Patents by Inventor Edward W. Kluger
Edward W. Kluger has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5591833Abstract: Colorants and compositions useful as a fugitive or permanent colorant for a variety of substrates, or as intermediates for their manufacture, and having one or more improved properties of enhanced aqueous washability, compatibility with and non-extractibility from thermoplastic resins, or reactivity with resins having reactive functionality, said composition having the formula C(Z).sub.Type: GrantFiled: August 10, 1993Date of Patent: January 7, 1997Assignee: Milliken Research CorporationInventors: John B. Hines, David J. Moody, Edward W. Kluger
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Patent number: 5290921Abstract: The present invention provides primary hydroxyl enhanced colorants having markedly improved reactivities in e.g., polyurethane foams for imparting permanent coloring thereto, the colorants having the formulaC--(Z).sub.1-4are provided wherein C is an azo, methine, or azamethine chromogen and Z is a poly(oxyalkylene) moiety comprised of (1) at least two (A) units independently selected from those of the formulae--CH.sub.2 CH(O--T)CH.sub.2 O-- or --CH.sub.2 CH(O--T)CH.sub.2 O--Tand (2) from none to about 200 (B) units of the formula (--RO--) wherein R is straight or branched chain hydrocarbon of 2-4 carbons, T is a moiety of the formula--CH.sub.2 CH(R.sub.1)--O--(RO).sub.0-40 --CH.sub.2 CH.sub.2 OHwherein R.sub.1 is selected from unsubstituted or substituted alkyl, aryl, alkenyloxyalkyl, alkoxyalkyl or aryloxyalkyl, and wherein the A units comprise at least 0.5 percent of the total A+B units.Type: GrantFiled: January 8, 1990Date of Patent: March 1, 1994Assignee: Milliken Research CorporationInventors: David J. Moody, Edward W. Kluger, John W. Rekers
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Patent number: 5270363Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula A--[SO.sub.2 --N(R.sub.2)--Y].sub.1-4 ; wherein: R.sub.2 is selected for example from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl.Type: GrantFiled: August 24, 1992Date of Patent: December 14, 1993Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, David J. Moody
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Patent number: 5240464Abstract: The process for chemically modifying metal-free, organic material for improving one or more properties thereof such as water dispersibility, compatibility with other organics, or increased chemical reactivity, wherein the process includes providing material with from 1-6 sulfonylhalide groups or sulfonate ester groups or mixtures thereof, and contacting the material under sulfonamido forming conditions with one or more reactants containing one or more poly(oxyalkylene) moieties, each of the reactants having from 1 to 4 functional amine groups, and each of the poly(oxyalkylene) moieties being comprised of from about 4 to about 200 epoxide reactant residues at least about 50 mole percent of which residues contain 2-4 carbons.Type: GrantFiled: June 2, 1992Date of Patent: August 31, 1993Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Max A. Weaver, Jeffery R. Harris, David J. Moody
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Patent number: 5177200Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula A--[SO.sub.2 --N(R.sub.2)--Y].sub.1-4 ; wherein: R.sub.Type: GrantFiled: May 19, 1989Date of Patent: January 5, 1993Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, David J. Moody
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Patent number: 5149800Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula:A--[D--Z--SO.sub.2 --N(R.sub.2)--Y].sub.1-16wherein; R.sub.2 is selected from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl, alkoxy, alkylthio, or aryloxy; Z is an arylene moiety; D is a linking group being or containing at least one of --O--, --S--, --SO.sub.2 --, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloalkyl or aryl, and R.sub.3 is R.sub.Type: GrantFiled: June 26, 1989Date of Patent: September 22, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Max A. Weaver
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Patent number: 5135972Abstract: Colorants and compositions containing the same, including polymeric substrates, especially polyurethane foams which are tinted or deeper colored with the colorants which have the general formula: ##STR1## wherein R.sub.2 is selected from hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aryl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted or unsubstituted; Z is an arylene moiety; each D or D' is selected from a covalent bond or a linking group consisting of or containing at least one of --O--, --S--, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloaliphatic or aryl, and R.sub.3 is R.sub.Type: GrantFiled: July 15, 1991Date of Patent: August 4, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, Max A. Weaver
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Patent number: 5082938Abstract: Enhanced branched chain hydroxyl compounds are provided of formulaY--(Z).sub.1-6wherein Y is the residue of a nucleophile devoid of conjugated divalent linking moieties, and each Z is a poly(oxyalkylene) moiety having a molecular weight of from about 200-10,000 and containing at least one glycidol residue, wherein at least one of the primary oxy sites of said glycidol residue is linked preferably directly to a first epoxide residue of three or more carbons, and wherein said first epoxide residue is linked through a secondary oxy site preferably directly to a second epoxide reside having a primary terminal hydroxyl.Type: GrantFiled: March 1, 1990Date of Patent: January 21, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, David J. Moody
