Purification Or Recovery Patents (Class 534/887)
-
Publication number: 20120271020Abstract: A method for producing a copolymer for semiconductor lithography containing less metal impurities, and a method for purifying a polymerization initiator for production of the copolymer, are provided. The method for purifying a polymerization initiator to be used for production of a polymer includes a filtering step wherein a solution of a polymerization initiator dissolved in an organic solvent is allowed to pass through a filter having a nominal pore size of not more than 1.0 ?m, to reduce the sodium content of the polymerization initiator solution to not more than 300 ppb with respect to the weight of the polymerization initiator. Further, the method for producing a copolymer for semiconductor lithography includes a polymerization step wherein the polymer for semiconductor lithography is synthesized by a radical polymerization reaction in the presence of a polymerization initiator purified by the above purification method.Type: ApplicationFiled: April 20, 2012Publication date: October 25, 2012Applicant: Maruzen Petrochemical Co., Ltd.Inventor: Youji SUZUKI
-
Patent number: 7999086Abstract: The invention provides a method of conditioning azo pigments containing carboxylic ester groups, using glycol monoalkyl ethers or mixtures of glycols and glycol dialkyl ether.Type: GrantFiled: January 30, 2009Date of Patent: August 16, 2011Assignee: Clariant Finance (BVI) LimitedInventors: Jens Paetzold, Carsten Plueg, Frank Alfter
-
Patent number: 7982019Abstract: The present invention provides a method for producing dry organic pigment, comprising the successive steps of, in this order: a first step wherein a wet organic pigment is obtained by drying an organic pigment presscake at 70 to 150° C. to a moisture content of 5 to 30%, and a second step wherein a dry organic pigment is obtained by pulverizing and drying the wet organic pigment at a temperature that is higher than the temperature employed in the first step but lower than the decomposition temperature of the organic pigment. The method for producing dry organic pigment enables the dry organic pigment to be obtained with superior productivity while consuming less energy than conventional methods.Type: GrantFiled: October 16, 2007Date of Patent: July 19, 2011Assignee: DIC CorporationInventors: Akihiro Ogata, Nagatoshi Kobayashi
-
Patent number: 7923540Abstract: The present invention is directed to 2-[[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxo-propyl]azo]-benzoic acid (C.I. Pigment Yellow 151): (I), characterized by a ?E* (black/white) in masstone below 22.0±0.7, a process for its preparation and its use for pigmenting macromolecular organic materials of natural or synthetic origin. The pigment has high opacity and high color strength.Type: GrantFiled: January 8, 2007Date of Patent: April 12, 2011Assignee: BASF SEInventors: Hans Reichert, Max Hügin, Ulrich Veith, Sibylle Soder, Thomas Eichenberger
-
Patent number: 7847073Abstract: A process for producing a liquid formulation of salts of sulfonated azo dyes by coupling an at least equimolar amount of diazotized aminoarylsulfonic acids I H2N—Ar—SO3H??(I), where Ar is phenylene (which may be monosubstituted by sulfo) or naphthylene (which may be mono- or disubstituted by sulfo and/or monosubstituted by hydroxyl) onto the coupling product of an unsubstituted or methyl-substituted phenylenediamine with itself comprises dissolving the azo dye in a basic medium and then subjecting the solution to a nanofiltration.Type: GrantFiled: May 18, 2005Date of Patent: December 7, 2010Assignee: BASF AktiengesellschaftInventors: Gunter-Rudolf Schroeder, Juergen Decker, Helmut Reichelt, Ingo Klopp, Armin Diefenbacher, Hartwig Voss
-
Patent number: 7709614Abstract: Novel crystalline modifications (eta, theta, iota, kappa) of the C.I. Pigment Yellow 181, obtained when one of the known phases or another inventive phase of said pigment is treated with specific solvents. The novel crystalline phases are characterized by yellow shades and excellent coloring properties.Type: GrantFiled: June 15, 2005Date of Patent: May 4, 2010Assignee: Clariant Produkte (Deutschland) GmbHInventors: Martin U. Schmidt, Gerald Mehltretter
-
