Additional Hetero Ring Or Polycyclo Ring System Which Contains A Hetero Ring As One Of The Cyclos Bonded Directly To The Azo Group Patents (Class 534/765)
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Patent number: 10968147Abstract: The invention relates to a pyrotechnic agent containing at least one azotetrazolate as a component thereof.Type: GrantFiled: June 2, 2006Date of Patent: April 6, 2021Assignee: RUAG AMMOTEC GMBHInventors: Ulrich Bley, Rainer Hagel, Julia Havlik, Aleksej Hoschenko, Peter Simon Lechner
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Publication number: 20150080561Abstract: The present invention relates to laundry care compositions comprising carboxylate dyes. The laundry care compositions can be laundry detergent compositions, laundry additive compositions such as fabric enhancer compositions or bleach additive compositions. Preferably, the laundry care composition is a laundry detergent composition. The composition can be a solid, such as a powder, tablet or bar, or a liquid. The composition can be in the form of a unit dose, such as pouch. Suitable unit dose pouches include single compartment and multi-compartment pouches.Type: ApplicationFiled: September 4, 2014Publication date: March 19, 2015Inventors: Eduardo Torres, Sanjeev Kumar Dey, Gregory Scot Miracle
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Publication number: 20110177281Abstract: An aspect of the present invention relates to an optical information recording medium comprising a recording layer on a surface of a support, wherein the surface of the support has pregrooves with a track pitch ranging from 50 to 500 nm, the recording layer comprises an azo metal complex dye being a complex of six azo dyes and seven transition metal ions. A further aspect of the present invention relates to a method of recording information onto the optical information recording medium and a novel azo metal complex dye.Type: ApplicationFiled: September 25, 2009Publication date: July 21, 2011Applicant: FUJIFILM CORPORATIONInventors: Kousuke Watanabe, Taisuke Fujimoto, Tetsuya Watanabe, Masashi Ogiyama, Seiji Hatano, Taro Hashizume, Hirokazu Hashimoto
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Patent number: 7947815Abstract: An azo dye represented by the following formula (I): wherein, in formula (I), R1, R2, R3, and R4 each independently represent a hydrogen atom, an aliphatic group, an aryl group, a halogen atom, an acyl group, a cyano group, an acylamino group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an aliphatic sulfonyl group, an arylsulfonyl group, a sulfamoyl group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, a sulfo group, a carboxyl group, a carbamoylamino group, a sulfamoylamino group, or an aliphatic- or aromatic-sulfonylamino group, wherein R1 and R2 and/or R3 and R4 may be combined with each other to form a five- or six-membered aromatic ring or non-aromatic ring; X represents a carbon atom or a nitrogen atom, wherein n is 0 when X is a nitrogen atom and n is 1 when X is a carbon atom; A, B, C, and D each represent a carbon atom or a nitrogen atom, provided that at least one of A, B, C and D represents a nitrogen atom; Y represents a substituent; andType: GrantFiled: June 29, 2005Date of Patent: May 24, 2011Assignee: FUJIFILM CorporationInventor: Yasuhiro Ishiwata
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Publication number: 20110069595Abstract: To provide a dye to be used for an optical recording medium excellent in both high speed recording characteristics and reproduction durability. A dye having an azo compound represented by the following formula coordinated to a metal ion: wherein the ring A represents a nitrogen-containing heteroaromatic ring containing a carbon atom and a nitrogen atom; X represents C—R1R2, an oxygen atom, a sulfur atom or N—R3, wherein each of R1, R2 and R3 which are independent of one another, represents a hydrogen atom, a linear or branched alkyl group, an aralkyl group, a cycloalkyl group, a linear or branched alkenyl group, an aryl group or an acyl group represented by —COR4, wherein R4 is a hydrocarbon group or a heterocyclic group which may be substituted; and the benzene ring B represents a benzene ring which may have a substituent(s), provided that adjacent substituents in the benzene ring B may be mutually bonded to form a ring.Type: ApplicationFiled: May 20, 2009Publication date: March 24, 2011Applicant: Mitsubishi Kagaku Media Co., Ltd.Inventors: Hisashi Shoda, Kan Takeshita, Naoyuki Uchida, Takashi Miyazawa
