The Hetero Ring Is In A Bicyclo Ring System (e.g., Quinoline, Benzomorpholine, Etc.) Patents (Class 534/768)
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Patent number: 7601819Abstract: A dye represented by the following formula (1-1), a colored curable composition using the same, and a colored curable composition including a dye represented by the following formula (1) and at least one dye represented by the following formula (2) or (3): wherein Ra1 is an aliphatic group, an aryl group, a heterocyclic group, an acyl group or the like; Xa1 is —CRa3? or N; Ra2 and Ra3 are each H or a substituent; B is a coupler residue; A is a residue of a 5-membered heterocyclic diazo component A-NH2; B1 and B2 is —CR1?, —CR2? or N; R5 and R6 is H, an aliphatic group, an aromatic group, a heterocyclic group or the like; G, R1 and R2 is H, halogen, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a carboxyl group, a carbamoyl group, an alkoxycarbonyl group or the like; Rd1 to Rd4 is H or an aliphatic group; Rd5 is a sulfo group or a sulfamoyl group; Rd6 to Rd10 is a substituent; m, n, p and q=0 to 3; r=0 to 4.Type: GrantFiled: January 28, 2005Date of Patent: October 13, 2009Assignee: FUJIFILM CorporationInventors: Nobuo Seto, Nobuo Suziki
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Patent number: 7144993Abstract: The present invention relates to a process for the preparation of a compound of the general formula (I), which comprises converting a compound of the general formula (II), in an aprotic organic solvent in the presence of a catalytically active amount of a strong acid (catalyst) or of an agent that liberates a strong acid or of an ammonium salt of a strong acid, it also being possible for the catalyst to be part of the starting material/product, into a compound of formula I, wherein R5, R6 and R8 are each independently of the others a hydrogen atom, a nitro group, a sulfo group, a halogen atom, a pseudohalogen, a group COOR1 or CONHR2 or a C1-8 alkyl, C1-8 alkoxy or aryloxy radical, an amide group, a thioalkyl or thioaryl radical, an alkyl- or aryl-sulfonyl radical, an alkyl- or aryl-sulfinyl radical, a trifluoromethyl group or a phosphono group, R1 and R2 being a hydrogen atom or a C1-8 alkyl radical or an aryl or aralkyl radical, R10 is a group —C(O)CH2C(O)CH3 and R11 is a hydrogen atom or an acyl radical, oType: GrantFiled: December 3, 2002Date of Patent: December 5, 2006Assignee: Ciba Specialty Chemicals Corp.Inventors: Johannes Benkhoff, Bernd Lamatsch
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Patent number: 7105503Abstract: Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.Type: GrantFiled: February 15, 2002Date of Patent: September 12, 2006Assignee: QLT Inc.Inventors: Zaihui Zhang, Timothy S. Daynard, Serguei V. Sviridov, Mikhail A. Chafeev, Shisen Wang
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Patent number: 6989439Abstract: A color-developing agent of the formula (1-1): wherein X represents a hydrogen atom or a substituent, and Z represents a carbamoyl, acyl, alkoxycarbonyl, or aryloxycarbonyl group. An azo dye of the formula (2-1): wherein R1 represents a hydrogen atom or a substituent, and A represents a group of atoms necessary to form the azo dye by the compound of formula (2-1). A silver halide photographic light-sensitive material containing any of the color-developing agent and the azo dye in at least one photographic constitutional layer.Type: GrantFiled: February 6, 2003Date of Patent: January 24, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Osamu Uchida, Yasuhiro Ishiwata, Takayuki Ito, Nobutaka Fukagawa
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Patent number: 6855195Abstract: An ink composition comprising at least one of water-soluble dyes represented by the following formulae (1) to (3) and a surfactant:Type: GrantFiled: July 23, 2002Date of Patent: February 15, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Nobuhiro Nishita, Junichi Yamanouchi, Toshiki Fujiwara
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Publication number: 20030176400Abstract: Indole derivatives represented by formula (I): 1Type: ApplicationFiled: December 13, 2002Publication date: September 18, 2003Inventors: Kazuhiko Torisu, Kaoru Kobayashi, Fumio Nambu
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Publication number: 20030089274Abstract: An ink composition comprising at least one of water-soluble dyes represented by the following formulae (1) to (3) and a surfactant: 1Type: ApplicationFiled: July 23, 2002Publication date: May 15, 2003Inventors: Nobuhiro Nishita, Junichi Yamanouchi, Toshiki Fujiwara
