Alkylene, Alkenyl Or Alkenylene Bonded Directly To Carboxamido, Urea Or -c(=x)-, Wherein X Is Chalcogen, Which Group Is Between A Ring And The Alkylene, Alkenyl Or Alkenylene Patents (Class 534/643)
-
Patent number: 9085697Abstract: A polymerizable yellow dye which is used to block or lower the intensity of blue light transmitted through ophthalmic lenses and is represented by the following formula (I): wherein R1 is hydrogen or —NHCOCH3; R2 is hydrogen or C1-C3 alkyl groups; R3 and R4 are independently hydrogen or —OCO—R5, wherein R5 is isopropenyl group or a substituted isopropenyl group represented as —R6—(R7O)n—COC(CH3)CH2, R6 is NH or R7 is C1-C5 alkylene groups and n is an integer of 1-40.Type: GrantFiled: June 21, 2013Date of Patent: July 21, 2015Assignee: BENQ MATERIALS CORPORATIONInventors: Fan-Dan Jan, Hsia-Hao Chang
-
Patent number: 8815485Abstract: A compound that can improve azo pigment dispersibility in a non-water-soluble solvent. The compound is represented by formula (1): wherein R1 to R4 represent hydrogen or halogen; R5 to R9 represent hydrogen, COOR17 or CONR18R19, and at least one of R5 to R9 represents COOR17 or CONR18R19, where R17 to R19 represent hydrogen or an alkyl group having 1 to 3 carbons; R10 represents an alkyl group having 1 to 6 carbons or a phenyl group; R11 to R15 represent a hydrogen, L1R20 or L2R21R22, and at least one of R11 to R15 represents L1R20 or L2R21R22, where L1 represents a divalent linking group, L2 represents a trivalent linking group, and R20 to R22 represent an alkyl group having 8 or more carbons or an alkenyl group having 8 or more carbons; and R16 represents an alkyl group having 1 to 6 carbons or a phenyl group.Type: GrantFiled: August 11, 2011Date of Patent: August 26, 2014Assignee: Canon Kabushiki KaishaInventors: Masatake Tanaka, Masashi Kawamura, Yuki Hasegawa, Takayuki Toyoda, Yasuaki Murai, Masashi Hirose, Takeshi Miyazaki
-
Patent number: 8142520Abstract: The present invention concerns dyes of the general formula I where X and Y represent hydrogen, bromine or chlorine, but not simultaneously hydrogen; R represents F, Cl, Br, COOR1 or CF3; R? represents H or F; R1 represents C1-C6-alkyl; and one of W1 and W2 represents hydroxyl and the other nitro and Y is always ortho to the hydroxyl group; but not compounds in which R represents Cl attached to the phenyl nucleus in a is position ortho to the NH group nor compounds in which W1 represents nitro, W2 represents hydroxyl, Y represents hydrogen, X represents chlorine and R represents bromine attached to the phenyl nucleus in a position meta to the NH group, mixtures with further dyes, and also their preparation and use.Type: GrantFiled: August 24, 2007Date of Patent: March 27, 2012Assignee: DyStar Colours Deutschland GmbHInventors: Hartwig Jordan, Andreas Endres
-
Publication number: 20110041264Abstract: wherein D is a chromophore; L is a linking group selected from SO2, NHCO, and NHSO2; Q is a hydrogen or halogen atom; and R is selected from C1-C4 alkyl, (CH2)nCOOH, (CH2)nCONH2, (CH2)nSO3H, (CH2)nCOOM, (CH2)nPO3H, (CH2)nOH, (CH2)nSSO3?, (CH2)nNR12, (CH2)nN+R1H2, (CH2)nNHCOR1, PhSSO3?, PhSO3H, PhPO3H, PhNR12, PhN+R13, (CH2)2CH(SH)R1(CH2)3COOH, and n is an integer in the range of 1 to 4 wherein within the same molecule each n is not necessarily the same integer; M is a cation of an alkaline earth metal, alkali metal, NH4+ or NR13+; and R1 is C1-C4 alkyl.Type: ApplicationFiled: March 10, 2009Publication date: February 24, 2011Applicant: PERACHEM LIMITEDInventors: Jamie Anthony Hawkes, David Malcolm Lewis, Celine Gauche
-
Patent number: 7619074Abstract: The present invention relates to a novel reactive dyestuff with an N,N-dialkylamino bridge group, represented by the following formula (I): wherein R, B, B?, E1, E2, Z, Z?, i, j, R1, R2, m and n are defined the same as the specification. The reactive dyestuff of the present invention is suitable for exhaust dyeing, cold batch-up dyeing, continuous dyeing, printing and digital spray printing materials that contain hydroxyl group or polyamine fibers.Type: GrantFiled: May 20, 2008Date of Patent: November 17, 2009Assignee: Everlight USA, Inc.Inventors: Wen-Jang Chen, Ya-Cing Yu, Hong-Chang Huang, Chien-Yu Chen, Chen-Lung Kao, Hsien-Chung Hsia
-
