Patents Assigned to Pittsburg State University
  • Patent number: 9238618
    Abstract: Processes for the production of polyols from sources such as dried distillers grains plus solubles (DDGS) make use of a two-stage reaction scheme. In the first stage, the proteinaceous starting material is reacted with an aminating agent, such as diethanolamine (DEOA), to generate amino-amides and amides. These products are then reacted with an alkoxylating agent, preferably a substituted or unsubstituted epoxide to yield polyols. These polyols may be further reacted with isocyanates to give low-cost rigid polyurethane foams. In alternate forms, lignin may be directly converted to polyols by reaction with an alkoxylating agent, optionally followed by reaction with an isocyanate to produce polyurethanes.
    Type: Grant
    Filed: October 16, 2014
    Date of Patent: January 19, 2016
    Assignees: MGPI Processing, Inc., Pittsburg State University
    Inventors: Sukh Bassi, Michael Douglas Parker, Mihail Ionescu, Zoran Petrovic
  • Publication number: 20140221696
    Abstract: A new class of polyols derived from renewable resources, including polyglycerol and vegetable oils, the use of such polyols in polyurethane foams and cast resins, and methods for making the polyols and polyurethanes are provided.
    Type: Application
    Filed: April 9, 2014
    Publication date: August 7, 2014
    Applicant: Pittsburg State University
    Inventors: Zoran S. PETROVIC, Mihail IONESCU, Ivan JAVNI
  • Publication number: 20140200324
    Abstract: Processes for the production of polyols from sources such as dried distillers grains plus solubles (DDGS) make use of a two-stage reaction scheme. In the first stage, the proteinaceous starting material is reacted with an aminating agent, such as diethanolamine (DEOA), to generate amino-amides and amides. These products are then reacted with an alkoxylating agent, preferably a substituted or unsubstituted epoxide to yield polyols. These polyols may be further reacted with isocyanates to give low-cost rigid polyurethane foams. In alternate forms, lignin may be directly converted to polyols by reaction with an alkoxylating agent, optionally followed by reaction with an isocyanate to produce polyurethanes.
    Type: Application
    Filed: February 1, 2013
    Publication date: July 17, 2014
    Applicants: PITTSBURG STATE UNIVERSITY, MGPI PROCESSING, INC.
    Inventors: Sukh Bassi, Michael Douglas Parker, Mihail Ionescu, Zoran Petrovic
  • Patent number: 8692030
    Abstract: A method of making a biobased-petrochemical hybrid polyol is provided. This method includes reacting a cyclic ether with a vegetable oil-based polyol in the presence of a cationic catalyst or a coordinative catalyst that includes a vegetable oil-based polyol ligand to form the biobased-petrochemical hybrid polyol. The biobased-petrochemical hybrid polyol that is created has a number average molecular weight of about 3,000 to about 6,000 and has a structure that is about 22% to about 36% biobased. In one aspect of the present invention, the cyclic ether is propylene oxide, and the propoxylated polyol formed from the propylene oxide and vegetable oil-based polyol is then reacted with ethylene oxide in the presence of a superacid catalyst to create a block copolymer with a terminal polyethylene oxide block having a high percentage of terminal primary hydroxyl groups.
    Type: Grant
    Filed: April 20, 2006
    Date of Patent: April 8, 2014
    Assignee: Pittsburg State University
    Inventors: Mihail Ionescu, Zoran S. Petrovic, Ivan Javni
  • Patent number: 8013088
    Abstract: A polymerization reaction mixture for the cationic polymerization of unsaturated biological oils (e.g. vegetable oils and animals oils) based on the cationic reaction of double bonds initiated by superacids is provided. The polymerized oils have a viscosity about 10 to 200 times higher than the initial oil and relatively high unsaturation (only about 10-30% lower than that of initial oils).
    Type: Grant
    Filed: March 9, 2009
    Date of Patent: September 6, 2011
    Assignee: Pittsburg State University
    Inventors: Mihail Ionescu, Zoran S. Petrovic
  • Patent number: 7795311
    Abstract: Improved methods and compositions for protecting plants or seeds from soil-borne fungal diseases. The composition may include a triterpenoid isolated from Glycyrrhiza glabra and a polymer. The triterpenoid may be Carbenoxolone disodium salt, and the polymer may be a water-insoluble, water-soluble or flowable, seed coating polymer. The methods may comprise the steps of applying the composition to the plant's seeds, roots, tubers and/or foliage, and may also include applying the composition to the soil surround surrounding the plant. The composition may be applied as an aqueous solution or as dry particulates, and may be used for the treatment of soybean plants and seeds.
    Type: Grant
    Filed: October 15, 2007
    Date of Patent: September 14, 2010
    Assignee: Pittsburg State University
    Inventor: Nancy L. Brooker
  • Patent number: 7786239
    Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.
    Type: Grant
    Filed: June 24, 2005
    Date of Patent: August 31, 2010
    Assignee: Pittsburg State University
    Inventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
  • Publication number: 20090099262
    Abstract: Improved methods and compositions for protecting plants or seeds from soil-borne fungal diseases. The composition may include a triterpenoid isolated from Glycyrrhiza glabra and a polymer. The triterpenoid may be Carbenoxolone disodium salt, and the polymer may be a water-insoluble, water-soluble or flowable, seed coating polymer. The methods may comprise the steps of applying the composition to the plant's seeds, roots, tubers and/or foliage, and may also include applying the composition to the soil surround surrounding the plant. The composition may be applied as an aqueous solution or as dry particulates, and may be used for the treatment of soybean plants and seeds.