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Publication number: 20020052343Abstract: The present invention provides novel compounds of Formula I: 1Type: ApplicationFiled: December 14, 2000Publication date: May 2, 2002Inventors: Darin Arthur Allen, Danny Peter Claude McGee, Jeffrey R. Spencer
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Patent number: 5763588Abstract: Compounds having particular interest as labels and various novel uses in diagnostics and therapeutics are provided which have structure (1) ##STR1## wherein R.sup.1 is a binding partner, a linker or H; a and b are 0 or 1, provided that the total of a and b is 0 or 1;A is N or C;X is S, O, --C(O)--, NH or NCH.sub.2 R.sup.6 ;Y is --C(O)--;Z is taken together with A to form an aryl or heteroaryl ring structure comprising 5 or 6 ring atoms wherein the heteroaryl ring comprises a single O ring heteroatom, a single N ring heteroatom, a single S ring heteroatom, a single O and a single N ring heteroatom separated by a carbon atom, a single S and a single N ring heteroatom separated by a carbon atom, 2 N ring heteroatoms separated by a carbon atom, or 3 N ring heteroatoms at least two of which are separated by a carbon atom, and wherein the aryl or heteroaryl ring carbon atoms are unsubstituted with other than H or at least 1 nonbridging ring carbon atom is substituted with R.sup.6 or .dbd.O;R.sup.Type: GrantFiled: June 7, 1995Date of Patent: June 9, 1998Assignee: Gilead Sciences, Inc.Inventors: Mark D. Matteucci, Robert J. Jones
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Patent number: 5760197Abstract: Hydroxyquinolone monoazo dyestuffs of the formula I ##STR1## in which D is an organic radical such as one of the disclosed aromatic radicals, and R is substituted or unsubstituted alkyl, benzyl, phenyl, phenoxy, or alkoxy (most preferably C.sub.1 -C.sub.6 -alkyl) are especially well suited to dyeing and printing of hydrophobic materials and other dyeing or printing applications. The dyestuffs are prepared by diazotizing an amine (D--NH.sub.2) and coupling the diazotization product to a hydroxyquinolone compound.Type: GrantFiled: July 3, 1996Date of Patent: June 2, 1998Assignee: Dystar Japan Ltd.Inventor: Ulrich Buhler
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Patent number: 5723586Abstract: Disperse dyes of the general formula I ##STR1## wherein D signifies a diazo component which is usual with disperse dyes,K signifies an aromatic radical of formula ##STR2## Y signifies ##STR3## and the other symbols have the meanings as defined in claim 1, are useful for dyeing or printing hydrophobic, fully or half-synthetic organic fiber materials.Type: GrantFiled: June 14, 1996Date of Patent: March 3, 1998Assignee: Clariant Finance (BVI) LimitedInventor: Ruedi Altermatt
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Patent number: 5633355Abstract: The disperse dyes of formula I ##STR1## wherein the symbols D, K, R.sub.3-5, R.sub.10, m, z, n and Y possess the significances given in claim 1, are eminently suitable for dyeing or printing hydrophobic, fully or semi-synthetic, organic fiber materials.Type: GrantFiled: November 7, 1995Date of Patent: May 27, 1997Assignee: Sandoz Ltd.Inventor: Ruedi Altermatt
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Patent number: 5623060Abstract: Dye mixtures comprising at least 4 dyes of the same color having the formula ##STR1## where D is the radical of a diazo component of the aminoanthraquinone, aniline, aminothiophene, aminothiazole, aminoisothiazole, aminothiadiazole or aminobenzisothiazole series,one of X1 and X2 is substituted or unsubstituted phenylamino while the other is a radical of the formula NH--L--O--R, where L is substited or unsubstituted C.sub.2 -C.sub.8 -alkylene, andR is hydrogen, C.sub.1 -C.sub.4 or C.sub.1 -C.sub.3 -alkanoyl,are useful for dyeing or printing textile materials.Type: GrantFiled: February 20, 1996Date of Patent: April 22, 1997Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Hermann Loeffler, Helmut Reichelt
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Patent number: 5532342Abstract: An azo metal chelate compound of an azo compound of the formula (I) with a metal: ##STR1## wherein A is a residue forming a heterocyclic ring together with the carbon atom and the nitrogen atom to which it is bonded, X is a residue forming an aromatic group together with the two carbon atoms to which it is bonded, R.sup.1 is an alkyl group which may be substituted, an aryl group which may be substituted, an alkenyl group which may be substituted, or a cycloalkyl group which may be substituted, Y is a hydrogen atom or a cation, and n is an integer of from 1 to 3.Type: GrantFiled: April 17, 1995Date of Patent: July 2, 1996Assignee: Mitsubishi Chemical CorporationInventors: Tameichi Ochiai, Yutaka Kurose, Takumi Nagao, Takako Tsukahara, Satoru Imamura
