Replacement Of Halogen By Cyano Group Patents (Class 534/597)
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Publication number: 20090209742Abstract: The present invention relates to dyes of the general formula (I) where X1 and X2 are both hydrogen or both cyano; R1 is ethyl, straight-chain or branched (C3-C10)-alkyl or —(CH2)nCOO6; R2 is hydrogen, methyl, cyanomethyl, halomethyl, ethyl, cyanoethyl, haloethyl, halogen, —NH—CO—R7 or —NH—SO2—R7; R3 is (C1-C8)-alkyl or hydroxyl-, (C1-C4)-alkoxy-, cyano-, halogen-, R7OCO—, R7OOC—, vinyl- or phenyl-substituted (C1-C8)-alkyl; R4 is hydrogen, (C1-C8)-alkyl or hydroxyl-, (C1-C4)-alkoxy-, cyano-, halogen-, R7OCO—, R7OOC—, vinyl or phenyl-substituted (C1-C8)-alkyl; R5 is hydrogen, halogen, (C1-C4)-alkyl, (C1-C8)-alkoxy or halogen-, cyano- or phenyl-substituted (C1-C8)-alkoxy; R6 is (C1-C4)-alkyl; R7 is (C1-C8)-alkyl or halogen- or cyano-substituted (C1-C8)-alkyl; and n is 1, 2, 3, 4 or 5. The invention also relates to the process of the preparation of the dyes of formula (I) and their use.Type: ApplicationFiled: June 6, 2007Publication date: August 20, 2009Applicant: DyStar Textilfarben GmbH & Co. Deutschland KGInventor: Andreas Endres
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Patent number: 7087731Abstract: The present invention relates to dyes of formula wherein R1 is hydrogen, methyl or —BHCO—C1–C4alkyl, R2 is C1–C4alkyl, it being possible for the alkyl chain, from C2 upwards, optionally to be interrupted by an oxygen atom, and R3 has, independent of R2, any of the meanings of R2, and to the process for the preparation thereof and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydmophobic fiber materials, especially textile materials.Type: GrantFiled: January 29, 2002Date of Patent: August 8, 2006Assignee: Ciba Specialty Chemicals CorporationInventors: Antoine Clément, Jean-Claud Wilhelm, Alfons Arquint, Urs Lauk
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Patent number: 6673906Abstract: The present invention relates to the &bgr; modification of the dye of the formula IType: GrantFiled: January 11, 1996Date of Patent: January 6, 2004Assignee: DyStar Textifarben GmbH & Co. Deutschland KGInventor: Ulrich Bühler
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Patent number: 5292872Abstract: A Monoazo dye of the general formula I ##STR1## in which X is methyl, chlorine or bromineR.sup.1 is ethyl, n-propyl, i-propyl, n-butyl or i-butylR.sup.2 is methyl, ethyl, n-propyl, i-propyl, n-butyl or i-butyl andn is 2 or 3,mixtures containing dyes of the general formula I and the preparation of these dyes and their mixtures and their use for the dyeing of hydrophobic synthetic materials, in particular for automotive cover fabrics.Type: GrantFiled: November 24, 1992Date of Patent: March 8, 1994Assignee: Hoechst Mitsubishi Kasei Co.Inventor: Ulrich Buhler
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Patent number: 5218095Abstract: The novel dispersion dyes of the formula ##STR1## in which R.sub.1 is a C.sub.2 -C.sub.8 alkyl radical which is substituted by hydroxyl, halogen, a radical --X--C.sub.1 -C.sub.8 alkyl or --X--phenyl, in which X is a bridging member of the formula --O--, ##STR2## and R.sub.2 and R.sub.3, independently of one another, are each an unsubstituted C.sub.1 -C.sub.8 alkyl radical or a C.sub.2 -C.sub.8 alkyl radical which is substituted as mentioned for R.sub.1, or in which R.sub.1 and R.sub.2 together with the nitrogen atom linking them are a heterocyclic radical, are suitable in particular for the dyeing of polyester textile material.Type: GrantFiled: February 15, 1991Date of Patent: June 8, 1993Assignee: Ciba-Geigy CorporationInventor: Martin Trottmann
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Patent number: 5216140Abstract: The monoazo dye of the formula ##STR1## is highly suitable for dyeing and printing hydrophobic fibres.Type: GrantFiled: August 17, 1992Date of Patent: June 1, 1993Assignee: Cassella AktiengesellschaftInventor: Ulrich Buhler