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Patent number: 5043013Abstract: A washable aqueous ink composition having a viscosity of from about 1.0 to about 6.0 centipoises and containing from about 10 to about 50% by weight of one or more polymeric colorants of the formula: ##STR1## wherein: X is a polar group such as sulfonic acids, sulfonic acid salts, sulfonamides, sulfonates or the like;R is alkylene; Y is H, alkanoyl, carbamoyl, or the like;R.sub.1 is nitrogen, oxygen, sulfur, or a sulfur-containing divalent linking group;a is an integer of from six to about forty;b and c are each independently selected from one or two;d is an integer of from one to four; the product of (a) (b) (c) is an integer of from 6 to about 40;and CHROM is a chromophore such as nitro, nitroso, monoaxo, disazo and trisazo, diarylmethane, triarylmethane, xanthane, acridine, methine, thiazole, indamine, azine, oxazine, or anthraquinone, wherein the (RO).sub.a moiety is bonded to a carbocyclic aromatic ring of the (CHROM) through R.sub.1.Type: GrantFiled: August 15, 1989Date of Patent: August 27, 1991Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore, Judy A. Wagner
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Patent number: 4992204Abstract: A method for tagging one or a mixture of natural or synthetic materials comprising contacting the same with one or a mixture of tagging compounds containing one or more non-ionic luminophore moieties attached to at least one poly(oxyalkylene) moiety by means of a linking moiety; wherein said tagging compound has substantial absorbance within the range of from about 300 to about 400 nm and reemits substantial visible light, said contacting effecting at least a temporary association between said material and said compound wherein said compound is present in an amount between about 0.0001 and about 10 percent by weight of said material.Type: GrantFiled: August 22, 1989Date of Patent: February 12, 1991Assignee: Miliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore, John B. Hines, John G. Lever
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Patent number: 4981516Abstract: A washable ink composition is provided which is an aqueous mixture containing water soluble, ester-terminated, poly(alkyleneoxy)-substituted methine colorant of the formula: ##STR1## wherein: AR is an unsubstituted or substituted aromatic or hetero-aromatic group; X is nitrogen or oxygen; R is unsubstituted or substituted straight or branched alkylene of 2-4 carbons or mixtures thereof; R.sub.1 is H or an unsubstituted or substituted alkyl, cycloalkyl or phenyl moiety containing one to about 10 carbons, or a group of the formula: ##STR2## wherein: R.sub.3 is H or alkyl of one to about ten carbons, and d is zero when X is oxygen and one when X is nitrogen; R.sub.Type: GrantFiled: September 21, 1989Date of Patent: January 1, 1991Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers, Judy A. Wagner
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Patent number: 4978362Abstract: A thermoplastic resin composition is provided which contains a thermoplastic resin and a colorant in the form of a polyalkyleneoxy-trifluoromethyl aniline colorant provided in said thermoplastic resin in a minor amount sufficient to provide coloration to said resin, said colorant having the formula: ##STR1## wherein R.sub.1 is selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 OH, phenyl or ##STR2## wherein R.sub.4 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is H, CF.sub.3, a lower alkyl group containing from 1 to about 9 carbon atoms, Cl or Br; R.sub.3 is an aromatic or heteroaromatic containing group, and n is an integer from 2 to about 75.Type: GrantFiled: October 11, 1988Date of Patent: December 18, 1990Assignee: Milliken Research CorporationInventors: Edward W. Kluger, John W. Rekers
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Patent number: 4962142Abstract: Triazine compounds are disclosed which are useful for imparting UV screening properties to polymers of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H, ##STR2## where R.sub.3 is an alkyl group having from one to about six carbon atoms; and R.sub.2 is selected from H and CH.sub.3, also disclosed are polymer compositions having improved UV screening properties containing said triazine compounds.Type: GrantFiled: November 14, 1988Date of Patent: October 9, 1990Assignee: Milliken Research CorporationInventors: Cyril A. Migdal, John B. Hines, Edward W. Kluger
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Patent number: 4912203Abstract: Thiophene based colorants useful for coloring thermoset resins such as polyurethanes being the formula; ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from halogen, carboxylic acid, alkanoyl, aryloyl, carbocyclic forming polymethylene chains, alkyl, aryl, cyano, thioalkyl, dithioalkyl, thioaryl, dithioaryl, thiocyano, carboxyalkyl, carboxyaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, oxyalkyl, thioamidoalkyl, thioamidodialkyl, or hydrogen when an adjacent group is isobutyryl; R.sub.4, R.sub.5, and R.sub.7 are selected from hydrogen alkyl, oxyalkyl, sulfonamidoalkyl, sulfonamidoaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, halogen, thioalkyl and thioaryl; and R.sub.8 and R.sub.9 are selected from polyalkylene oxide, copolymers of polyalkylene oxides, and hydroxyalkylenes.Type: GrantFiled: May 17, 1988Date of Patent: March 27, 1990Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore