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Patent number: 5466790Abstract: Azo dyes of the formula ##STR1## where L.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl or phenyl,L.sup.2 and L.sup.3 are each substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, or together a radical of the formula ##STR2## where n is 0, 1 or 2, Y.sup.1 and Y.sup.4 are hydrogen, hydroxymethyl, 1,2-dihydroxyethyl or a radical of the formula COO.sym.M.sup..crclbar. or SO.sub.3.sup..crclbar. M.sup..sym., Y.sup.2 and Y.sup.3 are halogen or hydroxymethyl, and M.sup..sym. is the equivalent of a cation,L.sup.4 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, substituted or unsubstituted phenyl, halogen, C.sub.1 -C.sub.8 -alkoxy, substituted or unsubstituted phenoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylsulfonyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl or phenoxycarbonyl,X is nitrogen or the radical C--L.sup.5, where L.sup.Type: GrantFiled: September 30, 1994Date of Patent: November 14, 1995Assignee: BASF AktiengesellschaftInventors: Sabine Gruettner-Merten, Helmut Reichelt, Arno Lange, Helmut Degen
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Patent number: 5391720Abstract: Disclosed is an imidazole azo dye of formula (I), which is useful for image formation and as a filter dye, which has a sharp absorption wave and which is fast to light, heat, air, moisture and chemicals. Also disclosed is a thermal transfer dye-donating material containing imidazole azo dye(s) of formula (I) preferably along with aminopyrazole azo dye(s) of formula (II). The material gives a high-density image with good color reproduction, and the image formed has improved storage stability. ##STR1## In (I), B and C independently represent a hydrogen atom or a substituent capable of being substituted in the imidazole ring; A represents an aryl or heterocyclic group; provided that when B is a hydrogen atom, C is not a hydrogen atom nor an alkyl group having from 1 to 3 carbon atoms; provided that when C is a hydrogen atom, B is not a substituted nor unsubstituted alkyl group; provided that C is not a mercapto group or an alkylthio group; and provided that B is not a carboxyl group.Type: GrantFiled: December 3, 1992Date of Patent: February 21, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Hisashi Mikoshiba, Tomomi Tateishi
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Patent number: 5324826Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-18 alkyl, substituted C.sub.1-18 alkyl, phenyl, substituted phenyl, C.sub.3-6 alkenyl, substituted C.sub.3-6 alkenyl, C.sub.3-6 alkynyl or substituted C.sub.3-6 alkynyl,R.sub.2 is an electron withdrawing substituent; andK is the residue of a coupling component that is free of any water solubilizing groups.The compounds are disperse dyes which can be used to dye, print or pad fully synthetic or semi-synthetic hydrophobic high molecular weight organic material.Type: GrantFiled: August 10, 1992Date of Patent: June 28, 1994Assignee: Sandoz Ltd.Inventor: Peter Matzinger
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Patent number: 5310888Abstract: Disclosed are arylazo chromoionophores characterized by the formula: ##STR1## wherein X is hydrogen or a monovalent cation, Y is H or methoxy and R is a ringed aromatic organic structure which affects the optical absorption properties of the compounds. Also disclosed is a method for the detection of calcium ion using these compounds.Type: GrantFiled: October 22, 1992Date of Patent: May 10, 1994Assignee: Miles Inc.Inventors: Michael L. Bloczynski, Thomas Boecker, Paul F. Corey
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Patent number: 5306815Abstract: Azo dyes useful for dyeing or printing textile fibers or fabrics and for thermal transfer have the formula ##STR1## where R.sup.1 and R.sup.2 are each substituted or unsubstituted C.sub.1 -C.sub.10 -alkyl or substituted or unsubstituted C.sub.3 -C.sub.4 -alkenyl or R.sup.1 may also be hydrogen,R.sup.3 is hydrogen or C.sub.1 -C.sub.6 -alkyl,R.sup.4 and R.sup.5 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, halogen, C.sub.1 -C.sub.6 -alkoxy, amino or mono- or di(C.sub.1 -C.sub.4 -alkyl)amino, andD is a radical of the thiophene, thiazole, isothiazole, benzothiophene, thienothiophene or thienothiazole series.Type: GrantFiled: September 21, 1992Date of Patent: April 26, 1994Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Clemens Grund, Andreas Geisberger, Helmut Reichelt, Andreas Guldner, Mathias Wiesenfeldt, Karl-Heinz Etzbach, Ruediger Sens, Helmut Hagen
