Formation Of Quaternary Ammonium Or Hydrazinium Group Patents (Class 534/589)
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Publication number: 20120217151Abstract: A photoresponsive ionic organic compound of formula (I); a method of producing the same; a photoresponsive carbon nanotube (CNT) dispersant; a CNT dispersion containing the dispersant; and a method of separating a CNT from the dispersion: wherein R1, R2, and R3 each represent a hydrogen atom or an alkyl group; A represents —CH— or a nitrogen atom; X represents an anion; and n is a number to give a charge of ?2 to nX.Type: ApplicationFiled: October 26, 2010Publication date: August 30, 2012Inventors: Yoko Matsuzawa, Masaru Yoshida, Harumi Ohyama, Haruhisa Kato
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Patent number: 7648790Abstract: An electrolyte for a fuel cell comprising a proton conducting resin comprising a backbone comprising a polyurea resin and side chains that comprise an active hydrogen group at a terminal and a fuel cell employing the same are provided. The electrolyte has improved proton conductivity, heat resistance, and mechanical strength.Type: GrantFiled: July 26, 2005Date of Patent: January 19, 2010Assignee: Samsung SDI Co., Ltd.Inventors: Atsuo Sonai, Toshihiko Matsuda
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Patent number: 6130319Abstract: A flocculating dye reduces bleed between two inks when they are applied side by side. A first ink comprises the flocculating dye which flocculates the dispersant-pigment of the second ink.Type: GrantFiled: April 3, 1998Date of Patent: October 10, 2000Assignee: Lexmark International, Inc.Inventors: James F. Feeman, Jing X. Sun
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Patent number: 5929216Abstract: Disclosed are dyes having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkoxy or chlorine,R.sub.2 is C.sub.1 -C.sub.4 alkyl,R.sub.3 is C.sub.1 -C.sub.4 alkyl,R.sub.4 is C.sub.1 -C.sub.4 alkyl,R.sub.5 is hydroxyethyl or hydroxypropyl, andAn.sup..crclbar. is an anion, in which R.sub.3 and R.sub.4 are not both ethyl at the same time, compositions containing the dyes and methods of using and preparing the dyes. The dyes are especially useful for dyeing polyacrylonitrile.Type: GrantFiled: September 10, 1997Date of Patent: July 27, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Wilfried Herter, Josef Koller
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Patent number: 5708151Abstract: The cationic imidazole azo dyes of the formulae ##STR1## in which A and A.sub.1 independently of one another are each a radical of the formula ##STR2## Z is the radical of an aliphatic or aromatic diamine, R.sub.1 and R.sub.2 are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or, together with the two nitrogen atoms to which they are attached and with Z, form a 5-, 6- or 7-membered ring, X is the radical of a bridging member, n is 2, 3 or 4, Z.sub.1 is the radical of an aromatic diamine, Z.sub.2 is the radical of an aliphatic diamine, KK is the radical of a coupling component, R.sub.3 and R.sub.4 are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, R.sub.5 and R.sub.6 independently of one another are each hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and An.sup..crclbar. is a colorless anion, are particularly suitable for the dyeing of paper in red or violet shades having good fastness properties.Type: GrantFiled: November 2, 1995Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Peter Mockli
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Patent number: 5635607Abstract: The cationic or basic aminobenzothiazole dyes disclosed herein are particularly suitable for dyeing paper.Paper is dyed with these dyes in blue or violet shades of good fastness properties.Type: GrantFiled: April 21, 1995Date of Patent: June 3, 1997Assignee: Ciba-Geigy CorporationInventor: Adolf Kaser
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Patent number: 5552531Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1.Type: GrantFiled: April 6, 1993Date of Patent: September 3, 1996Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K.-M. Cheng
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Patent number: 5436323Abstract: Cationic 1,3,4-thiadiazolyldiphenylamine dyestuffs and corresponding anhydro bases, the dyestuffs having the formula (I) ##STR1## their preparation and their use, and materials dyed with such dyestuffs.Type: GrantFiled: July 1, 1993Date of Patent: July 25, 1995Assignee: Bayer AktiengesellschaftInventors: Horst Berneth, Werner Hartwich, Karl-Heinrich Lange
