Patents Represented by Attorney Edward M. Roberts
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Patent number: 4891153Abstract: Mixtures of fluorescent whitening agents consisting of 51 to 99% by weight of a symmetrically or unsymmetrically substituted first 1,4-bis(cyanostyryl)benzene and 49 to 1% by weight of an unsymmetrically substituted second 1,4-bis(cyanostyryl)benzene that differs from the first, a process for the preparation of said mixtures by condensing terephthalaldehyde with a di(C.sub.1 -C.sub.4)alkylphosphonomethylbenzonitrile to cyano-4-formylstilbene, which is further condensed, either direct or after isolation, with at least one other di(C.sub.1 -C.sub.4)alkylphosphonomethylbenzonitrile, the use of these mixtures for whitening polyester fibres, and compositions containing said mixtures for whitening polyester fibres.Type: GrantFiled: August 5, 1988Date of Patent: January 2, 1990Assignee: CIBA-GEIGY CorporationInventors: Leonardo Guglielmetti, Hans R. Meyer, Dieter Reinehr, Kurt Weber
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Patent number: 4859687Abstract: The described novel pyridine derivatives are those of the general formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3, or benzyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3,R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy,R.sub.3, R.sub.4 and R.sub.5 independently of one another are each hydrogen, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, NO.sub.2 and/or CF.sub.3,U and V independently of one another are each C.sub.1 -C.sub.6 -alkyl, or alkyl substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or together form one of the following alkylene bridges: ##STR2## R.sub.a is hydrogen, C.Type: GrantFiled: February 20, 1986Date of Patent: August 22, 1989Assignee: Ciba-Giegy CorporationInventor: Peter Riebli
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Patent number: 4859207Abstract: A process for dyeing textile planar fabrics made from natural or synthetic polyamides with anionic dyes by(a) locally applying a resist agent by itself or in conjunction with an anionic dye of fluorescent whitening agent,(b) subjecting the textiles to a heat treatment, and(c) carrying out ground dyeing with a dye liquor that contains a further anionic dye,which process comprises using, as resist agent, a melamine compound of formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently phenyl or naphthyl, each of which may be substituted by halogen, hydroxy, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, Z is an acid water-solubilizing group, and m is 1 to 6.Type: GrantFiled: July 19, 1988Date of Patent: August 22, 1989Assignee: Ciba-Geigy CorporationInventors: Thys Bouwknegt, Heinz Abel
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Patent number: 4847404Abstract: The invention relates to novel sulfone compounds of formula I ##STR1## wherein R.sub.1 is an unsubstituted or substituted phenyl or naphthyl radical,R.sub.2 is hydrogen or the radical of the formula ##STR2## R.sub.3 and R.sub.4 are --CN or --COOR.sub.5, in which R.sub.5 is C.sub.1 -C.sub.4 alkyl, with the proviso that, if R.sub.2 is the radical of the formula ##STR3## R.sub.3 and R.sub.4 in formula I may be identical or different. The compounds of the invention are valuable intermediates for the preparation of fluorescent whitening agents of the stilbene series.Type: GrantFiled: July 25, 1988Date of Patent: July 11, 1989Assignee: Ciba-Geigy CorporationInventors: Kurt Burdeska, Kurt Weber, Dieter Reinehr
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Patent number: 4806657Abstract: A process for the preparation of fluoran compounds which are substituted by basic groups and have the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen, halogen or lower alkyl, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached are a fused benzene nucleus,X.sub.1 and X.sub.2 are each independently hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, orX.sub.1 and X.sub.2 together with the nitrogen atom to which they are attached are a 5- or 6-membered heterocyclic radical, andY is unsubstituted or substituted alkyl, cycloalkyl, aryl or aralkyl, andthe ring A is unsubstituted or substituted, which process comprises reacting a ketonic acid of the formula ##STR2## with a substituted 4-formylaminophenol derivative of the formula ##STR3## wherein A, R.sub.1, R.sub.2, R.sub.3, X.sub.1, X.sub.Type: GrantFiled: May 5, 1986Date of Patent: February 21, 1989Assignee: Ciba-Geigy CorporationInventor: Rudolf Zink