Patent number: 7109313Abstract: The present invention relates to dyes of the general formula (I) where X1 is a radical —CH2CH2Z or —CH?CH2, Z being analkali-eliminable group, X2 is alkyl, alkoxy, halogen, COOM or SO3M, X3 is a heterocyclic reactive group of the general formula (IIa) or (IIb) ?or a reactive group of the formula (IIc), (IId) or (IIe) the stated variables being as defined in claim 1, to processes for preparing them and to their use for dyeing and printing hydroxyl-containing and/or carboxamido-containing material.Type: GrantFiled: March 18, 2003Date of Patent: September 19, 2006Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Stefan Meier, Werner Russ, Stefan Ehrenberg
-
Patent number: 6518408Abstract: Compounds of formula (1) wherein K1 and K2 are each independently of the other the radical of a coupling component from the series benzene, naphthalene, 4-alkyl-6-hydroxypyridone-(2), 2,5-diamino-4-alkylpyridine, 1-arylpyrazolone-(5) and 1-aryl-5-aminopyrazole, at least one of which contains a fiber-reactive group, with the proviso that (i) the fiber-reactive group is not 2-(&bgr;-sulfatoethylsulfonyl)ethylamino when K1 and K2 are phenyl substituted by a fiber-reactive group, and (ii) the fiber-reactive group is not &bgr;-sulfatoethylsulfonyl when K1 and K2 are N-(&bgr;-sulfatoethyl)aniline substituted on the phenyl ring by a fiber-reactive group, are suitable for dyeing a wide variety of fiber materials, especially cellulosic fiber materials, and yield dyeings having good allround properties.Type: GrantFiled: March 19, 2001Date of Patent: February 11, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Rolf Deitz
-
Patent number: 6392021Abstract: Reactive dyes of formula (1) wherein b is the number 1 or 2, A is the radical of formula (2) or (3) D1, D2, R1, R2, X1, Y, l, m and n are as defined in the specification, are especially suitable for dyeing cotton and wool and yield dyeings having good all round properties.Type: GrantFiled: September 24, 2001Date of Patent: May 21, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Athanassios Tzikas, Rolf Deitz, Herbert Klier
-
Patent number: 6281339Abstract: Monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes comprising at least one structural unit of formula (1) wherein Z is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen; phenoxy unsubstituted or substituted in the phenyl ring; C1-C4alkylthio unsubstituted or substituted in the alkyl moiety; phenylthio unsubstituted or substituted in the phenyl ring; amino; N-mono- or N,N-di-C1-C24-alkylamino, unsubstituted or substituted in the alkyl moiety, or uninterrupted or interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or C1-C4alkyl; C10-C20terpeneamino; C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring; phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino, each unsubstituted or substituted in the aryl moiety; morpholino; piperazin-1-yl or piperidin-1-yl, and X is hydType: GrantFiled: September 13, 2000Date of Patent: August 28, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Marcel Frick
-
Patent number: 6239263Abstract: Novel water-soluble azo compounds useful as raw materials for preparing dyes excellent in dyeing properties and fastness and prepared from a coupler consisting of 2-hydroxynaphthalene-3,6-dicarboxylic acid or an ester thereof or an amide derivative of the same and a diazonium compound having a group of the general formula: —B—(CH2)2- Q or —B′—(CH2)2-Q′ (wherein B and B′ are each an electron-attracting group; and Q and Q′ are each a group capable of forming a vinyl group through the elimination with an alkali, provided the groups Q and Q′ are each bonded at the &bgr;-position of the ethyl group).Type: GrantFiled: August 26, 1999Date of Patent: May 29, 2001Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Masaharu Kittaka
-