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Patent number: 5290347Abstract: The present invention provides a novel salt-forming type dye represented by the formula: ##STR1## wherein D is a residue of a monoazo or disazo dye, m is an integer of 1 to 3, n is an integer of 1 to 4, and M.sup.+ is a cation selected from the group consisting of cations represented by the formulas: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and represent hydrogen, an alkyl group, an alkoxyalkyl group, a cyclohexyl group, an aralkyl group or a hydroxyalkyl group, and at least one of R.sup.1 to R.sup.4 is a branched or non-branched alkyl, alkoxyalkyl, cycloalkyl, aralkyl or polyoxyalkylene group having not less than 4 carbon atoms, ##STR3## wherein R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are the same or different and represent hydrogen, an alkyl group, or a substituted or non-substituted phenyl group, and at least one of R.sup.5 to R.sup.8 is a substituted or non-substituted phenyl group, and ##STR4## wherein R.sup.9 and R.sup.Type: GrantFiled: April 9, 1992Date of Patent: March 1, 1994Assignee: Orient Chemical Industries, Ltd.Inventors: Takashi Ono, Tatsuya Yagyu, Katsumi Fukuda
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Patent number: 5284939Abstract: There is described a process for the preparation of highly concentrated aqueous solutions of specific cationic azo dyes. The solutions are prepared by diazotising a diazo component in a solution which contains sulfuric acid, coupling the diazotised component to a coupling component, treating the resultant azo dye with a bicarbonate, and converting the dye bicarbonate with an organic acid into the dye salt of said acid.Type: GrantFiled: May 14, 1992Date of Patent: February 8, 1994Assignee: Ciba-Geigy CorporationInventors: Alex Nicopoulos, Hanspeter Birri, Gerhard Hanika
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Patent number: 5264560Abstract: Quaternized azo dyes whose diazo components are derived from a five-membered nitrogen-containing aromatic aminoheterocycle and whose coupling components are derived from the aniline series are prepared by reacting to corresponding neutral dye-bases with an alkylating agent in .gamma.-butyrolactone as inert diluent.Type: GrantFiled: July 17, 1992Date of Patent: November 23, 1993Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Johannes P. Dix, Helmut Reichelt, Clemens Grund
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Patent number: 5239063Abstract: Fiber reactive azo dyestuffs of the formula ##STR1## in which R=H or C.sub.1 -C.sub.6 alkyl, which can be substituted with OH, Hal, SO.sub.3 H or OSO.sub.3 H;Z=heterocyclic five or six membered ring;n, m=0, 1 or 2, wherein n+m=0, 1 or 2;Y=OH, OR, NR.sub.2 R.sub.3, OMe; andR.sub.2, R.sub.3, =H, R and R.sub.2, R.sub.3 and N can form a heterocyclic 5 or 6-membered ring.Type: GrantFiled: January 9, 1992Date of Patent: August 24, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
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Patent number: 5208325Abstract: Cationic 1,3,4-thiadiazole dyestuff of the formula ##STR1##in whichR.sup.1 and R.sup.2, independently of one another, denote hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, a heterocycle, said heterocycle having a direct bond to the nitrogen atom, or being bound through a methylene or ethylene group, or R.sup.1 and R.sup.2, together with the nitrogen atom to which they are attached form a heterocycle,R.sup.3 denotes alkyl, alkenyl or aralkyl,R.sup.4 denotes hydrogen or alkyl,R.sup.5 denotes acyl,R.sup.6 and R.sup.7, independently of one another, denote hydrogen, alkyl, alkoxy, aryloxy or halogen andR.sup.8 and R.sup.9, independently of one another, denote hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, a heterocycle, said heterocycle having a direct bond to the nitrogen atom, or being bound through a methylene or ethylene group, or R.sup.8 and R.sup.9, together with the nitrogen atom to which they are attached form a heterocycle, orR.sup.6 and R.sup.8 together with the nitrogen to which R.sup.Type: GrantFiled: December 11, 1991Date of Patent: May 4, 1993Assignee: Bayer AktiengesellschaftInventors: Horst Berneth, Klaus Leverenz