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Publication number: 20100146716Abstract: A hair dye composition containing an azo dye represented by any one of the formulas (1) to (5): [wherein R1, R2a, and R2b each represents a hydrogen atom or a substituent, A and A? each represents an aromatic heterocyclic residue (having a free valence at carbon atom thereof) and these groups have, in the structure thereof, none of a carboxy group, a sulfo group, and a quaternary ammonium group]; [R represents a coupler component, X1 to X4 represent atoms coupled together with the carbon atom sandwiched between X1 and X4 to form a 5-membered heteroaromatic ring, V1 and V2 each represents a substituent, and a1 and a2 each stands for from 0 to 3]; and [R3 represents a hydroxy group, an alkylsulfonylamino group, an arylsulfonylamino group, or —CH(R4)(R5) (R4 and R5 each representing a substituent having a Hammett's constant ? of 0.2 or greater and less than 1.Type: ApplicationFiled: June 27, 2008Publication date: June 17, 2010Applicants: KAO CORPORATION, FUJIFILM CORPORATIONInventors: Masakazu Yamaguchi, Osamu Takiguchi, Masaaki Tsukase, Yasuhiro Ishiwata
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Publication number: 20100132856Abstract: A subject matter of the present invention is: the compounds of formula (I): in which: and Het is an azolyl radical: nitroazolyl or tetrazolyl; with the exception of 3-nitro-4-(4-nitro-1,2,3-triazol-1-yl)furazan; the preparation of said compounds; and the energetic compositions including at least one compound chosen from said compounds of formula (I) and 3-nitro-4-(4-nitro-1,2,3-triazol-1-yl)furazan.Type: ApplicationFiled: January 15, 2008Publication date: June 3, 2010Applicant: SNPE MATERIAUX ENERGETIQUESInventors: Guy Jacob, Gregoire Herve, Guy Cagnon, Frederic Alvarez
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Publication number: 20090133787Abstract: The invention relates to a pyrotechnic agent containing at least one azotetrazolate as a component thereof.Type: ApplicationFiled: June 2, 2006Publication date: May 28, 2009Applicant: RUAG AMMOTEC GMBHInventors: Ulrich Bley, Rainer Hagel, Julia Havlik, Aleksej Hoschenko, Peter Simon Lechner
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Patent number: 7416593Abstract: The invention relates to novel azo dyestuffs of formula (I), the use of such compounds and/or mixtures for printing recording materials, especially paper or papery substrates, textile fiber materials, plastic films and plastic transparencies by the inkjet printing process and also to the recording materials printed therebyType: GrantFiled: November 11, 2003Date of Patent: August 26, 2008Assignee: Clariant Finance (BVI) LimitedInventor: Ludwig Hasemann
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Patent number: 7125966Abstract: The present invention relates to novel dyestuffs of formula (I) wherein the substituents have the meanings defined in the claims, the production of such dyestuffs, the use of these dyestuffs and material dyed or printed by such dyestuffsType: GrantFiled: October 17, 2003Date of Patent: October 24, 2006Assignee: Clariant Finance (BVI) LimitedInventor: Robert Egli
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Patent number: 7041809Abstract: A light-resistant, metal complex dye for inkjet printing comprising a substituted 8-heterocyclic azo-5-aminoquinoline of the following structural formula:Type: GrantFiled: June 25, 2004Date of Patent: May 9, 2006Assignee: Lexmark International, Inc.Inventors: Bradley Leonard Beach, James F. Feeman, Kelly Ann Killeen
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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: 20040034011Abstract: Compounds of formula (I′), wherein A, R1 to R3 and t are as defined in the disclosure, exhibit COMT enzyme inhibiting activity so that they are useful as COMT inhibitors.Type: ApplicationFiled: July 9, 2003Publication date: February 19, 2004Inventors: Reijo Bckstrm, Jarmo Pystynen, Timo Lotta, Martti Ovaska, Jyrki Taskinen
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Publication number: 20030232830Abstract: &bgr;-lactamases are the most widespread resistance mechanism to &bgr;-lactam antibiotics, such as penicillins and cephalosporins. In response to these enzymes, inhibitors have been introduced. Unfortunately, these inhibitors are also &bgr;-lactams, and resistance to them has developed rapidly. Consequently, the present invention provides a novel structure-based approach to inhibitors of these enzymes.Type: ApplicationFiled: February 19, 2003Publication date: December 18, 2003Inventors: Brian K. Shoichet, Rachel A. Powers
