Purification Or Recovery Patents (Class 534/887)
  • Patent number: 4946948
    Abstract: Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Hari, Fridolin Babler
  • Patent number: 4942225
    Abstract: Preparation of diazo compounds by transfer of diazo groups to activated methylene compounds, characterized in that an azidoformamidinium salt is used as the diazo group transferring agent, and also preparation of azo compounds by this route.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: July 17, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Manfred Lorenz
  • Patent number: 4939242
    Abstract: A process for the preparation of the lithium azo compound of the formula ##STR1## having an Na content of less than 0.2% by weight, in particular less than 0.1% by weight, in which the lithium salt of 4-(.beta.-sulfatoethylsulfonyl)-aniline is diazotized in an aqueous solution or in an aqueous solution containing a water-miscible organic solvent by means of nitrosylsulfuric acid, and the product is coupled with the lithium salt of 1-hydroxy-7-acetylaminonaphthalene-3-sulfonic acid.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: July 3, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad Opitz, Marcos Segal
  • Patent number: 4937325
    Abstract: 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: Grant
    Filed: December 12, 1988
    Date of Patent: June 26, 1990
    Assignees: Cassella Aktiengesellschaft, Tokico Ltd.
    Inventors: Ulrich Buhler, Klaus Hofmann, Hiroshi Mitsuhashi, Harutsugu Ushiota, Akiharu Odagiri, Gen Kano, Susumu Sakamoto
  • Patent number: 4935502
    Abstract: When a diamine of the formula ##STR1## in which n is 1 to 4, is bis-diazotized and the resulting bis-diazo compound is coupled with 2 moles of one or more coupling components of the formula ##STR2## in which R.sup.1 is hydrogen, chlorine, bromine, methyl or methoxy and R.sup.2 is hydrogen or, if R.sup.1 is hydrogen, also methyl or ethyl, disazo compounds are obtained which are colorants. Due to their high fastness to light and to migration and their heat stability and dispersibility, these compounds are useful for pigmenting high molecular weight materials, especially polyolefins.
    Type: Grant
    Filed: August 22, 1989
    Date of Patent: June 19, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4933436
    Abstract: Azo dyes are obtained by diazotizing an aromatic amine and combining the resulting diazonium salt solution with a sulpho-containing coupling component when the sole acid donor used for the diazotization reaction--instead of the otherwise customary mineral or fatty acids--is a low molecular weight, nonsurfactantlike aromatic sulphonic acid.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: June 12, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Wolff, Karl-Heinz Wolf, Reinhold M. Klipper
  • Patent number: 4933437
    Abstract: The invention relates to a process for the preparation of asymmetrical 1:2 chromium complex azo dyes of not less than 90% purity and containing at least one water-solubilizing group, which process comprises reacting a mixture of two metallizable azo dyes that contain identical diazo components or identical coupling components, in the molar ratio of 0.85:1.0 to 1.2:1.0, with the proviso that only one of said two azo dyes contains at least one water-solubilizing group, with a chromium donor, under pressure and at a temperature above 100.degree. C. and in the pH range from 0 to 2, and subsequently carrying out further reaction in a weakly acid, neutral or weakly alkaline pH range, utilizing a single vessel for all stepsThe dyes obtained by the process of the invention are particularly suitable for dyeing wool or polyamide materials.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: June 12, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Iff, Daniel Parisot, Hans Schaller
  • Patent number: 4927538
    Abstract: The present invention provides a process for highly purifying C.I. Solvent Black 3 using specific aromatic hydrocarbons or petroleum hydrocarbons. The process comprises dissolving C.I. Solvent Black 3 represented by ##STR1## in an organic solvent selected from the group consisting of aromatic hydrocarbons having 6 to 12 carbon atoms and petroleum hydrocarbons having 6 to 10 carbon atoms followed by filtering, and then removing the solvent.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: May 22, 1990
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Hisashi Senshu, Masahiro Otsuka
  • Patent number: 4923972