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Patent number: 5194598Abstract: Azo dyestuffs of the formula ##STR1## in which X denotes H, F, Cl, Br, I, R, CO.sub.2 R, CN, CF.sub.3 and the like,Y/Z denotes H, CH.sub.3, Cl or Br,R.sup.1, R.sup.2 and R denote C.sub.1 -C.sub.4 -alkyl andR.sup.3 and R.sup.4 denote H or CH.sub.3, are highly suitable for the dyeing of polyester fibres, where they are distinguished by a high thermomigration fastness.The preparation of the dyestuffs is preferably carried out by so-called "halogen/cyano exchange".Type: GrantFiled: February 20, 1991Date of Patent: March 16, 1993Assignee: Bayer AktiengesellschaftInventor: Rainer Hamprecht
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Patent number: 5160495Abstract: Monoazo dyestuffs useful for dyeing and printing hydrophobic fibers have the formula ##STR1## in which R.sup.1 denotes alkyl having 1 to 3 carbon atoms, R.sup.2 and R.sup.3 independently of one another denote alkyl having 2 to 5 carbon atoms and R.sup.4 denotes methyl or ethyl.Type: GrantFiled: October 29, 1990Date of Patent: November 3, 1992Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Reinhard Kuhn, Margareta Boos
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Patent number: 5028701Abstract: Disperse dyestuffs of the formula ##STR1## in which A/B denotes H, alkyl, C1 or O-alkyl,R.sub.1, R.sub.2, R.sub.3 denote H or alkyl,R.sub.4 denotes alkyl, aryl or COO-alkyl,R.sub.5 denotes alkyl or aryl,Y denotes H or CN,X denotes NO.sub.2, Cl, Br, CN or SO.sub.2 -alkyl,V denotes NO.sub.2, Cl, Br, COOR.sub.5, COR.sub.5 CF.sub.3 or alkyl andZ denotes H, Cl, Br, SCN or CN,are very color-strong and are suitable in particular for the dyeing of polyester by a wide range of methods.Type: GrantFiled: June 15, 1989Date of Patent: July 2, 1991Assignee: Bayer AktiengesellschaftInventors: Rainer Hamprecht, Manfred Hoppe
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Patent number: 4985045Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety, has improved dyeing properties compared with the individual dyestuffs when used to dye or print hydrophobic fiber materials.Type: GrantFiled: October 30, 1989Date of Patent: January 15, 1991Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Klaus Hofmann
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Patent number: 4937325Abstract: A monoazo dyestuff composition comprising at least two different individual compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are linear or branched alkyl having 1 to 4 carbon atoms and R is linear or branched alkyl having 1 to 5 carbon atoms, and where said individual compounds differ from each other in at least the R moiety. The monoazo dyestuff mixtures are used for the dyeing and printing of hydrophobic fibers such as high molecular weight polyesters of their mixtures with natural fiber material.Type: GrantFiled: December 12, 1988Date of Patent: June 26, 1990Assignees: Cassella Aktiengesellschaft, Tokico Ltd.Inventors: Ulrich Buhler, Klaus Hofmann, Hiroshi Mitsuhashi, Harutsugu Ushiota, Akiharu Odagiri, Gen Kano, Susumu Sakamoto
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Patent number: 4923974Abstract: A monoazo compound of the following formula, ##STR1## wherein X is a hydrogen or halogen atom, or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, nitro, cyano or trifluoromethyl group, Y is a hydrogen or chlorine atom or a methyl or acylamino group, and Z is a hydrogen or chlorine atom or a methyl, methoxy or ethoxy group, which is useful for dyeing or printing hydrophobic fibers with superior level dyeing and build-up properties to give dyed products of a brilliant color superior in fastness properties.Type: GrantFiled: July 19, 1988Date of Patent: May 8, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuyoshi Ueda, Hideo Hattori, Jun Yamamoto, Kiyoyasu Hashimoto
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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