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Patent number: 5298608Abstract: A metal chelate compound comprising a monoazo compound of the following formula (I): ##STR1## (wherein A is a residue forming a hetero ring together with the carbon atom and the nitrogen atom to which it is bonded, B is a residue forming an aromatic group together with the two carbon atoms to which it is bonded, and X is a hydrogen atom or a cation), and a metal, and an optical recording medium comprising a substrate and a recording layer formed thereon for information to be written in and/or read out by laser, wherein said recording layer contains the metal chelate compound comprising a monoazo compound of the above formula (I) and a metal.Type: GrantFiled: January 16, 1992Date of Patent: March 29, 1994Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Murayama, Shuichi Maeda, Chiyoko Fukabori, Takumi Nagao
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Patent number: 5283326Abstract: The compounds of the general formula ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are very useful for dyeing synthetic fibers or plastics.Type: GrantFiled: May 13, 1992Date of Patent: February 1, 1994Assignee: Sandoz AGInventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
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Patent number: 5235047Abstract: Provided are certain bathochromic azo dyes which are prepared by reacting 2-aminothiphenes or 2-aminothiazoles, which contain a primary amino group, with 2-chloro-3-negatively-substituted maleimides. These compounds are then diazotized and coupled with azo components, for example, anilines, 1,2,3,4-tetrahydroquinolines, 2,3-dihydroindiles, and 3,4-dihydro-2H-1,4-benzoxazines to form blue-cyan azo dyes.Type: GrantFiled: September 3, 1992Date of Patent: August 10, 1993Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Max A. Weaver
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Patent number: 5179207Abstract: Provided are certain substituted 2-aminothiazoles and 2-aminothiophenes which are useful as red colorants and as intermediates in the synthesis of bathochromic azo dyes. These compounds are prepared by reacting 2-aminothiophenes or 2-aminothiazoles, which contain a primary amino group, with 2-chloro-3-negatively-substituted maleimides. These compounds can be diazotized and coupled with azo components, for example, anilines, 1,2,3,4-tetrahydroquinolines, 2,3-dihydroindoles, and 3,4-dihydro-2H-1,4-benzoxazines to form bathochromic blue-cyan azo dyes.Type: GrantFiled: August 19, 1991Date of Patent: January 12, 1993Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Max A. Weaver
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Patent number: 5144015Abstract: A process for preparing a 1-alkyl-3-secondary or tertiary alkyl-4-cyano-pyrazol-5-yl azo dye or a 1-alkyl-3-aryl-4-cyano-pyrazol-5-yl azo dye comprising:a) reacting a 3-secondary or tertiary alkyl-4-cyano-5-amino pyrazole or a 3-aryl-4-cyano-5-amino pyrazole with a diazotizing reagent to form a pyrazol-5-yl diazonium salt;b) allowing said diazonium salt to react with an aromatic coupling component to form a 3-secondary or tertiary alkyl-4-cyano-pyrazol-5-yl azo dye or a 3-aryl-4-cyano-pyrazol-5-yl azo dye; andc) reacting the product of step b) with an aklylating agent in the presence of a base to form a 1-alkyl-3-secondary or tertiary alkyl-4-cyano-pyrazol-5-yl azo dye or a 1-alkyl-3-aryl-4-cyano-pyrazol-5-yl azo dye.Type: GrantFiled: July 31, 1991Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventor: Derek D. Chapman