    Abstract: Liquid formulations of basic azo dyes are prepared from unsubstituted or C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted m-phenylenediamine by diazotizing and coupling in carboxylic acid solution, which comprises performing the reaction with 0.76 to 0.95 mole of nitrile, calculated as nitrous acid and based on 1 mole of m-phenylenediamine, and then heating the resulting reaction mixture at from 60.degree. C. to the boiling point of the reaction mixture.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: May 8, 1990
    Assignee: BASF Aktiengesellschaft
    Inventor: Karl Schmeidl
  • Patent number: 4923974
    Abstract: 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: Grant
    Filed: July 19, 1988
    Date of Patent: May 8, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuyoshi Ueda, Hideo Hattori, Jun Yamamoto, Kiyoyasu Hashimoto
  • Patent number: 4920205
    Abstract: Azo pigments are made by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65.degree. C. in the aqueous/acid and aqueous/netural pH-ranges. More specifically, an aqueous/alkaline solution of the coupling component is continuously mixed in a first reaction step with an aqueous solution of acetic acid, boric acid, phosphoric acid, hydrochloric acid or sulfuric acid at a temperature lower than 65.degree. C. within a period of less than 1 minute, during which the coupling component commenences precipitating at least partially as reactive matter; next, the suspension obtained is continuously mixed, in a second reaction step immediately following the first reaction step, with an aqueous/acid solution of the diazo component at a temperature of less than 65.degree. C.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: April 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinrich Rehberg, Hartmut Behringer
  • Patent number: 4920206
    Abstract: Azo Pigments are made by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65.degree. C. in the aqueous/acid and aqueous/neutral pH-ranges. More specifically, an aqueous/acid-solution of the diazo component is continuously mixed at a temperature of less than 65.degree. C. within a period of less than 1 minute with the aqueous/alkaline solution of the coupling component and a predetermined pH between 2 and 9 is established by controlling the flow of the mass streams of diazo component and coupling component; in this way a portion of the coupling component is caused to undergo immediate reaction to the azo pigment to be made whereas the balance portion of the coupling component simultaneously commences precipitating as finely crystalline reactive matter, which is reacted in a post-reaction phase with unreacted diazo component to give the azo pigment to be made.
    Type: Grant
    Filed: March 29, 1989
    Date of Patent: April 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Behringer, Heinrich Rehberg
  • Patent number: 4916215
    Abstract: Water-soluble disazo compounds of the general formula ##STR1## in which D.sub.1 and D.sub.2 are each a phenylene or naphthylene radical which can be substituted by 1 or 2 substituents from the group consisting of 1 chlorine, 1 bromine, 2 sulfo, 2 carboxyl, 2 alkyl of 1 to 4 carbon atoms and 2 alkoxy of 1 to 4 carbon atoms, R' and R" each denote an amino or hydroxyl group, R.sup.+ and R* each represent methyl, carboxyl or lower carbalkoxy, R.sup.1 and R.sup.3 are each hydrogen, lower alkyl, lower alkoxy, chlorine or bromine, R.sup.2 and R.sup.4 each denote hydrogen, lower alkyl, lower alkoxy or chlorine, X denotes a vinyl, .beta.-sulfatoethyl,.beta.-thiosulfatoethyl or .beta.-chloroethyl group and Y is a chlorine, fluorine or bromine atom or a sulfo, hydroxyl, aliphatic or aromatic ether group or thioether group or a primary, secondary or tertiary amino group.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: April 10, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Hoyer, Rudolf Fass
  • Patent number: 4916216
    Abstract: Granules of azobisamidine salt can be produced by granulating a powder of azobisamidine salt using a limited amount of water or a mixture of water and a water-soluble organic solvent such as methanol are convenient in handling without deteriorating the quality and can be used as a water-soluble polymerization initiator.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: April 10, 1990
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoaki Tanaka, Takanori Toyama, Hiroki Sugioka
  • Patent number: 4910298