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Patent number: 4804757Abstract: The invention relates to novel suylfonylureas of the formula I ##STR1## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.2 and R.sub.3, each independently of the other, are hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkylthio, C.sub.1 -C.sub.5 haloalkyl, halogen, C.sub.1 -C.sub.5 haloalkylthio, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, an alkoxyalkyl group or alkoxyalkoxy group, each containing not more than 6 carbon atoms,Z is oxygen or sulfur,E is --CH.dbd. or --N.dbd., andQ is an unsubstituted or substituted 6-membered heterocyclic radical containing 2 to 3 nitrogen atoms and bound through a carbon atom,and the salts thereof.A process for the preparation of the novel compounds and the use thereof are also described. The compounds of formula I can be used in the form of agriculturally useful compositions for controlling weeds and/or for selectively influencing plant growth.Type: GrantFiled: May 18, 1987Date of Patent: February 14, 1989Assignee: Ciba-Geigy CorporationInventors: Beat Bohner, Werner Fory, Rolf Schurter, Georg Pissiotas
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Patent number: 4784805Abstract: A novel process for the preparation of anthraquinoid intermediates and vat dyes by alkali fusion of suitable precursors in the presence of alcohol. The process comprises starting from benzanthrone, pyrazolanthrone or anthraquinone derivatives and carrying out the reaction in a machine with kneading action and in the presence of an alkali metal hydroxide and an aliphatic alcohol with a boiling point below 120.degree. C., at elevated temperature, to effect dimerization or cyclization, the weight ratio of alkali metal hydroxide to benzanthrone, pyrazolanthrone or anthraquinone derivative being <1:1.The process makes it possible to prepare in good quality anthraquinoid intermediate which can be further processed to dyes, as well as vat dyes which are suitable for dyeing or printing cellulosic material.Type: GrantFiled: May 7, 1987Date of Patent: November 15, 1988Assignee: Ciba-Geiby CorporationInventor: Rudolf Blattner
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Patent number: 4778928Abstract: The preparation of 4,4'-stilbenedialdehydes by reduction of 4,4'-stilbenedinitriles with an aluminium hydride.Type: GrantFiled: December 10, 1986Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventor: Dieter Reinehr
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Patent number: 4766253Abstract: The invention relates to a novel process for preparing chlorodiphenyl ethers of the formula I ##STR1## in which R is hydrogen or chlorine, which comprises heating a material of the formula III ##STR2## in which X is one equivalent of an alkali metal or alkaline earth metal ion and R is as defined above, in an excess of a dichlorobenzene of the formula II ##STR3## in the presence of a copper catalyst and of an aprotic solvent as cocatalyst at temperatures of 120.degree.-220.degree. C.Type: GrantFiled: May 4, 1987Date of Patent: August 23, 1988Assignee: Ciba-Geigy CorporationInventor: Peter Rauber
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Patent number: 4758667Abstract: There is disclosed a process for the preparation of 2-(imidazolin-2-yl)-3-pyridine and -3-quinolinecarboxylic acids of formula ##STR1## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.4 alkoxy, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.2 and R.sub.3 together are 1,3-butadienylene which can be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, nitro, cyano, phenyl, phenoxy, or phenyl or phenoxy, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: February 5, 1987Date of Patent: July 19, 1988Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Dieter Durr
