Chain Containing At Least Fifteen Alkylene Oxide Groups Patents (Class 534/729)
  • Patent number: 11198838
    Abstract: This invention relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two components: at least one chromophore component and at least one polymeric component. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to ultraviolet light, or they may absorb light to reflect these same shades. The whitening agents are further characterized by having a dispersion component value of the Hansen Solubility Parameter of less than or equal to about 17 MPa0.5. This invention also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: November 19, 2019
    Date of Patent: December 14, 2021
    Assignee: The Procter & Gamble Company
    Inventors: Eugene Steven Sadlowski, Mark Robert Sivik, Michael David Cummings, Donna D'Angelo Morrall, Kevin Lee Kott, Keith Homer Baker, Brian Joseph Loughnane, Michael A. Valenti, Laurent D. Kieken, Xiayong Michael Hong, Eduardo Torres, Dominick J. Valenti, Patrick D. Moore, Leonard J. Starks
  • Patent number: 10597614
    Abstract: The present application relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two constituents: at least one chromophore constituent and at least one polymeric constituent. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to light, or they may absorb light to reflect these same shades. This disclosure also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: March 24, 2020
    Assignee: The Procter & Gamble Company
    Inventors: Gregory Scot Miracle, Sanjeev Kumar Dey, Eduardo Torres, Dominick Joseph Valenti
  • Patent number: 10526566
    Abstract: This invention relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two components: at least one chromophore component and at least one polymeric component. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to ultraviolet light, or they may absorb light to reflect these same shades. The whitening agents are further characterized by having a dispersion component value of the Hansen Solubility Parameter of less than or equal to about 17 MPa0.5. This invention also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: January 7, 2020
    Assignee: The Procter & Gamble Company
    Inventors: Eugene Steven Sadlowski, Mark Robert Sivik, Michael David Cummings, Donna D'Angelo Morrall, Kevin Lee Kott, Keith Homer Baker, Brian Joseph Loughnane, Michael A. Valenti, Laurent D. Keiken, Xiayong Michael Hong, Eduardo Torres, Dominick J. Valenti, Patrick D. Moore, Leonard J. Starks
  • Patent number: 10155868
    Abstract: The present application relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two constituents: at least one chromophore constituent and at least one polymeric constituent. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to light, or they may absorb light to reflect these same shades. The whitening agents are further characterized by the polymeric component comprising at least two repeating glycerol units. This disclosure also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: October 3, 2016
    Date of Patent: December 18, 2018
    Assignee: Milliken & Company
    Inventors: Eduardo Torres, Gregory Scot Miracle
  • Patent number: 9777250
    Abstract: The present application relates to novel whitening agents for cellulosic substrates. The whitening agents are comprised of at least two constituents: at least one chromophore constituent and at least one polymeric constituent. Suitable chromophore components generally fluoresce blue, red, violet, or purple color when exposed to light, or they may absorb light to reflect these same shades. This disclosure also relates to laundry care compositions including but not limited to liquid and/or powder laundry detergent formulations and rinse added fabric softening (RAFS) compositions that comprise such whitening agents.
    Type: Grant
    Filed: October 3, 2016
    Date of Patent: October 3, 2017
    Assignee: Milliken & Company
    Inventors: Sanjeev K. Dey, Gregory Scot Miracle
  • Publication number: 20150080560
    Abstract: Laundry care compositions comprising thiophene azo carboxylate fabric shading dyes and methods of treating a textile comprising such laundry care compositions.
    Type: Application
    Filed: September 4, 2014
    Publication date: March 19, 2015
    Inventors: Eduardo Torres, Gregory Scot Miracle
  • Patent number: 8802829
    Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.
    Type: Grant
    Filed: May 16, 2012
    Date of Patent: August 12, 2014
    Assignee: Spectra Colors Corp.
    Inventors: Mark Berenfeld, Sai Harfouch, Peter Caputo
  • Patent number: 8772545
    Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: July 8, 2014
    Assignee: Spectra Colors Corp.
    Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
  • Patent number: 8664371
    Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: March 4, 2014
    Assignee: Spectra Colors Corp.
    Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
  • Patent number: 8378083
    Abstract: This invention relates to bis-azo colorants for use as bluing agents, laundry care compositions comprising bis-azo colorants that may serve as bluing agents, processes for making such bluing agents and laundry care compositions and methods of using the same. The bluing agents are generally comprised of at least two components: at least one chromophore component and at least one polymeric component. These bluing agents are advantageous in providing a whitening effect to fabrics, while not building up over time and causing undesirable blue discoloration to the treated fabrics.
    Type: Grant
    Filed: October 22, 2010
    Date of Patent: February 19, 2013
    Assignee: Milliken & Company
    Inventors: Robert L. Mahaffey, Jr., Xiaoyong Michael Hong, Eduardo Torres, Dominick J Valenti, Gregory S Miracle
  • Publication number: 20120101264
    Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.
    Type: Application
    Filed: December 2, 2011
    Publication date: April 26, 2012
    Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
  • Publication number: 20120004400
    Abstract: Rinsable dyes with improved fugitivity are formulated by attaching dyestuff compounds with amine-capped sulfonic solubilizing groups to commercially available ethoxylated aniline, so that the surfactant effect of the ethoxylated aniline counteracts the substantivity of the dyestuff compound, while the neutralization of the sulfonic solubilizing groups reduces substantivity.
    Type: Application
    Filed: July 2, 2010
    Publication date: January 5, 2012
    Inventors: Mark Berenfeld, Sal Harfouch, Peter Caputo
  • Patent number: 7772377
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: January 25, 2008
    Date of Patent: August 10, 2010
    Assignee: Xerox Corporation
    Inventors: Jeffrey H Banning, Donald R Titterington, Clifford R King
  • Patent number: 7619075
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: August 16, 2005
    Date of Patent: November 17, 2009
    Assignee: Xerox Corporation
    Inventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
  • Patent number: 6969759
    Abstract: Disclosed is a colorant composition of the formula wherein R is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and wherein R can be joined to the phenyl moiety to form a ring, R? is an aromatic- or heteroaromatic-containing group, each Ra, independently of the others, is a halogen atom, an alkyl group, an alkoxy group, a nitrile group, a nitro group, an amide group, or a sulfonamide group, w is an integer of 0, 1, 2, 3, or 4, n is an integer representing the number of carbon atoms in each repeat alkylene oxide unit, and x is an integer representing the number of repeat alkylene oxide units, wherein said colorant has no more than one —OH, —SH, or primary or secondary amino group per molecule.
    Type: Grant
    Filed: May 25, 2004
    Date of Patent: November 29, 2005
    Assignee: Xerox Corporation
    Inventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
  • Patent number: 6870036
    Abstract: Novel addition products of hydroxyl-protecting groups (such as isocyanates) with oxyalkylene-substituted intermediates, such as poly(oxyalkylenated) aniline compounds, for the eventual production of substituted, and substantially pure, colorants, particularly diazo and triphenylmethane derivatives, through the reaction of such intermediates with certain reactants are provided. These new colorants exhibit improved wax and/or oil solubility and high purity, particularly due to the inability of certain impurities to deleteriously react with the protected hydroxyl groups of either the intermediate or the colorant during and/or after formation thereof. A method for producing such novel colorants through utilization of these novel substantially pure colorant intermediates is also provided.
    Type: Grant
    Filed: May 1, 2003
    Date of Patent: March 22, 2005
    Assignee: Milliken & Company
    Inventor: Rajnish Batlaw
  • Patent number: 6667392
    Abstract: This invention relates to colorants comprising a chromophore having a single azo acetoacetanilide moiety, wherein said moiety each have at least one poly(oxyalkylene) chain. Such colorants exhibit extremely good base stability and lightfastness, particularly when incoporated within certain media and/or on the surface of certain substrates. These poly(oxyalkylene) chains provide solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or or diverse substrates. Compositions and articles comprising such colorants are provided as are methods for producing such inventive colorants.
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: December 23, 2003
    Assignee: Milliken & Company
    Inventors: Jusong Xia, Eric B. Stephens, Mary G. Mason, John W. Miley, Leonard J. Starks, Eugene K. Stephenson
  • Publication number: 20020177640
    Abstract: This invention relates to colorants comprising a chromophore having a single azo acetoacetanilide moiety, wherein said moiety each have at least one poly(oxyalkylene) chain. Such colorants exhibit extremely good base stability and lightfastness, particularly when incoporated within certain media and/or on the surface of certain substrates. These poly(oxyalkylene) chains provide solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or or diverse substrates. Compositions and articles comprising such colorants are provided as are methods for producing such inventive colorants.
