Polymer From Isocyanate And Polyol, E.g., Polyurethane, Etc., Substrate Patents (Class 8/515)
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Patent number: 9358578Abstract: An image article comprises a substrate having a security image coated on at least a portion thereof, which security image effects less than 50% reflectance of radiation of a wavelength between 800 and 900 nm, wherein the security image comprises a defined infrared-absorbing compound, for example Pigment Green 8, wherein said infrared-absorbing compound does not create a strongly colored security image.Type: GrantFiled: January 31, 2014Date of Patent: June 7, 2016Assignee: INOVINK LIMITEDInventors: David Malcolm Lewis, Peter Jeffrey Broadbent
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Publication number: 20140250611Abstract: A polyurethane is dyed with an aqueous solution of an acid dye compound, a quaternary ammonium compound selected from soluble tetrabutylammonium compounds and tetrahexylammonium compounds, and, optionally, an water-soluble organic solvent.Type: ApplicationFiled: March 5, 2013Publication date: September 11, 2014Applicant: NIKE, INC.Inventor: NIKE, INC.
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Publication number: 20140256468Abstract: A golf ball of a first color is dyed to a second color with an anionic or nonionic disperse dye. Either or both of the cover or an optional clear coating layer on the cover comprises a member selected from the group consisting of polyurethanes, polyureas, polyamides, and combinations thereof, which can be dyed by the anionic or nonionic disperse dye.Type: ApplicationFiled: March 5, 2013Publication date: September 11, 2014Applicant: NIKE, INC.Inventor: NIKE, Inc.
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Publication number: 20140250609Abstract: A golf ball of a first color is dyed to a second color with an anionic or nonionic disperse dye. Either or both of a pigmented coating layer or an optional clear coating layer on the pigmented coating layer comprises a member selected from the group consisting of polyurethanes, polyureas, polyamides, and combinations thereof, which can be dyed by the anionic or nonionic disperse dye.Type: ApplicationFiled: March 5, 2013Publication date: September 11, 2014Applicant: NIKE, INC.Inventor: NIKE, Inc.
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Patent number: 8206463Abstract: A process for making a colored article of manufacture is disclosed. Accordingly an article of manufacture is first prepared of a material selected from the group consisting of metal, wood, glass, ceramic, masonry and polymeric materials. A polymeric coating (superstrate) is then applied to at least a portion of the surface of the article. At least a portion of the superstrate is brought into contact with a material system that contains (i) water, (ii) a carrier, (iii) a dye and (iv) a diol, under conditions calculated to bring about diffusion of said dye into said superstrate.Type: GrantFiled: May 4, 2006Date of Patent: June 26, 2012Assignee: Bayer MaterialScience LLCInventors: Mark W. Witman, Robert A. Pyles, Rick L. Archey, Joseph D. Ventura
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Patent number: 7691155Abstract: Disclosed herein is a composition for the oxidation dyeing of keratin fibers, for example of human keratin fibers, such as the hair, containing, in a medium that is suitable for dyeing, a) at least one oxidation dye, b) at least one associative polymer, and c) at least one aminosilicone, wherein the at least one aminosilicone/at least one associative polymer weight ratio is greater than or equal to 1.Type: GrantFiled: July 7, 2008Date of Patent: April 6, 2010Assignee: L'Oreal S.A.Inventors: François Cottard, Christine Rondeau
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Patent number: 7687411Abstract: The speaker member includes: a base material; and a resin film layer laminated on the base material through an adhesive layer. The adhesive layer has a heat shrinkage ratio of 0.5 to 1.0%; the resin film layer has a heat shrinkage ratio of 0.8 to 1.3%; and the heat shrinkage ratio of the adhesive layer is smaller than the heat shrinkage ratio of the resin film layer. The method of manufacturing a speaker comprises the steps of: applying a predetermined resin composition on a release material; drying the resin composition, so as to form a resin film layer on the release material; applying a predetermined adhesive on the resin film layer, so as to form an adhesive layer; attaching together the resin film layer formed on the release material and a base material through the adhesive layer, so as to form a laminate; subjecting the laminate to aging; and molding the laminate subjected to aging by using a metal mold having a predetermined shape.Type: GrantFiled: February 16, 2006Date of Patent: March 30, 2010Assignee: Onkyo CorporationInventors: Takeshi Fujitani, Masahiro Yoshida
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Patent number: 7611547Abstract: A process for dyeing a thermoplastic elastomeric substrate comprising immersing the substrate into a dye system comprising at least one metal complex dye and a solvent system comprising water and an organic solvent. The organic solvent may be soluble, partially miscible with water or insoluble or nearly insoluble in water. In particular, the substrate is an inflated bladder such as an airbag used in athletic shoes.Type: GrantFiled: October 30, 2006Date of Patent: November 3, 2009Assignee: Nike, Inc.Inventors: Anna Bracken, Chang Yihua
