Oxidation Dye, E.g., Aniline, Nitroaniline, Etc. Patents (Class 8/649)
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Publication number: 20120110751Abstract: The present invention is concerned with a dye system for application to a substrate, the dye system comprising: (a) at least one dye precursor; (b) an oxidising agent; and (c) a catalyst, wherein the catalyst is a homogeneous catalyst or a heterogeneous catalyst. Preferably, the catalyst comprises at least one metal-containing compound. The invention also envisages a method for the coloration of a substrate, the method comprising treating the substrate with the dye system of the invention. In preferred embodiments of the invention, the substrate comprises human hair, natural or synthetic polymers, or textile fibres. In further preferred embodiments, the at least one dye precursor is an organic precursor, the at least one metal derivative for use as a catalyst comprises at least one inorganic metal compound or at least one metal complex comprising at least one organic ligand, and the oxidising agent is hydrogen peroxide.Type: ApplicationFiled: June 30, 2010Publication date: May 10, 2012Applicant: UNIVERSITY OF LEEDSInventors: Richard Simon Blackburn, Patrick Columba McGowan, Christopher Martin Pask, Christopher Mark Rayner
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Patent number: 7799095Abstract: A subject-matter of the present invention is an anhydrous composition in the form of a paste or in the pulverulent form for the coloring of the keratinous human fibers comprising at least one oxidation dye, at least one complex of hydrogen peroxide and a specific polymer and at least one alkaline agent. A subject-matter of the invention is likewise a method for coloring keratinous fibers in which the following stages are carried out: —The above mentioned anhydrous composition is mixed with an aqueous composition advantageously devoid of hydrogen peroxide, and the resulting composition is applied to the keratinous fibers, the composition is left to stand and the fibers are rinsed.Type: GrantFiled: June 27, 2008Date of Patent: September 21, 2010Assignee: L'Oreal S.A.Inventors: Maud Mario, Patricia Desenne, Jean-Marie Millequant
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Patent number: 7740665Abstract: By combining a hydrogen peroxide liberating complex with hair coloring dyes, a highly effective hair coloring composition is obtained which comprises a stable dry powder composition which can be stored in a single container. When use is desired, the stable dry powder composition of the present invention is mixed with water, activating the liberation of hydrogen peroxide and allowing the desired hair coloring effect to be achieved. In addition to providing a single stable dry powder formulation, the composition of the present invention is capable of achieving a wide array of shades and coloring effects.Type: GrantFiled: September 15, 2008Date of Patent: June 22, 2010Assignee: Zotos International, Inc.Inventors: Zubaida Khan, Marina Azizova, Rushi Tasker
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Patent number: 7621967Abstract: A dye base sulfate and method of making are described. The dye base sulphate of formula (I) is produced with a residual amine content of less than 2000 ppm, as determined by HPLC, by precipitation of the dye base, made by Friedel-Crafts alkylation, substitution and hydrolysis, as the dye base sulphate is a) taken up in water and subjected to a first steam distillation then filtered and optionally dried at 50 to 180° C., b) the pressed cake is treated with water or the optionally dried dye base sulphate is moistened with water, c) subjected to a further steam distillation and filtration and d) dried at 50 to 180° C.Type: GrantFiled: October 21, 2003Date of Patent: November 24, 2009Assignee: Clariant Produkte (Deutschland) GmbHInventors: Eduard Michel, Ruediger Baur, Hans-Tobias Macholdt, Norbert Kohl
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Publication number: 20090119850Abstract: According to the invention, a metal salt and an oxygen source are applied to penetrate or impregnate a suitable substrate sequentially in effective amounts so as to react in contact with the substrate and produce a mineral compound fixed within the surface of the substrate. The inventive combination of a mutually compatible metal salt, oxygen source, and substrate brings about an in situ reaction, and modifies the substrate to bring about a lasting desired effect. The mineral compound that is produced according to the invention is linked to the substrate, is stable and long-lasting or permanent, and is immobilized or insolubilized in the substrate. The mineral compound is bound or contained within and on the surface of the substrate, so it may be said to be ingrained in the fibers or matrix of the substrate, or embedded within the substrate. The desired effect is preferably a color. A wide variety of metal salts may be used depending on the desired effect.Type: ApplicationFiled: January 16, 2009Publication date: May 14, 2009Applicant: Purecolor, IncorporatedInventor: Stephen B. Auger