    Type: Application
    Filed: November 21, 2001
    Publication date: November 28, 2002
    Inventors: Jusong Xia, Eric B. Stephens, Mary G. Mason, John W. Miley, Leonard J. Starks, Eugene K. Stephenson
  • Patent number: 6479647
    Abstract: Novel addition products of hydroxyl-protecting groups (such as isocyanates) with oxyalkylene-substituted intermediates, such as poly(oxyalkylenated) aniline compounds, for the eventual production of substituted, and substantially pure, colorants, particularly diazo and triphenylmethane derivatives, through the reaction of such intermediates with certain reactants are provided. These new colorants exhibit improved wax and/or oil solubility and high purity, particularly due to the inability of certain impurities to deleteriously react with the protected hydroxyl groups of either the intermediate or the colorant during and/or after formation thereof. A method for producing such novel colorants through utilization of these novel substantially pure colorant intermediates is also provided.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: November 12, 2002
    Assignee: Milliken & Company
    Inventor: Rajnish Batlaw
  • Patent number: 6479648
    Abstract: This invention relates to colorants comprising a chromophore having two azo acetoacetanilide moieties, wherein said moieties each have at least one poly(oxyalkylene) chain, preferably at least two such chains. Such colorants exhibit extremely good base stability and lightfastness, particularly when incorporated within certain media and/or on the surface of certain substrates. These poly(oxyalkylene) chains provide solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or or diverse substrates. Compositions and articles comprising such colorants are provided as are methods for producing such inventive colorants.
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: November 12, 2002
    Assignee: Milliken & Company
    Inventors: Jusong Xia, Eric B. Stephens, Mary G. Mason, John W. Miley, Leonard J. Starks
  • Patent number: 6069276
    Abstract: This invention relates to very specific oxyalkylene-substituted m-amidoaniline compounds as intermediates for the production of poly(oxyalkylene)-substituted diazo (or other type) colorants. Such an inventive intermediate compound is produced in a single step by reacting an oxyalkylene oxide or alkoxy oxyalkylester having at least three carbon atoms (branched or unbranched), glycidol, or a glycidyl group directly with m-acetoamidoaniline (as a preferred example) at a relatively low temperature. Propylene oxide is the preferred compound. The propylene oxide selectively reacts with the amine group on the base compound without propoxylating the amido group. Such a specific method thus does not require extra time- and cost-consuming steps of protecting the amido nitrogen from attack. After production, this intermediate may be reacted with, for example, a diazotized aromatic amine to ultimately form a diazo colorant.
    Type: Grant
    Filed: March 5, 1999
    Date of Patent: May 30, 2000
    Assignee: Milliken & Company
    Inventor: Rajnish Batlaw
  • Patent number: 5994486
    Abstract: A fluorine-containing macroazo compound having a fluorine segment in the molecule is useful as a polymerization initiator for producing, for example, fluorine-containing block polymers.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: November 30, 1999
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Kazuo Shiraki, Nobutaka Shimamura
  • Patent number: 5955523
    Abstract: Disazo chromphores having at least two different poly(oxyalkylene) substituents are linked together by a covalent bond or by an intervening connecting group to form dimers. The preferred poly(oxyalkylene) substituents are straight chain polymers consisting of ethylene oxide and propylene oxide. The disazo colorants are useful for coloring thermoplastic resins such as polypropylene and polyethylene and show improved extraction, migration, clarity and thermal stability characteristics as compared to standard monoazo colorants.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: September 21, 1999
    Assignee: Milliken Research Corporation
    Inventors: Eric B. Stephens, Mark E. Ragsdale
  • Patent number: 5925150
    Abstract: 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: Grant
    Filed: August 20, 1997
    Date of Patent: July 20, 1999
    Assignee: Milliken & Company
    Inventors: Mark Edward Ragsdale, David Jesse Moody, Eric B. Stephens
  • Patent number: 5766268