    Abstract: A monoazo compound of the following formula, ##STR1## wherein D is sulfonaphthyl, sulfophenyl or carboxyphenyl, any one of A.sub.1 and A.sub.2 is sulfo and the other is hydrogen, methoxy or ethoxy, R.sub.1 and R.sub.2 are independently hydrogen or alkyl, B.sub.1 and B.sub.2 are independently phenylene or naphthylene, and Y.sub.1 and Y.sub.2 are independently vinyl, .beta.-sulfatoethyl or the like, which is useful for dyeing or printing fiber materials to give dyed or printed products of a deep color excellent in fastness properties.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: March 20, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
  • Patent number: 4910299
    Abstract: Disperse dyes suitable for dyeing textile material composed of polyester dyes of the formula ##STR1## in which D is the radical of a substituted or unsubstituted, homocyclic or heterocyclic diazo component belonging to the series comprising thienyl, thiazolyl, isothiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, imidazolyl or phenyl,X is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, acylamino, halogen or a group of the formula -NH-CO-NHQ in which Q is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxy,R is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl or phenyl, or Y and R, together with the nitrogen atom and the two C atoms linking them, form a 5-membered ring or 6-membered ring,B is a l inear or branched C.sub.2 -C.sub.6 -alkylene radical,W is halogen, C.sub.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo D. Casa, Peter Liechti, Max Dempfle
  • Patent number: 4908437
    Abstract: The invention relates to novel thienone compounds useful in dyeing fibers, of the formula: ##STR1## where R.sup.1 is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or C.sub.1 -C.sub.4 -monoalkylcarbamoyl or -dialkylcarbamoyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.8 -alkyl, substituted or unsubstituted phenyl, furyl, thienyl or halogen,X is nitrogen or CR.sup.4 where R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano or substituted or unsubstituted phenyl, andR.sup.3 is an aniline, thiazole, indole, styrol or isoindole radical, with the proviso that if R.sup.1 is cyano, X is CH and R.sup.3 is 4-dimethylaminophenyl or styryl, then R.sup.2 is not methyl or phenyl and that if R.sup.1 is cyano, X is CH and R.sup.3 is phenyl or 4-methoxyphenyl, then R.sup.2 is not phenyl.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: March 13, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Johannes P. Dix, Helmut Reichelt, Masahiro Hayashi
  • Patent number: 4908435
    Abstract: An azo compound of the formula:A--N.dbd.N--B--N.dbd.N--Dwherein:A is (i) a phenyl group containing at least two unsaturated electron-withdrawing groups in ortho or para positions with respect to the azo link, (ii) an aromatic heterocycle, or (iii) the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine;B is an substituted or unsubstituted thien-2,5-ylene or thiazol-2,5-ylene group; andD is the residue of an aromatic coupling component having a group displaceable by a diazotized aromatic amine.The azo compound has a significant absorption band extending into the near infra-red region of the spectrum and has utility in applications, such as solar screening, electronic, optical character recognition, printing, reprographic and security systems, where enhanced infra-red absorption is necessary or desirable.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: March 13, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Peter Gregory
  • Patent number: 4906739
    Abstract: A fibre-reactive azo dyestuff of the formula ##STR1## in which X is alkyl or alkoxy with 1 to 4 carbon atoms, carboxyl or halogen, n is 1, 2 or 3, m is 0 or 1, p is 0 or 1 and q is 0 or 1 and the benzene or naphthalene rings A, B and B' can contain further substituents in addition to SO.sub.3 H groups. The dyestuffs of the invention are suitable inter alia, for dyeing and printing silk, leather, wool, high molecular weight polyamide fibres and high molecular weight polyurethanes, but especially cellulose-containing materials having a fibrous structure.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: March 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Seiler, Gert Hegar
  • Patent number: 4906741
    Abstract: The invention is directed toward compounds having the formula: ##STR1## wherein A is a substituent independently selected from the group consisting of lower alkyl having from 1 to 3 carbon atoms, chloro or fluoro; n is an integer independently selected from 0 to 2; and X is a halogen selected from the group consisting of chloro and fluoro.Compounds of this invention are useful as intermediates in the preparation of the corresponding diamine compounds resulting from the reductive cleavage of the azo linkage. They may also be used to prepare dyestuffs and photosensitive materials.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: March 6, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Hazen, William R. Lee