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Patent number: 7452386Abstract: The present disclosure relates to a composition for bleaching and simultaneously dyeing keratin fibers, comprising at least one dye chosen from meta-substituted ortho-nitroanilines and addition salts thereof, at least one peroxygenated salt and at least one alkaline agent. The present disclosure further relates to the process for bleaching and dyeing keratin fibers using this composition, and also to the use of this composition for bleaching and simultaneously dyeing keratin fibers.Type: GrantFiled: December 5, 2005Date of Patent: November 18, 2008Assignee: L'Oreal S.A.Inventors: Sylvain Kravtchenko, Valérie Bonnardel
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Publication number: 20080115296Abstract: The present invention relates to symmetrical tetraazo cationic compounds of formula (I) Dye1-L-Dye1 in which formula: Dye1 represents: in which: W1, which are identical, represent: W2, which are identical, represent: W3, which are identical, represent: L represents an optionally substituted C1-C60 hydrocarbon-based chain, optionally bearing at least one cationic charge, optionally interrupted with and/or terminated at one and the other of the ends with at least one hetero atom or group comprising at least one hetero atom; the electrical neutrality of the compounds being ensured by means of one or more cosmetically acceptable, identical or different anions An. A subject of the invention is similarly a composition comprising such a dye as direct dye, and also a process using the said composition for dyeing keratin fibres.Type: ApplicationFiled: November 24, 2005Publication date: May 22, 2008Inventors: Andrew Greaves, Herve David
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Patent number: 7300469Abstract: The invention relates to novel diaminopyrazole having formula (I), wherein: R1, R2, identical or different, represent a C3 C5 mono- or polyhydroxyalkyl, isopropyl, n-propyl or ethyl group, said groups being linear or branched, and their physiologically acceptable salts. The invention also relates to a composition for dyeing keratinous fibres containing a compound having formula (I) and the method for using same.Type: GrantFiled: February 14, 2002Date of Patent: November 27, 2007Assignee: L'Oreal, SAInventors: Thilo Fessmann, Eric Terranova
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Patent number: 7285136Abstract: The invention relates to novel diaminopyrazole compounds having formula (I): wherein R1 represents a linear or branched C4-C5 alkyl or n-propyl group, or a linear or branched C3-C5 mono or polyhydroxy alkyl group, and the addition salts thereof with a physiologically acceptable acid. The invention also relates to the compositions containing such a compound for the dyeing of keratinous fibres and the method for using said compositions.Type: GrantFiled: February 14, 2002Date of Patent: October 23, 2007Assignee: L'Oreal, SAInventors: Thilo Fessmann, Eric Terranova
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Patent number: 6793687Abstract: The object of the invention is an agent for oxidatively dyeing keratin fibers, wherein it contains (a) at least one 4,5-diaminopyrazole derivative of Formula (I), (II) or (III) or its salt with organic or inorganic acids, as well as (b) at least one pyrazol-5-one derivative of the general formula (IV), (V) or (VI), or its salt with organic or inorganic acids,Type: GrantFiled: October 8, 2002Date of Patent: September 21, 2004Assignee: Wella AktiengesellschaftInventors: Manuela Javet, Christel Dousse, Dominique Le Cruer
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Patent number: 6666898Abstract: An adhesive-tape cutting device of an adhesive-tape holder includes a side plate provided on one side of a blade holder of the adhesive-tape holder. The side plate is provided with a support rod and a pivotal shaft. A press plate is formed with a push plate at its lower end to push a slide base together with a blade to move forward, with a curved support member formed between the press plate and the push plate and rested against the support rod of the side plate. The curved support member rests against the support rod serving as a fulcrum, operating the press plate with a little force to let the blade cut off an adhesive tape easily. The press plate is sandwiched between the support rod and the slide base, so it is needless to be additionally provided with any fixing member, economizing cost and facilitating assembling.Type: GrantFiled: January 30, 2002Date of Patent: December 23, 2003Inventor: Hsiu-Man Yu Chen