    Abstract: A colorant composition which can be liquid in the neat form at 25.degree. C., having the structure ABXYZ, whereA is an organic chromophore;B is an electrophilic reactive group covalently bonded to A directly or through a linking group;X is a nucleophilic linking group covalently bonding B and Y;Y is a poly(oxyalkylene)-containing moiety comprising the formula (C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n where a and b are different and from 1 to 8, m is at least 3, n is 0 to 15; andZ is a terminal group for Y.The colorant composition can be prepared from a reactive dye AB which is reacted with XYZ, a poly(oxyalkylene)-containing moiety containing a nucleophilic group.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: June 16, 1998
    Assignee: Milliken Research Corporation
    Inventor: John D. Bruhnke
  • Patent number: 5591833
    Abstract: 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: Grant
    Filed: August 10, 1993
    Date of Patent: January 7, 1997
    Assignee: Milliken Research Corporation
    Inventors: John B. Hines, David J. Moody, Edward W. Kluger
  • Patent number: 5532346
    Abstract: A coupling component for use in the synthesis of azo colorants, selected from compounds having the formula: ##STR1## wherein R.sub.1 is Y or arylene-(Y).sub.n, where n is an integer from 1-4; R.sub.2 is H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, aryl, or Y; provided that if R.sub.1 is arylene-(Y).sub.n, then R.sub.2 is not aryl; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, SO.sub.3 H, Br, Cl, OH, or NO.sub.2 and m is an integer from 0-3; and Y is a poly(oxyalkylene) substituent having from 4-200 oxyalkylene units which are the addition products of compounds selected from the group consisting of ethylene oxide and propylene oxide.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: July 2, 1996
    Assignee: Milliken Research Corporation
    Inventors: Patrick D. Moore, Michael A. Valenti, Richard A. VanDahm
  • Patent number: 5456725
    Abstract: A process for temporarily coloring a polyamide substrate is provided whereby a poly(oxyalkylene) substituted methine colorant is applied to the substrate followed by heating the substrate with superheated steam at a temperature of 250.degree. F. or greater, which effectively decolorizes the methine colorant.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: October 10, 1995
    Assignee: Milliken Research Corporation
    Inventor: John D. Bruhnke
  • Patent number: 5310887
    Abstract: As aqueous ink composition is provided having up to 5 wt. % of a colorant of the formula:A--{Y--X--C(O)--R.sub.1 --C(O)O.sup.- }.sub.pwhere A is an organic chromophore; Y is a polyoxyalkylene substituent; X is a radical of a reactive hydroxy, amino or thio group; and R.sub.1 is C.sub.2-30, substituted or unsubstituted alkylene, alkenylene, or phenylenealkylene. A counter ion selected from alkaline metal ions, alkaline earth metal ions, ammonium ions, amine salts, and zinc ammonium complexes is present in approximately stoichiometric proportion or greater relative to the colorant in the ink composition.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: May 10, 1994
    Assignee: Milliken Research Corporation
    Inventors: Patrick D. Moore, Clifford R. King, Raj Batlaw
  • Patent number: 5290921
    Abstract: 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: Grant
    Filed: January 8, 1990
    Date of Patent: March 1, 1994
    Assignee: Milliken Research Corporation
    Inventors: David J. Moody, Edward W. Kluger, John W. Rekers
  • Patent number: 5176745
    Abstract: An aqueous ink composition is provided having up to 50 wt. % of a colorant of the formula:A--{Y--X--C(O)--R.sub.1 --C(O)O.sup.- }.sub.pwhere A is an organic chromophore; Y is a polyoxyalkylene substituent; X is a radical of a reactive hydroxy, amino or thio group; and R.sub.1 is C.sub.2-30, substituted or unsubstituted alkylene, alkenylene, or phenylenealkylene. A counter ion selected from alkaline metal ions, alkaline earth metal ions, ammonium ions, amine salts, and zinc ammonium complexes is present in approximately stoichiometric proportion or greater relative to the colorant in the ink composition.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: January 5, 1993
    Assignee: Milliken Research Corporation
    Inventors: Patrick D. Moore, Clifford R. King, Raj Batlaw
  • Patent number: 5101041
    Abstract: A group of functionalized triamine chelants and their derivatives that form complexes with radioactive metal ions are disclosed. The complexes can be covalently attached to a protein or an antibody or antibody fragment and used for therapeutic and/or diagnostic purposes.