    Type: Application
    Filed: October 15, 2007
    Publication date: April 16, 2009
    Applicant: PITTSBURG STATE UNIVERSITY
    Inventor: Nancy L. Brooker
  • Patent number: 7501479
    Abstract: A method for the cationic polymerization of unsaturated biological oils (e.g., vegetable oils and animal oils) based on the cationic reaction of double bonds initiated by superacids is provided. The process occurs under very mild reaction conditions (about 70-110° C. and atmospheric pressure) and with short reaction times. The polymerized oils have a viscosity about 10 to 200 times higher than the initial oil and relatively high unsaturation (only about 10-30% lower than that of initial oils).
    Type: Grant
    Filed: May 7, 2007
    Date of Patent: March 10, 2009
    Assignee: Pittsburg State University
    Inventors: Mihail Ionescu, Zoran S. Petrovic
  • Patent number: 6686435
    Abstract: A method for making natural oil-based polyols directly from vegetable or animal oil using a consecutive two-step process involving epoxidation and hydroxylation is provided. Specifically, this process comprises adding a peroxyacid to a natural oil wherein said natural oil and said peroxyacid react to form an epoxidized natural oil and adding said epoxidized natural oil to a mixture of an alcohol, water, and a fluoboric acid catalyst. The catalytic amount of fluoboric acid is less than about 0.5% by weight of the entire reaction mixture, and the amount of water is about 10 to 30% by weight of the entire mixture. The epoxidized natural oil undergoes hydroxylation and forms a natural oil-based polyol. The present invention further includes a method for making natural oil-based polyols from epoxidized oil by hydroylating the epoxidized oil in the presence of fluoboric acid, alcohol and water in the amounts discussed above.
    Type: Grant
    Filed: June 20, 2002
    Date of Patent: February 3, 2004
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Ivan Javni, Andrew Guo, Wei Zhang
  • Patent number: 6573354
    Abstract: A vegetable oil-based polyol is made by adding a peroxyacid to vegetable oil wherein said peroxyacid reacts with said vegetable oil to form epoxidized vegetable oil and adding said epoxidized vegetable oil to a mixture of an alcohol, water, and a catalytic amount of fluoboric acid so as to form a vegetable oil-based polyol. A further embodiment of the present invention involves making a vegetable oil-based polyol using an epoxidized vegetable oil as the starting material. The epoxidized vegetable oil undergoes hydroxylation by the same process as outlined above. According to another aspect of the present invention, the vegetable oil-based polyol formed by the novel methods of this invention may be reacted with an isocyanate to form a polyurethane. Alternatively, a filler such as silica may be combined with the vegetable oil-based polyol before it is reacted with the isocyanate. These polyurethanes made from vegetable oil-based polyols may be used to form electroinsulating casting resins.
    Type: Grant
    Filed: May 10, 2000
    Date of Patent: June 3, 2003
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Andrew Guo, Ivan Javni
  • Patent number: 6433121
    Abstract: A method for making natural oil-based polyols directly from vegetable or animal oil using a consecutive two-step process involving epoxidation and hydroxylation is provided. Specifically, this process comprises adding a peroxyacid to a natural oil wherein said natural oil and said peroxyacid react to form an epoxidized natural oil and adding said epoxidized natural oil to a mixture of an alcohol, water, and a fluoboric acid catalyst. The catalytic amount of fluoboric acid is less than about 0.5% by weight of the entire reaction mixture, and the amount of water is about 10 to 30% by weight of the entire mixture. The epoxidized natural oil undergoes hydroxylation and forms a natural oil-based polyol. The present invention further includes a method for making natural oil-based polyols from epoxidized oil by hydroylating the epoxidized oil in the presence of fluoboric acid, alcohol and water in the amounts discussed above.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: August 13, 2002
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Ivan Javni, Andrew Guo, Wei Zhang
  • Patent number: 6399698
    Abstract: An isocyanate prepolymer for application in polyurethanes. The prepolymer is synthesized by combining epoxidized natural oils with isocyanates and a catalyst. The prepolymer contains oxazolidone rings that will react with polyols to form polyurethane. The invention provides a method of using a renewable resource in a fast, simple process to produce substantial amounts of isocyanate prepolymer and a minimum of homopolymers.
    Type: Grant
    Filed: October 26, 2000
    Date of Patent: June 4, 2002
    Assignee: Pittsburg State University
    Inventors: Zoran S. Petrovic, Ivan J. Javni
  • Patent number: 6107433
    Abstract: A vegetable oil-based polyol is made by adding a peroxyacid to vegetable oil wherein said peroxyacid reacts with said vegetable oil to form epoxidized vegetable oil and adding said epoxidized vegetable oil to a mixture of an alcohol, water, and a catalytic amount of fluoboric acid so as to form a vegetable oil-based polyol. A further embodiment of the present invention involves making a vegetable oil-based polyol using an epoxidized vegetable oil as the starting material. The epoxidized vegetable oil undergoes hydroxylation by the same process as outlined above. According to another aspect of the present invention, the vegetable oil-based polyol formed by the novel methods of this invention may be reacted with an isocyanate to form a polyurethane. Alternatively, a filler such as silica may be combined with the vegetable oil-based polyol before it is reacted with the isocyanate. These polyurethanes made from vegetable oil-based polyols may be used to form electroinsulating casting resins.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: August 22, 2000
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Andrew Guo, Ivan Javni