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Patent number: 5175260Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.Type: GrantFiled: August 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Udo Mayer
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Patent number: 4997918Abstract: Novel cationic azo compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 -alkylene, R.sub.2 is C.sub.1 -C.sub.4 -alkyl, R.sub.3 is C.sub.1 -C.sub.4 -alkyl, R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino or halogen, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 - alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, one or more or R.sub.5 independently of each other being present on the ring to which R.sub.5 is attached, and A is an anion. Also provided is the production, and the use of these novel compounds as dyes for dyeing and/or printing, especially polyacrylonitrile materials, neutral blue dyeings having in particular good fastness to light being obtained.Type: GrantFiled: May 6, 1987Date of Patent: March 5, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 4992495Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.Type: GrantFiled: June 16, 1988Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh
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Patent number: 4956456Abstract: The present invention is directed towards a betaine-type monoazo dye for dying and printing fibrous materials, represented by formula (I):Dye--X--Y (I)wherein Dye represents a cyan dye anion represented by formula (II);X represents a bond or linking group;Y represents quaternary ammonium; andDye and X are bonded to each other via A, B.sup.1, B.sup.2, B.sup.3, B.sup.4 or B.sup.5 in formula (II): ##STR1## wherein B.sup.1, B.sup.2, B.sup.3, B.sup.4 and B.sup.5 are the same or different, and each represents a member selected from the group consisting of a bond, hydrogen, alkyl, halogen, --OR.sup.4, --CO.sub.2 R.sup.4, ##STR2## wherein R.sup.4 and R.sup.5 are the same or different and each represents a member selected from the group consisting of hydrogen, alkyl and aryl, or R.sup.4 and R.sup.Type: GrantFiled: December 1, 1989Date of Patent: September 11, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Masaaki Tsukase, Kozo Sato
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Patent number: 4940783Abstract: Disazo dyes which are suitable for dyeing and printing, especially of paper of all kinds. The dyes correspond to the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each an alkyl radical,A is an alkylene radical,X and Y are nonionic substituents customarily in azo dyes andAn.sup..crclbar. is an anion.Type: GrantFiled: August 30, 1988Date of Patent: July 10, 1990Assignee: Ciba-Geigy CorporationInventor: Willy Stingelin
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Patent number: 4925926Abstract: The invention relates to a continuous process for the preparation of cationic azo or hydrazone dyes from heterocyclic diazo components and coupling components. The diazo component is diazotised in water and an acid, the diazo solution is coupled with the coupling component and continuously alkylated, preferably using sufficient acid that, after the alkylation, a two-phase system forms, consisting of an aqueous solution which is substantially free from dye and a highly concentrated oil phase or solid dye.Type: GrantFiled: December 7, 1987Date of Patent: May 15, 1990Assignee: Ciba-Geigy CorporationInventors: Roland Ronco, Ermanno Ciapponi, Pierre Pessonneaux
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Patent number: 4880916Abstract: Azo dyes of the formula ##STR1## or tautomers thereof, wherein Z is N,S or CH,X is O,S,NR.sup.2 or N, V is N or CH, W is N or C, K is a coupling component from the group consisting of acylacetarylamides, phenols, pyridones, quinolines, pyrazoles, indoles, diphenylamines, aminopyridines, pyrimidines, pyrimidones, naphthols, naphthylamines, aminoathiozoles, thiophenes and hydroxypyridines, R is unsubstituted or substituted alkyl or alkenyl, R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, --CN, --NHR.sup.2, --NH--acyl, phenoxy, --COOR.sup.2, --COOR.sup.2 --CONHR.sup.2 or substituted or unsubstituted phenyl, R.