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Patent number: 4731092Abstract: Textile cellulose material is printed or dyed with reactive dyes with the aid of foam. The foam is applied by applying to the cellulose material a foamed, aqueous preparation which contains in addition to dyes and fixing alkalis(1) a foam-forming agent(2) a homopolymer or copolymer of acrylamide or methacrylamide or preferably a graft polymer which is obtained from an addition product of an alkylene oxide, preferably propylene oxide, on an at least trihydric aliphatic alcohol, e.g. glycerol, and acrylamide or methacrylamide, and(3) an anionic graft polymer which has as grafting base a copolymerization product from (A) an alkyl acrylate or methacrylate, the alkyl radical having at least 8 carbon atoms, with (B) a dicarboxylic acid diester of an ethylenically unsaturated aliphatic dicarboxylic acid and a polyethylene glycol, a terminal hydroxyl group of the diol having been etherified with a C.sub.1 -C.sub.Type: GrantFiled: April 20, 1987Date of Patent: March 15, 1988Assignee: Ciba-Geigy CorporationInventor: Hans-Ulrich Berendt
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Patent number: 4681596Abstract: The invention relates to a process for dyeing natural or synthetic polyamide fibre material levelly from an aqueous liquor, with 1:1 metal complex dyes and at least one metal free dye, all of which contain sulfo groups, in the presence of an alkali metal salt or an ammonium salt and optionally in the presence of an assistant, which comprises carrying out dyeing in the presence of an alkali metal fluoride or ammonium fluoride, or an alkali metal fluorosilicate or ammonium fluorosilicate, or of an alkali metal fluoroborate or ammonium fluoroborate, at a pH in the range from 3 to 7.The process of this invention is suitable for dyeing natural or synthetic polyamide material in level shades of good fastness properties.Type: GrantFiled: May 9, 1986Date of Patent: July 21, 1987Assignee: Ciba-Geigy CorporationInventors: Gerhard Back, Walter Mosimann
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Patent number: 4676823Abstract: When applied as safeners, the haloacylaminoalkylphosphinates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides of the formula I below are able to protect cultivated plants from the phytotoxic effects of herbicides. Suitable crops are preferably sorghum, cereals, rice, maize and soya beans and the herbicides employed are chloroacetanilides and thiocarbamates.The haloacylaminoalkylphosphonates, haloacylaminoalkylphosphinates and haloacylaminoalkylphosphine oxides have the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkoxy or C.sub.1 -C.sub.4 cyanoalkoxy,R.sub.2 is hydrogen or a substitutent as defined for R.sub.1,R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or one of R.sub.3 and R.sub.4 is also a radical ##STR2## or both taken together with the carbon atom to which they are attached are also a C.sub.3 -C.sub.Type: GrantFiled: January 8, 1986Date of Patent: June 30, 1987Assignee: Ciba-Geigy CorporationInventors: Ludwig Maier, Hans Moser
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Patent number: 4605511Abstract: Stilbene fluorescent brightener solutions which are stable to metal ions and metal catalysts and contain a stilbene fluorescent brightener substituted by sulfo groups and a fatty amine oxyalkylation product of the formula ##STR1## in which Q is an aliphatic hydrocarbon radical having 12 to 22 carbon atoms, M is hydrogen or an alkali metal ion, ammonium ion or amine salt ion and m and n are integers, the sum of m and n being at least 2 and not more than 50, and their use for the fluorescent brightening of natural and synthetic fibrous materials.Type: GrantFiled: July 12, 1982Date of Patent: August 12, 1986Assignee: Ciba-Geigy CorporationInventor: Werner Fringeli
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Patent number: 4589911Abstract: Fused N-phenylsulfonyl-N'-triazinylurea of formula I ##STR1## wherein Z is oxygen or sulfur,R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, or a --X--R.sup.5, --CO--X--R.sup.6, --CO--NR.sup.7 R.sup.8, --SO--R.sup.9 or --SO.sub.2 --R.sup.10 group,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy,R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C.sub.3 -C.sub.6 cycloalkyl,R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 alkoxyalkoxy, C.sub.3 -C.sub.6 cycloalkyl or --NR.sup.11 R.sup.12,R.sup.5 is C.sub.3 -C.sub.5 alkynyl or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or is C.sub.3 -C.sub.5 alkenyl, which is unsubstituted or is substituted by halogen or C.sub.1 -C.sub.4 -alkoxy,R.sup.6 and R.sup.9 are each independently C.sub.1 -C.sub.Type: GrantFiled: May 1, 1984Date of Patent: May 20, 1986Assignee: Ciba-Geigy CorporationInventors: Josef Ehrenfreund, Werner Fory