  • Patent number: 4906735
    Abstract: An improved process for the manufacture of a monoazo acetoacetylaminobenzimidazolone pigment of the formula ##STR1## by coupling the components in an aqueous medium in the presence of an oxethylation product of an alcohol or alcohol mixture having from 8 to 14 carbon atoms and 3 to 10 mols of ethylene oxide, and heating the aqueous pigment suspension after complete coupling. The pigment thus obtained avoids an after-treatment in anhydrous organic solvents and has good tinctorial strength, high hiding power and good properties with respect to flow and dispersibility.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: March 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Klaus Hunger
  • Patent number: 4906736
    Abstract: Water-soluble copper complex formazan compounds which conform to the general formula (1) below and have useful fiber-reactive dye properties and dye carboxamido- and/or hydroxy-containing material, in particular cellulose fibers, in fast blue shades. ##STR1## in which: M is hydrogen or a salt-forming metal atom,k, m and n each denote the number zero, 1 or 2, the sum (k+m+n) being equal to 1 to 4,A is a benzene or napththalene ring which additionally can contain the fiber-reactive group --NH--Q and further substituents,B is a benzene or naphthalene ring which additionally contains the fiber-reactive group --NH--Q and further substituents,D is substituted or unsubstituted alkylene of 1 to 8 carbon atoms or is a benzene or naphthalene ring having optionally additional substituents or is a heterocyclic radical,X is a sulfo group or an oxy or carbonyloxy group,r is the number 1 or 2,Q is a radical of the formula (2) ##STR2## in which Y is halogen, Z is vinyl or a .beta.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: March 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer, Werner H. Russ
  • Patent number: 4904777
    Abstract: A thiophene-containing azo dye of the formula ##STR1## where R is substituted or unsubstituted alkyl, alkenyl, cycloalkyl or phenyl, X is hydrogen, halogen, hydroxyl, unsubstituted or substituted alkoxy, cycloalkoxy, phenoxy, mercapto, alkylthio, phenylthio, alkylsulfonyl, phenylsulfonyl or phenyl and Y is cyano, nitro, alkanoyl, substituted or unsubstituted benzoyl, alkylsulfonyl, phenylsulfonyl, Co-Z, where Z is unsubstituted or substituted phenoxy, amino, mono- or dialkyl-amino, pyrrolidino, piperidino, morpholino or N-alkyl-piperazino, and K is the radical of a coupling component is used as dyes for dyeing fiber material.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: February 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4904766
    Abstract: A monoazo compound represented by the following formula in a free acid form, ##STR1## wherein D is a sulfophenyl or sulfonaphthyl, R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen or alkyl; B.sub.1 and B.sub.2 are independently phenylene, naphthylene, or alkylene, provided that at least one of B.sub.1 and B.sub.2 is phenylene or naphthylene, Y.sub.1 and Y.sub.2 are independently vinyl or --CH.sub.2 CH.sub.2 Z in which Z is splittable by the action of an alkali, and n is 0 or 1, and the monoazo compound is useful for dyeing or printing fiber materials to obtain dyed or printed products of extremely deep scarlet color excellent in various fastness with superior build-up property.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: February 27, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazufumi Yokogawa, Toshihiko Morimitsu, Naoki Harada, Takashi Omura, Sadanobu Kikkawa
  • Patent number: 4900812
    Abstract: Compounds of the formula ##STR1## and water-soluble salts thereof each cation of which is independently a non-chromophoric cation, whereinMe is cobalt, copper or nickel,Pc is the phthalocyanine radical,each R.sub.1 and R.sub.2 is independently hydrogen or C.sub.1-6 alkyl,each R.sub.4 is independently hydrogen, halo, hydroxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, carboxy or sulfo,each R.sub.6 is hydrogen, cyano, carbamoyl or ##STR2## wherein An .crclbar. is a non-chromophoric anion,each R.sub.7 is hydrogen, C.sub.1-4 alkyl, C.sub.5-6 cycloalkyl, phenyl, benzyl, phenylethyl or carboxy,each W is linear or branched C.sub.2-6 alkylene; linear or branched C.sub.3-6 alkylene monosubstituted by hydroxy; linear or branched C.sub.2-6 alkylene interrupted by ##STR3## wherein R.sub.11 is linear or branched C.sub.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: February 13, 1990
    Assignee: Sandoz Ltd.