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Publication number: 20090089942Abstract: A method of tinting a plastic article is provided. The method comprises the steps of (a) providing a plastic article comprising a thermoset or thermoplastic polymer; (b) contacting at least a portion of the surface of said plastic article with a treatment composition comprising at least one dye and water; (c) maintaining said portion of said plastic article in contact with said treatment composition for a period of time at least sufficient to form a tinted plastic article; (d) removing said tinted plastic article from contact with said treatment composition; and (e) rinsing said tinted plastic article with water to remove excess dye. The method is carried out in the absence of an organic solvent, without the need for fixing or further processing steps.Type: ApplicationFiled: October 9, 2007Publication date: April 9, 2009Inventors: Robert A. Pyles, Rick L. Archey
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Publication number: 20090064425Abstract: A colored polymeric material having improved light fastness is generally provided. The colored polymeric material generally comprises a polymer, a colorant, and natural nanoparticles. The colorant can be a dye, such as an acid dye. In one embodiment, the dye can be susceptible to degradation when exposed to light in the presence of oxygen, such as many azo dyes. The natural nanoparticles can include many natural clays.Type: ApplicationFiled: April 10, 2006Publication date: March 12, 2009Applicant: UNIVERSITY OF SOUTH CAROLINAInventors: Walter Scrivens, Dongling Fei
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Publication number: 20080295261Abstract: The invention relates to a dye of the formula I wherein the phenylene ring A is unsubstituted or singly or multiply substituted by C1-C4-alkyl, halogen, aryl, CF3, CN, C1-C4-alkoxy, COR1, COOR1, CONR2R3, SO2R1 or SO2NR2R3, wherein R1 is C1-C4-alkyl, which is optionally substituted, or is aryl, R2 and R3 are independently hydrogen, C1-C4-alkyl, which is optionally substituted, or aryl; R4 is C1-C4-alkyl; X is hydrogen, Cl or Br, Y is OH or NHR4; and Z1 and Z2 are independently hydrogen or halogen. The invention also relates to a method for the production of the dye of the formula (I). The invention further relates to a colored polyurethane and method of producing the colored polyurethane.Type: ApplicationFiled: December 1, 2006Publication date: December 4, 2008Applicant: DyStar Textifarben GmbH & Co. Deutschland KGInventors: Hartwig Jordan, Werner Russ
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Publication number: 20080250574Abstract: The present invention is directed to processes for colorization of molded articles made from engineering plastics. In particular, the processes are used to colorize ice skate blade holders and goalie skate cowlings.Type: ApplicationFiled: November 5, 2007Publication date: October 16, 2008Applicant: PROHOLDERS, INC.Inventors: Michael Benoit, Dennis Doherty, Greg Royer
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Patent number: 7422610Abstract: In a method of coloring a dye coating-formed lens by heating, the lens is subjected to half dyeing by changing the heating temperature depending on the lens site. This dyeing method involves heating a lens having a dye coating-formed on the surface thereof in a heating furnace to diffuse a dye into the lens. This method is carried out in a heating furnace having a frame section having the shape of a cube or rectangular parallelepiped, a heating section provided within the frame section, and an insertion port for inserting the lens provided on the bottom surface of the frame section. All or a part of the lens is inserted from the insertion port into a furnace inside of the heating furnace from the lower portion of the heating furnace and heated.Type: GrantFiled: January 10, 2006Date of Patent: September 9, 2008Assignee: Hoya CorporationInventors: Takaaki Kubodera, Masahiko Samukawa
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Patent number: 7410505Abstract: Disclosed herein is a composition for the oxidation dyeing of keratin fibers, for example of human keratin fibers, such as the hair, containing, in a medium that is suitable for dyeing, a) at least one oxidation dye, b) at least one associative polymer, and c) at least one aminosilicone, wherein the at least one aminosilicone/at least one associative polymer weight ratio is greater than or equal to 1.Type: GrantFiled: December 8, 2003Date of Patent: August 12, 2008Assignee: L'Oreal, S.A.Inventors: François Cottard, Christine Rondeau
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Patent number: 7306630Abstract: A composition comprising at least one coupler chosen from 2-chloro-6-methyl-3-aminophenol and addition salts thereof, at least one oxidation base and at least one associative polymer comprising at least one C8-C30 fatty chain; the use of the composition for the oxidation dyeing of keratin fibres; the dyeing process using this composition; and multi-compartment devices comprising the composition.Type: GrantFiled: April 29, 2004Date of Patent: December 11, 2007Assignee: L'Oreal S.A.Inventor: Marie-Pascale Audousset