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Patent number: 4826978Abstract: Triazine compounds are disclosed which are useful for imparting UV screening properties to polymers of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H, ##STR2## where R.sub.3 is an alkyl group having from one to about six carbon atoms; and R.sub.2 is selected from H and CH.sub.3, also disclosed are polymer compositions having improved UV screening properties containing said triazine compounds.Type: GrantFiled: December 29, 1987Date of Patent: May 2, 1989Assignee: Milliken Research CorporationInventors: Cyril A. Migdal, John B. Hines, Edward W. Kluger
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Patent number: 4775748Abstract: Novel reactive colorants being the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from halogen, carboxylic acid, alkanoyl, aryloyl, carbocyclic forming polymethylene chains, alkyl, aryl, cyano, thioalkyl, dithioalkyl, thioaryl, dithioaryl, thiocyano, carboxyalkyl, carboxyaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, oxyalkyl, thioamidoalkyl, thioamidodialkyl, or hydrogen when an adjacent group is isobutyryl; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are selected from hydrogen, alkyl, oxyalkyl, oxyaryl, sulfonamidoalkyl, sulfonamidoaryl, amidoalkyl, amidodialkyl, amidoaryl, amidodiaryl, halogen, thioalkyl and thioaryl; and R.sub.8 and R.sub.9 are selected from polyalkylene oxide, copolymers of polyalkylene oxides, and hydroxyalkylenes.Type: GrantFiled: June 1, 1987Date of Patent: October 4, 1988Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore
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Patent number: 4761502Abstract: Polyalkyleneoxytrifluoromethylaniline compounds are provided of the formula: ##STR1## wherein R.sub.1 is independently selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 Br, CH.sub.2 OH, phenyl or ##STR2## where R.sub.5 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is selected from H, a lower alkyl group containing from 1 to about 9 carbon atoms, alkylaryl containing from 7 to about 11 carbon atoms, cyanoalkyl, or acyl; R.sub.3 is selected from a lower alkyl group containing from 1 to about 9 carbon atoms, cyanoalkyl, acetoxyalkyl or ##STR3## wherein R.sub.1 and R.sub.2 are as given above; R.sub.4 is H, CF.sub.3, a lower alkyl group containing from 1 to about 9 carbon atoms, Cl or Br and n is 0 or an integer from 1 to about 125.Type: GrantFiled: September 8, 1986Date of Patent: August 2, 1988Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore, Joe T. Burchette
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Patent number: 4751254Abstract: This invention relates to a process for coloring polyurethane resins during the production of same with reactive colorants derived from novel polyalkoxytrifluoroaniline intermediates. These colorants impart increased brightness in shade for both aromatic and heteroaromatic derivatives and increased resistance to stannous octanoate catalyst over conventional polymeric colorants derived for heteroaromatic compounds. These novel colorants have the structure: ##STR1## wherein R.sub.1 is selected from H, a lower alkyl group containing from 1 to about 10 carbon atoms, CH.sub.2 Cl, CH.sub.2 OH, phenyl or ##STR2## where R.sub.6 is H or a lower alkyl group containing from 1 to about 9 carbon atoms; R.sub.2 is selected from OH, NH.sub.2 or SH; R.sub.3 is selected from a lower alkyl group containing from 1 to about 9 carbon atoms, cyanoalkyl, acetoxyalkyl or ##STR3## where R.sub.1 and R.sub.2 are as given above; R.sub.4 is H, CF.sub.Type: GrantFiled: January 20, 1987Date of Patent: June 14, 1988Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Patrick D. Moore, Joe T. Burchette
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Patent number: 4624980Abstract: An N-t-alkyl-N-sec-alkyl secondary amine compound of the formula: ##STR1## wherein X, Y and Z are each independently selected from --H, --OH, or an alkyl group having from 1 to about 15 carbon atoms; and n is an integer of from 3 to about 6.Type: GrantFiled: March 28, 1985Date of Patent: November 25, 1986Assignee: Milliken Research CorporationInventors: John W. Rekers, Edward W. Kluger
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Patent number: 4601725Abstract: Fugitive colorants having the general formula:A--N.dbd.N--B--[(C)H].sub.nwherein A is thiophene or a thiophene derivative, N is nitrogen, B is a nitrogen containing organic dyestuff coupling component, C is a polymer chain bound to nitrogen in the dyestuff coupling component; said polymer chain being selected from polyethylene oxide, polypropylene oxide, polybutylene oxide and copolymers of polyethylene oxide, polypropylene oxide, and/or polybutylene oxide, said polymer chain having about x repeating monomeric units, n is an integer from 1 to 6 and the product of n times x is from about 50 to about 250. A coloration process is also disclosed and claimed.Type: GrantFiled: August 27, 1984Date of Patent: July 22, 1986Assignee: Milliken Research CorporationInventors: Margaret S. Keller, Edward W. Kluger