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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: 20030040559Abstract: The present invention provides Pigment Yellow 180 having an excellent transparency produced by using a fine slurry of 5-acetoacetylamino-benzimidazolone as a coupling component when Pigment Yellow 180 is produced by coupling reaction of 5-acetoacetylamino-benzimidazolone and diazo component obtained by diazotization of 1,2-bis(2-aminophenoxy)ethane.Type: ApplicationFiled: August 15, 2002Publication date: February 27, 2003Inventors: Isao Hashimoto, Noboru Tsuda, Hiroshi Ohsawa, Tomonori Okazaki, Manabu Shiga, Kohei Ohtsuki
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Publication number: 20020103234Abstract: Described is a heterocycle-containing carboxylic acid derivative represented by the following formula (I): 1Type: ApplicationFiled: July 23, 2001Publication date: August 1, 2002Applicant: Eisai Co. Ltd.Inventors: Kouichi Kikuchi, Katsuya Tagami, Hiroyuki Yoshimura, Shigeki Hibi, Mitsuo Nagai, Shinya Abe, Makoto Okita, Takayuki Hida, Seiko Higashi, Naoki Tokuhara, Seiichi Kobayashi
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Patent number: 5919914Abstract: Clathrates of bis?6-hydroxy-4-methyl-5-(3-methyl-imidazolium-1-yl)-3-(phen-4-ylazo)pyrid in-2-one!ethylene with aromatics of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -hydroxyalkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -hydroxyalkoxy, C.sub.1 -C.sub.10 -alkyl which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.10 -alkoxy which is interrupted by 1, 2 or 3 non-neighboring oxygen atoms and is unsubstituted or substituted by hydroxyl, or is C.sub.1 -C.sub.6 -alkanoyl, hydroxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, phenylcarbonyl or C.sub.1 -C.sub.6 -alkenyl andR.sup.2 is R.sup.1, hydrogen or phenoxy,a process for their preparation and their use for the preparation of formulations of the dye.Type: GrantFiled: March 17, 1998Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Manfred Ruske, Peter Erk, Heidi Hengelsberg
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Patent number: 5877300Abstract: A process for the preparation of a guanidinium 5,5'-azotetrazolate by reacting 5-aminotetrazolate monohydrate with potassium permanganate in an aqueous hydroxide solution to form sodium 5,5'-azotetrazolate dihydrate as an intermediate, then reacting 5,5'-azotetrazolate dihydrate with guanidine nitrate or guanidine chloride to obtain guanidinium 5,5'-azotetrazolate.Type: GrantFiled: June 19, 1998Date of Patent: March 2, 1999Assignee: Chung Shan Institute of Science & TechnologyInventors: Yu-Lin Peng, Chi-Wung Wong
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Patent number: 5789560Abstract: Azo dyes of the formula ##STR1## where D is the radical of a diazo component of the aniline series or the series of the aromatic heterocyclic amines,R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.10 -alkyl, which may be substituted, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.4 -alkenyl, substituted or unsubstituted phenyl, or are together with the nitrogen atom joining them together a heterocyclic radical, andR.sup.3 is tert-butyl or tert-pentyl,are useful for thermal transfer and for dyeing or printing synthetic materials.Type: GrantFiled: January 22, 1997Date of Patent: August 4, 1998Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Rudiger Sens
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Patent number: 5777089Abstract: Phenol derivatives of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, X, Y and Z have the meanings stated in the description, are used in particular in nonlinear optics.Type: GrantFiled: October 15, 1996Date of Patent: July 7, 1998Assignee: BASF AktiengesellschaftInventors: Stefan Beckmann, Karl-Heinz Etzbach, Rudiger Sens
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Patent number: 5739296Abstract: Polarizing coatings are formed from dyestuffs which provide a stable liquid crystalline phase in a wide range of concentrations, temperatures and pH-values. Particles formed by aggregates of the liquid crystal molecules are oriented in a predetermined direction to polarize light. The stability of the liquid crystalline state allows orienting the particles by mechanical forces such as a shearing force applied when the liquid crystal (10) is spread on a support surface (20) by a knife-like doctor (90) or a tension deformation force acting on the meniscus of the liquid crystal deposited between two surfaces (20, 30) as the surfaces are peeled off one another. As a result, the polarizing coatings are formed in some embodiments by simple methods. In some embodiments, the polarizing coatings have a high lightfastness, a high thermal stability, and a high dichroic ratio.Type: GrantFiled: November 20, 1995Date of Patent: April 14, 1998Assignee: Russian Technology GroupInventors: Khan Ir Gvon, Yuri A. Bobrov, Victor A. Bykov, Leonid Y. Ignatov, Tatiana D. Ivanova, Sergei I. Popov, Elena Y. Shishkina, Georgiy N. Vorozhtsov