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Patent number: 7300470Abstract: The present disclosure relates to a composition for oxidation dyeing keratin fibers, for instance, human keratin fibers such as the hair, comprising 2-chloro-6-methyl-3-aminophenol as a coupler, para-phenylenediamine or para-tolylenediamine as at least one first oxidation base, N,N-bis(?-hydroxyethyl)-para-phenylenediamine or 2-(?-hydroxyethyl)-para-phenylenediamine as at least one second oxidation base, and at least one associative thickening polymer. The present disclosure also relates to a multi-compartment device or kit for the oxidation dyeing of keratin fibers comprising the compositions disclosed herein, and to the dyeing process using these compositions.Type: GrantFiled: April 29, 2004Date of Patent: November 27, 2007Assignee: L'Oreal S.A.Inventor: Marie-Pascale Audousset
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Patent number: 7276087Abstract: The present disclosure relates to a composition for oxidation dyeing keratin fibers, for instance human keratin fibers such as the hair, comprising 2-chloro-6-methyl-3-aminophenol as at least one coupler, para-aminophenol as at least one first oxidation base, 3-methyl-4-aminophenol as at least one second oxidation base, and an associative thickening polymer. The present disclosure also relates to a multi-compartment device or kit for the oxidation dyeing of keratin fibers comprising the compositions disclosed herein, and to the dyeing process using these compositions.Type: GrantFiled: April 29, 2004Date of Patent: October 2, 2007Assignee: L'Oreal S.A.Inventor: Marie-Pascale Audousset
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Patent number: 7198731Abstract: The present invention relates to the use of compounds of formula (I) wherein all substituents are as defined in the claims as optical brighteners as well as to new mixtures of optical brighteners.Type: GrantFiled: November 18, 2002Date of Patent: April 3, 2007Assignee: Clariant Finance (BVI) LimitedInventor: Andrew Clive Jackson
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Patent number: 7175675Abstract: In the method of the present invention a plastic article (e.g., a molded article of thermoplastic polycarbonate) is immersed at least partially in a dye bath which includes one or more dyes, water, at least one carrier, and at least one diol. The dye bath contains: (i) at least one dye (e.g., a static and/or photochromic dye); (ii) water; (iii) at least one carrier represented by the following general formula I, R—O—(CH2)n—OHI wherein R is a radical selected from linear or branched C1–C18 alkyl, benzyl, benzoyl and phenyl, and n is 2 or 3; and (iv) a diol selected from at least one of linear or branched C2–C20 aliphatic diols, poly(C2–C4 alkylene glycol), cycloaliphatic diols having from 5 to 8 carbon atoms in the cyclic ring, monocyclic aromatic diols, bisphenols and hydrogenated bisphenols. In an embodiment of the present invention, the carrier is ethyleneglycol butyl ether, and the diol is diethylene glycol.Type: GrantFiled: December 11, 2003Date of Patent: February 13, 2007Assignee: Bayer MaterialScience LLCInventors: Robert A. Pyles, Rick L. Archey, David M. Derikart
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Patent number: 7160335Abstract: The present invention relates to a compound of formula I wherein R1 and R3 are each independently of the other —NHR5, NHSO2R5, —NHCOR5, —OR6 or —SR7, R2 and R4 are each independently of the other —OR6 or —SR7, with the proviso that not all of the substituents R1 to R4 are —SR7, R5 is hydrogen, alkyl, aryl, aralkyl or a group of formula —(CnH2nX)m—H wherein X is —O—, —S—, —SO2—, —NH—, —NR8—, —CONH— or —CONR8— and R8 is alkyl or aryl, n is a number from 2 to 6 and m is a number from 1 to 10, R6 is aryl or heteroaryl and R7 is alkyl, aryl, heteroaryl or a group of formula —(CnH2nX)m—H wherein X is —O—, —S—, —SO2—, —NH—, —NR8—, CONH— or —CONR8— and R8 is alkyl or aryl, to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles.Type: GrantFiled: March 13, 2003Date of Patent: January 9, 2007Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Lauk, Patric Nowack, Alfons Arquint
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Patent number: 6994735Abstract: A process for tinting a molded article is disclosed. The process entails applying by spraying or by flow coating a hot, dye-solution onto at least a portion of the surface of a molded article to obtain a tinted article and washing the tinted article. In addition to the dissolved dye, the dye solution that is substantially free of particulate matter contains an aqueous solution of a carrier and an optional emulsifier. The article is one molded of a thermoplastic molding composition. In an embodiment of the invention, the dye solution is prepared by filtering a hot aqueous solution through a bag filter that contains a dye to obtain a hot, dye-solution. In a further embodiment, activated carbon is used to purify the dye solution to obtain a dye-free aqueous solution.Type: GrantFiled: May 8, 2003Date of Patent: February 7, 2006Assignee: Bayer Materialscience LLCInventors: Robert A. Pyles, David M. Derikart, Rick L. Archey, Michael Nikolakopoulos