Patent number: 7342062Abstract: Monoazo metal complex compound containing composition, the incidence of skin sensitization in a skin sensitization potential test based on the maximization method of said composition being not more than 20% and method for producing said composition which comprises a step for removing impurity substances using an alcoholic organic solvent; charge control agent comprising said composition and toner containing said charge control agent; coloring agent containing said composition and colored thermoplastic resin composition containing said coloring agent.Type: GrantFiled: November 12, 2003Date of Patent: March 11, 2008Assignee: Orient Chemical Industries, LtdInventors: Akihiro Tada, Tohru Tsuruhara
-
Patent number: 7262284Abstract: A method for the production of a diazo pigment, or a mixture of diazo pigments, according to formula (I) of the specification by azo coupling, wherein the azo coupling product is subjected to a finish in an organic solvent or in an agueous organic solvent with a neutral or alkaline pH.Type: GrantFiled: May 27, 2003Date of Patent: August 28, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Olaf Schupp, Felix W. Grimm, Manfred Opravil, Joachim Weber
-
Patent number: 6335431Abstract: A method of separation of a racemic isomer and a meso isomer from a mixture of a racemic isomer and a meso isomer of a compound shown by the general formula [1] (wherein R1 and R2 are each independently a lower alkyl group or a cyano group, which are different from each other, R3 and R4 are each independently a lower alkyl group, and R5 is a hydrogen atom or a lower alkoxy group), which comprises treating the mixture with a water soluble organic solvent.Type: GrantFiled: January 10, 2001Date of Patent: January 1, 2002Assignee: Wako Pure Chemical Industries, Ltd.Inventor: Toshiyasu Ito
-
Publication number: 20010020088Abstract: A method for separation of a racemic isomer and a meso isomer from a mixture of a racemic isomer and a meso isomer of a compound shown by the general formula [1] 1Type: ApplicationFiled: January 10, 2001Publication date: September 6, 2001Applicant: Wako Pure Chemical Industries, Ltd.,Inventor: Toshiyasu Ito
-
Patent number: 6031083Abstract: The new disazo dyestuffs of the formula (I) ##STR1## wherein the substituents and the indices have the meanings given in the description,wherein more than 25 equivalent % of all the M cations in the molecule are alcohol ammonium radicals of the formula .sup..sym. NR.sub.1 R.sub.2 R.sub.3 R.sub.4 whereinR.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another represent hydrogen, C.sub.1 -C.sub.4 -alkyl and C.sub.2 -C.sub.4 -hydroxyalkyl, with the proviso that at least one of the radicals R.sub.1 -R.sub.4 denotes C.sub.2 -C.sub.4 -hydroxyalkyl,are excellently suitable for dyeing cellulose-containing materials, and in particular paper, and are distinguished by high degrees of fastness.Type: GrantFiled: March 19, 1999Date of Patent: February 29, 2000Assignee: Bayer AktiengesellschaftInventors: Klaus Kunde, Wolfgang Zarges
-
Patent number: 5958128Abstract: In the method of manufacturing a disazo pigment according to the present invention, a superior coupling reaction rate during the coupling reaction process makes it possible to manufacture a disazo pigment having superior transparency, brightness, color strength and gloss for the case in which a color strength agent is used. In this method, a coupling reaction is carried out while continuously feeding a coupler aqueous solution comprising a coupler component having the general formula (I) shown below and a tetrazo aqueous solution comprising a benzidine derivative tetrazo component at a molar ratio of 2:0.8.about.0.99 into an acidic aqueous solution held in a batch type mixing vessel. ##STR1## (where each of X, Y, Z independently represents H, CH.sub.3, OCH.sub.Type: GrantFiled: October 24, 1997Date of Patent: September 28, 1999Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yoshimi Kikuchi, Hitoshi Sugamo
-
Patent number: 5910577Abstract: Compounds of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are Cl, COO(C.sub.1 -C.sub.4)-alkyl, CONH.sub.2, CONCH.sub.3, CON(CH.sub.3).sub.2 or SO.sub.2 NRR', where R and R' are identical or different and are hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl, it being possible for phenyl to be substituted by methyl, ethyl, methoxy, ethoxy or halogen,R.sup.3 is hydrogen, methyl, methoxy, ethoxy, chloro or bromo, andR.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, chloro or bromo,are useful yellow pigments with high light fastness and weather fastness properties.Type: GrantFiled: July 31, 1998Date of Patent: June 8, 1999Assignee: Clariant GmbHInventors: Hans Joachim Metz, Joachim Weber
-