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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: 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: 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: 5254674Abstract: A diaminoazothiophene compound represented by the formula (I): ##STR1## salts thereof or metal complexes thereof and a method for preparing the same.Type: GrantFiled: November 6, 1992Date of Patent: October 19, 1993Assignee: Osaka Gas Company, LimitedInventors: Yasunori Yokomichi, Shinichi Tada, Hitoshi Nishino, Kenji Seki
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Patent number: 5216139Abstract: Thiopheneazo dyes of the formula ##STR1## where R.sup.1 is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylazo, phenylsulfonyl, formyl or the radical ##STR2## where R.sup.7 and R.sup.8 are independently of the other cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, halogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, or R.sup.1 and R.sup.2 together are the radical (CH.sub.2).sub.3 --CO, which may be substituted by 1 or 2 methyl groups and whose carbonyl group is bonded to the thiophene ring in the ortho position relative to the sulfur atom,R.sup.3 is cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.4 is C.sub.1 -C.sub.8 -alkyl, cyclohexyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted thienyl,R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.7 -alkyl whose alkyl chain is interrupted by 1 or 2 oxygen atoms, or C.sub.1 -C.sub.4 -alkoxy andR.sup.6 is cyanoethyl, phenylethyl or C.sub.3 -C.sub.Type: GrantFiled: December 4, 1990Date of Patent: June 1, 1993Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Guenter Hansen, Gunther Lamm, Helmut Reichelt
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Patent number: 5198046Abstract: A stable, nitrogen-rich organic compound in the form of diguanidinium-5,5zotetrazolate having the empirical formula C.sub.4 H.sub.12 N.sub.16, is with a pulverulent, chemically stable oxidizer as a pyrotechnic mixture for spontaneously generating environmentally friendly, non-toxic gases.Type: GrantFiled: March 10, 1992Date of Patent: March 30, 1993Assignee: Fraunhofer-Gesellschaft zur Forderung der Angewandten Forschund e.V.Inventors: Klaus M. Bucerius, Friedrich-Wilhelm Wasmann, Klaus Menke
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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: 5132412Abstract: Thiazoleazo dyes of the formula ##STR1## where X is nitrogen or a radical C--R.sup.5, R.sup.5 being cyano, halogen, alkoxycarbonyl or thiocyanato, R.sup.1 is cyano, chlorine, unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted thienyl, unsubstituted or substituted pyridyl or unsubstituted or substituted alkylthio, alkylsulfinyl or alkylsulfonyl, R.sup.2 is unsubstituted or substituted alkyl, cycloalkyl, unsubstituted or substituted phenyl, furyl, unsubstituted or substituted thienyl or pyridyl and R.sup.3 and R.sup.4 independently of one another are each unsubstituted or substituted alkyl, or R.sup.3 and R.sup.4, together with the nitrogen atom which links them, form a heterocyclic radical, are used for dyeing textile fibers having good wet fastness and color build-up.Type: GrantFiled: September 15, 1989Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
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Patent number: 5059684Abstract: Thiazole-azo dyes of the formula ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms, phenyl, halogen, cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.2 is formyl, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl or a radical of the formula --CH.dbd.CX.sup.1 X.sup.2, where X.sup.1 and X.sup.2 independently of each other are cyano or C.sub.1 -C.sub.4 -alkoxycarbonyl,R.sup.3 is C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms or substituted by phenyl or phenoxy, C.sub.5 -C.sub.7 -cycloalkyl, substituted or unsubstituted phenyl, furyl, thienyl, C.sub.1 -C.sub.4 -alkylthienyl or pyridyl, andR.sup.4 and R.sup.5 independently of each other are C.sub.1 -C.sub.12 -alkyl, which may be interrupted by oxygen atoms and/or substituted,with the proviso that in at least one of R.sup.1, R.sup.4 and R.sup.5 the alkyl chain is interrupted by oxygen atoms, are useful for dyeing textile fibers.Type: GrantFiled: March 5, 1990Date of Patent: October 22, 1991Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Karl H. Etzbach, Matthias Wiesenfeldt, Guenter Hansen, Helmut Reichelt