Patent number: 6187912Abstract: Disazo compounds, processes for their preparation and their use as dyestuffs Described are fiber-reactive, water-soluble disazo compounds corresponding to the formula (1) given below, which are capable of dyeing fiber material containing hydroxy, amino, thiol and/or carboxamido groups, such as cellulose fibers, for example cotton, regenerated cellulose fibers, wool and synthetic polyamide fibers, in a high intensity and with good fastness properties. in which: W2 is a particular fiber-reactive grouping, D1 is phenyl or naphthyl, each optionally substituted by substituents customary in dyestuffs, and D2 is phenylene or naphthylene optionally substituted by substituents customary in dyestuffs, M is hydrogen or an alkali metal, R is hydrogen or sulfo and R1 is hydrogen, optionally substituted lower alkyl or optionally substituted phenyl.Type: GrantFiled: January 7, 2000Date of Patent: February 13, 2001Assignee: Dystar Textifarben GmbH & Co.Inventor: Joachim Steckelberg
-
Patent number: 5849887Abstract: Dye mixtures comprising at least one reactive dye of formula ##STR1## together with at least one reactive dye of formula ##STR2## give dyeings having good fastness properties on nitrogen-containing or hydroxyl group-containing fiber materials.Type: GrantFiled: March 30, 1998Date of Patent: December 15, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lehmann, Rolf Deitz, Hans Reichert, Athanassios Tzikas
-
Patent number: 5710258Abstract: The invention relates to compounds of formula ##STR1## The compounds of formula (1) are suitable as dye for dyeing or printing hydroxyl group-containing or nitrogen-containing fibre materials and give dyeings of prints having good allround fastness properties.Type: GrantFiled: February 5, 1996Date of Patent: January 20, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Jean-Marie Adam, Peter Sutter
-
Patent number: 5703215Abstract: A process for the coloration of a substrate, especially a textile, comprising the steps of:(a) applying to the substrate a mixture comprising an aqueous solvent and a water-soluble dye comprising molecules which contain a nucleophilic group and an electrophilic group; and(b) heating or basifying or heating and basifying the dye thereby causing molecules of the dye to join together.Also claimed are dyes, polymers and oligomers.Type: GrantFiled: May 30, 1995Date of Patent: December 30, 1997Assignee: Zeneca LimitedInventors: Andrew Hunter Morris Renfrew, Andrew Paul Shawcross
-
Patent number: 5691459Abstract: Azo dyes of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are unsubstituted or hydroxy-, C.sub.1 -C4-alkoxy- or halogen-substituted C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;unsubstituted or C.sub.1 -C4-alkyl-, C.sub.1 -C4-alkoxy- or halogen-substituted phenyl or phenoxy; ora radical of the formula --N(R.sub.3)R.sub.4, in which R.sub.3 und R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, or C.sub.2 -C.sub.4 -alkanoyl which is unsubstituted or further substituted in the alkyl part by hydroxyl or C.sub.1 -C.sub.4 -alkoxy,with the proviso that R.sub.1 and R.sub.2 are not simultaneously methyl, produce dyeings with good fastnesses on fibre materials containing nitrogen or containing hydroxyl groups.Type: GrantFiled: July 15, 1996Date of Patent: November 25, 1997Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Peter Sutter
-
Patent number: 5616695Abstract: The invention relates to azo dyes of formula ##STR1## wherein R.sub.1 is acryloyl, .alpha.-haloacryloyl, .alpha.-methylacryloyl or .alpha.,.beta.-dihalopropionyl, R.sub.2 is C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen, cyano, hydroxy, sulfo, sulfato or C.sub.1 -C.sub.4 alkoxy, n is 0 or 1 and m is 1;or wherein R.sub.1 is acryloyl, .alpha.-haloacryloyl, .alpha.-methylacryloyl or .alpha., .beta.-dihalopropionyl, R.sub.2 is C.sub.2 -C.sub.8 alkylene which is unsubstituted or substituted by hydroxy, halogen, C.sub.1 -C.sub.4 alkoxy, n is 0 or 1 and m is 2.The dyes are suitable for dyeing nitrogen-containing or hydroxyl group-containing fibre materials.Type: GrantFiled: August 25, 1995Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventor: Peter Aeschlimann
-
Patent number: 5597904Abstract: Reactive dyes of formula ##STR1## wherein Z is a group of formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, and Y is a leaving group, and K is a radical of formula ##STR2## wherein X is a radical of formula --(CH.sub.2).sub.n --Cl, ##STR3## or --CH.dbd.CH.sub.2 ; Hal is halogen; and n is 1, 2, 3 or 4; R is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl; R.sub.1 is amino or hydroxyl; R.sub.2 is methyl or carboxyl; and R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, halogen or carboxyl, are particularly suitable for dyeing or printing cellulosic fibre materials or natural or synthetic polyamide fibre materials in high tinctorial yield, and give dyeings and printings with good fastness properties.Type: GrantFiled: March 12, 1996Date of Patent: January 28, 1997Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Claudia Carisch