Patent number: 5874547Abstract: A process for diazotizing an amine comprises the steps of oxidizing nitric oxide in solution with an oxidizing agent to maintain an equilibrium concentration of a diazotizing agent and reacting a primary aromatic amine in situ with said diazotizing agent in said solution.Type: GrantFiled: June 5, 1997Date of Patent: February 23, 1999Assignee: Crompton & Knowles CorporationInventors: John W. Larsen, Tracey McCracken, Jay E. Rowe, Lee A. Schaeffer
-
Patent number: 5852179Abstract: The use of alkoxylated acetylenic diol surfactants in the aqueous synthesis of disperse azo dyes provides a simple process for improving filtration properties of dyestuff. The surfactants may be added prior to the coupling step of the synthesis or prior to heat treatment of the dye slurry. Advantages that are realized by incorporation of the surfactants into the synthesis include decreased filtration time, increased solid content in filter cake, improved washing properties of filter cake, and increased dye yield. In addition, for azo dyes that are synthesized as non-heat-stable crystal modifications, the presence of alkoxylated acetylenic diol surfactants in the dye slurry is effective in promoting the conversion of the dye to the desired thermally stable crystal modification.Type: GrantFiled: May 27, 1998Date of Patent: December 22, 1998Assignee: Air Products and Chemicals, Inc.Inventor: Gregory Paul Dado
-
Patent number: 5834603Abstract: A polymerization initiator composition, comprising an azobisamidine salt represented by the general formula (1) ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group or a cycloalkyl group, providing that R.sup.1 and R.sup.2 may together form an aliphatic ring, and Y represents --C(.dbd.NR.sup.3)--NH--R.sup.4 or a guanyl group represented by the formula (2) ##STR2## wherein R.sup.3 and R.sup.4 independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, an allyl group, a phenyl group, or a substituted phenyl group, R.sup.5 represents a lower alkylene group optionally containing a substituent group, and R.sup.6 represents a hydrogen atom or a hydroxyalkyl group, and X represents a chlorine atom, a bromine atom, or a CH.sub.3 COO-- group, and a hydrophilic organic compound.Type: GrantFiled: November 19, 1997Date of Patent: November 10, 1998Assignee: Nippoh Chemicals Co., Ltd.Inventors: Tsuneo Tsubakimoto, Toshiyasu Sato, Hisayuki Suzuki
-
Patent number: 5650498Abstract: The present invention provides a process for producing a spherical granule of a water-soluble azo compound, which comprises dispersing a water-soluble azo compound in a water-insoluble solvent and then add dropwise water or a hydrophilic solvent dissolving the water-soluble azo compound with stirring to granulate the water-soluble azo compound in the solution, and produce the spherical granule of the water-soluble azo compound.Type: GrantFiled: October 19, 1994Date of Patent: July 22, 1997Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Hideo Amo, Masaya Kajimoto, Akihiko Goto
-
Patent number: 5559216Abstract: An ecologically and economically advantageous process for preparing a disazo pigment of the formula (I) or a mixture of said disazo pigments ##STR1## where D.sup.1 and D.sup.2 are identical or different and each is unsubstituted phenyl, phenyl with from 1 to 5 substituents, unsubstituted naphthyl, naphthyl with from 1 to 3 substituents, unsubstituted anthraquinonyl, anthraquinonyl with from 1 to 3 substituents, or a radical of a fused aromatic heterocycle which contains from 1 to 3 identical or different heteroatoms from nitrogen or oxygen and sulfur and is unsubstituted or has from 1 to 3 substituents,R.sup.1 and R.sup.2 are identical or different and each is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.Type: GrantFiled: September 1, 1993Date of Patent: September 24, 1996Assignee: Hoechst AGInventors: Ruediger Jung, Joachim Weide, Hans J. Metz
-
Patent number: 5532344Abstract: A process for producing a monoazodye of the following formula (III): ##STR1## wherein X.sup.1 is nitro or halogen, X.sup.2 is halogen, R.sup.1 is lower alkoxy, R.sup.2 is lower alkyl, each of R.sup.3 and R.sup.4, which are independent of each other, is alkyl, cyanoalkyl or alkylcarbonyloxyalkyl, and each of m and n, which are independent of each other, is 0 or 1, which comprises diazotizing an aniline derivative of the following formula (I): ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, followed by coupling with an aniline derivative of the following formula (II): ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, m and n are as defined above, wherein a reaction mixture obtained by the coupling reaction is heat-treated in the presence of a polyoxyethylene higher fatty acid ester type nonionic surfactant, followed by filtration to obtain said monoazo compound in the form of a cake.Type: GrantFiled: March 29, 1993Date of Patent: July 2, 1996Assignee: Dystar Japan Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara, Yoshiharu Hamano, Shinji Kubo
