Patents by Inventor Harlan G. Freeman

Harlan G. 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: 3947425
    Abstract: Described herein are hydrophilic resin products having particular utility in rapid curing adhesives for wood and other materials. Processes for producing these resins and hydrophilic adhesives produced therefrom are also described. The resins are prepared by reacting an aldehyde condensation polymer, such as a phenol-formaldehyde condensation polymer, with a strong mineral acid salt, i.e., a hydrochloric, nitric, or sulfuric acid salt, of m-hydroxy aniline, 2,6-diaminopyridine or 4,4'-diaminodiphenylmethane. When these resins are blended with an appropriate curing agent, such as an aldehyde, the resulting adhesives cure very rapidly at ambient temperatures. While uncured, these adhesives are hydrophilic and thus water washable, but when cured, they are insoluble in water and common organic solvents.
    Type: Grant
    Filed: September 13, 1973
    Date of Patent: March 30, 1976
    Assignee: Weyerhaeuser Company
    Inventors: Harlan G. Freeman, Maurice F. Gillern, Harry A. Smith
  • Patent number: 3931110
    Abstract: This invention describes resin products having particular utility as rapid curing adhesives for wood and other materials, and processes for making the resin compositions. The reaction products are made by reacting an aldehyde condensation polymer, such as a phenol-formaldehyde condensation polymer, with a primary aromatic amine having the formula: ##SPC1##WhereX.sub.1 is --NH.sub.2 --CH.sub.2 NH.sub.2 ;X.sub.2 is --X.sub.1 --OH--alkoxy;X.sub.3 is -X.sub.1 COOH NHCOCH.sub.3 NO.sub.2 OH C.sub.1 to C.sub.5 alkyl H -halogen halogenated alkyl alkoxyX.sub.4 is C.sub.1 to C.sub.4 alkyl, --H--aryl; andA is ##EQU1## where Y.sub.1 and Y.sub.2 are hydrogen or alkyl radicals having from 1 to 3 carbon atoms and Z is an integer from 0 to 2,--SO.sub.2 ----NH----O----S---- C----S--S----N=N--, to obtain an amine-modified polymer. On blending an appropriate hardening agent with the amine-modified polymer, the composition cures very rapidly at ambient temperature.
    Type: Grant
    Filed: October 23, 1973
    Date of Patent: January 6, 1976
    Assignee: The Dow Chemical Company
    Inventors: Harlan G. Freeman, Gene F. Baxter, George Graham Allen