-
Patent number: 5565553Abstract: Reactive dyes of the formula ##STR1## where A, K and Z are each as defined in the claims, are especially useful for dyeing or printing cellulosic fiber materials, producing dyeings and prints having good fastness properties in a high yield.Type: GrantFiled: January 11, 1996Date of Patent: October 15, 1996Assignee: Ciba-Geigy CorporationInventors: Rolf Deitz, Paul Herzig, Athanassios Tzikas
-
Patent number: 5523397Abstract: Reactive dyes of formula ##STR1## wherein Z is a group of formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, and Y is a leaving group, and K is a radical of formula ##STR2## wherein X is a radical of formula ##STR3## Hal is halogen; and n is 1, 2, 3 or 4; R is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl; R.sub.1 is amino or hydroxyl; R.sub.2 is methyl or carboxyl; and R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, halogen or carboxyl, are particularly suitable for dyeing or printing cellulosic fiber materials or natural or synthetic polyamide fiber materials in high tinctorial yield, and give dyeings and printings with good fastness properties.Type: GrantFiled: October 7, 1994Date of Patent: June 4, 1996Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Claudia Carisch
-
Patent number: 5480976Abstract: Reactive dyes of formula ##STR1## wherein X, Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and m are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fiber materials or natural or synthetic polyamide fiber materials in high tinctorial yield, and give dyeings and prints with good fastness properties.Type: GrantFiled: October 7, 1994Date of Patent: January 2, 1996Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Claudia Carisch
-
Patent number: 5449762Abstract: Reactive dyes of the formula I ##STR1## where n is 0 or 1R.sup.1, R.sup.2 and R.sup.3 are in each case hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridge member, A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, Q being a group which can be removed under alkaline reaction conditions, andD is phenyl or naphthyl, it being possible for these radicals to be substituted, and a process for preparing reactive dyes by oxidation of the abovementioned compounds are described.Type: GrantFiled: February 1, 1995Date of Patent: September 12, 1995Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Bernd Siegel, Manfred Patsch
-
Patent number: 5432266Abstract: Preparation of water-soluble reactive dyes containing vinylsulphonyl and .beta.-sulphatoethylsulphonyl groups by the oxidation of dyes containing .beta.-hydroxyethylmercapto radicals, and then sulphation and, if appropriate, conversion of the .beta.-sulphatoethylsulphonyl radical to the vinylsulphonyl radical with bases.Type: GrantFiled: April 1, 1993Date of Patent: July 11, 1995Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Peter Roschger
-
Patent number: 5428140Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1R.sup.1, R.sup.2 and R.sup.3 are in each case hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridge member, A is unsubstitued or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, Q being a group which can be removed under alkaline reaction conditions, andD is phenyl or naphthyl, it being possible for these radicals to be substituted,and a process for preparing reactive dyes by oxidation of the abovementioned compounds are described.Type: GrantFiled: June 6, 1994Date of Patent: June 27, 1995Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Bernd Siegel, Manfred Patsch
-
Patent number: 5424405Abstract: The fibre-reactive dyes of the formula ##STR1## where the variables are each as defined in the claims, are suitable in particular for dyeing nitrogen-containing and hydroxyl-containing fibre materials.Type: GrantFiled: November 19, 1993Date of Patent: June 13, 1995Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Guido Jordine