-
Patent number: 5508389Abstract: If highly concentrated aqueous solutions of azo dyes are prepared directly by diazotization and coupling reactions, appreciable difficulties generally result as a consequence of the fact that the diazotization and coupling reactions give rise to viscous phases which lead to stirring problems in the reaction apparatus used, which in turn results in an incomplete synthesis. The novel process for preparing concentrated aqueous dye solutions of an anionic dye in an aqueous medium overcomes this disadvantage by carrying out the diazotization of the aromatic amine diazo component and/or the coupling reaction between the diazonium salt and the coupling component in the presence of an auxiliary which exerts a viscosity-reducing effect on pasty phases. Examples of such auxiliaries are optionally alkyl-substituted naphthalenesulfonic acid-formaldehyde condensation products, ligninsulfonates, polyacrylates and copolymers of maleic anhydride and methacrylic acid or acrylic acid.Type: GrantFiled: March 26, 1993Date of Patent: April 16, 1996Assignee: Hoechst AktiengesellschaftInventors: Peter Mischke, Kurt Hohmann, Eckhard Schwab, Manfred Sittig
-
Patent number: 5504199Abstract: A dye which is either 2-naphthalenol (phenylazo) phenyl azo alkyl derivatives and 1,4-dialkylamino anthraquinone is added to sufficient non-ionic surfactant to compatibilize it with ethanol and an solvent to produce a homogeneous solution. The homogeneous solution is added to ethanol in an amount to provide a desired amount of coloration to the ethanol.Type: GrantFiled: October 28, 1994Date of Patent: April 2, 1996Assignee: Morton International, Inc.Inventors: Alejandra Zimin, Peter A. Caputo, Michael R. Friswell, David L. Booth, Michael P. Hinton
-
Patent number: 5502170Abstract: Azo dyes of the formula ##STR1## where L.sup.1, L.sup.2, L.sup.3, L.sup.4, X and K are as defined in the specification, and crystal forms of thienylazobenzene dyes are useful for dyeing or printing textile materials such as polyesters, fibers or fabrics made of cellulose esters or polyamides or blend fabrics from polyester and cellulose fibers with high color strength, good fastness properties and brilliant hues.Type: GrantFiled: May 17, 1995Date of Patent: March 26, 1996Assignee: BASF AktiengesellschaftInventors: Sabine Gruettner-Merten, Helmut Reichelt, Arno Lange, Helmut Degen
-
Patent number: 5502173Abstract: 2,4,6-trifluoro-5-chloro-pyrimidine and the aqueous solution of a salt of 2-amino-5-aminomethyl-naphthalene-1-sulphonic acid are simultaneously metered into a reactor in approximately equimolar amounts and afford a valuable intermediate for the preparation of high-purity dyes.Type: GrantFiled: September 27, 1994Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventors: Horst Ja/ ger, Siegbert Arnold, Richard Sommer
-
Patent number: 5493011Abstract: Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings.These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides.Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.Type: GrantFiled: November 6, 1992Date of Patent: February 20, 1996Assignee: Hoechst AGInventors: Rudiger Jung, Reinhold Deubel
-
Patent number: 5489672Abstract: A process for the production of a dis-azo pigment which is excellent in sanitary condition and almost free of a residual coupler component and decomposition products derived from the residual coupler component, and has a reduced aromatic amine content, and a dis-azo pigment produced by the said process, the process comprising the steps of (a) coupling-reacting a solution of a tetrazonium salt of benzidine with a slurry of acetoacetanilide of which the amount is stoichiometrically excess relative to an amount of said tetrazonium salt, to prepare a dis-azo pigment slurry, and (b) adding a halogen to the dis-azo pigment slurry to treat the acetoacetanilide in said slurry.Type: GrantFiled: October 26, 1994Date of Patent: February 6, 1996Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Osamu Shiromaru, Hitoshi Sugamo
-
Patent number: 5459246Abstract: New reactive dyestuffs which, in the form of the free acid, correspond to the following formula ##STR1## wherein the substituents have the meaning given in the description, are suitable for dyeing and printing materials containing hydroxyl groups or amide groups, in particular cellulose materials.Type: GrantFiled: May 4, 1993Date of Patent: October 17, 1995Assignee: Bayer AktiengesellschaftInventors: Horst Jager, Klaus Wunderlich