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Patent number: 6949127Abstract: A process of dyeing a molded article is disclosed. The process entails immersing at least a portion of the article in a dyeing bath, retaining the portion in the bath for a period of time sufficient to allow an amount of dye to diffuse into the article, and removing said article from the bath. The molded article comprises a polymeric resin such as (co)polyester, (co)polycarbonates, acrylonitrile-butadiene-styrene, polyamide, polyurethane, polyalkyl(meth)-acrylate, allyldiglycol carbonate and styrene copolymers. The dyeing bath contains in addition to dye, water, a plasticizing agent and a leveling agent.Type: GrantFiled: March 9, 2004Date of Patent: September 27, 2005Assignee: Bayer MaterialScience LLCInventors: Robert A. Pyles, Rick L. Archey
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Patent number: 6758866Abstract: Hair coloring compositions which comprise: (A) non-nitrogenous chelating agents from the group consisting of polyphosphate; phosphonates; hydroxycarboxylates; polyacrylates; zeolite; and mixtures thereof; (B) an oxidative dye primary intermediate; and (C) an oxidative dye coupler; (D) and water are described. The present invention also relates to a method for coloring hair which comprises contacting said hair with a hair coloring composition as described above.Type: GrantFiled: December 21, 2001Date of Patent: July 6, 2004Assignee: Unilever Home & Personal Care USA, Division of Conopco, Inc.Inventors: Jiang Yang, John Brian Bartolone, Gabriela Wis-Surel, Alexander C Chan
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Patent number: 6749646Abstract: A process for tinting of articles molded from a polymeric resin is disclosed. Preferably, the article is molded from polycarbonate and the process entails immersing the molded article in a dye bath that contains water, dye, a carrier and an optional surfactant. The carrier is a compound conforming to R1[—O—(CH2)n]mOR2 (i) wherein R1 and R2 independently denote H or C1-18 alkyl, benzyl, benzoyl or phenyl radical which may be substituted in the aromatic ring by alkyl and or halogen, preferably R1=butyl, R2=H, n is 2 or 3 and m is 2 to 35. The method is especially useful in the manufacture of tinted lenses.Type: GrantFiled: November 7, 2001Date of Patent: June 15, 2004Assignee: Bayer Polymers LLCInventors: Robert A. Pyles, Rick L. Archey
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Patent number: 6733543Abstract: A process of dyeing a molded article is disclosed. The process entails immersing at least a portion of the article in a dyeing bath, retaining the portion in the bath for a period of time sufficient to allow an amount of dye to diffuse into the article, and removing said article from the bath. The molded article comprises a polymeric resin such as (co)polyester, (co)polycarbonates, acrylonitrile-butadiene-styrene, polyamide, polyurethane, polyalkyl(meth)acrylate, allyldiglycol carbonate and styrene copolymers. The dyeing bath contains in addition to dye, water, a plasticizing agent and a leveling agent.Type: GrantFiled: March 26, 2002Date of Patent: May 11, 2004Assignee: Bayer Polymers LLCInventors: Robert A. Pyles, Rick L. Archey
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Patent number: 6610876Abstract: A yellow colorant comprising a chromophore having at least one poly(oxy-C2-C4-alkylene) chain attached to an aromatic methine backbone having at least one cyanoester moiety attached thereto is provided. The ester portion must include a C1-C8 (such as ethyl, butyl, hexyl, or ethyl-hexyl) pendant group and the poly(oxyalkylene) chain must be at most 10 monomers and at least 3 monomers, with ethylene oxide as the capping group. Such a specific group of coloring agents provides the best overall yellow colorations or effects (either alone or in blends with other coloring agents, particularly at low color loadings) as well as the best overall low extraction levels when present within clear polyester (such as polyethylene terephthalate, for example), when compared to all other known polymeric yellow colorants for the same end-use. Compositions and articles comprising such colorants are provided as well as methods for producing such inventive colorants.Type: GrantFiled: February 6, 2003Date of Patent: August 26, 2003Assignee: Milliken & Co.Inventor: Eric B. Stephens
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Publication number: 20030110580Abstract: A process for dyeing certain textile fibers, utilizing vat acid dyeing and specific additional (second) reducing agents such as &agr;-hydroxyalkylsulfinic acids, their salts and 1,2,4-trithiolane, resulting in excellent depth of shade and washfastness, is provided.Type: ApplicationFiled: August 20, 2002Publication date: June 19, 2003Inventors: Stephen M. Burkinshaw, Samit N. Chevli, Michael O. Hunt, Lee D. Jones, David M. Lewis, David J. Marfell