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl or substituted or unsubstituted phenyl, D is a 1,4-phenylene radical which can be substituted further and AN.THETA.Type: GrantFiled: March 24, 1988Date of Patent: November 14, 1989Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4845202Abstract: Water-soluble disazo compounds having useful fiber-reactive dye properties, which conform to the general formula (1) defined hereinafter and dye carboxamido- and/or hydroxy-containing materials in fast shades. Fast dyeings on cellulose fiber materials can also be obtained in a weakly acid to neutral pH range, for example together with disperse dyes for dyeing a polyester fiber portion. ##STR1## in which: A is phenylene which may be substituted by methyl, ethyl, methoxy, chlorine or sulfo, or is a radical of the formula ##STR2## in which G is a direct bond or a group of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R.sup.1 and R.sup.Type: GrantFiled: October 23, 1987Date of Patent: July 4, 1989Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Hartmut Springer, Reinhard Hahnle
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Patent number: 4839468Abstract: Triazine compounds which in their betaine form correspond to the formula ##STR1## wherein Y denotes hydrogen or the radical of an azo dye-stuff,R denotes hydrogen or alkyl,Ar denotes arylene,Z denotes halogen, hydroxyl, alkoxy, alkyl, aryl or an amino group which may be monosubstituted or disubstituted,m denotes 0 or 1 andX.sup.(+) denotes an ammonium groupamd whereimthe cyclic and acyclic radicals can carry further substituents,are used for dyeing/coloring natural and synthetic substrates and compositions, in particular paper.Type: GrantFiled: November 13, 1984Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventors: Horst Nickel, Peter Wild, Frank-Michael Stohr
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Patent number: 4820806Abstract: Metal-free monoazo and disazo compounds of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --W.sub.1 --D--N.dbd.N--K--(W.sub.2 --Z).sub.n,1:1 and 1:2 metal complexes of such metallizable metal-free compounds and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes, whereinD is the radical of a diazo component of the benzene, naphthalene or tetrahydronaphthalene series,K is the radical of a coupling component of the benzene, naphthalene, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzeneazobenzene, benzeneazonaphthalene, naphthaleneazobenzene, naphthaleneazonaphthalene, tetrahydronaphthaleneazobenzene, tetrahydronaphthaleneazonaphthalene or acetoacetamide series,W.sub.1 is a direct bond or a divalent bridging radical,each W.sub.Type: GrantFiled: February 28, 1986Date of Patent: April 11, 1989Assignee: Sandoz, Ltd.Inventors: Werner Baumann, Joseph V. Diest, Herbert Eichenberger, Max Oppliger
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Patent number: 4818815Abstract: The invention relates to novel 1,2,3-thiadiazole-axo compounds of formula ##STR1## wherein R is unsubstituted or substituted alkyl or alkenyl,R.sub.1 is hydrogen or unsubstituted or substituted alkyl or alkenyl,R.sub.2 is hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl or phenyl, orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, are a 5- or 6-membered heterocyclic ring which may contain one or two additional hetero atoms as ring members and/or may be substituted, or R.sub.1 together with R.sub.3 ortho to the amino group form a partially hydrogenated, unsubstituted or substituted 5-or 6-membered heterocyclic ring which may contain an additional N or O atom as ring member,R.sub.3 and R.sub.4 are each independently of the other hydrogen, alkyl, alkoxy, alkanoylamino or halogen,R.sub.5 is hydrogen or together with R.sub.4 in ortho-position forms the member which completes a fused benzene ring,R.sub.7 is hydrogen, optionally substituted phenyl or alkyl, andX.Type: GrantFiled: July 17, 1986Date of Patent: April 4, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Moser
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Patent number: 4760132Abstract: Cationic hydrazone dyestuffs of the general formula ##STR1## in which R.sub.1 stands for hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy, nitro or halogen,R.sub.2 stands for hydrogen, C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy, halogen or phenylazo,R.sub.3 stands for C.sub.1 - to C.sub.3 -alkyl andA.sup.- stands for an anion,are prepared by quaternarizing azo bases of the general formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 have the abovementioned meaning, with dialkyl sulphates of the general formula(R.sub.3 --O).sub.2 SO.sub.2 IIIin whichR.sub.3 has the abovementioned meaning,in the presence of water and alkali metal sulphate or alkaline earth metal sulphate and, where appropriate, by replacing the alkylsulphate anion by another anion.Type: GrantFiled: December 16, 1986Date of Patent: July 26, 1988Assignee: Bayer AktiengesellschaftInventors: Hans-Lothar Dorsch, Dietmar Kalz, Volker Huhne, Roderich Raue