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Patent number: 5132411Abstract: Compounds of the formula ##STR1## wherein R is halo,R.sub.1 is cyano; (C.sub.1-6 alkoxy)carbonyl; (C.sub.3-6 alkenyl)oxycarbonyl; C.sub.1-4 alkylsulfonyl; phenylsulfonyl; (C.sub.1-4 alkyl)carbonyl; benzoyl; carbamoyl; (C.sub.1-4 alkyl)carbamoyl; N,N-di-(C.sub.1-4 alkyl)carbamoyl; phenylcarbamoyl; benzyloxycarbonyl; or (C.sub.1-6 alkoxy)carbonyl, (C.sub.3-6 alkenyl)oxycarbonyl, C.sub.1-4 alkylsulfonyl, phenylsulfonyl or (C.sub.1-4 alkyl)carbamoyl substituted by one or two substituents independently selected from chloro, bromo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, cyano and acyl, andR.sub.2 is formyl, cyano, --CH.dbd.C(R.sub.4).sub.2 or --CH.dbd.N--OH,wherein (1) each R.sub.4 is independently cyano; (C.sub.1-6 alkoxy)carbonyl; (C.sub.3-6 alkenyl)oxycarbonyl; (C.sub.3-6 alkynyl)oxycarbonyl; or (C.sub.1-6 alkoxy)carbonyl, (C.sub.3-6 alkenyl)oxycarbonyl or (C.sub.3-6 alkynyl)oxycarbonyl substituted by one or two substituents independently selected from chloro, bromo, C.sub.1-4 alkyl, C.sub.Type: GrantFiled: March 19, 1990Date of Patent: July 21, 1992Assignee: Sandoz Ltd.Inventors: Robert Egli, Beat Henzi
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Patent number: 5128457Abstract: Newly synthesized chromogenic thiol-indicating benzoisthiazolone derivatives having the structure: ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, are useful in the detection of thiols, particularly in an aqueous system. This process comprises contacting the aqueous system with a chromogenic thiol-indicating benzoisothiazolone derivative as described herein. Chromophoric changes due to thiol-mediated reduction of the benzothiazolone derivative then occur. Such changes can be in a solution or on an indicator surface in contact or having been in contact with the aqueous system. The chromophoric changes, due to a bathochromic shift in characteristics light absorption upon reduction of the benzoisothiazolone derivative, are proportional to the amount or rate of appearance of thiols in the aqueous system.Type: GrantFiled: December 5, 1991Date of Patent: July 7, 1992Assignee: Miles Inc.Inventors: James P. Albarella, David L. Garling, Robert P. Hatch
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Patent number: 5075429Abstract: A monoazo compound of the formula, ##STR1## wherein D is a heterocyclic or carbocyclic compound residue such as benzothiazolyl and phenyl, X is hydrogen, alkyl, alkoxy, halogeno, acylamino or the like, Y is hydrogen, halogeno, alkyl, alkoxy and the like, R.sub.1 is alkyl, R.sub.2 is C.sub.2 -C.sub.4 alkylene, B is a bridging group such as ##STR2## --O--, --S--, C.sub.1 -C.sub.6 alkylene and the like, and W.sub.1, W.sub.2, W.sub.3, Z.sub.1, Z.sub.2 and Z.sub.3 are independently hydrogen, alkyl, halogeno or the like, which is useful for dyeing hydrophobic fiber materials to give dyed or printed product of a deep color excellent in fastness properties, particularly those such as washing fastness, even after various finishing treatments of the product.Type: GrantFiled: October 10, 1989Date of Patent: December 24, 1991Assignee: Sumitomo Chemical Company LimitedInventors: Jun Yamamoto, Yasuyoshi Ueda, Takashi Omura, Yosuke Yamamoto, Hideo Hattori, Junichi Sekihachi
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Patent number: 5071968Abstract: Azo dyes of the formula ##STR1## where D is a diazo component, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.8 alkyl, and n is 1,2,3,4 or 5, produce dyeings of good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: March 5, 1990Date of Patent: December 10, 1991Assignee: Ciba-Geigy CorporationInventor: Harald Walter
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Patent number: 5013826Abstract: The azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.2 is a group of the formula, --CN, --CON(R.sub.8)R.sub.9, --COR.sub.10, --COOR.sub.11, --SO.sub.2 R.sub.12 or --CONHNHR.sub.13, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.10 alkoxy or phenoxy, R.sub.4 is substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.5 is C.sub.1 -C.sub.4 alkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8, R.sub.9 and R.sub.13, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, R.sub.10, R.sub.11 and R.sub.12 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, X is an oxygen atom or a group of the formula --CH(R.sub.14)-- in which R.sub.14 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: February 21, 1989Date of Patent: May 7, 1991Assignee: Ciba-Giegy CorporationInventor: Harald Walter