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Patent number: 6136043Abstract: The present invention is directed to polishing pads useful in determining an end to the useful wear life thereof. In a simple embodiment of the present invention, a polishing pad that is used with slurries is dyed on one side in a manner that causes the dye to permeate the pad to a limited depth that does not cause total coloring. Another embodiment of the present invention involves a fixed abrasive pad that has fixed abrasives embedded into the pad to a selected depth where at least one color level is within the portion of the pad that contains the fixed abrasives. After dyeing the pad, the pad is attached to the polishing platen. During the polishing operation, a color change signals a time to stop the polishing operation and change the pad. With multiple colors in the pad, limited only by the ability to dye the pad with uniform depth levels, characteristic wear patterns can be observed and adjustments made accordingly to prolong and optimize pad life.Type: GrantFiled: April 20, 1999Date of Patent: October 24, 2000Assignee: Micron Technology, Inc.Inventors: Karl M. Robinson, Michael A. Walker, John K. Skrovan
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Patent number: 5876466Abstract: Suede-like artificial leather is described that is treated with at least one dye selected from the group consisting of sulfur dyes, vat dyes and sulfur vat dyes, and 2,2',4,4'-tetrahydroxy benzophenone. The suede-like artificial leather has excellent color resistance to light and color fastness to both washing and dry-cleaning.Type: GrantFiled: September 29, 1997Date of Patent: March 2, 1999Assignee: Kuraray Co., Ltd.Inventors: Hitoshi Nakashima, Hisao Yoneda
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Patent number: 5864002Abstract: A method of providing for manufacturing a colored polymer resin having the steps of:(a) blending a disazo colorant into a mixture of monomers, the colorant having a poly(oxyalkylene) substituent comprising from 2 to 200 alkylene oxide residues, bonded to each end of the disazo chromophore, the poly(oxyalkylene) substituent having a nucleophilic terminal group which is capable of reacting with at least a portion of the monomers;(b) providing conditions under which the monomers and disazo colorant polymerize to form a colored polymer resin.Type: GrantFiled: October 18, 1996Date of Patent: January 26, 1999Assignee: Milliken Research CorporationInventors: Eric B. Stephens, Mark E. Ragsdale, David J. Moody
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Patent number: 5731398Abstract: A black colorant composition useful for coloring polyurethanes is provided having a red benzothiazole azo colorant which, when combined with a complementary blue and yellow colorant, exhibits low flairing.Type: GrantFiled: May 31, 1996Date of Patent: March 24, 1998Assignee: Milliken Research CorporationInventors: Mark Edward Ragsdale, David Jesse Moody, Eric B. Stephens
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Patent number: 5679418Abstract: A polyurethane composition suitable for producing leather-like sheets having a soft hand and excellent durability and being dyeable with acid dyes comprising a mixture of:a first polyurethane (a) obtained by reacting:an intermediate product diol (D) with both ends thereof substantially being OH and obtained by reacting a tertiary amino group-containing diol (A), a polymer diol (B) having a number average molecular weight of 500 to 3,000 selected from the group consisting of polyesters, polycarbonates, polylactones and polyethers and an organic diisocyanate (C1), in such stoichiometric amounts as to make the molar ratio of NCO/OH 0.5 to 0.Type: GrantFiled: November 7, 1995Date of Patent: October 21, 1997Assignee: Kuraray Co., Ltd.Inventor: Toshiyuki Akasawa
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Patent number: 5432266Abstract: Preparation of water-soluble reactive dyes containing vinylsulphonyl and .beta.-sulphatoethylsulphonyl groups by the oxidation of dyes containing .beta.-hydroxyethylmercapto radicals, and then sulphation and, if appropriate, conversion of the .beta.-sulphatoethylsulphonyl radical to the vinylsulphonyl radical with bases.Type: GrantFiled: April 1, 1993Date of Patent: July 11, 1995Assignee: Bayer AktiengesellschaftInventors: Karl-Josef Herd, Peter Roschger
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Patent number: 5030243Abstract: There is disclosed a process for the photochemical stabilization of undyed and dyeable artificial leather, which comprises treating said artificial leather in an aqueous liquor which contains a light stabilizer. A composition for carrying out the process is also described.Type: GrantFiled: December 27, 1989Date of Patent: July 9, 1991Assignee: Ciba-Geigy CorporationInventor: Gerhard Reinert
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Patent number: 4992495Abstract: Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.Type: GrantFiled: June 16, 1988Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Stefan Hari, Georg Cseh
