanoethyl; or mixtures of at least two species of said formula are used for dyeing and printing hydrophobic fiber materials.
    Type: Grant
    Filed: February 5, 1987
    Date of Patent: September 6, 1988
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Manfred Hahnke, Michael Kunze, Albert Bode
  • Patent number: 4767844
    Abstract: An azo lake pigment is obtained by coupling an aromatic diazo component having a sulfonic acid group with a mixture of 2-hydroxy-3-naphthoic acid and a 2-hydroxy-3-naphthoic acid derivative represented by formula [I] ##STR1## wherein R represents a hydrogen atom, a naphthalene residue, a cyclohexyl group, or a group of the formula ##STR2## in which each of X, Y and Z represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, an acetylamino group, a benzoylamino group, a carbomoyl group or a phenylcarbamoyl group, and X and Y together may form a cyclized benzimidazolone, benzthiazole or benzoxazole group,and laking the resulting dye with an alkaline earth metal salt or a manganese salt.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: August 30, 1988
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hirohito Ando, Zenji Takada, Shigeto Aoki, Yuko Shigeta
  • Patent number: 4754020
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: June 28, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Wolff, Karlheinz Wolf, Reinhold M. Klipper, Peter M. Lange
  • Patent number: 4749813
    Abstract: 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: Grant
    Filed: December 30, 1982
    Date of Patent: June 7, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Gerhard Wolfrum
  • Patent number: 4743683
    Abstract: 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: Grant
    Filed: December 3, 1986
    Date of Patent: May 10, 1988
    Assignee: Ciba-Geigy AG
    Inventor: Paul Tschopp
  • Patent number: 4742160
    Abstract: 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: Grant
    Filed: February 28, 1986
    Date of Patent: May 3, 1988
    Assignee: Sandoz Ltd.
    Inventors: Jacky Dore, Reinhard Pedrazzi
  • Patent number: 4740592
    Abstract: 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: Grant
    Filed: September 30, 1986
    Date of Patent: April 26, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Michael Kunze, Marcos Segal, Werner H. Russ
  • Patent number: 4737581
    Abstract: 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: Grant
    Filed: April 18, 1985
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Stefan Hari
  • Patent number: 4732975
    Abstract: 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: Grant
    Filed: December 21, 1981
    Date of Patent: March 22, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Manfred Pesenacker
  • Patent number: 4730037
    Abstract: 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: Grant
    Filed: August 22, 1986
    Date of Patent: March 8, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Ferenc Rakoczi, Rudiger Oxenius
  • Patent number: 4716220
    Abstract: The present invention provides a tetrazoneum salt compound represented by the general formula (I): ##STR1## (wherein, X stands for an anion functional group); a disazo compound represented by the general formula (II): ##STR2## wherein, A stands for ##STR3## (wherein, R stands for an alkyl group, an alkoxy group, a nitro group, halogen, a cyano group or a halomethyl group, n stands for an integer of 0, 1, 2 or 3, and in case n is an integer of 2 or 3 R may be the same or different); a method for the production thereof, and electrophotographic elements using the same or like disazo compounds as the charge carrier generating materials.
    Type: Grant
    Filed: July 9, 1985
    Date of Patent: December 29, 1987
    Assignee: Ricoh Co., Ltd.
    Inventor: Kyoji Tsutsui
  • Patent number: 4709019
    Abstract: 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: Grant
    Filed: April 21, 1983
    Date of Patent: November 24, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Meinhard Rolf, Rutger Neeff, Walter Muller
  • Patent number: 4703112
    Abstract: 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: Grant
    Filed: October 30, 1986
    Date of Patent: October 27, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Mischke, Ludwig Schlafer
  • Patent number: 4701524
    Abstract: 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: Grant
    Filed: November 5, 1985
    Date of Patent: October 20, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Hirokazu Sawamoto, Takashi Omura, Naoki Harada, Akira Takeshita
  • Patent number: 4701523
    Abstract: 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: Grant
    Filed: May 13, 1986
    Date of Patent: October 20, 1987
    Inventors: Marcos Segal, Michael Kunze
  • Patent number: 4686287
    Abstract: 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: Grant
    Filed: April 3, 1985
    Date of Patent: August 11, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Klaus Hunger
  • Patent number: 4677200
    Abstract: The invention relates to aminoazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, chlorine, bromine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A represents hydrogen, methyl or ethyl, and Z in the 6- or 7-position of the heteroaromatic ring system is hydrogen, chlorine or bromine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro.The compounds of the formula I are prepared 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 and Z analogously to the formula I. In the case where X, Y or Z does not denote a nitro group, it is possible to use in place of the p-diaminobenzene derivative a p-aminonitrobenzene derivative which is disubstituted by X and Y in the 2- and 5-positions.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: June 30, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Klaus Hunger
  • Patent number: 4665163
    Abstract: Diaryl pigments having an excellent stability to heat are obtained by carrying out the coupling of bis-diazotized 3,3'-dichloro-4,4'-diaminobiphenyl with acetoacetanilides in the presence of an added quantity of acetoacetanilides which are monosubstituted or disubstituted in the 3-position or 4-position of the nucleus. As a result of their good heat stability, these pigments are particularly suitable for pigmenting plastics having processing temperatures above 200.degree. C.