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Patent number: 4994564Abstract: Thien-3-ylazo dyes of the formula: ##STR1## where X is cyano, nitro, C.sub.1 -C.sub.6 -alkanoyl, substituted or unsubstituted benzoyl, substituted or unsubstituted phenyl or the radical COOR.sup.1 or CONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are identical or different and each is independently of each other substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.4 -alkenyl, substituted or unsubstituted phenyl or together with the nitrogen atom linking them a 5- or 6-membered saturated heterocyclic radical, and R.sup.2 may additionally be hydrogen, Y is hydrogen, cyano, C.sub.1 -C.sub.6 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl, substituted or unsubstituted phenyl or the radical COOR.sup.1 or CONR.sup.1 R.sup.2 where R.sup.1 and R.sup.2 are each as defined above, Z is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.Type: GrantFiled: November 10, 1988Date of Patent: February 19, 1991Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Helmut Reichelt, Guenter Hansen, Ernst Schefczik, Helmut Hagen, Gunther Lamm
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Patent number: 4962040Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.Type: GrantFiled: August 10, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Herbert Hugl, Aloysius Engel, Klaus Wehling
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Patent number: 4952681Abstract: Compounds of the formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are disclosed. They are useful for dyeing synthetic fibers or plastics.Type: GrantFiled: July 27, 1988Date of Patent: August 28, 1990Assignee: Sandoz AGInventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
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Patent number: 4888432Abstract: 2-Aminothiophenes of the formula ##STR1## wherein R=substituent and n=0-4, are prepared by dehydrogenating ring closure of thioamides of the formula ##STR2## The 2-aminothiophenes are useful for preparing useful azo dyestuffs. A process for preparing a compound of the formula ##STR3## comprising reacting a compound of the formula ##STR4## in which R and n have the abovementioned meanings with a compound of the formula ##STR5## in which T denotes NH.sub.2, aryl or alkyl, in the presence of an acid. An azo dyestuff of the formula ##STR6## in which V denotes Cl, Br or CF.sub.3,W denotes Cl, Br or NO.sub.2,R.sub.1 denotes hydrogen, halogen, alkyl, alkoxy, alkoxyalkyl or aryloxy,R.sub.2 denotes alkenyl or OH-, halogen-, CN-, CO.sub.2 -alkyl-, aryl-, cycloalkyl-, alkoxy-, aryloxy-, OCO-alkyl-, OCO-aryl-, OCONH-alkyl- or OCO.sub.2 -alkyl-substituted alkyl,R.sub.3 denotes hydrogen or identical or different R.sub.2 andR.sub.2 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, alkoxy, halogen, CF.sub.Type: GrantFiled: October 15, 1987Date of Patent: December 19, 1989Assignee: Bayer AktiengesellschaftInventor: Rainer Hamprecht
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Patent number: 4837308Abstract: A universally usable process for preparing azo dyestuffs by oxidative coupling consists in carrying out the oxidation in the presence of redox mediators with a standard potential of 0.2-1.5 volts and, if appropriate, an additional oxidizing agent with a standard potential of 0.25-2.5 volts, wherein the sum of the oxidation equivalents should be at least 4. The preferred redox mediator is iodine. The process is particularly suitable for the preparation of heteroaromatic azo dyestuffs using an aniline coupling component.Type: GrantFiled: January 12, 1988Date of Patent: June 6, 1989Assignee: Bayer AktiengesellschaftInventor: Rainer Gerlach
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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: 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: 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: 4685934Abstract: Monoazo compounds of formula ##STR1## wherein R.sub.1 is a coupling component radical,R.sub.1 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by 1 or 2 substituents selected from chloro, cyano, hydroxy, C.sub.1-4 alkoxy, phenyl and phenyl substituted by 1 or 2 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy, sulfo, sulfamoyl and acetamido; C.sub.5-7 cycloalkyl; C.sub.5-7 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl; phenyl substituted by 1 to 3 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetamido (maximum of 1), carboxy (maximum of 1), sulfo (maximum of 1) and --SO.sub.2 NR.sub.7 R.sub.8 (maximum of 1); 1- or 2-naphthyl or 1- or 2-naphthyl substituted by sulfo,whereineach of R.sub.7 and R.sub.8 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy or phenyl; cyclohexyl; phenyl or phenyl monosubstituted by chloro, methyl or methoxy, or--NR.sub.7 R.sub.Type: GrantFiled: July 12, 1985Date of Patent: August 11, 1987Assignee: Sandoz Ltd.Inventors: Francois Benguerel, Roland Mislin