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Patent number: 6596035Abstract: A single composition for simultaneous coloring and highlighting hair to provide hair fibers having variations in tonality and hue, comprising, 1-10% inorganic persulfate, 1-20% hydrogen peroxide, 0.001-20% of at least one primary intermediate and, optionally, at least one coupler for the formation of oxidation dyes; and 0.01-20% of one or more surfactants; as well as a one step method for simultaneously color and highlighting hair to provide hair fibers having variations in tonality and hue comprising, combining, immediately prior to use, a powder composition comprised of at least one alkali metal or alkaline earth metal persulfate, an aqueous developer composition comprised of hydrogen peroxide; and an aqueous based colorant composition comprised of at least one primary intermediate and, optionally, at least one coupler for the formation of oxidation dyes; and applying the mixture to the hair for a period of time sufficient to cause coloration and highlighting of the hair.Type: GrantFiled: April 30, 2001Date of Patent: July 22, 2003Assignee: Revlon Consumer Products CorporationInventors: Glen Alan Gutkowski, Alexander Chan, Shailendra Kumar Singh
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Patent number: 6572843Abstract: A method for treating hair, combining permanent dyeing and straightening of hair, without significantly damaging the hair. According to the method of the present invention the hair is treated by chemically reducing covalent disulfide linkages in the hair, and contacting said hair with at least one oxidoreductase, at least one mediator, and at least one chemical oxidizing agent in an amount equivalent to 0.001-1% hydrogen peroxide calculated by weight of the dyeing formulation.Type: GrantFiled: March 10, 2000Date of Patent: June 3, 2003Assignee: Novozymes, A/SInventors: Niels Henrik Sorensen, Jason Patrick McDevitt
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Patent number: 6447552Abstract: A simplified process is presented for the preparation of stable, aqueous hair dyeing emulsions, comprising at least one oxidation hair dyestuff precursor, by first preparing a homogenous oily phase comprising at least one oil-soluble emulsifier by mixing the oil components at an increased temperature between 40° and 80° C., and subsequently mixing this oily phase with an aqueous phase, comprising at least one water-soluble emulsifier under shearing force at a temperature between 15° and 30° C. Compared to conventional processes of hot emulsification, this process substantially reduces the preparation time.Type: GrantFiled: March 19, 1999Date of Patent: September 10, 2002Assignee: Goldwell GmbHInventor: Frank Golinski
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Patent number: 6432147Abstract: A hair coloring composition comprising: (a) from about 0.0003 moles (per 100 g of composition) to less than about 0.09 moles (per 100 g of composition) of an inorganic peroxygen oxidizing agent; and (b) an oxidative hair coloring agent; wherein the pH of each of (a) and (b) is in the range of from about 1 to about 6 and wherein the combined mixture of (a) and (b) has a pH in the range of from about 1 to about 6. The products can provide excellent hair coloring and in-use efficacy benefits including excellent initial color and good wash fastness in combination with reduced hair damage at low pH.Type: GrantFiled: June 23, 1999Date of Patent: August 13, 2002Assignee: The Procter & Gamble CompanyInventors: Louis Carlos Dias, James Charles Dunbar, Dominic Pratt
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Patent number: 6409772Abstract: The invention relates to the use of hydroxystilbenes for dyeing, to ready-to-use dye compositions comprising them, to a dyeing process using them and to a multi-compartment device containing the compositions used in the processes of the invention.Type: GrantFiled: December 21, 1999Date of Patent: June 25, 2002Assignee: L'OrealInventors: Francis Pruche, Didier Saint Leger, Bruno Bernard
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Patent number: 6398821Abstract: A hair coloring composition comprising: (a) an inorganic peroxygen oxidizing agent; and (b) an oxidative hair coloring agent; wherein the pH of each of components (a) and (b) is in the range of from about pH 1 to about pH 4.5 and wherein the pH of the composition is in the range of from about pH 1 to about pH 4.5. The products can provide excellent hair coloring and in-use efficacy benefits including excellent initial color and good wash fastness in combination with reduced hair damage at low pH.Type: GrantFiled: June 23, 1999Date of Patent: June 4, 2002Assignee: The Procter & Gamble CompanyInventors: Louis Carlos Dias, James Charles Dunbar, Dominic Pratt
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Patent number: 6306179Abstract: The present invention relates to a new method for the synthesis of 2-hydroxyalkyl-para-phenylenediamines which are substituted or unsubstituted at the 5-position of the benzene ring, new 2-hydroxyalkyl-para-phenylenediamines which are substituted or unsubstituted at the 5-position of the benzene ring, their use for the oxidation dyeing of keratinous fibers, the dyeing compositions containing them, as well as the methods of dyeing using them.Type: GrantFiled: October 22, 1998Date of Patent: October 23, 2001Assignee: L'Oreal S.A.Inventors: Alain Genet, Alain Lagrange