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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: 4960873Abstract: Isothiazoleazo dyes I ##STR1## where R.sup.1 is H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and A is the radical of a coupling component are used predominantly as disperse dyes for dyeing hydrophobic organic fibers and fiber materials.Type: GrantFiled: March 9, 1989Date of Patent: October 2, 1990Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
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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: 4929720Abstract: 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: GrantFiled: November 10, 1988Date of Patent: May 29, 1990Assignee: Basf AktiengesellschaftInventors: Guenter Hansen, Ernst Schefczik, Helmut Reichelt
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Patent number: 4908435Abstract: An azo compound of the formula:A--N.dbd.N--B--N.dbd.N--Dwherein:A is (i) a phenyl group containing at least two unsaturated electron-withdrawing groups in ortho or para positions with respect to the azo link, (ii) an aromatic heterocycle, or (iii) the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine;B is an substituted or unsubstituted thien-2,5-ylene or thiazol-2,5-ylene group; andD is the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine.The azo compound has a significant absorption band extending into the near infra-red region of the spectrum and has utility in applications, such as solar screening, electronic, optical character recognition, printing, reprographic and security systems, where enhanced infra-red absorption is necessary or desirable.Type: GrantFiled: February 12, 1988Date of Patent: March 13, 1990Assignee: Imperial Chemical Industries PLCInventor: Peter Gregory
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Patent number: 4855412Abstract: Compounds of the general formula ##STR1## where D is a radical of the formula ##STR2## and one of the two radicals L.sup.1 and L.sup.2 is unsubstituted amino and the other the radical ##STR3## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl or C.sub.1 -C.sub.8 -acyloxy-C.sub.2 -C.sub.4 -alkyl,R.sup.2 is C.sub.2 -C.sub.10 -alkylene or C.sub.2 -C.sub.10 -alkylene is interrupted by oxygen,T is C.sub.1 -C.sub.8 -alkanoyl which is unsubstituted or is substituted by chlorine or methoxy,B.sup.1 is C.sub.1 -C.sub.4 -alkyl or benzyl or phenyl, which are each unsubstituted or are each substituted by methyl, methoxy or chlorine,B.sup.2 is B.sup.1, hydrogen, halogen, cyano or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.1 is hydrogen, nitro, cyano, C.sub.1 -C.sub.9 -alkoxycarbonyl, C.sub.1 -C.sub.9 -mono- or -dialkylaminocarbonyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl,X.sup.2 is nitro or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.3 is X.sup.Type: GrantFiled: April 24, 1987Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
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Patent number: 4820809Abstract: Novel compounds of the general formula I ##STR1## where X is hydrogen, nitro or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aryl or hetaryl, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, R is unsubstituted or substituted alkyl or aryl, R.sup.1 is hydrogen or R.sup.2, and R.sup.2 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl, are useful for dyeing textile fibers, in particular polyesters.Type: GrantFiled: January 11, 1988Date of Patent: April 11, 1989Assignee: BASF AktiengesellschaftInventors: Udo Bergmann, Erwin Hahn, Guenter Hansen
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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: 4740604Abstract: There are disclosed benzanthrone lactones of formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in claim 1. The benzanthrone lactones of formula (1) are important intermediates for the synthesis of novel dyes which are obtained by coupling suitable diazo components to said compounds of formula (1).Type: GrantFiled: May 15, 1987Date of Patent: April 26, 1988Assignee: Ciba-Geigy CorporationInventors: Claus D. Weis, Peter Sutter
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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