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Patent number: 4754022Abstract: The invention relates to novel cationic isothiazolazo compounds of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted C.sub.1 -C.sub.4 alkylR.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, cyano, C.sub.1 -C.sub.4 alkoxy or by phenyl which is in turn unsubstituted or substituted by methyl, methoxy and/or halogen,R.sub.5 and R.sub.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkylR.sub.7 is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl,Y is the direct bond or the group ##STR2## wherein R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8 and R.sub.9 are each hydrogen and, if Y is the direct bond, they are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl, andX.sup..crclbar. is an anion. These compounds can be used as dyes for dyeing or printing in particular polyacrylonitrile materials in blue shades.Type: GrantFiled: October 24, 1985Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventor: Peter Moser
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Patent number: 4754021Abstract: Methine-azo compounds of the formulae ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted and/or be fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 -C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,m and n independently of each other are the numbers 1 or 2, in the formula (I) at least one of the two symbols m and n being the number 2 and where in the case m=2 the two B's are identical or different,KK is the radical of a coupling componentX.sup..crclbar. is an anion and Y is a bridge member. These compounds can be used for dyeing and printing in particular polyacrylonitrile, acid-modified polyester and especially paper.Type: GrantFiled: August 21, 1985Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventor: Peter Mockli
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Patent number: 4742162Abstract: Condensates of an azo compound of the formula ##STR1## wherein n is 1 or 2, with the stilbene compound of the formula ##STR2## in the molar ratio of 1:1 to 2:1, dye leather in a yellowish-brown shade, which penetrate deeply into the leather, and give fast dyeings.Type: GrantFiled: April 6, 1984Date of Patent: May 3, 1988Assignee: Ciba-Geigy CorporationInventor: Ulrich Schlesinger
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Patent number: 4736021Abstract: There are described azo compounds of the formula ##STR1## wherein K is an optionally quaternized basic group,X is the radical COOR, in which R is an alkyl group or a substituted or unsubstituted phenyl group, or X is the radical CONHR', in which R' is an alkyl group or a substituted or unsubstituted phenyl group; and wherein the benzene rings B and/or D can be further substituted;and the use thereof as dyes for the dyeing of textile materials, and particularly for the dyeing of paper of all types, especially bleached, lignin-free, unsized paper.Type: GrantFiled: September 13, 1982Date of Patent: April 5, 1988Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Pierre Galafassi
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Patent number: 4694075Abstract: The compounds of the formula ##STR1## where Y is hydrogen, chlorine, bromine or nitro, Z is hydrogen, chlorine, bromine, a sulfonic ester group or unsubstituted or substituted sulfamyl, X is --O-- or ##STR2## R is alkylene which may or may not be interrupted by oxygen or ##STR3## m is 0 or 1, p is 1 or 2, R.sup.1 and R.sup.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl, or aryl, or R.sup.1 and R.sup.2 together with the nitrogen form a heterocyclic structure, R.sup.3 is hydrogen or unsubstituted or substituted alkyl, R.sup.6 and R.sup.7 independently of one another are each hydrogen, unsubstituted or substituted alkyl, alkoxy or acylamino, K is a radical of a coupling component, A.crclbar. is an anion, R.sup.4 is unsubtituted or substituted alkyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: January 21, 1986Date of Patent: September 15, 1987Assignee: BASF AktiengesellschaftInventors: Horst Colberg, Erwin Hahn