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Patent number: 6296672Abstract: The present invention relates to methods of dyeing a material which involve contacting the material with a dyeing system which comprises: (a) a mixture of (i) an aromatic diamine and (ii) one or more of a naphthol and an aminonaphthalene and (b) an oxidation system comprising (i) a hydrogen peroxide source and an enzyme exhibiting peroxidase activity or (ii) an enzyme exibiting oxidase activity on one or more of the compounds of mixture (a). The material may be a fabric, yarn, fiber, garment or film made of fur, hide, leather, silk or wool, or made of cationic polysaccharide, cotton, diacetate, flax, linen, lyocel, polyacrylic, synthetic polyamide, polyester, ramie, rayon, triacetate, or viscose.Type: GrantFiled: December 14, 1999Date of Patent: October 2, 2001Assignees: Novozymes A/S Patents, Novozymes North AmericaInventors: Martin Barfoed, Ole Kirk, Sonja Salmon
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Patent number: 6129769Abstract: The present invention relates to methods for dyeing a material, comprising (a) treating the material with a dyeing system which comprises one or more reduced vat dyes and/or one or more reduced sulfur dyes; and (b) oxidizing the one or more reduced vat dyes or one or more reduced sulfur dyes adsorbed onto the treated material with an oxidation system comprising (i) an oxygen source and one or more enzymes exhibiting oxidase activity or (ii) a hydrogen peroxide source and one or more enzymes exhibiting peroxidase activity, to convert the one or more reduced dyes to their original oxidized insoluble colored forms; wherein the material is a fabric, yarn, fiber, garment or film made of cotton, diacetate, flax, fur, hide, leather, linen, lyocel, polyacrylic, polyamide, polyester, ramie, rayon, silk, tencel, triacetate, viscose or wool.Type: GrantFiled: August 24, 1999Date of Patent: October 10, 2000Assignee: Novo Nordisk Biotech, Inc.Inventors: Feng Xu, Sonja Salmon, Heinz-Josef Wilhelm Deussen, Henrik Lund
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Patent number: 6036729Abstract: The present invention relates to methods of dyeing a material, comprising (a) soaking the material in an aqueous solution which comprises one or more mono-, di- or polycyclic aromatic or heteroaromatic compounds; and (b) treating the soaked material in an aqueous solution with (i) a hydrogen peroxide source and an enzyme exhibiting peroxidase activity or (ii) an enzyme exibiting oxidase activity on the one or more aromatic or heteroaromatic compounds; wherein the material is a fabric, yarn, fiber, garment or film made of fur, hide, leather, silk or wool.Type: GrantFiled: December 19, 1996Date of Patent: March 14, 2000Assignees: Novo Nordisk A/S, Novo Nordisk Biochem North America, Inc.Inventors: Martin Barfoed, Ole Kirk
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Patent number: 6024768Abstract: A diaminoalkane of general formula (I) in which R.sub.1 to R.sub.10 stand independently of each other for hydrogen, a (C.sub.1 -C.sub.4)-alkyl group, a hydroxy-(C.sub.2 -C.sub.3)-alkyl group, a (C.sub.1 -C.sub.4)-alkoxy-(C.sub.2 -C.sub.3) alkyl group, an amino- (C.sub.2 -C.sub.3) alkyl group or a 2,3-dihydroxypropyl group and n is a number from 1 to 6 with the proviso that the --NR.sub.1 R.sub.2 and --NR.sub.7 R.sub.8 groups are either in positions 4 and 4' or in positions 5 and 5'. Salts of the diaminoalkane which are physiologically compatible with inorganic and organic acids. Method of coloring keratin fiber.Type: GrantFiled: December 30, 1998Date of Patent: February 15, 2000Assignee: Hans Schwarzkopf GmbH & Co. KGInventors: Andreas Joachim Bittner, Astrid Kleen
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Patent number: 5972042Abstract: Methods of dyeing a material, comprising treating the material with a dyeing system which comprises (a) one or more mono-, di- or polycyclic aromatic or heteroaromatic compounds, and (b) (i) a hydrogen peroxide source and an enzyme exhibiting peroxidase activity or (ii) an enzyme exhibiting oxidase activity on the one or more aromatic or heteroaromatic compounds; wherein the material is a fabric, yarn, fiber, garment or film made of cotton, diacetate, flax, linen, lyocel, polyacrylic, synthetic polyamide, polyester, ramie, rayon, tencel, or triacetate.Type: GrantFiled: December 19, 1996Date of Patent: October 26, 1999Assignees: Novo Nordisk A/S, Novo Nordisk Bio-Chem North AmericaInventors: Martin Barfoed, Ole Kirk
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Patent number: 5925148Abstract: The present invention relates to methods of overdyeing a warp dyed denim textile, comprising treating the textile in an aqueous dye liquor with a dye system which comprises an effective amount of (a) one or more mono-, di- or polycyclic aromatic or heteroaromatic compounds and (b) (i) a hydrogen peroxide source and at least one enzyme exhibiting peroxidase activity and/or (ii) at least one enzyme exhibiting oxidase activity on the one or more aromatic or heteroaromatic compounds.Type: GrantFiled: July 28, 1997Date of Patent: July 20, 1999Assignee: Novo Nordisk A/SInventors: Martin Barfoed, Ole Kirk