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Patent number: 4588412Abstract: The invention relates to solid formulations of dyes which are insoluble or sparingly soluble in water, which formulations contain a dialkyl sulfosuccinate having 3 to 8 carbon atoms in each alkyl moiety, or a C.sub.3 -C.sub.6 alkylnaphthalenesulfonate and/or a branched or unbranched acetylene glycol containing 8 to 20 carbon atoms, in addition to the dye and one or more anionic dispersants, optionally together with further auxiliaries conventionally employed in powdered formulations.These formulations are characterized by very good wettability, excellent dispersibility and good redispersibility. The dyebaths and padding liquors prepared with these formulation are non-foaming or only low foaming and are in addition stably disperse. They are suitable for dyeing and printing natural and synthetic fibres.Type: GrantFiled: December 14, 1984Date of Patent: May 13, 1986Assignee: Ciba-Geigy CorporationInventor: Paul Hugelshofer
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Patent number: 4566901Abstract: The invention relates to novel oxime ethers of the formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R.sub.2 and R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical.These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides.Type: GrantFiled: April 29, 1983Date of Patent: January 28, 1986Assignee: Ciba-Geigy CorporationInventors: Henry Martin, Urs Fricker
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Patent number: 4560516Abstract: Ethylenediamine tetraacetonitrile is prepared in a two stage process by cyanomethylating an ethylenediamine formaldehyde adduct with hydrocyanic acid at 30.degree. C. or less under basic conditions (pH 8 to 10) to form, in a first discrete stage, ethylenediamine diacetonitrile (EDDiN) which is soluble in the reaction mixture. The solution of EDDiN is then further cyanomethylated under acidic conditions with formaldehyde and hydrocyanic acid in slight excess to form ethylenediamine tetraacetonitrile (EDTN). The precipitated EDTN, with or without isolation, can be hydrolyzed to form ethylenediamine tetraacetic acid in a stock solution for further processing. The process reduces the need for toxic cyanide waste treatment and greatly simplifies the procedures needed to protect the environment.Type: GrantFiled: January 31, 1985Date of Patent: December 24, 1985Assignee: Ciba-Geigy CorporationInventor: John J. Singer
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Patent number: 4519834Abstract: The ethynyl-phenylureas of the formula I ##STR1## wherein X is hydrogen, halogen, lower alkyl, lower alkoxy, haloalkyl or nitro, Y is oxygen or sulfur, R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, phenyl or benzyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or benzyl, R.sub.1 and R.sub.2 together with the nitrogen atom to which they are bound are also a pyrrolidine, piperidine, morpholino or piperazine ring, R.sub.3 is hydrogen or lower alkyl, and R.sub.4 is hydrogen, alkyl, phenyl, pyridyl, alkenyl, cycloalkyl or cycloalkenyl, are novel substances. They are characterized by strong herbicidal activity.Type: GrantFiled: July 11, 1983Date of Patent: May 28, 1985Assignee: Ciba-Geigy CorporationInventor: Henry Szczepanski
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Patent number: 4507240Abstract: A process for purifying crude monochloro- or monobromoanthraquinone is described. In this process, monochloro- or monobromoanthraquinone which contains by-products as impurities is mixed with a hot non-polar aliphatic solvent in such a ratio that more than half of the crude product goes into solution and the remainder which contains the impurities forms a second lower phase, said eutectic melt is separated, and the saturated solution is allowed to cool, and the monochloro- or monobromoanthraquinone, which precipitates in pure form, is isolated.Type: GrantFiled: November 23, 1983Date of Patent: March 26, 1985Assignee: Ciba-Geigy AGInventors: Tibor Somlo, Johann Regli