-
Patent number: 5446135Abstract: Dyes having the specific structural formula (1) set out below, their copper salt dyes, water-soluble azo dyes containing the dyes or the copper salt dyes, and polarizing films containing the water-soluble azo dyes: ##STR1## wherein A means a benzene or naphthalene ring having a sulfone group or a base thereof, Y and Z individually denote a group of the following formula (a); ##STR2## wherein R.sup.2 is a hydrogen atom, a methyl group, a methoxyl group or an ethoxyl group and R.sup.3 is a methyl, methoxyl or ethoxyl group,R.sup.1 represents an amino, C.sub.1-4 alkylamino, C.sub.2-4 alkylcarboxyamino, benzoylamino or phenylamino group bonded to the 6 or 7 position of the naphthalene ring, and X denotes a hydrogen, sodium, potassium or lithium atom, with the proviso that Y and Z are different but, when both R.sup.2 s are hydrogen atoms and both R.sup.3 s are methoxyl groups, Y and Z may be the same.Type: GrantFiled: March 14, 1994Date of Patent: August 29, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
-
Patent number: 5428136Abstract: Disazo compounds of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are a hydrogen or halogen atom or a C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyl, nitro, cyano or trifluoromethyl group and the rings A, B, C and D independently of one another are unsubstituted or contain one or more substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.5 -carbalkoxy, C.sub.2 -C.sub.5 -alkanoyl, benzoyl, acyloxy, acylamino, unsubstituted or N-mono- or N,N-disubstituted carbamoyl or unsubstituted or N-mono- or N,N-disubstituted sulfamoyl, possible substituents being C.sub.1 -C.sub.4 -alkyl or mono- to trisubstituted phenyl; C.sub.1 -C.sub.4 -alkylamino or phenylamino; C.sub.1 -C.sub.Type: GrantFiled: July 29, 1993Date of Patent: June 27, 1995Assignee: Hoechst AGInventors: Rudiger Jung, Joachim Weide, Hans J. Metz
-
Patent number: 5356440Abstract: The invention relates to a process for the dyeing of synthetic polyamide fibre materials, which comprises dyeing these fibre materials with a reactive dye of the formulaHO.sub.3 S--Fa--X--SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H).sub.m(1),in which Fa is a dye radical, X is a direct bond or a radical of the formula --CONHCH.sub.2 CH.sub.2 -- and m is the number 1 or 2, the dye of the formula (1) containing only one sulfo group, from an aqueous liquor at a pH of 5 to 9 and, to set the dyeing temperature, raising the temperature from 80.degree. C. to at least 95.degree. C. over a period of at least 20 minutes. The process according to the invention produces level dyeings on synthetic polyamide fibre materials.Type: GrantFiled: July 22, 1993Date of Patent: October 18, 1994Assignee: Ciba-Geigy CorporationInventors: Pierre Galafassi, Jean-Marie Adam
-
Patent number: 5354850Abstract: Water-soluble disazo compounds, a process for their preparation and their use as dyes.Disazo compounds are described which have the formula (1) given and defined below and are used in their function as fiber-reactive dyes for the dyeing of hydroxy- and/or carboxamido-containing fiber material, such as cellulose fiber materials and synthetic and natural polyamide fiber materials, such as wool. They produce brown dyeings and prints having high color strength and good color fastness by the application and fixation methods customary for fiber-reactive dyes ##STR1## in which R is hydrogen or sulfo,R.sup.1 is hydroxy, methoxy or ethoxy,is hydrogen or an alkali metal and the non-fixed sulfo group in the naphthylene radical is in the 6 or 7 position.Type: GrantFiled: June 24, 1993Date of Patent: October 11, 1994Assignee: Hoechst AGInventors: Andreas von der Eltz, Werner H. Russ
-
Patent number: 5258505Abstract: Disclosed herein is an azo compound represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each are a group or atom selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 4 carbon atoms, a methoxy group, halogen atoms, COOM and COOR.sub.4 in which R.sub.4 is an alkyl group having 1 to 4 carbon atoms, and M denotes an alkali metal atom, or an ammonium or organic ammonium ion. An ink containing this compound is suitable for use in an ink-jet recording.Type: GrantFiled: March 27, 1992Date of Patent: November 2, 1993Assignee: Canon Kabushiki KaishaInventors: Tsuyoshi Eida, Mayumi Yamamoto, Takao Yamamoto
-