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Patent number: 5922085Abstract: A process of preparing a dye composition and a resultant dye composition. The process includes preparing a mixture comprising a triphenylmethane dye and oxidation products by reacting methylenedianiline, aniline, an oxidation catalyst, and an oxidant; separating the oxidation products from the triphenylmethane dye to produce an aqueous solution of oxidation products; treating the solution of oxidation products with a basic compound; separating unreacted aniline from the solution of oxidation products and forming a mixture of oxidation products; and sulfonating the mixture of oxidation products to form a dye composition.Type: GrantFiled: September 30, 1997Date of Patent: July 13, 1999Assignee: BASF CorporationInventors: Gray D. Ellis, Belinda J. DiMarcello, Debra J. Bradshaw
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Patent number: 5865854Abstract: The invention provides compositions and methods containing novel bis-(2,4-diaminophenoxy)benzene coupling compounds, and cosmetically acceptable salts thereof, for use with conventional primary intermediate dye compounds and oxidizing agents for the oxidative coloring of human hair. The compositions of the invention may also contain other components typically used in oxidative hair dye preparations to impart intense and lasting coloration to hair.Type: GrantFiled: November 21, 1997Date of Patent: February 2, 1999Assignee: Bristol-Myers Squibb CompanyInventors: Mu-Iii Lim, Yuh-Guo Pan, Linas R. Stasaitis
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Patent number: 5865856Abstract: The oxidation hair dye composition is based on a combination of coupler substance and developer substance, and includes, as developer substance, at least one 2,5-diaminobenzonitrile compound of the formula (I), ##STR1## in which R.sup.1 and R.sup.2, independently of each other, are selected from the group consisting of H, alkyl groups having 1 to 6 carbon atoms, hydroxyalkyl groups having 2 to 4 carbon atoms and dihydroxyalkyl groups having 3 to 4 carbon atoms, with the proviso that both of the R.sup.1 and R.sup.2 groups are not both hydrogen at the same time, or a physiologically compatible water-soluble salt thereof. The invention also includes new 2,5-diaminobenzonitrile compounds of formula I.Type: GrantFiled: March 17, 1997Date of Patent: February 2, 1999Assignee: Wella AktiengesellschaftInventors: Helmut Keller, Wolfgang Balzer
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Patent number: 5792221Abstract: A hydroxypropylated 2-nitro-p-phenylenediamine of formula (I), wherein R1 is a C1-4 alkyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl or .gamma.-hydroxypropyl radical; R2 and R3 independently represent a .beta.-hydroxyethyl, .beta.-hydroxypropyl, .gamma.-hydroxypropyl or .beta.,.gamma.-dihydroxypropyl radical, with the proviso that at least one of R1, R2 and R3 is a .gamma.-hydroxypropyl radical, while the other two are not both a .beta.-hydroxyethyl radical; and cosmetically acceptable salts thereof. This compound may be used for directly dyeing hair to give blue through purplish blue shades which are wash-fast, light-fast, waterproof and sweat resistant.Type: GrantFiled: November 25, 1996Date of Patent: August 11, 1998Assignee: L'OrealInventors: Alain Lagrange, Alex Junino, Alain Genet, Jean Cotteret
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Patent number: 5739343Abstract: Nitro dyes of the formula ##STR1## where X.sup.1 and X.sup.2 are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or pyrrolidin-2-on-1-yl,X.sup.3 is hydrogen or C.sub.1 -C.sub.6 -alkyl, andX.sup.4 is a radical of the formula ##STR2## where R.sup.1 is hydrogen, substituted or unsubstitued C.sub.1 -C.sub.12 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or substituted or unsubstituted phenyl,R.sup.2 and R.sup.3 are hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy,R.sup.4 is hydrogen, methyl, ethyl, methoxy or ethoxy, andR.sup.5 is hydrogen or C.sub.1 -C.sub.6 -alkyl,are useful for dyeing or printing textile materials.Type: GrantFiled: January 21, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Helmut Reichelt, Clemens Grund
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Patent number: 5670099Abstract: Process for obtaining submicronic particles, for example, pigments in the presence of lipidic vesicles having a lamellar structure, starting with at least one precursor of said particles involves preparing a dispersion of vesicles starting with at least one lipid capable of forming the walls of the vesicles and an aqueous phase E intended to be encapsulated in the said vesicles, and optionally an aqueous phase D, intended to form a dispersion medium of the said vesicles, at least one precursor of the said vesicles being dissolved in phase E and/or D, before and/or during and/or after the preparation of the vesicular phase, at least one agent capable of transforming the said precursor(s) into sought after particles being reacted with it (them) after introduction into the preparation medium.Type: GrantFiled: September 30, 1994Date of Patent: September 23, 1997Assignee: L'OrealInventors: Jean-Luc Morancais, Alain Lety, Guy Vanlerbergue