    Type: Grant
    Filed: June 23, 1983
    Date of Patent: May 12, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Hunger, Heinrich Frolich, Hans-Joachim Lenz
  • Patent number: 4652633
    Abstract: 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: Grant
    Filed: February 15, 1985
    Date of Patent: March 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventor: Gunther Lamm
  • Patent number: 4642339
    Abstract: This invention relates to thiazoleazophenylaminoethyl carbonyloxy-C.sub.8 -C.sub.10 -alkyl compounds useful as dyes for polyester fibers represented by the formula: ##STR1## wherein X represents hydrogen, chlorine, methyl, methoxy or ethoxy; Y represents methyl, acetylamino or propionylamino; and R.sup.1 represents C.sub.8 -C.sub.10 alkyl.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: February 10, 1987
    Assignee: Research Association of Synthetic Dyestuffs
    Inventors: Toshio Niwa, Kiyoshi Himeno, Junji Yoshihara
  • Patent number: 4628082
    Abstract: Azobarbituric acid derivatives characterized in that in their free acid form they have the following tautomeric structure are disclosed: ##STR1## The azobarbituric acid derivatives are characterized in that X and Y rings can each carry one or two substituents from the series comprising .dbd.O, .dbd.S, .dbd.NR.sub.7, --NR.sub.6 R.sub.7, --OR.sub.6, --SR.sub.6, --COOR.sub.6, --CN, --CONR.sub.6 R.sub.7, --SO.sub.2 R.sub.8, ##STR2## alkyl, cycloalkyl, aryl and aralkyl, the total number of the endocyclic and exocyclic double bonds for each of the rings X and Y being three.The new azobarbituric acid derivatives are other than those of azobarbituric acid, azouracil and uracil-5-azobarbituric acid and their salts. The compounds are useful as pigments which pigments are useful for pigmented paints, in printing inks, distempers or emulsion paints, inter alia.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: December 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Karl H. Schundehutte
  • Patent number: 4623397
    Abstract: 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: Grant
    Filed: October 10, 1984
    Date of Patent: November 18, 1986
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4622391
    Abstract: New inclusion compound, intercalation compounds or solid solutions which are the nickel salts or nickel complexes of a compound which, in one of its tauteromeric structures, corresponds to the formula ##STR1## which contain at least one other included compound, except for one composition of matter which consists of 45 to 82% by weight of azobarbituric acid/nickel 1:1 complex, 3 to 15% by weight of benzene-sulphonamide, 5 to 20% by weight of nickel acetate and 10 to 20% by weight of water and the use of these materials as pigments are disclosed.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: November 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lorenz, Karl H. Schundehutte
  • Patent number: 4609726
    Abstract: 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: Grant
    Filed: March 14, 1984
    Date of Patent: September 2, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Kemper, Egon Liedek
  • Patent number: 4607096
    Abstract: 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: Grant
    Filed: November 4, 1982
    Date of Patent: August 19, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Josef Landler, Klaus Hunger, Erhard Worfel
  • Patent number: 4605734
    Abstract: A compound, useful as an anti-cancer drug or agent, having the formula: ##STR1## where X represents hydroxyl, amino or alkylamino, Y represents one member selected from ##STR2## or alkylated derivatives thereof, and Z represents hydrogen or one of the basic groups of Y, an acid addition salt of the said compound, a nitrogen oxide derivative of the said compound in the case where it contains a ring nitrogen atom or atoms.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: August 12, 1986
    Inventor: Douglas Shortridge
  • Patent number: 4585460
    Abstract: Reactive dyes of the formula ##STR1## wherein Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, in which X is a leaving group, and Z is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or carboxy, and K is the radical of a coupling component which couples at pH.ltoreq.7, are suitable for dyeing and printing textile fibre material and give dyeings and prints of good fastness properties.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: April 29, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Hansrudolf Schwander, Jurgen Markert, Peter Aeschlimann
  • Patent number: 4530996
    Abstract: A compound represented by a free acid of the formula: ##STR1## wherein D is ##STR2## (R.sub.1 and R.sub.2 independently represent hydrogen, methyl or methoxy) or ##STR3## (n is 0 or 1, the mark * signifies the position of linkage to --N.dbd.N-- and the mark # signifies the position of linkage to Q mentioned below); Q is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 R (R is a group capable of being split off by the action of alkali); one of X.sub.1 and X.sub.2 is hydrogen and the other is a sulfonic acid group; and m is 0 or 1, which is useful for dyeing cellulose fibers a blue-black color with good dyeability and excellent fastnesses, particularly chlorine fastness.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: July 23, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Omura, Naoki Harada, Yasuo Tezuka
  • Patent number: 4515639
    Abstract: Intense azo pigment formulations which have good flow and are readily dispersible are obtained on adding a long-chain aliphatic primary amine and a diamine of the formulaH.sub.2 N--A--NH.sub.2in which A is an aliphatic hydrocarbon radical having 6 to 30 C atoms, before, during or preferably after the coupling. The formulations are in particular suitable for intaglio printing inks which produce glossy prints which do not even strike through thin papers.
    Type: Grant
    Filed: February 5, 1982
    Date of Patent: May 7, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Dopfer, Johann Ostermeier, Siegfried Schwerin