-
Patent number: 5352247Abstract: Anthraquinone dyes of the formula ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3 and n are as defined in claim 1, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: November 30, 1993Date of Patent: October 4, 1994Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
-
Patent number: 5278293Abstract: Azo dyestuffs of the formula ##STR1## having the substituent meanings given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups and amide groups.Type: GrantFiled: October 31, 1990Date of Patent: January 11, 1994Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Manfred Hoppe, Hermann Henk, Klaus Kunde, Frank-Michael Stuohr
-
Patent number: 5278292Abstract: Water-soluble fiber-reactive dyes are described conforming to the below-indicated formula (1) which are capable of dyeing hydroxyl- and/or carboxamido-containing material, in particular fiber material, such as wool and in particular cellulose fiber materials, in strong, fast shades. ##STR1## in which F is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, triphenoldioxazine, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, formazan, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye;R.sup.x is hydrogen or alkyl of 1 to 4 carbon atoms;R is hydrogen, sulfo, carboxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or chlorine;w is 1, 2, 3 or 4;Y is vinyl or an ethyl group which contains in the .beta.-position a substituent which is eliminable by alkali to form a vinyl group;n is 1 or 2.Type: GrantFiled: July 17, 1992Date of Patent: January 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Hartmut Springer, Rolf Gleissner, Gunther Schwaiger
-
Patent number: 5276148Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, whereQ is a group which can be eliminated under alkaline reaction conditions,D.sup.1 is phenyl or naphthyl, where these radicals may be substituted,D.sup.2 is phenylene or naphthylene, where these radicals may be substituted, andZ is a reactive radical,with the proviso thata) n is zero when D.sup.1 is substituted by unsubstituted or substituted phenylazo or by unsubstituted or substituted naphthylazo andb) the reactive radical Z is not devised from the triazine series when n is zero and D.sup.1 is dihydroxysulfonylphenyl or trihydroxysulfonylnaphthyl,are used for dyeing and printing organic substrates containing hydroxyl groups or nitrogen atoms.Type: GrantFiled: May 22, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch
-
Patent number: 5262526Abstract: A fluorescent compound, which is readily capable of forming a stable complex with a rare-earth metal ion having fluorescence with satisfactory intensity even in an aqueous system and long fluorescence lifetime when formed a complex with the rare-earth metal ion, a complex of the fluorescent compound and the rare-earth metal ion, and a labelled reagent made therefrom, together with a specific binding assay using said labelling agent.A fluorescent compound expressed by the following formula A, typically exemplified by 2,15-diaza[3,3](2,9)-1,10-phenanthrolinophane-N.sup.2,N.sup.15 -diacetic acid.Type: GrantFiled: December 20, 1991Date of Patent: November 16, 1993Assignees: Dojindo Laboratories, Mochida Pharmaceutical Co., Ltd.Inventors: Kazumi Sasamoto, Daikichi Horiguchi, Masahiro Nobuhara, Hiroshi Mochizuki
-
Patent number: 5183881Abstract: The new o-aminoazo compounds of the formula ##STR1## in which the substituents D, A, R and R.sub.1 and the index n have the meaning given in the description are valuable intermediates for the preparation of metal complex dyestuffs and are also highly suitable for the dyeing of wool and polyamide.Type: GrantFiled: August 22, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventor: Horst Jager
-
Patent number: 5106960Abstract: The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series.These dyes yield dyeings of good light- and wetfastness on polyamide material.Type: GrantFiled: March 22, 1991Date of Patent: April 21, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Hurter, Dieter Mausezahl
-