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Patent number: 4863479Abstract: An improved process is described for obtaining synthetic hides similar to natural hides by application, to a composite sheet material formed of a porous polymeric matrix within which are embedded fibres, preferably polyamides, of a tanning phase entirely similar to that utilized on natural hides, followed by a treatment with an aqueous solution of a di- or polyaldehide and by a stuffing phase, also entirely similar to that utilized on natural hides; the improved principle consists in effecting, between the tanning phase and the treatment with the di- or polyaldehide, a filling phase in which synthetic polymeric resins mixed with synthetic and/or natural tannins are introduced and fixed into the porous matrix.Type: GrantFiled: June 16, 1988Date of Patent: September 5, 1989Assignee: Lorica S.p.A.Inventor: Giorgio Poletto
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Patent number: 4846846Abstract: A process for coloring polyurethane resins made by a polyaddition reaction of a polyol and an isocyanate is provided, which comprises adding to the reaction mixture before or during the polyaddition reaction a reactive coloring agent suitable for incorporation in the resin with the formation of covalent bonds, said coloring agent having the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently selected from an alkyl group having from 1 to about 12 carbon atoms, X is --CH.sub.2 --, a and a' are integers from 1 to about 6, and Y and Y' are independently selected from polymeric units of hydroxy alkylenes or alkylene oxide monomers selected from ethylene oxide, propylene oxide, butylene oxide, cyclohexene oxide, or glycidol, b and b' are independently either 0 or 1, and Z and Z' are reactive groups independently selected from --OH, --NH.sub.2, or --SH.Type: GrantFiled: June 20, 1988Date of Patent: July 11, 1989Assignee: Milliken Research CorporationInventors: John W. Rekers, John W. Miley
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Patent number: 4756947Abstract: Artificial leather and a dyeing method therefor; the leather includes ultrafine polyamide fibers and is particularly a grained artificial leather having bright, deep color, good color fastness to dry cleaning with charged soap, a delicate touch free from any undesirable rubber-like feeling, as well as high durability.A super-entangled fiber base is provided comprising ultrafine polyamide fibers and/or bundles thereof; polyurethane including polyoxyethylene of molecular weight of 500-5,000 is applied. The polyamide ultrafine fibers are dyed with a metal-dye complex and a fixing agent.Type: GrantFiled: July 9, 1986Date of Patent: July 12, 1988Assignee: Toray Industries, Inc.Inventors: Toshio Nishikawa, Shiro Imai, Kenkichi Yagi, Yuriko Yoshida, Masato Shimada, Junnosuke Nagashima, Teruo Nakamura
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Patent number: 4737581Abstract: Azo compounds of the formula I ##STR1## wherein X is --H, --CH.sub.3, --CF.sub.3, --NO.sub.2, --COOR.sub.1, --NHCOR.sub.2 or --COHN.sub.2, and R.sub.1 and R.sub.2 are as defined in claim 1, are suitable for pigmenting high-molecular organic material.Type: GrantFiled: April 18, 1985Date of Patent: April 12, 1988Assignee: Ciba-Geigy CorporationInventor: Stefan Hari
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Patent number: 4722738Abstract: A waterless dye composition for apparel and other articles, made from thermoplastic materials, comprises an aliphatic polyester of a higher alkanoic acid and a polyol, of the formula (ACOO).sub.2-6 B, wherein A is alkyl of 8-22 carbon atoms and B is the residue of a polyhydric alcohol, other than glycerol, of 2-6 hydroxyl groups and an organic colorant. The compositions can further comprise an aromatic polyester of the formula C.sub.6 H.sub.z' --COOR.sub.1).sub.z, wherein z is 3, 4, 5, or 6; z' is 6-z; and R.sub.1 is higher alkyl; and/or a cycloaliphatic diester of the formula ##STR1## wherein R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C.sub.x H.sub.y O).sub.n C.sub.x H.sub.y --or phosphated polyoxyalkylene of the formula (HO).sub.2 P(.dbd.O)O(C.sub.x H.sub.2x O).sub.n C.sub.x H.sub.2x or a salt thereof, wherein (C.sub.x H.sub.2x O).sub.n is (CH.sub.2 CH.sub.2 O).sub.n, (C.sub.3 H.sub.6 O).sub.n or (CH.sub.2 CH.sub.2 O).sub.p (C.Type: GrantFiled: July 25, 1986Date of Patent: February 2, 1988Assignee: Crucible Chemical CompanyInventor: Robert B. Wilson
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Patent number: 4661117Abstract: A waterless dip dye composition for non-textile and general-utility articles comprises an aromatic ester of the formula ArCOOR.sub.2, ArCOO--R.sub.1 --OOCAr or (ArCOO).sub.z --R.sub.3, wherein R.sub.1 is alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula --C.sub.r H.sub.2r (OC.sub.r H.sub.2r).sub.s, in which r is 2 or 3 and s is 1 to 15; R.sub.2 is substituted or unsubstituted alkyl or alkenyl of 8-30 carbon atoms; R.sub.3 is the residue of a polyhydric alcohol having z hydroxyl groups; Ar is substituted or unsubstituted mono- or bicyclic aryl of up to 15 carbon atoms and z is 3-6, admixed with at least 0.5% by weight of a dyeing assistant agent and an organic colorant.A process for coloring non-textile and general-utility articles, fabricated from polyester, polyamide, polyurethane, acrylic, halogenated polyolefin or epoxy plastic, comprises exposing an article to the foregoing compositions, maintained at a temperature from about 100.degree. C.Type: GrantFiled: November 8, 1984Date of Patent: April 28, 1987Assignee: Crucible Chemical CompanyInventors: Robert B. Wilson, William F. Pomeroy, Louis T. Sovey, Jr.