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Patent number: 5554196Abstract: Method of marking a surface of an object by means of a laser light beam.A description is given of a method of decorating or marking, for example, synthetic resin objects by means of an UV-laser or IR-laser by coating the object with a layer of a dye precursor and a coupler in a binder. For the precursor use is made of a heterocyclic mono- or bis-arylsulphonylhydrazone and for the coupler use is made of, for example, an indole, aniline, pyrazoline or malonitrile, so that after irradiation with UV-laser light or IR-laser light an azo-dye (XXX) is formed.Type: GrantFiled: August 1, 1995Date of Patent: September 10, 1996Assignee: U.S. Philips CorporationInventor: Ytsen Wielstra
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Patent number: 5516916Abstract: A process for preparing dye compositions which comprises hydrolyzing an O-protected 5,6-dihydroxyindole with an alkaline material under anaerobic condition and the products made by such process.Type: GrantFiled: May 31, 1995Date of Patent: May 14, 1996Assignee: Clairol IncorporatedInventors: Bryan P. Murphy, Keith C. Brown, Thomas M. Schultz, Alice A. Meyer
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Patent number: 5053078Abstract: An ink is provided which comprises a liquid medium containing at least water and an organic solvent and containing therein a water-soluble dye oxidizable to be water-insoluble and an antioxidant in combination. The ink can be fixed on a recording medium by oxidation, and is suitable for ink-jet printing. An ink-jet printing process employing the ink also provided.Type: GrantFiled: April 9, 1990Date of Patent: October 1, 1991Assignee: Canon Kabushiki KaishaInventors: Shoji Koike, Yasuko Tomida
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Patent number: 5034016Abstract: Dyed denim cotton yarns capable of meeting the market demand for color jeans can be provided by immersing denim cotton yarns in a dye bath containing a dye or dye composition comprising a specific indirubin derivative(s), a specific quinophthalone derivative(s) and/or an indigo dye, squeezing and air-oxidizing the dyed yarns, and repeating a series of these steps.Type: GrantFiled: May 24, 1989Date of Patent: July 23, 1991Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hitoshi Koshida, Tetsuo Sakagawa, Takayuki Nakayama, Hiroshi Suwa, Masao Imai, Akio Karasawa
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Patent number: 5019130Abstract: The coloring of human hair and other keratinaceous substrates can be carried out efficiently using compositions containing certain N-aryl pyrroles as dye couplers or developers.Type: GrantFiled: November 3, 1989Date of Patent: May 28, 1991Assignee: Clairol IncorporatedInventor: Lawrence A. Flood
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Patent number: 5019131Abstract: A process for redyeing partially bleached fabric or garments to yield sharply-etched multicolored designs comprises the steps of:(a) dyeing the fabric, or purchasing a commercial garment, with a background first color;(b) gathering selected areas of the dyed fabric with ligatures to restrict access of further reagents;(c) bleaching the gathered background dyed to remove the first color from the areas outside the gathered areas; and(d) redyeing the bleached areas with a second color,whereby sharply defined multicolored patterns are formed having from about 0.2 mm to about 2 mm of white gap between each color.Type: GrantFiled: July 9, 1990Date of Patent: May 28, 1991Assignee: MMOQ, Ltd.Inventor: James L. Nitsch, Jr.
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Patent number: 4941887Abstract: Disclsoed herein is dye suitable for use in dyeing denim cotton yarns. The dye comprises at least one quinophthalone derivative represented by the following general formula (I) or (II): ##STR1## wherein X means H, Br or Cl and Y denotes H, COOR or --COOC.sub.2 H.sub.4 OR (R: alkyl), or a combination of said at least one quinophthalone derivative and an idigo dye. A dyeing process making use of the above dye and denim cotton yarns thus dyed are also disclosed.Type: GrantFiled: January 22, 1988Date of Patent: July 17, 1990Inventors: Tetsuo Sakagawa, Takayuki Nakayama, Hisanobu Kunihiro, deceased, by Masako Kunihiro, legal representative