Patent number: 5023274Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where X is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano or nitro, Y is .beta.-haloethyl or vinyl, m is 1, 2 or 3, n is 3 or 4, p is 0, 1 or 2 and q is 0 or 1, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: April 25, 1989Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Alois Puntener, Urs Lehmann, Peter Scheibli, Josef Koller
-
Patent number: 5023326Abstract: Reactive dyes of the formula ##STR1## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, D is a phenyl or naphthyl radical, which can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo, and which contains at least one reactive radical bound direclty or via a bridge member to a ring carbon atom, or to which a further radical is bound which contains a reactive radical, and u is the number 2, 3, 4 or 5, are suitable in particular for the dyeing or printing of cellulose-containing fiber materials by the exhaust method or by the continuous method and product in combination with a high colorisitc yield dyeings and prints which have good fastness properties.Type: GrantFiled: November 9, 1989Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Herbert Seiler
-
Patent number: 5023325Abstract: A reactive dye of the formulaD--U--R).sub.nin which D is the radical of an anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is a polymethylene radical having 1 to 6 C atoms or its branched isomers; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl;or a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: May 11, 1988Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
-
Patent number: 5021558Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.Type: GrantFiled: March 20, 1990Date of Patent: June 4, 1991Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
-
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
-
Patent number: 5003052Abstract: A reactive dye of the formula ##STR1## in which R is a radical of the formula ##STR2## or Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; V is hydrogen or a radicalZ--SO.sub.2 --CH.sub.2 --CH.sub.2 --in which z is as defined above; R.sub.1 is hydrogen or C.sub.1-6 -alkyl; alk, independently of each other, are polymethylene radicals having 2 to 6 C atoms or their branched isomers; K is a benzene, naphthalene or heterocyclic radical; m is 1 to 6, p is 1 to 6 and q is 1 to 6; and the benzene or naphthalene radical A is further unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.8 -acylamino, C.sub.1 -C.sub.4 -alkylamino, phenylamino, N,N-di-.beta.-hydroxyethylamino, N,N-di-.beta.-sulfatoethylamino, sulfobenzylamino, N,N-disulfobenzylamino, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, trifluoromethyl, nitro, cyano, halogen, carbamoyl, N-C.sub.1 -C.sub.Type: GrantFiled: May 11, 1988Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
-
Patent number: 4994563Abstract: The azo dyes of the formula ##STR1## in which D is a diazo component, R.sub.1 and R.sub.2 independently of one another are each a C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical each of which is substituted or unsubstituted, or R.sub.1 and R.sub.2, together with the nitrogen atom linking them, are a 5-membered, 6-membered or 7-membered ring each of which is unsubstituted or substituted by heteroatoms, R.sub.3 is hydrogen, halogen or a C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or phenoxy radical each of which is substituted or unsubstituted, X is --CO-- or --SO.sub.2 --, n is the number 1, 2, 3, 4, 5 or 6 and M is a cation, produce dyeings of good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups. This application also relates to the preparation and use of said azo dyes and to intermediates utilized in the preparation of said azo dyes.Type: GrantFiled: June 27, 1989Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Harald Walter, Rudolf Hurter
-
Patent number: 4994562Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where B is an aliphatic or sulfo-free aromatic bridge member, R is .alpha.,.beta.-dihalopropionyl, .alpha.-haloacryloyl or haloacetyl, T.sub.1 is halogen, X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano or nitro, Y is --CO-- or --SO.sub.2 --, Z is nitrogen or --C--T.sub.2, T.sub.2 is halogen, hydrogen, C.sub.1 -C.sub.4 alkylthio, cyano, formyl or C.sub.1 -C.sub.4 alkylsulfonyl, m is 1, 2 or 3, n is 0, 1 or 2, qu is 0 or 1 and r and s are each eitehr 0 or 1 but never the same as each other, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: June 29, 1989Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventor: Urs Lehmann