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Patent number: 4889923Abstract: Azo compounds corresponding to the general formula (1) ##STR1## in which m represents the number 1 or 2, the cyano groups being attached to D in the ortho-position relative to the azo group,n denotes the number 1 or 2,Y is the vinyl group or a .beta.-sulfatoethyl group,D denotes a radical of a diazo component of the benzene or naphthalene series which is optionally additionally substituted, but is otherwise free from anionic groups, andK denotes a radical of a coupling component which is optionally additionally substituted, but is otherwise free from anionic groups.The compounds have valuable fiber-reactive dyestuff properties and are suitable for dyeing both hydrophilic and hydrophobic materials, in particular fiber materials, such as, for example, cellulose, wool, synthetic polyamide and polyester.Type: GrantFiled: December 16, 1987Date of Patent: December 26, 1989Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Hans J. Schladetsch
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Patent number: 4839469Abstract: Dyestuffs of the formula ##STR1## wherein B=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 OSO.sub.3 H,u and v=H or SO.sub.3 H, with u=v,R=Cl, Br, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, COOH, SO.sub.3 H, NHCOCH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 Hn=0, 1 or 2 ##STR2## These dyestuffs are outstandingly suitable for the dyeing and printing of materials containing hydroxyl groups or amide groups, such as cellulose, wool and polyamide, and give dyeings with good wet and light fastness properties.Type: GrantFiled: November 13, 1987Date of Patent: June 13, 1989Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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Patent number: 4837309Abstract: A monoazo dyestuff of the formula: ##STR1## wherein D represents substituted or unsubstituted phenyl, imidazolyl, pyridyl, thiazolyl, thiadiazolyl, thienyl, benzoisothiazolyl, pyridinoisothiazolyl, thienoisothiazolyl, thienothiazolyl or benzothiazolyl, R.sup.1 represents substituted or unsubstituted alkyl, cyclohexyl, alkenyl, aralkyl or aryl, R.sup.2 and R.sup.3 each represents hydrogen, alkyl optionally substituted by cyano, hydroxy, alkoxy or alkoxyalkoxy, alkenyl, cyclohexyl, aryl or aralkyl, or together represent a 5- or 6-membered nitrogen-containing heterocyclic ring formed by combining R.sup.2 and R.sup.3, A represents ##STR2## X represents fluorine or chlorine, and Y.sup.1 represents hydrogen, chlorine, methyl or acylamino. The monoazo dyestuff is especially useful in the dyeing of cellulose-containing fibers and exhibits good fastness properties including good wet color fastness and good light fastness.Type: GrantFiled: February 24, 1984Date of Patent: June 6, 1989Assignee: Mitsubishi Chemical Industries LimitedInventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Yutaka Kurose, Yukiharu Shimizu
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Patent number: 4835261Abstract: Azo compounds of the formula I ##STR1## where D=diazo componentR.sub.1 and R.sub.2 =alkyl or aralkylX=H, hydrocarbon radical or acylare useful dyestuffs or dyestuff intermediates.Type: GrantFiled: March 12, 1987Date of Patent: May 30, 1989Assignee: Bayer AktiengesellschaftInventor: Klaus Leverenz
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Patent number: 4802889Abstract: Monoazo dyestuff of the formula ##STR1## wherein R.sup.1 is 4 alkyl having 1 to 3 carbon atoms, andR.sup.2 is methyl, ethyl or alkoxy having 1 to 4 carbon atoms hich is unsubstituted or substituted by methoxy or ethoxy is useful for dyeing and printing hydrophobic fibers a blue color.Type: GrantFiled: August 24, 1987Date of Patent: February 7, 1989Assignee: Cassella AktiengesellschaftInventors: Ulrich Bte,uml/u/ hler, Horst Tappe, Reinhard Kuhn, Albert Bode, Margareta Boss
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Patent number: 4769449Abstract: Azo dyes of the formula ##STR1## wherein R.sup.1 is alkyl having 1 to 4 carbon atoms; R.sup.2 is alkyl having 1 to 3 carbon atoms; R.sup.3 is alkylcarbonyloxyethyl having 1 to 3 carbon atoms in the alkyl moiety, alkoxycarbonyloxyethyl having 1 to 4 carbon atoms in the alkoxy moiety, methoxyethoxycarbonyloxyethyl or ethoxyethoxycarbonyloxyethyl; and R.sup.4 is one of the definitions of R.sup.3 or cyanoethyl; or mixtures of at least two species of said formula are used for dyeing and printing hydrophobic fiber materials.Type: GrantFiled: February 5, 1987Date of Patent: September 6, 1988Assignee: Cassella AktiengesellschaftInventors: Ulrich Buhler, Manfred Hahnke, Michael Kunze, Albert Bode