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Patent number: 4620852Abstract: Artificial leather and a dyeing method therefor; the leather includes ultrafine polyamide fibers and is particularly a grained artificial leather having bright, deep color, good color fastness to dry cleaning with charged soap, a delicate touch free from any undesirable rubber-like feeling, as well as high durability.A super-entangled fiber base is provided comprising ultrafine polyamide fibers and/or bundles thereof; polyurethane including polyoxyethylene of molecular weight of 500-5,000 is applied. The polyamide ultrafine fibers are dyed with a metal-dye complex and a fixing agent.Type: GrantFiled: June 19, 1984Date of Patent: November 4, 1986Assignee: Toray Industries, Inc.Inventors: Toshio Nishikawa, Shiro Imai, Kenkichi Yagi, Yuriko Yoshida, Masato Shimada, Junnosuke Nagashima, Teruo Nakamura
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Patent number: 4609375Abstract: A waterless dip dye composition for apparel- and textile-related articles comprises an aromatic ester of the formula ArCOOR.sub.2, ArCOO--R.sub.1 --OOCAr or (ArCOO).sub.z --R.sub.3, wherein R.sub.1 is alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula --C.sub.r H.sub.2r (OC.sub.r H.sub.2r).sub.s, in which r is 2 or 3 and s is 1 to 15; R.sub.2 is substituted or unsubstituted alkyl or alkenyl of 8-30 carbon atoms; R.sub.3 is the residue of a polyhydric alcohol having z hydroxyl groups; Ar is substituted or unsubstituted mono- or bicyclic aryl of up to 15 carbon atoms and z is 3-6, admixed with at least 0.5% by weight of a dyeing assistant agent and an organic colorant.A process for coloring apparel- and textile-related articles, fabricated from polyester, polyamide, polyurethane, acrylic, halogenated polyolefin or epoxy plastic, comprises exposing an article to the foregoing compositions, maintained at at a temperature between 100.degree. C.Type: GrantFiled: November 8, 1984Date of Patent: September 2, 1986Assignee: Crucible Chemical CompanyInventors: Robert B. Wilson, William F. Pomeroy, Louis T. Sovey, Jr.
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Patent number: 4608056Abstract: A waterless dye composition for apparel and other thermoplastic articles comprises an aromatic polyester of the formula C.sub.6 H.sub.z' --(COOR.sub.1).sub.z, wherein z is 3, 4, 5, or 6; z' is 6 - z; and R.sub.1 is higher alkyl; and/or a cycloaliphatic diester of the formula ##STR1## wherein R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C.sub.x H.sub.y O).sub.n C.sub.x H.sub.y -- or phosphated polyoxyalkylene of the formula(HO).sub.2 P(.dbd.O)O(C.sub.x H.sub.2x O).sub.n C.sub.x H.sub.2xor a salt thereof, wherein (C.sub.x H.sub.2x O).sub.n is (CH.sub.2 CH.sub.2 O).sub.n, (C.sub.3 H.sub.6 O).sub.n or (CH.sub.2 CH.sub.2 O).sub.p -- (C.sub.3 H.sub.6 O).sub.q, n is 2-22, and the sum of p+q is n; and an organic colorant.Type: GrantFiled: February 15, 1985Date of Patent: August 26, 1986Inventor: Robert B. Wilson
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Patent number: 4602916Abstract: A waterless dye composition for apparel and other articles, made from thermoplastic materials, comprises an aliphatic polyester of a higher alkanoic acid and a polyol, of the formula (ACOO).sub.2-6 B, wherein A is alkyl of 8-22 carbon atoms and B is the residue of a polyhydric alcohol, other than glycerol, of 2-6 hydroxyl groups and an organic colorant. The compositions can further comprise an aromatic polyester of the formula C.sub.6 H.sub.z' --(COOR.sub.1).sub.z, wherein z is 3, 4, 5, or 6; z' is 6-z; and R.sub.1 is higher alkyl; and/or a cycloaliphatic diester of the formula ##STR1## wherein R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C.sub.x H.sub.y O).sub.n C.sub.x H.sub.y -- or phosphated polyoxyalkylene of the formula (HO).sub.2 P(.dbd.O)O(C.sub.x H.sub.2x O).sub.n C.sub.x H.sub.2x or a salt thereof, wherein (C.sub.x H.sub.2x O).sub.n is (CH.sub.2 CH.sub.2 O).sub.n, (C.sub.3 H.sub.6 O).sub.n or (CH.sub.2 CH.sub.2 O).sub.Type: GrantFiled: August 26, 1985Date of Patent: July 29, 1986Assignee: Crucible Chemical CompanyInventor: Robert B. Wilson