-
Patent number: 4990599Abstract: The invention relates to a process for dyeing or printing natural or synthetic polyamide fibre materials which comprises dyeing or printing these fibre materials with reactive dyes of the formula ##STR1## where each M is a cation, R.sub.1 and R.sub.2 are independently of each other hydrogen or C.sub.1 -C.sub.4 alkyl, and X.sub.1 and X.sub.2 are independently of each other .alpha.,.beta.-dibromopropionyl, .alpha.-bromoacryloyl, chloroacetyl or a mono-, di- or trihalopyrimidinyl radical.Type: GrantFiled: December 20, 1989Date of Patent: February 5, 1991Assignee: Ciba-Geigy CorporationInventors: Dieter Mausezahl, Peter Loew
-
Patent number: 4975530Abstract: Intermediates useful for the preparation of fiber-reactive dyes having the formula ##STR1## in which Q is phenyl unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, sulfo or trihalomethyl; 1- or 2-naphthyl; or unsubstituted or C.sub.1 -C.sub.4 alkyl, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylthio substituted furanyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl or 1,3,5-triazinyl, and A.sub.1 and A.sub.2 independently of one another are a radical of the formula ##STR2## in which R.sub.1 and R.sub.2 independently of one another are hydrogen; C.sub.1 -C.sub.4 alkyl unsubstituted or substituted by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.Type: GrantFiled: November 22, 1989Date of Patent: December 4, 1990Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Kurt Burdeska
-
Patent number: 4975539Abstract: Water-soluble azo compounds which have fiber-reactive and dye properties and dye carboxamido- and/or hydroxyl-containing materials, such as fiber materials, in particular cellulose fiber materials, in strong, predominantly bluish red to orange hues which have good fastness properties; they conform to the general formula (1) ##STR1## in which the symbols have the following meaning: M is a hydrogen atom or an alkali metal,T is a covalent bond or a methylene group or an amino group --N(R)--, in which R is alkyl of 1 to 4 carbon atoms,D is a group of the formula ##STR2## in which R.sup.1 is alkyl of 1 to 4 carbon atoms, hydroxy, nitro, hydrogen, alkoxy of 1 to 4 carbon atoms, chlorine, bromine or carboxy,R.sup.2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, chlorine or sulfo,R.sup.3 is hydrogen or sulfo,k is the number zero or 1,p is the number zero, 1 or 2 andM has the abovementioned meaning;m is the number zero, 1 or 2;W has one of the meanings of T;X is vinyl, .beta.-chloroethyl, .Type: GrantFiled: August 31, 1989Date of Patent: December 4, 1990Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Werner H. Russ
-
Patent number: 4968782Abstract: Reactive dyes of the formula ##STR1## in which D is the radial of an anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; Q is hydrogen or alkyl which has 1 to 4 carbon atoms and can be substituted by carboxyl, sulfo, cyano, hydroxyl, C.sub.1- C.sub.4 alkoxy or halogen; B is a radical --CH.sub.2n, --O--CH.sub.2n or --NH --CH.sub.2n and n is 1 to 6; R is a radical of the formula ##STR2## Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl; alk is an alkylene radical having 1 to 6 C atoms or branched isomers thereof; Y is hydrogen, chlorine, bromine, flourine, hydroxyl, sulfato, acyloxy having 1 to 4 C atoms, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.Type: GrantFiled: October 13, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann
-
Patent number: 4968781Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.Type: GrantFiled: March 28, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Karl Hoegerle
-