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Patent number: 4687842Abstract: Compounds of the formula ##STR1## wherein each of R and R.sub.1 is independently hydrogen, C.sub.1-4 alkyl, phenyl or phenyl substituted by 1 to 3 C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo substitutents orR and R.sub.1 taken together are trimethylene or tetramethylene,each of R.sub.2 and R.sub.3 is independently allyl, C.sub.1-4 alkyl, phenyl (C.sub.1-4 alkyl) or C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or carbamoyl, ##STR2## wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined in the specification, andA.sup..crclbar. is an anion, and mixtures thereof with cationic 5-hydroxypyrazole dyes, are useful for dyeing and printing materials dyeable with basic dyes, e.g., homopolymers and copolymers of acrylonitrile and asymmetrical dicyanoethylene, polyamides and polyesters modified to contain acidic groups, leather and paper.Type: GrantFiled: January 14, 1980Date of Patent: August 18, 1987Assignee: Sandoz Ltd.Inventor: Beat Henzi
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Patent number: 4670546Abstract: Compounds of the formula ##STR1## in metal-free, 1:1 or 1:2 metal complex form, or in acid addition salt form, where the symbols are defined in the specification, useful as dyes for, for example, regenerated cellulose, cotton, synthetic polyamides and polyesters modified to contain acid groups and polymers and copolymers of acrylonitrile and 1,1-dicyanoethylene.Type: GrantFiled: June 28, 1984Date of Patent: June 2, 1987Assignee: Sandoz Ltd.Inventors: Jacky Dore, Reinhard Pedrazzi
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Patent number: 4665162Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula --Y--Z,whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group, ##STR2## wherein each of the variables is as defined above or below, x is a direct bond or a bridging radical,x is hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.Type: GrantFiled: June 18, 1985Date of Patent: May 12, 1987Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4654384Abstract: Novel water-soluble triazine compounds of the formula ##STR1## in which D and D.sub.1 independently of one another are radicals of diazo components, R and R.sub.1 independently of one another are hydrogen or C.sub.1 -C.sub.4 -aklyl, X is a monosubstituted or disubstituted amino group, a C.sub.1 -C.sub.4 -alkoxy group or an aryloxy group, the symbols Y are basic or cationic groups, which can be identical or different, l is 2, 3, 4, 5 or 6 and n is 0 or 1, and the number of basic and/or cationic groups Y in the molecule must be equal to or greater than the number of SO.sub.3 H groups are useful as dyes for dyeing and printing textile materials, leather and in particular, paper. The dyeings have good general fastness properties and the effluents remain colorless.Type: GrantFiled: January 12, 1984Date of Patent: March 31, 1987Assignee: Ciba-Geigy CorporationInventors: Visvanathan Ramanathan, Peter Mockli
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Patent number: 4638053Abstract: Chlorozincate salts of benzothiazonium azo compounds are prepared by reacting benzothiazolium azo compounds with an dialkylsulfate having from 1 to 4 carbon atoms in the alkyl radicals, which process comprises carrying out the reaction in an aqueous medium at a temperature of from 10.degree. to 80.degree. C. in the presence of an acid acceptor and the alkylation with the use of from 1.8 to 2.5 mols of the dialkylsulfate, calculated on the starting azo dyestuff, at a pH not exceeding 7. The prepared benzothiazolium azo compound is precipitated as chlorozincate salt, especially with the use of an alkali metal chloride. According to this process, the chlorozincate salts are obtained in higher purity. A perceptible decomposition of the benzothiazolium azo compound does not occur. Chemicals, for example the alkylation agent and acid-binding agents need be used in a small quantity.Type: GrantFiled: September 11, 1985Date of Patent: January 20, 1987Assignee: HoechstaktiengesellschaftInventors: Rudolf Neeb, Reinhard Mohr