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Patent number: 4668775Abstract: A compound of the formula: ##STR1## wherein K is a radical of a coupling component, R is a radical of a methylene-active compound, X is hydrogen or unsubstituted or substituted alkyl, aryl, or hetaryl and Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl. The present compound is useful for the dyeing of polyesters, nylons, cellulose esters and blends of polyesters and cellulose fibers.Type: GrantFiled: July 24, 1985Date of Patent: May 26, 1987Assignee: BASF AktiengesellschaftInventors: Udo Bergmann, Erwin Hahn, Guenter Hansen
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Patent number: 4650860Abstract: A compound having the formula: ##STR1## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R.sup.1 or R.sup.2 is phenyl which is unsubtituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C.sub.2 -C.sub.8 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.8 -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR2## The compounds of formula (I) are used as dyes, preferably for cellulose and cellulose-containing fabrics.Type: GrantFiled: June 26, 1985Date of Patent: March 17, 1987Assignee: BASF AktiengesellschaftInventors: Johannes Dehnert, Gunther Lamm
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Patent number: 4628082Abstract: 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: GrantFiled: May 14, 1985Date of Patent: December 9, 1986Assignee: Bayer AktiengesellschaftInventors: Manfred Lorenz, Karl H. Schundehutte
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Patent number: 4619992Abstract: A compound of the formula: ##STR1## where R is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R.sup.1 is allyl, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkyl substituted by C.sub.1 -C.sub.8 -alkoxy, phenoxy, phenyl or C.sub.1 -C.sub.8 -alkanoyloxy, cyclopentyl, cyclohexyl, methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R.sup.2 is C.sub.1 -C.sub.10 -alkanoyl, C.sub.1 -C.sub.10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C.sub.1 -C.sub.8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH.sub.3 NHCO, C.sub.2 H.sub.5 NHCO, C.sub.3 H.sub.7 NHCO, C.sub.4 H.sub.9 NHCO, (CH.sub.3).sub.2 NCO, CH.sub.3 SO.sub.2, C.sub.6 H.sub.5 SO.sub.2 or p--CH.sub.3 --C.sub.6 H.sub.4 --SO.sub.2 ; or R.sup.1 and R.sup.2, together with the nitrogen atom, form a ring system, and K is a radical of a coupling component.Type: GrantFiled: March 12, 1985Date of Patent: October 28, 1986Assignee: BASF AktiengesellschaftInventors: Udo Bergmann, Johannes P. Dix, Guenter Hansen, Ernst Schefczik
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2-amino-cinnamoylthiophene azo dyes having aniline, tetrahydroquinoline, or benzomorpholine couplers
Patent number: 4593088Abstract: Disclosed are new disperse azo dyes prepared from 2-amino-cinnamoylthiophene compounds. These dyes give bright blue shades, for example, on polyester, cellulose acetate and other synthetic fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, migration, and the like. The dyes have the general formula: ##STR1## wherein each R is a substituent selected for example from alkyl, substituted alkyl, hydroxy, alkoxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, cyano, alkylamino, and dialkylamino, R.sup.14 is hydrogen or alkyl, C.sup.1 represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted, and each of R.sup.12 and R.sup.13 is hydrogen or a substituent such as acyl, acylamido, alkyl, halogen, and cyano.Type: GrantFiled: January 23, 1984Date of Patent: June 3, 1986Assignee: Eastman Kodak CompanyInventor: Robert N. Gourley -
Patent number: 4593087Abstract: Disclosed are azo dyes containing diazonium moieties from aminothiazoles, aminoisothiazoles, or aminothiadiazoles (1,2,4- or 1,3,4-), and certain coupler moieties from aniline, tetrahydroquinoline, and benzomorpholine type compounds, wherein the diazonium moieties have at least one cinnamoyl group, and wherein a wide variety of groups, e.g., one or more water-solubilizing substituents such as sulfonic acid groups or their metal or amine salts may be present in the dye molecule. These dyes are useful for dyeing materials selected from polyamide, cellulose ester, polyester, wool and other natural and synthetic fibers and generally exhibit improvements in dyeability and fastness properties.Type: GrantFiled: January 23, 1984Date of Patent: June 3, 1986Assignee: Eastman Kodak CompanyInventor: Robert N. Gourley