    Inventors: Helmut A. Moser, Roland Wald
  • Patent number: 4892936
    Abstract: A process is disclosed for the preparation of .alpha.-substituted carbonyl compounds, wherein .alpha.-substituted ketone is prepared by the following reaction: ##STR1## .alpha.-azo ester is prepared by the following reaction: ##STR2## and .alpha.-hydrozono ester is prepared by the following reaction: ##STR3## wherein the .alpha.-azo ester and .alpha.-hydrazono ester obtained by the above reactions include novel compounds, which are also disclosed.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: January 9, 1990
    Assignee: Agency of Industrial Science and Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4891424
    Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4886517
    Abstract: The present invention relates to a composition for dyeing keratinic fibres, and human hair in particular, comprising the azo dye of formula: ##STR1## optionally in combination with at least one nitro benzene dye or with at least one aminoanthraquinone dye or with at least one nitro benzene and at least one aminoanthraquinone dye. The azo dye of formula (II) is nonmutagenic, has good solubility properties in the usual dye carriers, and imparts to hair hues which are stable, particularly to washing. The invention also relates to a process for dyeing human hair by direct coloration which comprises applying the dyeing composition defined above onto the hair, leaving it on the hair for 3 to 60 minutes and then rinsing and drying the hair.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: December 12, 1989
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Alex Junino, Jean Cotteret
  • Patent number: 4880916
    Abstract: Azo dyes of the formula ##STR1## or tautomers thereof, wherein Z is N,S or CH,X is O,S,NR.sup.2 or N, V is N or CH, W is N or C, K is a coupling component from the group consisting of acylacetarylamides, phenols, pyridones, quinolines, pyrazoles, indoles, diphenylamines, aminopyridines, pyrimidines, pyrimidones, naphthols, naphthylamines, aminoathiozoles, thiophenes and hydroxypyridines, R is unsubstituted or substituted alkyl or alkenyl, R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, --CN, --NHR.sup.2, --NH--acyl, phenoxy, --COOR.sup.2, --COOR.sup.2 --CONHR.sup.2 or substituted or unsubstituted phenyl, R.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 alkyl or substituted or unsubstituted phenyl, D is a 1,4-phenylene radical which can be substituted further and AN.THETA.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: November 14, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean-Marie Adam
  • Patent number: 4879373
    Abstract: each of R.sub.2 and R.sub.3 is independently hydrogen, chloro, bromo, methyl, methoxy or ethoxy,useful as pigments for, for example, the mass pigmenting of viscose and surface coatings such as oil and water base paints, lacquers and inks, pigment printing, textile coating and pigmenting paper in the mass.
    Type: Grant
    Filed: February 19, 1987
    Date of Patent: November 7, 1989
    Assignee: Sandoz Ltd.
    Inventor: Bansi L. Kaul
  • Patent number: 4876333
    Abstract: A crystalline modification, designated ".beta.", of the dye of the structure ##STR1## The .beta.-crystalline modification of the dye is easier to isolate from water and gives filter cakes of higher solids and color content. The .beta.-form is also more suitable for making liquid formulations of the dye; the liquid formulations of the crystalline modification have lower viscosity and better dispersion stability than liquid formulations of non-modified form. The .beta.-modification of the dye is obtained by heating an aqueous slurry of the dye at about 90.degree.-95.degree. C. and pH of 8.5 to 9.5 until the modification is complete. The crystalline modification of the dye gives Debye-Scherrer X-ray diffraction patterns substantially different from the non-modified form.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: October 24, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Hoehener, Roy E. Smith
  • Patent number: 4873319
    Abstract: Disazo dyes which are suitable for dyeing and printing, especially of paper of all kinds. The dyes correspond to the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each an alkyl radical, A is an alkylene radical, n is 1 or 2, V, X, Y and Z are nonionic substituents customarily in azo dyes, K is a pyrimidine coupling and An is an anion.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: October 10, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Willy Stingelin
  • Patent number: 4870164