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Patent number: 4626589Abstract: A compound of the formula, ##STR1## wherein D is an organic dye moiety, R.sub.1 and R.sub.2 are independently hydrogen or a substituted or unsubstituted lower alkyl group, R.sub.3 is hydrogen or a substituted or unsubstituted lower alkyl, phenyl or naphthyl group, X.sub.1 and X.sub.2 are independently hydrogen, halogen or a lower alkyl, cyano, carbamoyl, vinyl, .beta.-hydroxyethyl, .beta.-sulfoethyl, .beta.-sulfatoethyl, carboxyl, carboxylic acid ester or sulfonic acid group, and Z is appended to the above-defined D or R.sub.3 and stands for --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali, which is useful for dyeing hydroxyl or amido group-containing fiber materials with excellent build-up properties, thereby giving dyed products having excellent various fastness properties.Type: GrantFiled: February 7, 1985Date of Patent: December 2, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Yutaka Kayane, Mikoto Takahashi, Tetsuya Miyamoto, Akira Takeshita, Naoki Harada, Katsumasa Otake
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Patent number: 4587292Abstract: Metal-free azo compounds of the formula ##STR1## wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification,R.sub.t is an arylazo group or a group of the formula --Y--Z, whereinY is a direct bond or a bridging radical, andZ is a basic amino or quaternary ammonium group,R is ##STR2## wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical,x is hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino or carboxy,ring B is further unsubstituted or further substituted,d is 0, 1 or 2, andn is 0 or 1,with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.Type: GrantFiled: August 18, 1982Date of Patent: May 6, 1986Assignee: Sandoz Ltd.Inventors: Paul Doswald, Emil Moriconi, Helmut Moser, Horst Schmid
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Patent number: 4581445Abstract: There are described novel cationic benzothiazole disazo compounds of the formula ##STR1## K independently of one another are each a coupling component, R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen,X is the direct bond, --(CH.sub.2).sub.y wherein y is a number from 1 to 4, --CH.dbd.CH--, a phenylene group, a naphthylene group, a heterocyclic radical, an --NH-alkylene-(C.sub.1 -C.sub.6)--NH-- radical or an --NH-arylene-NH-- radical, andAn is an anion, with the proviso that when the coupling component K is a dimethylaminophenyl radical, the divalent bridge member X is not the --(CH.sub.2).sub.2 -- group are useful for dyeing and printing textile materials, leather and in particular paper. The dyeings obtained have good fastness properties, especially good fastness on paper to light.Type: GrantFiled: September 16, 1983Date of Patent: April 8, 1986Assignee: Ciba-Geigy CorporationInventor: Visvanathan Ramanathan
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Patent number: 4525583Abstract: Benzthiazole compounds of the formula ##STR1## or a tautomeric form thereof, in which KK is the radical of a pyrimidine coupling compound as defined, W is a radical of the formula --CH.sub.2 --NH--CO--C.sub.1 --C.sub.4 -alkyl-Q.sup..sym. An.sup..crclbar. in which An is an anion and Q is a quaternary radical of the formula ##STR2## in which R.sub.1 to R.sub.6 independently of one another are a substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl radical, or the radicals R.sub.1 and R.sub.2, or R.sub.3 and R.sub.4, or R.sub.3 and R.sub.4 and R.sub.5, together with the N atom, form a heterocyclic ring, m is the number 1, 2 or 3 and n is the number 0 or 1, and in which the benzene radicals A, B and/or C may be further substituted are particularly suitable as dyes for paper, brilliant yellow to orange dyeings which have, in particular, good wet-fastness and light-fastness, being obtained.Type: GrantFiled: January 13, 1983Date of Patent: June 25, 1985Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4517358Abstract: Cationic disazo compounds of the formula ##STR1## wherein K independently of one another are each a coupling component,R independently of one another are each an unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl group,R.sub.1 independently of one another are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted C.sub.1 -C.sub.4 -alkoxy, or halogen, andAn is an anionare useful as dyes, in particular as paper dyes, whereby dyeings fast to water are obtained. The dyeings obtained have very good fastness to light and to wet processing.Disazo compounds of the formula ##STR2## wherein K and R, are as defined above are useful as disperse dyes and as intermediates in the preparation of the above cationic disazo compounds.Type: GrantFiled: September 14, 1982Date of Patent: May 14, 1985Assignee: Ciba-Geigy CorporationInventor: Visvanathan Ramanathan