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Patent number: 4912258Abstract: Fluorinated aniline derivatives of the general formula I are described ##STR1## in which R.sup.1 represents H or (CH.sub.2).sub.n -X, n is a whole number from 1 to 3, X is H, OH, NH.sub.2, CH.sub.3 CONH, CH.sub.3 SO.sub.2 NH, SO.sub.3 H or ArSO.sub.3 H, Ar is optionally substituted arylene radical, R.sup.1 is alternatively also a --(CH.sub.2).sub.3 -- group, which is bonded to the free o-position next to the N-atom, Y is H, --O--, --NH--, --S-- or a C--C single bond, R.sup.2, in the event that Y=H, is the same as or different from R.sup.1 and means one of the radicals shown for R.sup.1, and in the event that Y is a C--C single bond or --O--, --NH-- or --S--, is an alkylene group having 1 to 3 carbon atoms linked with Y, and R.sup.3 =H, alkyl having 1 to 3 carbon atoms, OCH.sub.3, CH.sub.3 CONH, CO.sub.2 H or SO.sub.3 H.Type: GrantFiled: February 5, 1988Date of Patent: March 27, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans-Georg Batz, Rupert Herrmann
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Patent number: 4624709Abstract: A novel substituted nigrosine dye represented by the formula D-R).sub.n wherein D is a nigrosine dye residue, R is C.sub.3 -C.sub.18 alkyl or alkenyl which may be straight or branched, or aralkyl or aralkenyl which may have a C.sub.1 -C.sub.8 alkyl substituent on the aryl moiety, the R in each case being the same as or different from the others, and n is a number of 1 to 4. The novel nigrosine dye is prepared by reacting a corresponding unsubstituted nigrosine dye with an alkyl halide, alkenyl halide, aralkyl halide, or aralkenyl halide, or with a mixture thereof, to form the substituted nigrosine dye. The novel dye has a high solubility in and compatability with organic solvents and/or resins and is oleophilic and stable and particularly useful for ink compositions and as a charge control agent for the toners of electrophotographic or electrostatic image developers.Type: GrantFiled: October 11, 1983Date of Patent: November 25, 1986Assignee: Orient Chemical IndustrieInventor: Masahiro Otsuka
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Patent number: 4619666Abstract: Hair coloring preparations containing substantive hair dyes corresponding to the following general formula ##STR1## in which A is an SO.sub.3 H group or a COOH group, and R.sup.1 and R.sup.2 are hydrogen or other substituents, show high fastness properties and favorable toxicological properties. The substantive hair dyes are preferably present in the hair coloring preparations in a quantity of from 0.01 to 5.0% by weight, optionally in conjunction with known oxidation hair dye precursors.Type: GrantFiled: July 8, 1985Date of Patent: October 28, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Edgar Lieske, Norbert Maak
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Patent number: 4599450Abstract: Acid nitro dyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent employed being a manganese-(VI) or manganese-(VII) compound and the reaction being carried out at a pH higher than 5 and at a temperature between 20.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full-grained chrome leather in full shades.Type: GrantFiled: May 10, 1984Date of Patent: July 8, 1986Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel
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Patent number: 4591359Abstract: Acid nitrodyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent being hypochlorous acid or its alkali metal or alkaline earth metal salts and the reaction taking place at above pH 4 and at a temperature between 0.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full chrome grained leather in deep shades.Type: GrantFiled: August 23, 1984Date of Patent: May 27, 1986Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel
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Patent number: 4532127Abstract: A composition for lightening or coloring hair comprising a liquid vehicle, an oxidizing agent and at least one di-long chain aliphatic hydrocarbon quaternary amine compound and a method for lightening or coloring hair using this composition.Type: GrantFiled: March 13, 1978Date of Patent: July 30, 1985Assignee: Clairol IncorporatedInventors: Raymond Feinland, Stanley Pohl, Michael Hnatchenko
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Patent number: 4466805Abstract: Compounds of the formulaR--C(R.sup.2).dbd.C(R.sup.3)--C(R.sup.4).dbd.C(R.sup.5)--Rwherein R is --CHO, --CH(OR.sup.6).sub.2, 1,3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl or 1,3-dioxan-2-yl; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently are hydrogen, methyl or ethyl; and R.sup.6 is C.sub.1-8 alkyl are highly useful as cosmetic active ingredients, e.g., as hair dyes and skin tanning agents. Compositions of these compounds with other active ingredients such as dihydroxyacetone are also quite effective.Type: GrantFiled: August 20, 1980Date of Patent: August 21, 1984Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Reiner Walters, Gernot Moschl, Hans-Dieter Allardt
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Patent number: 4430091Abstract: A dye solution for coloring a substrate, especially porous stone, comprising an oxidation base, acetic acid, and about 0.02 to about 0.3 mole, per mole of said oxidation base, of a C.sub.8-16 alkyl benzene sulfonic acid, especially dodecyl benzene sulfonic acid, in a volatile organic solvent medium, and a method of coloring a porous substrate therewith involving post-treatment with an oxidizing agent, especially aqueous hydrogen peroxide of about 1 to about 9 wt. % concentration.Type: GrantFiled: May 19, 1982Date of Patent: February 7, 1984Inventor: Clemens Streck