    Abstract: Symmetrical and asymmetrical disazo compounds of the formula: ##STR1## wherein: the R.sup.1 's are identical or different and are hydrogen, chlorine, bromine, methyl or methoxy;the R.sup.2 's are hydrogen, or, if the R.sup.1 's are hydrogen, the R.sup.2 's are hydrogen, methyl or ethyl, the two R.sup.2 radicals being identical or different; andn is 1 to 4and mixtures of such compounds as colorants, especially for pigmenting high molecular weight organic material.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: September 26, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Kuhne, Heinrich Hamal
  • Patent number: 4867789
    Abstract: A method for purifying a dye solution is provided. The method comprises the steps of dissolving an impure dye in a solvent. A flocculant is then added to the dye solution in order to flocculate the imprity so that the impurity may then be removed from the solution. A method for producing on ink utilizing the purification procedure is also provided.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tsuyoshi Eida, Makoto Shioya, Masatsune Kobayashi
  • Patent number: 4855411
    Abstract: This invention is directed to new water-soluble, monoazo dyes having the following general formula: ##STR1## in which: X and Y are independently selected from the group consisting of: ##STR2## R, R.sub.1, R.sub.2 are independently selected from H, lower alkyl of one to four carbons and sulfonated lower alkyl;A is a phenyl or napthyl radical optionally substituted with halogen, hydroxy, lower alkyl, lower alkoxy, carboxylic acid or sulfonic acid;W is a phenyl or naphthyl radical optionally substituted by carboxylic acid, sulfonic acid, amino, amido, lower alkyl, lower alkoxy, hydroxy or halogen groups;Z is a phenyl radical optionally substituted with halogen, lower alkoxy or lower alkyl groups; andcopper, chromium, cobalt and nickel metallized complexes of said dyestuffs.The dyes of this invention on cellulose textiles have high tinctorial strength, purity of shade, light and wash fastness particularly chlorine wash fastness.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: August 8, 1989
    Assignees: Hugh C. Crall, Hoechst Celanese Corp.
    Inventors: Glenn A. Thompson, Anthony J. Corso, Hans H. Steuernagel
  • Patent number: 4847365
    Abstract: The invention relates to novel 1:1 metal complexes of a divalent transition metal and an azo compound of the formula (1) ##STR1## wherein X is a hydrogen or a halogen atom, an alkyl, alkoxy, aryloxy, nitro, acylamino, ureido, arylureido, thioureido, thiocyano or sulfamoyl group or a phthalimido group which is unsubstituted or substituted by halogen atoms,Y is a hydrogen or halogen atom, an alkyl or alkoxy group, andR is an alkyl, alkoxycarbonyl, carbamoyl or alkylcarbamoyl group, orwherein X and Y, together with two vicinal carbon atoms of the benzene ring, form a fused benzene or imidazolone ring.These metal complexes, in particular the nickel and copper complexes, are suitable for the mass coloration of polymer fibres, especially polyolefins, polyamides or polyesters. The colored fibres have good fastness to heat, light and weather, as well as good rub- and wetfastness properties.
    Type: Grant
    Filed: February 17, 1988
    Date of Patent: July 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Paul Lienhard
  • Patent number: 4843151
    Abstract: The monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the aminobenzene, alkoxybenzene, hydroxybenzene, pyrazolone, aminopyrazole, pyrimmidine, indole, diphenylamine or acetoacetamide series, R is a substituted or unsubstituted C.sub.1-12 alkyl, cycloalkyl, aralkyl or aryl radical, X is a --CO-- or --SO.sub.2 -- group, a --COO-- group, R being attached to the oxygen atoms, or an --SO.sub.2 NH-- or ##STR2## group, R being attached to the nitrogen atom and Y being hydrogen or C.sub.1-4 alkyl, and Z is hydrogen or C.sub.1-4 alkyl, produce dyeings having good fastness to light and wet processing on polyamide material.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: June 27, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Hurter
  • Patent number: 4841032
    Abstract: A monoazo compound of the following formula in a free acid form, ##STR1## wherein A.sub.1 and A.sub.2 are phenylene or naphthylene, Z.sub.1 and Z.sub.2 are --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y in which Y is a splittable group, R.sub.1 and R.sub.2 are hydrogen or alkyl, and D is sulfophenyl or sulfonaphthyl, provided that --A.sub.1 --Z.sub.1 and --A.sub.2 --Z.sub.2 are different from each other when D is sulfophenyl and both R.sub.1 and R.sub.2 are hydrogen, which is useful for dyeing or printing fiber materials to give dyed products of high fastness properties with extremely high color depth.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiko Morimitsu, Sadanobu Kikkawa, Naoki Harada, Takashi Omura
  • Patent number: 4841027