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Patent number: 4582898Abstract: Aniline derivatives of the formula ##STR1## wherein X=alkyl,Z=H or alkyl, andY=S-alkyl, SO.sub.2 -alkyl, CO.sub.2 -R (R=alkyl, cycloalkyl, or H) or--if Z=H--Br,are diazo components for preparing valuable azo dyestuffs and starting materials for preparing compounds of the formula ##STR2## and new azo dyestuffs derived therefrom and which--in their nonionic form--are highly suitable for dyeing polyester fibres in blue shades having high tinctorial strength and high fastness levels.Type: GrantFiled: October 12, 1984Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventor: Rainer Hamprecht
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Patent number: 4562248Abstract: Azo dyes having the general formula ##STR1## in which each of X, Y and Z are independently selected from H and a variety of substituents, preferably provided that at least one of X and Y is a substituent selected, for example, from --CN, halogen, alkyl, and alkylsulfonyl, and C is the residue of a phenol, naphthol, indole, imidazothiazole, pyrazolone, thiazole, isothiazole or pyrazole type disperse dye coupling component. These dyes which are unexpectedly non-phototropic produce yellow to orange shades on hydrophobic fibers and exhibit improvements in one or more properties such as dyeability, dye exhaustion rate, light fastness, nonblooming, pH stability, build, fastness to ozone and nitrogen oxide, crock and wash fastness, migration, transfer, and pH stability on polyester, polyamide and other fibers including cellulose ester.Type: GrantFiled: November 25, 1983Date of Patent: December 31, 1985Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Jean C. Fleischer
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Patent number: 4554348Abstract: Disclosed are new acid azo dyes prepared from 2-amino-cinnamoylthiophene compounds. These dyes give bright red to blue shades, for example, on polyester, cellulose acetate, wool and particularly polyamide fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate, migration, and the like. The dyes have the general formula ##STR1## wherein: R.sup.14 is H or alkyl; R is a substituent selected, for example, from alkyl, substituted alkyl, hydroxy, alkoxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, cyano, alkylamino, and dialkylamino; C.sup.1 represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted; each of R.sup.12 and R.sup.13 is selected from H, alkyl, alkoxy, acyl, halogen, and the like; and at least one of the water solubilizing groups, --SO.Type: GrantFiled: January 23, 1984Date of Patent: November 19, 1985Assignee: Eastman Kodak CompanyInventor: Robert N. Gourley
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Patent number: 4552952Abstract: This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing diazonium moieties from 2-aminobenzothiazole or 2-aminobenzisothiazole type compounds, and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moieties have one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.Type: GrantFiled: January 23, 1984Date of Patent: November 12, 1985Assignee: Eastman Kodak CompanyInventor: Robert N. Gourley
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Patent number: 4530997Abstract: Disclosed are azo dyes in which the diazo component is a diazotized 3-amino-2,1-benzisothiazole compound bearing one or two sulfo groups, and the coupler is either a 1,2,3,4-tetrahydroquinoline or a 2,3-dihydro-1,4-benzoxazine compound. These dyes exhibit excellent dyeing and fastness properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. The dyes correspond to the general formula: ##STR1## wherein R.sup.5 is 0-3 substituents independently selected from halogen, cyano, alkyl, alkoxy, sulfo, and the like; M is H.sup.+, Na.sup.+, K.sup.+ or the like; and C is the coupler which may be substituted with groups known to the art.Type: GrantFiled: March 15, 1983Date of Patent: July 23, 1985Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Ralph R. Giles
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Patent number: 4528368Abstract: This invention relates to new azo dyes derived from 2-amino-5-cyanomethylthio-1,3,4-thiadiazole and aniline and tetrahydroquinoline couplers which may be extensively substituted. The dyes impart orange to violet shades on hydrophobic fibers, including polyesters, polyamides, and cellulose esters. They are of the particular interest for dyeing textured polyester fibers and have excellent properties such as fastness to light and sublimation.Type: GrantFiled: May 3, 1984Date of Patent: July 9, 1985Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Clarence A. Coates, Jr.