Patent number: 5243033Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently of one another, are C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, ureido, C.sub.1 -C.sub.4 acylamino, carboxyl and sulfo and n, m and p, independently of one another, are the number 0, 1, 2 or 3, X is fluorine or chorine and Z is an aliphatic, araliphatic, aromatic or heterocyclic amino group free from fibre-reactive radicals; or Z is the radical of an aliphatic or aromatic diamine which contains the radical of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3, n, m, p and X are as defined, bound via the second amino group; or Z is a radical of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3, n, m, and p are as defined; or Z is a radical --NH--SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 H; and the reactive dye of the formula (1) contains at least two sulfo groups, produce, on cellulose fibres, orange dyeings of high color strength and prints of good fastness properties.Type: GrantFiled: January 13, 1992Date of Patent: September 7, 1993Assignee: Ciba-Geigy CorporationInventor: Athanassios Tzikas
-
Patent number: 5241058Abstract: Azo dye salts corresponding to formula I are suitable as masking couplers. ##STR1## In Formula I, A denotes an optionally substituted aryl group;CC denotes a group optionally carrying a ballast group and capable of coupling under the conditions of photographic color development to produce a dye preferably a cyan dye (color coupler residue);L denotes a linking member which is attached at the coupling position of the color coupler residue by an oxygen, sulphur or nitrogen atom;Z denotes a group conferring solubility in alkalies;R denotes NH--CO--R.sup.1, NH--SO.sub.2 --R.sup.1, COOR.sup.2 or NR.sup.1 --R.sup.2 ;R.sup.1 denotes an optionally substituted alkyl or aryl group;R.sup.2 denotes H or a group such as R.sup.1 ;[M.sup..sym. ] denotes a mixture of organic and inorganic cations optionally containing protons, in which the proportion of organic cation amounts to at least 1/2 mol per mol of dye;m stands for 0, 1 or 2; andn stands for 1, 2, 3 or 4; n.gtoreq.m.Type: GrantFiled: May 15, 1991Date of Patent: August 31, 1993Assignee: Agfa-Gevaert AktiengesellschaftInventors: Gunter Renner, Hans Langen, Ulrich Klein
-
Patent number: 5239063Abstract: Fiber reactive azo dyestuffs of the formula ##STR1## in which R=H or C.sub.1 -C.sub.6 alkyl, which can be substituted with OH, Hal, SO.sub.3 H or OSO.sub.3 H;Z=heterocyclic five or six membered ring;n, m=0, 1 or 2, wherein n+m=0, 1 or 2;Y=OH, OR, NR.sub.2 R.sub.3, OMe; andR.sub.2, R.sub.3, =H, R and R.sub.2, R.sub.3 and N can form a heterocyclic 5 or 6-membered ring.Type: GrantFiled: January 9, 1992Date of Patent: August 24, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Hoppe, Martin Michna, Karl-Josef Herd, Frank-Michael Stohr
-
Patent number: 5229503Abstract: The invention relates to azo compounds, especially to compounds of formula ##STR1## wherein R.sub.1 is lower alkyl, R.sub.2 is lower alkyl, R.sub.3 is hydrogen, carboxy or sulfo, R.sub.4 is carboxy or sulfo, G is an unsubstituted or substituted 1,4-phenylene group or an unsubstituted or substituted 1,4-naphthylene group, and wherein either R.sub.5 and R.sub.6 together are an additional bond and L is an oxygen or sulfur atom or wherein R.sub.5 is hydrogen, R.sub.6 is halomethyl and L is an oxygen atom, and salts thereof, to the use of compounds I and their salts, to a process for the preparation of compounds I and their salts, to starting materials used in that preparation process, and salts thereof, to a process for the preparation of those starting materials and their salts, to a device in which the compounds I and their salts are used, and to a process in which that device is used.Type: GrantFiled: September 11, 1991Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventor: Jui Y. Chang
-
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
-
Patent number: 5216138Abstract: There are described water soluble azo compounds conforming to the formula (1)D--N.dbd.N--K (1)where D is a radical of the formula (2), (2a) or (2b) ##STR1##where Y is a substituent which is eliminable by alkali to form a vinyl group, Y.sup.2 has one of the meanings of Y or is hydroxyl, X is chlorine or bromine, and R is hydrogen, lower alkyl, phenyl or halogen, and K is a radical of a singly couplable coupling component which may additionally contain an azo group, or the radical of a doubly couplable coupling component.The compounds of the formula (1) have fiber-reactive properties and are very highly suitable for use as dyes for dyeing hydroxy- and/or carboxamido-containing material, in particular fiber material, for example cellulose-fiber materials, wool and synthetic polyamide fibers, in strong, fast shades.There are also described novel starting compounds of the formulae (7), (7a) and (7b) ##STR2##where Y.sup.2, X and R are each as defined above, x is zero or 2 and W is nitro or amino.Type: GrantFiled: November 27, 1991Date of Patent: June 1, 1993Assignee: Hoechst AktiengesellschaftInventor: Jorg Dannheim