    Abstract: Improvement in a process for producing an arylazo-aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR1## wherein A is a phenyl or naphthyl group unsubstituted or substituted by one to four members selected from alkyl, alkoxy, phenoxy, sulfonic acid, carboxylic acid, arylamino, amino, nitro and hydroxyl groups and halogen atoms, and m is 0 or 1, which comprises reacting an aminonaphtholsulfonic acid represented by a free acid of the formula, ##STR2## wherein m is as defined above, with a dibasic acid anhydride to obtain an acylaminonaphtholsulfonic acid, coupling a diazonium compound of amine of the formula,A'--NH.sub.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yutaka Kayane, Takashi Omura, Yasuo Tezuka, Hideharu Sone
  • Patent number: 4839469
    Abstract: 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: Grant
    Filed: November 13, 1987
    Date of Patent: June 13, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 4837308
    Abstract: A universally usable process for preparing azo dyestuffs by oxidative coupling consists in carrying out the oxidation in the presence of redox mediators with a standard potential of 0.2-1.5 volts and, if appropriate, an additional oxidizing agent with a standard potential of 0.25-2.5 volts, wherein the sum of the oxidation equivalents should be at least 4. The preferred redox mediator is iodine. The process is particularly suitable for the preparation of heteroaromatic azo dyestuffs using an aniline coupling component.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: June 6, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rainer Gerlach
  • Patent number: 4828622
    Abstract: According to the invention, addition of one or more surfactants having a cloud point in aqueous solution to an aqueous suspension of a solid gives after the isolation of the solid at a temperature above the cloud point aqueous press cakes containing a large amount of this solid. The direct processing of press cakes as obtained for example after the synthesis and isolation of dyes or pigments to give practical aqueous pastes or dispersions requires a minimum solids content in the press cakes. The minimum content is frequently not obtained when conventional methods of isolation are used, so that it is necessary to proceed via the indirect route of drying to obtain the powders and redispersing the powders. By using the process according to the invention it is possible to cut out the costly indirect route or, if desired, to reduce the expense of drying to obtain powders by an appreciable margin.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: May 9, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Joachim Weide, Erwin Dietz, Reinhold Deubel
  • Patent number: 4826976
    Abstract: This invention relates to a color-shifted dye compounds containing at least one thermally unstable carbamate moiety which are useful in thermal imaging. These compounds may be represented by the formula [M--(X).sub.q ].sub.p D wherein M is a carbamate moiety; X is --N.dbd., --SO.sub.2 -- or --CH.sub.2 --; D taken with X and M represents the radical of a color-shifted organic dye, said carbamate moiety M comprising a tert-alkoxycarbonyl group, ##STR1## wherein R' is halomethyl or alkyl.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: May 2, 1989
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Ernest W. Ellis, Donald A. McGowan
  • Patent number: 4826959
    Abstract: A mixture of an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a low melting point in an amount of about 70% by weight or more and an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a high melting point in an amount of about 30% by weight or less shows excellent solvent solubility, which is higher than that of the isomer having a low melting point. The mixture is useful as a polymerization initiator, and also as a blowing agent.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 2, 1989
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoaki Tanaka, Tsutomu Miyagawa, Hideo Takeuchi
  • Patent number: 4820806
    Abstract: Metal-free monoazo and disazo compounds of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --W.sub.1 --D--N.dbd.N--K--(W.sub.2 --Z).sub.n,1:1 and 1:2 metal complexes of such metallizable metal-free compounds and acid addition salts of such metal-free compounds and 1:1 and 1:2 metal complexes, whereinD is the radical of a diazo component of the benzene, naphthalene or tetrahydronaphthalene series,K is the radical of a coupling component of the benzene, naphthalene, pyrazol-5-one, pyridine, pyridone, barbituric acid, quinoline, isoquinoline, benzeneazobenzene, benzeneazonaphthalene, naphthaleneazobenzene, naphthaleneazonaphthalene, tetrahydronaphthaleneazobenzene, tetrahydronaphthaleneazonaphthalene or acetoacetamide series,W.sub.1 is a direct bond or a divalent bridging radical,each W.sub.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: April 11, 1989
    Assignee: Sandoz, Ltd.