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Patent number: 4581035Abstract: A waterless dye composition for apparel and other thermoplastic articles comprises a triglyceride fat or oil of the formula ##STR1## wherein acyl, acyl' and acyl" each are saturated or unsaturated substituted or unsubstituted linear alkanoyl of an even number of carbon atoms from 10-30 carbon atoms and an organic colorant.The composition can further contain one or more of:A. an aromatic polyester of the formula C.sub.6 H.sub.z' -(COOR.sub.1).sub.z, wherein z is 3, 4,5, or 6; z' is 6-z and R.sub.1 is higher alkyl;B. a cycloaliphatic diester of the formula ##STR2## wherein R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C.sub.x H.sub.y O).sub.n C.sub.x H.sub.y --or phosphated polyoxyalkylene of the formula(HO).sub.2 P(.dbd.O)O(C.sub.x H.sub.2x O).sub.n C.sub.x H.sub.2xor a salt thereof, wherein (C.sub.x H.sub.2x O).sub.n is (CH.sub.2 CH.sub.2 O).sub.n, (C.sub.3 H.sub.6 O).sub.n or (CH.sub.2 CH.sub.2 O).sub.p --(C.sub.3 H.sub.6 O).sub.Type: GrantFiled: November 8, 1984Date of Patent: April 8, 1986Assignee: Crucible Chemical CompanyInventor: Robert B. Wilson
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Patent number: 4531947Abstract: A thick coat of polyester powder is imparted onto a heated spectacle frame, some of the powder is removed from the frame hinges and replaced with a thin coat, the coated product is baked to fuse the powder and subsequently immersed in a heated aqueous dispersion of a disperse type dye, and the dyed product is subsequently reheated to a temperature sufficient to cause dye diffusion into the fused coating.Type: GrantFiled: March 26, 1984Date of Patent: July 30, 1985Assignee: R. Englehardt Nominees Pty. Ltd.Inventor: David R. Engelhardt
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Patent number: 4529405Abstract: A waterless dye composition for apparel and other thermoplastic articles comprises a bisterephthalate diester of an alkylphenoxypolyethoxyethanol and an organic colorant. Aromatic polyesters of the formula C.sub.6 H.sub.z' --(COOR.sub.1).sub.z, wherein z is 3, 4, 5, or 6; z' or 6 - z and R.sub.1 is higher alkyl and/or cycloaliphatic diesters of the formula ##STR1## wherein R is substituted or unsubstituted straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO(C.sub.x H.sub.y O).sub.n C.sub.x H.sub.y -- or phosphated polyoxyalkylene of the formula(HO).sub.2 P(.dbd.O)O(C.sub.x H.sub.2x O).sub.n C.sub.x H.sub.2xor a salt thereof, wherein (C.sub.x H.sub.2x O).sub.n is (CH.sub.2 CH.sub.2 O).sub.n, (C.sub.3 H.sub.6 O).sub.n or (CH.sub.2 CH.sub.2 O).sub.p --(C.sub.3 H.sub.6 O).sub.q, n is 2-22, and the sum of p+q is n can be admixed with the terephthalate composition.Type: GrantFiled: February 27, 1984Date of Patent: July 16, 1985Assignee: Crucible Chemical CompanyInventor: Robert B. Wilson
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Patent number: 4454170Abstract: A method of tinting a sheet of transparent polyurethane comprising a coloring operation followed by a fixation operation.The aforesaid coloring operation is carried out through immersion of the polyurethane into a bath maintained under continuous agitation and formed of a dispersion of one or several colorants in an aqueous solution containing a surfactant or wetting agent, while the aforesaid fixation operation is carried out through rinsing in a boiling aqueous solution of sodium alkyl sulfonate of the type known under the mark "Teepol".The application to a double or composite sheet preformed to a thin laminate, that is to say, one layer of a thermoplastic polyurethane and one other layer of a thermosetting polyurethane.In a particularly useful embodiment of the invention the tinted polyurethane serves as a selective filter having almost zero transmission in the so-called cutoff range of wavelengths lying between about 350-560 nm.Type: GrantFiled: October 12, 1982Date of Patent: June 12, 1984Assignee: Corning Glass WorksInventors: Serge Goepfert, Serge G. Marsaud, Serge A. M. Renault, Francoise M. M. Roger
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Patent number: RE31844Abstract: The method of treating open-celled polyurethane foam by the application of a modifying ingredient, such as a dye, pigment, color stabilizer or fire retardant, for example, wherein the method comprises the steps of (a) applying an excess of a liquid solution or dispersion of the modifying ingredient to a mass of the foam, (b) removing most of the excess of the liquid by squeezing the mass, (c) passing a gas, the temperature of which is between 350.degree. F. and 500.degree. F., through the material for a period of time sufficient (1) to raise the temperature of the polyurethane mass to a point at which the polyurethane will absorb the modifying ingredient, and (2) to vaporize the liquid present in the solution or dispersion, the period of time being insufficient to cause charring of the polyurethane, thereby accelerating the absorption of the modifying ingredient into the polyurethane, so as to permanently incorporate the modifying ingredient into the foam, and (d) allowing the mass to cool.Type: GrantFiled: October 26, 1983Date of Patent: March 5, 1985Assignee: Foam Cutting Engineers, Inc.Inventor: Winslow L. Pettingell