-
Patent number: 5212289Abstract: Dyestuffs in the form of their free acid have the following formula (1) ##STR1## in which the substituents have the meaning given in the description. The dyestuffs according to the invention are suitable for dyeing hydroxyl-containing fiber materials in yellow shades.Type: GrantFiled: June 10, 1991Date of Patent: May 18, 1993Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Karl-Heinz Schundehutte, deceased, Eva Schundehutte, heir, Horst Jager
-
Patent number: 5200512Abstract: There are described azo compounds which possess fiber-reactive groups and have valuable dye properties and are capable of dyeing hydroxy- and/or carboxamido-containing materials, in particular fiber materials, such as cellulose fibers and natural and synthetic polyamide such as wool, in strong, fast shades. They conform to the formula (1) ##STR1## where D is phenyl or naphthyl which are each substituted, at least one of these substituents being a water-solubilizing group or containing a water-solubilizing group;Y is fluorine, chlorine or a group of the formula--A--RwhereA is oxygen or the group NH andR is hydrogen, cycloalkyl or alkyl which may be interrupted by one or two hetero groups, or is benzyl, sulfomethyl, .beta.-sulfoethyl or cyano;X is fluorine, chlorine or a group conforming to the formula --NH--B, whereB is a group of the formula (3a), (3b) or (3c) ##STR2## where alk is alkylene which may be interrupted by one or two hetero groups,Z is a vinyl or an ethyl group which is substituted in the .beta.Type: GrantFiled: December 27, 1991Date of Patent: April 6, 1993Assignee: Hoechst AGInventor: Uwe Reiher
-
Patent number: 5175258Abstract: A process for the preparation of photogenerating pigments which comprises the reaction of a diaminofluorenone with an alkali nitrite, an acid, and a tetrafluoroborate; thereafter reacting the resulting product with an anilide coupler; and subsequently annealing the product obtained.Type: GrantFiled: December 14, 1990Date of Patent: December 29, 1992Assignee: Xerox CorporationInventors: Kock-Yee Law, Ihor W. Tarnawskyj
-
Patent number: 5136028Abstract: Novel reactive dyes of formula ##STR1## wherein Z is a radical of formula ##STR2## and R.sub.1, R.sub.2, R.sub.3, (R.sub.4).sub.2-3, (R.sub.5).sub.1-3, R.sub.7 and (R.sub.8).sub.1-3 are as defined in claim 1, give intense red dyeings and prints of good fastness properties on cellulosic fibres.Type: GrantFiled: November 9, 1990Date of Patent: August 4, 1992Assignee: Ciba-Geigy CorporationInventor: Herbert Seiler
-
Patent number: 5118737Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.Type: GrantFiled: June 22, 1990Date of Patent: June 2, 1992Assignee: Canon Kabushiki KaishaInventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
-
Monoazo pigments derived from diazotized di- or trichloroanilines, preparation thereof and their use
Patent number: 5086168Abstract: The invention relates to monoazo pigments prepared from dichloroanilines as diazo components and CH-acidic coupling components of the acetoacetarylamide or naphthol series, these pigments only containing an extremely low level of polychlorinated biphenyls (PCBs) (at most 25 .mu.g per g of pigment).The process for preparing the pigments takes the form of an azo coupling in an aqueous medium, whereina) azo coupling is effected by adding the diazonium salt solution to a suspension or solution of the coupling component or by simultaneously metering the aqueous suspensions or solutions of the diazonium salt and of the coupling component into the reaction mixture,b) azo coupling is effected at a pH or within a pH range of less than pH 7 andb1) between pH 4 and 7 during and after azo coupling less than 0.Type: GrantFiled: September 5, 1990Date of Patent: February 4, 1992Assignee: Hoechst AktiengesellschaftInventor: Wolfgang Rieper -
