Patents by Inventor Harold S. Freeman

Harold S. Freeman 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).

  • Patent number: 10640918
    Abstract: Functionalizing a fibrous material having a plurality of hydroxyl groups includes reacting the fibrous material with a compound of Formula I: where X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material. Also provided is a functionalized fibrous material prepared by any one of the methods described herein (e.g., a functionalized fiber including a moiety of Formula II: having an odor of free amine below the threshold of detection, or having an odor of free amine with degree of offensiveness of about 3 or less. The functionalized fibrous material may be dyed, and articles of clothing may be made from the dyed functionalized fibrous material.
    Type: Grant
    Filed: August 15, 2018
    Date of Patent: May 5, 2020
    Assignees: HBI Branded Apparel Enterprises, LLC, Cotton Incorporated, North Carolina State University
    Inventors: Harold S. Freeman, Malgorzata Szymczyk, Keith Zimmerman, Matthew J. Farrell
  • Publication number: 20190055692
    Abstract: Functionalizing a fibrous material having a plurality of hydroxyl groups includes reacting the fibrous material with a compound of Formula I: where X is a monovalent counteranion for the quaternary ammonium cation of Formula I and Hal is a halogen atom, to obtain the functionalized fibrous material. Also provided is a functionalized fibrous material prepared by any one of the methods described herein (e.g., a functionalized fiber including a moiety of Formula II: having an odor of free amine below the threshold of detection, or having an odor of free amine with degree of offensiveness of about 3 or less. The functionalized fibrous material may be dyed, and articles of clothing may be made from the dyed functionalized fibrous material.
    Type: Application
    Filed: August 15, 2018
    Publication date: February 21, 2019
    Applicant: HBI Branded Apparel Enterprises, LLC
    Inventors: Harold S. Freeman, Malgorzata Szymczyk, Keith Zimmerman
  • Publication number: 20080216256
    Abstract: The presently disclosed subject matter relates to heterobifunctional reactive dyes comprising nitrogen-containing heterocycles substituted by both halogen and vinyl sulfone moieties. In particular, the presently disclosed subject matter relates to reactive dye compounds comprising two or more halo-substituted, nitrogen-containing heterocycles and an asymmetric bridging group, wherein at least one of the two or more halo-substituted, nitrogen-containing heterocycles further comprises a vinyl sulfone substituent. In some embodiments, the bridging group has a structure based on cysteamine or cysteine. The heterobifunctional reactive dyes have high substrate affinity and can be applied to substrates, such as cotton fibers, under low salt conditions and with reduced dye material waste.
    Type: Application
    Filed: August 21, 2007
    Publication date: September 11, 2008
    Applicant: North Carolina State University
    Inventors: Harold S. Freeman, C. Brent Smith, Malgorzata Szymczyk, Mengnan Zhao
  • Patent number: 5965717
    Abstract: Nonmutagenic, highly twisted derivatives of benzidine of the following formula ##STR1## useful as intermediates for the preparation of various organic pigments were obtained. The benzidine derivatives are significantly rotated about the biphenyl linkage due to bulky substituents at the R.sub.2 and/or R.sub.4 positions. Bisazomethine, disaoacetoacetanilide, disazopyrazolone, disazobenzimidazolone and disazonaphthol pigments prepared from these highly twisted benzidines exhibit hypsochromic spectral shifts relative to pigments prepared from other benzidine compounds with less twist about the biphenyl linkage, for instance, other benzidine compounds in which all four R.sub.2 and R.sub.4 represent H. Greenish-yellow, yellow, orange, red and brown pigments obtained from the twisted benzidines are nonmutagenic in the standard Ames test and Prival modification.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: October 12, 1999
    Assignee: North Carolina State University
    Inventors: Harold S. Freeman, David Hinks, Jolanta Sokolowska-Gajda
  • Patent number: 5677434
    Abstract: A family of 1:2 Fe-complexed formazan dyes is described. The dyes unexpectedly afford reddish-violet, violet, blue and black shades on natural and synthetic substrates. Methods for synthesizing the dyes and for dyeing a substrate are described. The dyes represent environmentally friendly alternatives to conventional Cr- and Co-based azo and formazan dyes.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: October 14, 1997
    Assignee: North Carolina State University
    Inventors: Harold S. Freeman, Jolanta Sokolowska-Gajda, Abraham Reife
  • Patent number: 5376151
    Abstract: Disclosed is an original approach to solving the environmental problem associated with the use of Cr-based metallized azo dyes to deliver black shades on natural and synthetic substrates. This invention affords methods for both the synthesis of metallized dyes and the generation of black dyeings using those dyes without employing metals designated as priority pollutants at any stage in either method. The key element of the disclosure is the use of black 1:2 Fe complexes of azo dyes in lieu of currently used Cr-based complexes which are based on environmentally unfriendly priority pollutant metals without compromising the desirable high fastness properties of the latter complexes, an accomplishment heretofore assumed unachievable.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: December 27, 1994
    Assignee: North Carolina State University
    Inventors: Harold S. Freeman, Abraham Reife, Jolanta Sokolawska-Gajda
  • Patent number: 5194450
    Abstract: The present invention is concerned with compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen or C.sub.1-4 alkoxy;R.sub.2 is carbonyl, hydroxymethylene, or methylene; andR.sub.3 is hydrogen or hydroxy;and salts thereof, provided that when R.sub.1 is hydrogen and R.sub.2 is carbonyl, R.sub.3 is not hydroxy, with processes for preparing same and with their use in medicine for the treatment of hypertension.
    Type: Grant
    Filed: October 28, 1991
    Date of Patent: March 16, 1993
    Assignee: Burroughs Wellcome Co.
    Inventors: John D. McDermed, Anjaneyulu S. Tadepalli, Vincent H. Chang, Kevin P. Hurley, Harold S. Freeman
  • Patent number: 4902787
    Abstract: A method of producing a UV lightfast disperse dyestuff comprising selecting a disperse dyestuff having predetermined chromophoric groups, selecting a photostabilizer compound, designing a hybrid disperse dye molecular structure which contains the chromophoric groups of the selected disperse dyestuff and also contains the molecular structural features of the selected photostabilizer compound, and synthesizing the thus designed hybrid disperse dyestuff molecule. Such a method produces a hybrid dye molecule which is a UV lightfast analog of a disperse dyestuff having predetermined chromophoric groups, said hybrid dye molecule containing in its molecular structure the chromophoric groups of the selected disperse dyestuff and also containing the molecular structural features of a photostabilizer compound.
    Type: Grant
    Filed: April 21, 1988
    Date of Patent: February 20, 1990
    Assignee: North Carolina State University
    Inventor: Harold S. Freeman