    Inventors: Werner Baumann, Joseph V. Diest, Herbert Eichenberger, Max Oppliger
  • Patent number: 4818814
    Abstract: Water-soluble disazo compounds of the formula ##STR1## in which D is a benzene ring or a naphthalene ring which can both be substituted by substituents from the group consisting of chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy and sulfo, X is the vinyl group or a .beta.-sulfatoethyl group, R is a .beta.-sulfatoethylsulfonyl, 3-(.beta.-chloroethylsulfonyl)-benzoyl, 4-(.beta.-chloroethylsulfonyl)-benzoyl, 3-(.beta.-chloroethylsulfonylmethyl)-benzoyl, 4-(.beta.-chloroethylsulfonylmethyl)-benzoyl,4-(.beta.-chloroethylsulfonyl )-cinnamoyl, 3-(N-methyl-N-.beta.chloroethylsulfonyl)-aminobenzoyl or 4-(N-methyl-N-.beta.-chloroethylsulfonyl)-aminobenzoyl group, m is the number 1 or 2 and M denotes a hydrogen atom or an alkali metal.The disazo compounds are suitable for use as dyes having fiber-reactive properties for dyeing hydroxy- and/or carboxamido-containing fiber material, such as in particular cellulose fiber materials and polyamide fiber materials.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: April 4, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ludwig Schlafer
  • Patent number: 4810783
    Abstract: An azo dyestuff of the formula ##STR1## wherein D=a diazo component,R.sub.1 and R.sub.2 =alkyl or aralkyl,R.sub.3 =H, R or OR.sub.1 andR.sub.4 =a hydrocarbon radical or acyl,which are prepared in a simple manner by aminolysis with ammonia or an amine of the formula ##STR2## of an azo compound of the formula ##STR3## these dyestuffs dye polyester fibres in blue-green to green shades with good fastness to light.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: March 7, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Leverenz
  • Patent number: 4804747
    Abstract: (i) A compound of the formula: ##STR1## wherein R is H, a metal or a group containing a tetravalent N atom;X is S, O, ##STR2## R.sup.1 is NO.sub.2, CN or COOY; Y is H, C.sub.1-4 -alkyl, a metal or a group containing a tetravalent N atom;R.sup.2 and R.sup.3 are each independently H or a non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms;R.sup.4 and R.sup.5 are each independently H or a non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms; andR.sup.6 and R.sup.7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms; orR.sup.4 and R.sup.6 together comprise ring fused to Ring A and R.sup.5 and R.sup.7 are as hereinbefore defined; orR.sup.5 and R.sup.7 together comprise ring fused to Ring A and R.sup.4 and R.sup.6 are as hereinbefore defined; orR.sup.2 and R.sup.4 together with the N atom to which R.sup.2 is attached form a ring fused to Ring A and R.sup.3 and R.sup.5 are as hereinbefore defined; orR.sup.3 and R.sup.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: February 14, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Simon Allen, Paul F. Gordon, Richard A. Hann
  • Patent number: 4801702
    Abstract: A process for the preparation and conditioning of organic pigments, which comprises the use of at least one tricyclodecane alcohol or tricyclodecene alcohol.
    Type: Grant
    Filed: October 30, 1986
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • Patent number: 4801696
    Abstract: Disazo dyes for dyeing cellulose-containing fibers represented by the following general formula: ##STR1## wherein R.sup.1 and R.sup.2 each represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a thiocyanato group, a trifluoromethyl group, a formyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a sulfamoyl group, an N-lower alkylsulfamoyl group or an N,N-di-lower alkylsulfamoyl group, R.sup.3 represents a hydrogen atom, a methyl group, a chlorine atom, a lower alkoxy group or an acylamino group, R.sup.4 represents a hydrogen atom, a methyl group, a chlorine atom or a lower alkoxy group, R.sup.5 represents a hydrogen atom, a lower alkyl group or a halogen atom, --X-- represents ##STR2## --SO.sub.2 -- or --CH.sub.2 --, and n represents 0 or 1. These dyes are capable of dyeing cellulose-containing fibers, particularly fiber blends composed of cellulose fibers and polyester fibers, blue to bluish green with good fastness properties.
    Type: Grant
    Filed: June 22, 1987
    Date of Patent: January 31, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Kiyoshi Himeno, Toshio Hihara, Shuichi Maeda