Patent number: 5079347Abstract: Disazo compounds conforming to a general formula (1) shown below which have fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing fiber materials, such as wool and in particular cellulose, in strong fast shades. ##STR1## where R is a hydrogen atom or a sulfo group,R.sup.1 is a hydroxy group, a methoxy group or an ethoxy group,M is a hydrogen atom or an alkali metal,X is a chlorine atom or a fluorine atom,Y is a chlorine atom or an amino group or a group of the general formula (2) ##STR2## where R* is a hydrogen atom or a methyl or ethyl group,n is zero, 1 or 2,R.sup.2 is a hydrogen atom or a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group, andR.sup.3 is a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group,it being possible for R.sup.2 and R.sup.3 to be identical to or different from each other.Type: GrantFiled: December 6, 1988Date of Patent: January 7, 1992Assignee: Hoechst AktiengesellschaftInventor: Holger M. Buch
-
Patent number: 5073634Abstract: Basic dyes of the formulaChr.sup..sym.[FeCl.sub.4 ].sup..crclbar.where Chr.sup.a is a dye cation are useful for dyeing acrylonitrile polymers or acid-modified polyesters.Type: GrantFiled: May 1, 1990Date of Patent: December 17, 1991Assignee: BASF AktiengesellschaftInventors: Johannes P. Dix, Guenter Hansen, Hellmut Kast
-
Patent number: 5070189Abstract: Water-soluble azo compounds which have fiber-reactive dyestuff properties and dye materials containing carboxamide and/or hydroxyl groups, such as fiber materials, in particular cellulose fiber materials, in strong, fast, predominantly bluish-tinged red to orange shades; they correspond to the general formula (1) ##STR1## in which: M is a hydrogen atom or an alkali metal;R is alkyl having 1 to 4 carbon atoms;D is a group of the formula ##STR2## in which R.sup.1 is hydrogen, alkyl having 1 to 4 carbon atoms, hydroxy, nitro, alkoxy having 1 to 4 carbon atoms, chlorine, bromine or carboxy, R.sup.2 is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 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;m is the number zero or 1;n is the number zero or 1; andX and Y are both independently of one another vinyl, .beta.-thiosulfatoethyl or .beta.-sulfatoethyl.Type: GrantFiled: August 24, 1989Date of Patent: December 3, 1991Assignee: Hoechst AktiengesellschaftInventors: Ludwig Schlafer, Werner H. Russ
-
Patent number: 5068438Abstract: N-Alkyl-N'-phenyl-p-phenylenediamine particles, which are not easily broken during transportation or in a hopper and can be easily automatically metered, are prepared by a surface treating process wherein granulated N-alkyl-N'-phenyl-p-phenylenediamine particles are charged in a rotatable vessel and the vessel is then rotated at a temperature lower than the melting point of the N-alkyl-N'-phenyl-p-phenylenediamine, to cause the N-alkyl-N'-phenyl-p-phenylenediamine particles to freely flow.Type: GrantFiled: December 7, 1989Date of Patent: November 26, 1991Assignee: Mitsubishi Monsanto Chemical CompanyInventor: Katsumi Kobayashi
-
Patent number: 5053495Abstract: A dye which, in the free acid form, has the formula ##STR1## wherein W is COOHX is selected from H, COOH, SO.sub.3 H, halo, hydroxy, nitro, cyano, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy and C.sub.1-6 -acylamino;Y is H, COOH or SO.sub.3 H;Z is H, COOH or SO.sub.3 H;R & R.sup.1 are each independently H or C.sub.1-6 -alkyl substituted by 0, 1 or 2 --COOR.sup.2 groups; andR.sup.2 is H or C.sub.1-6 -alkyl;provided that there are at least two COOH groups and that the number of COOH groups is equal to or greater than the number of SO.sub.3 H groups.The dye is adapted for the preparation of inks for use in ink jet printing in which it displays high water-fastness on paper.Type: GrantFiled: August 24, 1989Date of Patent: October 1, 1991Assignee: Imperial Chemical Industries PLCInventors: David Greenwood, Nigel Hughes, Ronald W. Kenyon, Suraj L. Hindagolla
-
Patent number: 5053494Abstract: A polyazo compound of the following formula, ##STR1## wherein F is a bisazo or trisazo dye moiety, R.sub.1, R.sub.2 and R.sub.3 are independently of one another are each hydrogen or alkyl, B.sub.1 and B.sub.2 independently of one another are each phenylene or naphthylene, Y.sub.1 and Y.sub.2 independently of one another are each --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 L in which L is group capable of being split by the action of an alkali. The compound is useful for dyeing or printing fiber materials to give dyed or printed products with superior dye performance such as build-up property.Type: GrantFiled: October 20, 1989Date of Patent: October 1, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Omura, Naoki Harada, Hirokazu Sawamoto
-
Patent number: 5047514Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.Type: GrantFiled: November 5, 1987Date of Patent: September 10, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Scheibli, Karl Seitz