    Type: Grant
    Filed: April 26, 1989
    Date of Patent: March 31, 1992
    Assignee: The Curators of the University of Missouri
    Inventors: David E. Troutner, Christy S. John, Maroor R. A. Pillai
  • Patent number: 5062894
    Abstract: Diarylide pigment compositions useful for preparing storage stable printing inks (especially of the publication gravure type) are prepared using a poly (alkylene oxide) substituted acetoacetanilide together with a typical acetoacetanilide and coupling the mixture of acetoacetanilides with tetrazotized dichlorobenzidine.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: November 5, 1991
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
  • Patent number: 4985546
    Abstract: A substituted colorant which may be copolymerized with a condensation polymer to provide a covalently bound, nonextractable coloring, having the formula ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or lower alkyl; R.sub.4 is selected from hydrogen or lower alkyl; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N and M is from 3 to about 100. The hydroxyl groups are protected by formation of a ring structure during alkoxylation and amination of the substituent.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: January 15, 1991
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4978362
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: December 18, 1990
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, John W. Rekers
  • Patent number: 4977281
    Abstract: Primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane compounds are provided of the formula: ##STR1## wherein R and R.sub.1 are independently selected from hydrogen or a lower alkyl group; R.sub.2 and R.sub.3 are independently selected from hydrogen, phenyl or lower alkyl groups; R.sub.4 is selected from hydrogen or a lower alkyl group; x is 0 or 1; N and M are each integers of from 1 to about 100 and the sum of N an M is from 2 to about 100; also disclosed are polyoxyalkylene amino alcohol compounds which may be derived from the compounds of Formula I above having the formula: ##STR2## wherein R, R.sub.1, R.sub.4, x, N and M all have the values given above. Also provided is a process for preparing a primary amino polyoxyalkylene 1,3-dioxane or 1,3-dioxolane.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: December 11, 1990
    Assignee: Milliken Research Corporation
    Inventors: John W. Miley, John W. Rekers
  • Patent number: 4946509
    Abstract: Diarylide pigments modified with alkylene oxide polymers. The modified pigments are useful in both water-based and solvent-based coating and ink compositions.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: August 7, 1990
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Manuel Z. Gregorio, Anthony C. Zwirgzdas
  • Patent number: 4912203
    Abstract: 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: Grant
    Filed: May 17, 1988
    Date of Patent: March 27, 1990
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Patrick D. Moore
  • Patent number: 4871371
    Abstract: A two component tint composition is provided which comprises as a first component, a colorant of the formula: ##STR1## wherein X is a polar group selected from sulfonic acids, sulfonic acid salts, sulfonamides, sulfonates, carboxylic acids, carboxylic acid salts, carboxylic acid amides, carboxylic aldehydes, carboxylic acid esters, ureas, thioureas, nitro groups, hydroxy groups, polyethers, and hydroxyalkylethers;R.sub.1 is selected from nitrogen, oxygen, sulfur, or a sulfur, or a sulfur-containing divalent linking group;R.sub.
    Type: Grant
    Filed: October 24, 1988
    Date of Patent: October 3, 1989
    Assignee: Milliken Research Corporation
    Inventor: Jeffery R. Harris
  • Patent number: 4777248
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;X is the residue of a diazotisable amineY is NR.sup.1 R.sup.2 or non-chromophoric groups OR.sup.3 or NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are independently selected from H, alkyl and aryl, andZ is: ##STR2## wherein M is a monovalent cation, and an ink containing the dye suitable for use in an ink jet printing process.
    Type: Grant
    Filed: December 27, 1985
    Date of Patent: October 11, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Greenwood, David
  • Patent number: 4775748
    Abstract: 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: Grant
    Filed: June 1, 1987
    Date of Patent: October 4, 1988
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Patrick D. Moore
  • Patent number: 4726844
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ring a and b are different from 1 to 8m is from 1 to 10;n is from 0 to 9;X is the residue of a diazotizable amineY is NR.sup.1 R.sup.2 or non-chromophoric groups OR.sup.3 or NR.sup.3 R.sup.4 in which R.sup.3 and R.sup.4 are independently selected from H, alkyl and aryl; andZ is: ##STR2## wherein M is a monovalent cation, and an ink containing the dye suitable for use in an ink jet printing process.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: February 23, 1988
    Assignee: Canon Kabushiki Kaisha
    Inventor: David Greenwood
  • Patent number: 4601725
    Abstract: 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: Grant
    Filed: August 27, 1984
    Date of Patent: July 22, 1986
    Assignee: Milliken Research Corporation
    Inventors: Margaret S. Keller, Edward W. Kluger