Patent number: 4963659Abstract: Reactive dyes which are particularly suitable for the dyeing or printing of cellulose-containing fiber materials by the exhaust process or by the continuous process and give, at a high color yield, dyeings and prints having good fastness properties, having the formula ##STR1## in which D.sub.1 and D.sub.2, independently of one another, are each a radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R.sub.1, R.sub.2, B.sub.1 and B.sub.2, independently of one another, are hydrogen or alkyl having 1 to 4 carbon atoms, which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato; X is fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.Type: GrantFiled: March 14, 1989Date of Patent: October 16, 1990Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
-
Patent number: 4956457Abstract: The new azo compounds are represented by the following general formula I ##STR1## Wherein R and R.sup.1 are hydrogen, --COCR.sub.3.sup.4 --COCHR.sub.2.sup.4, --SO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 R.sup.4, --( CH.sub.2 CH.sub.2 R.sup.4).sub.2, --CH.sub.2 CH.sub.2 OH, --CONHCH.sub.2 CH.sub.2 R.sup.4 or --CH.sub.2 CH.sub.2 OCONH.sub.2 and R.sup.4 is Cl or a group of the formula ##STR2## --NHCO.sub.2 CH.sub.3 CH.sub.2 OH, --NHCO.sub.2 C.sub.2 H.sub.5, --NHOH, --NHCONHOH, or --NHCH.sub.3, whereby R.sup.1 and R.sup.2 are similar or dissimilar.Type: GrantFiled: August 10, 1989Date of Patent: September 11, 1990Inventor: Takeo Takayanagi
-
Fiber-reactive dyes containing an aniline radical which carries two different vinylsulfonyl moieties
Patent number: 4929719Abstract: Reactive dyes which are particularly suitable for dyeing and printing cellulose containing fiber materials by the cold padbatch process and which produce, in high dye yield, dyeings and prints having good fastness properties containing the radical of an amine of the formula ##STR1## in which R is hydrogen, halogen, hydroxyl or sulfo, Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, Y is a detachable group, R' is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by --COOH, --CN, --OH or --SO.sub.3 H, and E is a radical of the formula ##STR2## in which R' and Z are as defined above, alk, alk' and alk" independently of one another are a C.sub.1 -C.sub.6 alkylene radical, U is hydrogen, halogen, hydroxyl, sulfato, C.sub.1 -C.sub.4 alkanoyloxy, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above, V is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.Type: GrantFiled: August 10, 1989Date of Patent: May 29, 1990Assignee: Ciba-Geigy CorporationInventors: Hansrudolf Schwander, Athanassios Tzikas, Peter Aeschlimann -
Patent number: 4918169Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, napthoquinone, pyrenequinone or perylene-tetracarbimide dye radical, X is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphonic acid group or a quaternized ammonium group, r is 1 or 2, R is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, and A is a radical of the formula ##STR2## wherein R' is hydrogen, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxy or phenyl, C.sub.5 -C.sub.Type: GrantFiled: August 19, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Karl Hoegerle
-
Patent number: 4918183Abstract: The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted.These dyes give dyeings of good light- and wetfastness properties on polyamide material.Type: GrantFiled: October 24, 1985Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter
-
Patent number: 4906740Abstract: The present invention relates to monoazo dyes which dye polyamide material with good light- and wet-fastness and which have the formula ##STR1## in which K is the radical of an amino- or alkoxy-benzene, amino- or alkoxy-naphthalene, naphthol, aminonaphthol, pyrazolone, aminopyrazole, indole, naphthimidazole, diphenylamine, tetrahydroquinoline or acetoacetamide and can be further substituted, R is hydrogen, halogen, C.sub.1-6 -alkyl, trifluoromethyl, carboxyl or a --SO.sub.2 --C.sub.1-6 --alkyl, --SO.sub.2 --R.sub.1, ##STR2## --CO--R.sub.4 group, in which R.sub.1 is a substituted or unsubstituted phenyl- or naphthyl-C.sub.1-4 -alkyl radical, R.sub.2 and R.sub.3 independently of one another are hydrogen or a substituted or unsubstituted C.sub.1-6 -alkyl or C.sub.5-7 -cycloalkyl radical and R.sub.4 is a substituted or unsubstituted phenyl radical, and X is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or halogen, and in which R in formula (1) may not be hydrogen or chlorine if the radical --N.dbd.Type: GrantFiled: July 15, 1986Date of Patent: March 6, 1990Assignee: Ciba-Geigy CorporationInventor: Rudolf Hurter