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Patent number: 4405801Abstract: Disclosed are silicon-containing nitro dyes for dying organic polymers or organosiloxanes, which are reactive dyes for synthetic or natural fibers of vegetable or animal origin, having the formula: ##STR1## wherein the chromophore component is bonded with the Si-atom by homopolar bonds and wherein X represents the same or different hydrolyzable groups or a siloxane radical, Z is a bivalent alkylene radical with 1-10 carbon atoms which may be interrupted by NR' groups, R is a monovalent organic radical, R' is hydrogen, alkyl with 1-10 carbon atoms, aryl, aralkyl or said substituted radicals, Ar is a substituted or unsubstituted aryl radical, and a and b are integers from 1-3, and a process for making said dyes. Said dyes may be built into a large number of organic and inorganic molecules and color the same without fixation.Type: GrantFiled: June 24, 1982Date of Patent: September 20, 1983Assignee: VEB Chemiewerk NunchritzInventors: Bodo Hirsch, Gunter Horn, Hellmut Reuther
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Patent number: 4398915Abstract: There is disclosed a method for bleed-resistant coloring of cellulosic materials. The method comprises cross-linking to the cellulosic a water-insoluble colorant particle which is the cross-linkable reaction product of an organic polymer such as starch with a reactive dye compound. Representative of reactive dye compounds are Procion red, blue and yellow. Advantageous cross-linkers are urea-formaldehyde and melamine-formaldehyde resins. The cellulose materials colored by the method of the invention are new and are characterized-in-part in that they are bleed resistant.Type: GrantFiled: January 6, 1982Date of Patent: August 16, 1983Assignee: Albany International Corp.Inventors: Joseph S. Panto, Ernest R. Kaswell
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Patent number: 4378969Abstract: Fluid formulations of oxidation dyes, which are obtained by oxidizing a compound of the general formula I ##STR1## where R.sup.1 is unsubstituted or hydroxy-, C.sub.1 -C.sub.8 -alkoxy- or C.sub.1 -C.sub.8 -alkanoyloxy-substituted C.sub.2 -C.sub.13 -alkyl,R.sup.2 is hydrogen or unsubstituted or hydroxy- or C.sub.1 -C.sub.8 -alkoxy-substituted C.sub.1 -C.sub.13 -alkyl andX is hydroxyl, amino or ##STR2## in an organic solvent, are particularly suitable for dyeing mineral oil products, fats and waxes.Type: GrantFiled: May 6, 1981Date of Patent: April 5, 1983Assignee: BASF AktiengesellschaftInventors: Guenter Hansen, Hans J. Kolbinger, Rudolf Senninger, Georg Zeidler
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Patent number: 4373102Abstract: Novel dyes of the formula ##STR1## where A is cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, carbamyl, N-C.sub.1 -C.sub.4 -alkylcarbamyl, N-phenylcarbamyl, acetyl, benzoyl, 4-nitrophenyl or 4-cyanophenyl,X is hydrogen, chlorine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, and if n is 2 the substituents may be identical or different,n is 1 or 2,R.sup.1 is hydrogen, methyl, ethyl or 2-hydroxyethyl andR.sup.2 is phenyl or cyclohexyl, orR.sup.1 is hydrogen andR.sup.2 is C.sub.1 -C.sub.4 -alkyl, orR.sup.1 and R.sup.2 are C.sub.1 -C.sub.6 -alkyl, allyl or phenyl-C.sub.1 -C.sub.4 -alkyl orthe group ##STR2## is a saturated heterocyclic five-membered or six-membered ring which may additionally contain an oxygen or a further nitrogen as ring members,Y is hydrogen, hydroxyl, methyl or ethyl; ##STR3## where R.sup.3 is linear or branched C.sub.1 -C.sub.12 -alkyl, or is phenyl; ##STR4## where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.5 is hydrogen, linear or branched C.sub.1 -C.sub.Type: GrantFiled: March 7, 1980Date of Patent: February 8, 1983Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Wolfgang Elser, Gustav Bock, Wolf-Dieter Kermer
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Patent number: 4368054Abstract: Liquid compositions of nitro group-containing aniline compounds containing no sulfonic acid and/or carboxylic acid groups and having a melting point of below 140.degree. C., especially those suitable for use as diazo component in ice color dyeing, which contain 20 to 70% of this nitro-aniline, 5 to 80 weight % of a castor oil oxethylated with 25 to 60 mols of ethylene oxide, and 5 to 65 weight % of N-methyl-pyrrolidone as solvent. By simply mixing these components clear solutions are obtained which can be diazotized within a few seconds by means of an aqueous sodium nitrite solution and thus give diazonium salt solutions free from residue. These diazonium salt solutions can be used in simple manner and very advantageously as developing baths or liquors for producing water-insoluble azo dyestuffs on the fiber according to the ice color technique.Type: GrantFiled: January 29, 1982Date of Patent: January 11, 1983Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel