Diels-alder Adducts (e.g., Of Maleic Anhydride, Fumaric Acid, Etc., With Conjugated Dienes, Such As Rosin Acids, Terpenes, Etc.) Patents (Class 530/214)
  • Patent number: 9303195
    Abstract: Aliphatically modified rosin resins are prepared by reacting rosin esters with aliphatic monomers. These aliphatically modified rosin resins are compatible with metallocene catalyzed polyolefins and other aliphatic base polymers and are used as tackifiers in combination with metallocene catalyzed polyolefins and other aliphatic base polymers to form adhesive compositions for hot melt and pressure sensitive applications.
    Type: Grant
    Filed: August 26, 2014
    Date of Patent: April 5, 2016
    Assignee: Ingevity South Carolina, LLC
    Inventors: Brett A. Neumann, John C. Widders, Russ N. Fitzgerald
  • Patent number: 8901245
    Abstract: Methods for forming rosin-derived cationic compounds are provided. The method can include attaching a cationic group to a conjugated diene on a hydrophenathrene-based ring of a resin acid (e.g., levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof) to form a rosin-derived cationic compound. Attaching the cationic group to the conjugated diene on the hydrophenathrene-based ring of the resin acid can be achieved via a Diels-Alder reaction of a dienophile with the hydrophenathrene-based ring of the resin acid. Rosin-derived cationic compounds are also provided. The rosin-derived cationic compound can include a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the rosin-derived cationic compound further comprises a carboxylic acid group.
    Type: Grant
    Filed: December 10, 2013
    Date of Patent: December 2, 2014
    Assignee: University of South Carolina
    Inventors: Chuanbing Tang, Jifu Wang, Alan W. Decho, Yung Pin Chen
  • Patent number: 8604128
    Abstract: Methods for forming rosin-derived cationic compounds are provided. The method can include attaching a cationic group to a conjugated diene on a hydrophenathrene-based ring of a resin acid (e.g., levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof) to form a rosin-derived cationic compound. Attaching the cationic group to the conjugated diene on the hydrophenathrene-based ring of the resin acid can be achieved via a Diels-Alder reaction of a dienophile with the hydrophenathrene-based ring of the resin acid. Rosin-derived cationic compounds are also provided. The rosin-derived cationic compound can include a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the rosin-derived cationic compound further comprises a carboxylic acid group.
    Type: Grant
    Filed: February 15, 2012
    Date of Patent: December 10, 2013
    Assignee: University of South Carolina
    Inventors: Chuanbing Tang, Jifu Wang, Alan W. Decho, Yung Pin Chen
  • Patent number: 8383765
    Abstract: A polyester for a toner, obtainable by polycondensing an alcohol component and a carboxylic acid component containing a fumaric acid-modified rosin; and a toner containing the polyester for a toner. The polyester for a toner of the present invention is usable as a resin binder for a toner usable in, for example, developing electrostatic latent images formed in electrophotography, electrostatic recording method, electrostatic printing method or the like.
    Type: Grant
    Filed: April 16, 2007
    Date of Patent: February 26, 2013
    Assignee: Kao Corporation
    Inventors: Takashi Kubo, Yoshitomo Kimura, Yoshihiro Ueno, Yasunori Inagaki
  • Patent number: 8133970
    Abstract: Oxidized and maleated derivative compositions, such as chemically modified oxidized and maleated tall oil fatty acid compositions, can be prepared and used in a variety of industrial applications, including as emulsifiers, corrosion inhibitors, concrete admixtures, and in reverse flotation mining applications.
    Type: Grant
    Filed: January 30, 2009
    Date of Patent: March 13, 2012
    Assignee: Georgia-Pacific Chemicals LLC
    Inventors: Phillip W. Hurd, Roger Scott Johnson, John B. Hines, Brett A. Neumann
  • Publication number: 20120004390
    Abstract: A method for preparing pimaric acid type resin acids includes the following steps: step (1) adding refined resin acid, turpentine, or rosin along with maleic anhydride at a mass ratio of 1:0.3-1.5 into a reaction bottle, dissolving the ingredients into a C1-C10 lower fatty acid solvent, the mass ratio of the C1-C10 low fatty acid to refined resin acid is 0.05-30:1, then carrying out additional reaction by heating directly or with assistance of a microwave, subsequently cooling, crystallizing, filtering, and washing; and step (2) combining the filtrates collected in step (1), stripping the solvent by vacuum distillation to obtain pimaric acid type resin acid coarse product, dissolving the resulting coarse product in NaOH aqueous solution to prepare aqueous solution of pimaric acid type resin acid salt, adjusting the pH level to 6-14 with a mineral acid or an organic acid while stirring, and either directly purifying or acidifying followed by purifying, the resulting precipitation to obtain the final product.
    Type: Application
    Filed: March 18, 2010
    Publication date: January 5, 2012
    Inventors: Zhendong Zhao, Yuxiang Chen, Liangwu Bi, Yan Gu, Dongmei Li, Jing Wang, Yanju Lu
  • Patent number: 7910635
    Abstract: The specification describes a process for making gelled ink resins which exhibit improved properties such as lower viscosity under low shear and less viscosity decrease with increasing shear. In a preferred embodiment, a rosin-based or hydrocarbon-based resin is mixed with an organic solvent and reacted with a polyamine reactant, such as melamine-formaldehyde resin or hexamethylene diamine, under conditions sufficient to produce a substantially covalently cross-link gelled resin. The resulting gelled resin resists viscosity breakdown under high shear conditions and may be used directly for making ink compositions, obviating the need for further gelation and avoiding the use of conventional organo-metallic gelling agents.
    Type: Grant
    Filed: October 14, 2006
    Date of Patent: March 22, 2011
    Assignee: Lubrizol Advanced Materials, Inc.
    Inventors: John H. Larsen, Joshua M. Rosenheck, Robert E. Quinn
  • Patent number: 7709599
    Abstract: The present invention relates to terpene derivative compounds and rosins and sizing compositions comprising such compounds. Compounds of Formula (I) are disclosed in addition to rosins and sizing compositions comprising compounds of Formula (I). Fiber glass strands comprising a plurality of glass fibers at least partially coated with sizing compositions comprising compounds of Formula (I) are also disclosed.
    Type: Grant
    Filed: March 22, 2006
    Date of Patent: May 4, 2010
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Garry D. Puckett, Brian Woodworth
  • Patent number: 7411036
    Abstract: An ink formulation comprising an acrylated resin prepared by mixing a hydroxyalkyl acrylate and an isocyanate and reacting said mixture with a resin containing one or more hydroxyl functional groups and derived from a natural product.
    Type: Grant
    Filed: November 23, 2005
    Date of Patent: August 12, 2008
    Assignee: Sun Chemical Corporation
    Inventor: Kai-Uwe Gaudl
  • Patent number: 7411035
    Abstract: An acrylated resin prepared by mixing a hydroxyalkyl acrylate and an isocyanate and reacting said mixture with a resin containing one or more hydroxyl functional groups and derived from a natural product.
    Type: Grant
    Filed: November 23, 2005
    Date of Patent: August 12, 2008
    Assignee: Sun Chemical Corporation
    Inventor: Kai-Uwe Gaudl
  • Patent number: 7001981
    Abstract: A method of acrylating a resin containing one or more hydroxyl functional group and derived from a natural product, comprising preparing a mixture of a hydroxyalkyl acrylate and an isocyanate; and reacting said mixture with said resin.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: February 21, 2006
    Assignee: Sun Chemical Corporation
    Inventor: Kai-Uwe Gaudl
  • Patent number: 6590071
    Abstract: The present invention provides lipidized conjugates comprising an amino group-containing biologically active substance and a lipophilic group capable of penetrating a biological membrane. Under neutral or mildly acidic conditions, including those found in vivo, the free amino group-containing biologically active substance is released from the conjugate by hydrolysis of an amide bond. The present invention is also directed to methods of preparing lipidizing agents and lipidized conjugates, pharmaceutical compositions comprising lipidized conjugates and methods of increasing the delivery of amino group-containing substances into a cell. Preferred amino group-containing substances include peptides, proteins and derivatives thereof.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: July 8, 2003
    Assignee: University of Southern California
    Inventors: Wei-Chiang Shen, Hashem Heiati
  • Patent number: 6583263
    Abstract: A two-step method for introducing acrylic functions into high molecular weight natural resins, under mild conditions, without the risk of gellation, wherein an acrylated natural resin ester is prepared by esterifying one or more of the sterically hindered hydroxy groups of the natural resin ester in an inert solvent with a 3-halopropionic acid, to form a 3-halopropionate ester of the natural resin ester and dehydrohalogenated the 3-halopropionate ester by reacting it with an organic base.
    Type: Grant
    Filed: January 5, 2001
    Date of Patent: June 24, 2003
    Assignee: Sun Chemical Corporation
    Inventor: Kai-Uwe Gaudl
  • Patent number: 6407154
    Abstract: The present invention relates to rosin modified succinamic acid which is useful in lowering the rebound values of rubber and increases the traction of tires containing said compound in the tread. The rosin modified succinamic acids are prepared by reacting abietylamine and/or dehydroabietylamine with succinic anhydride.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: June 18, 2002
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Lawson Gibson Wideman, Paul Harry Sandstrom, Neil Arthur Maly
  • Patent number: 6241995
    Abstract: Novel Polygala senega saponin pharmaceutical compositions are disclosed. The P. senega saponins are useful as immunological adjuvants to enhance immune responses to a co-administered antigen.
    Type: Grant
    Filed: August 6, 1998
    Date of Patent: June 5, 2001
    Assignee: University of Saskatchewan
    Inventors: Alberto Estrada, Branka Barl, Georgios S. Katselis, Bernard Laarveld
  • Patent number: 6172174
    Abstract: This invention relates to novel phenolic rosin resin compositions. In particular, the invention relates to novel phenolic rosin resin compositions and dienophile-modified phenolic rosin resin compositions which exhibit properties that make them useful in formulating vehicles for lithographic printing inks and other coating applications.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: January 9, 2001
    Assignee: Westvaco Corporation
    Inventor: Michael D. Matzinger
  • Patent number: 6153693
    Abstract: This invention relates to novel rosin-based resins and the process for preparing them. In particular, the invention relates to elastomeric-modified pigment binder compositions which exhibit properties that make them useful in formulating vehicles for lithographic printing inks and other coating applications.
    Type: Grant
    Filed: February 11, 1999
    Date of Patent: November 28, 2000
    Assignee: Westvaco Corporation
    Inventors: Michael D. Matzinger, G. Frederick Hutter
  • Patent number: 5969071
    Abstract: This invention relates to novel phenolic rosin resins and the process for preparing them. In particular, the invention relates to novel phenolic rosin resin compositions which exhibit properties that make them useful in formulating vehicles for lithographic printing inks and other coating applications.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: October 19, 1999
    Assignee: Westvaco Corporation
    Inventor: Michael D. Matzinger
  • Patent number: 5594099
    Abstract: A modified resinate prepared by reactingA) rosins or rosin acids withB) aldehyde components and optionallyC) .alpha.,.beta.-olefinically unsaturated carboxylic acids or anhydrides thereof, subsequently reacting the resultant adduction products withD) phenols and optionallyE) alcohols containing at least two hydroxyl groups and subsequently forming resinates withF) basic compounds of divalent metals, useful as resin binders of high viscosity in low solid printing inks for intaglio printing of illustrations.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: January 14, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Albert Bender
  • Patent number: 5559206
    Abstract: The specification describes a process for making highly functionalized rosin ester resins; i.e., partially esterified rosin based resins. The resins are produced by reacting fortified rosin with a polyol at superatmospheric pressure in a closed reaction vessel while retaining at least a portion of the water formed during the esterification step in the reaction vessel, thereby limiting the reaction to a desired degree of partial esterification so that a relatively high degree of residual acid functionality is achieved in the final ester product. The process enables large scale production of resins with precise control of the degree of functionality of the resins thus produced. The products are particularly useful as binders in ink formulations.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: September 24, 1996
    Assignee: Arizona Chemical Company
    Inventor: Theodore J. Williams
  • Patent number: 5491215
    Abstract: This invention relates to rosin carboxypyrrolidinone adducts. In particular, this invention relates to water-soluble resins derived from the reaction product of a modified rosin with a hydroxyl-containing carboxypyrrolidinone derivative. These resins can be used to make acrylic latex compositions which can, in turn, be utilized to produce water-based flexographic and gravure ink formulations.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: February 13, 1996
    Assignee: Westvaco Corporation
    Inventor: G. Frederick Hutter
  • Patent number: 5224993
    Abstract: The present invention relates to a sizing agent which exerts excellent sizing efficiency even under severe conditions, namely, at an elevated temperature in the papermaking step, or at high conditions with a limited aluminum sulfate addition.The sizing agent for paper of the present invention is derived from i) dehydration condensation of an alkenylsuccinic anhydride and an organic carboxylic acid with a polyalkylene polyamine and ii) saponification of the remaining carboxyl groups with alkali following the dehydration condensation. More particularly, the present invention relates to a water-soluble sizing agent which is obtained by mixing an alkenylsuccinic anhydride with 1 to 20 times by molar equivalent, based on said alkenylsuccinic anhydride, as much as an organic carboxylic acid, adding 0.1 to 2.0 times by molar equivalent, based on said alkenylsuccinic anhydride, as much as a polyalkylene polyamine thereto so as to perform dehydration condensation.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: July 6, 1993
    Assignee: Mitsubishi Oil Co., Ltd.
    Inventors: Yoshio Takahashi, Shigeto Hatanaka
  • Patent number: 5208319
    Abstract: The invention is ink pigment grinding resins for waterbased printing inks which are produced by the amidation of maleated or fumarated rosin with a polyamine containing a primary amine group to produce the water soluble polyaminoamidoimide resin. The resulting rosin resin may be employed over a wide range of pH values to produce stable low or high viscosity grind bases.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: May 4, 1993
    Assignee: Westvaco Corporation
    Inventor: Peter Schilling
  • Patent number: 5134184
    Abstract: The present invention relates to rosin monomaleimides which are useful as a total or partial replacement for extender or processing oil in rubber formulations. Addition of the rosin monomaleimides improve peel adhesion in rubber compositions. The rosin monomaleimides are prepared by reacting abietylamine and/or dehydroabietylamide with maleic anhydride.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: July 28, 1992
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Paul H. Sandstrom, Lawson G. Wideman
  • Patent number: 5073623
    Abstract: A rosin based condensation product produced by reacting in a multistage process the following reactants, rosin, phenolic compounds, formaldehyde, unsaturated C.sub.3 -C.sub.4 dicarboxylic acid or maleic anhydride, monounsaturated or polyunsaturated aliphatic monohydric or dihydric alcohol or amine or a monounsaturated or polyunsaturated C.sub.2 -C.sub.12 aminoalcohol or C.sub.2 -C.sub.12 alkanediol or C.sub.2 -C.sub.12 aminoalcohol, monounsaturated or polyunsaturated C.sub.8 C.sub.40 fatty acid.
    Type: Grant
    Filed: September 6, 1989
    Date of Patent: December 17, 1991
    Assignee: BASF Lacke+Farben Aktiengesellschaft
    Inventors: Bernhard Prantl, Rolf Walz, Erwin Stark
  • Patent number: 4975503
    Abstract: Copolymerization of beta-phellandrene with maleic anhydride, preferably in the presence of a free radical initiator such as AIBN, to form high molecular weight polymers (weight average molecular weight over 1,000) is disclosed. The polymerization may be conducted at a temperature up to about 190.degree. C., preferably in the range of about 40.degree. to 130.degree. C., preferably in the presence of a polar solvent.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: December 4, 1990
    Assignee: Union Camp Corporation
    Inventor: David W. Parker
  • Patent number: 4975504
    Abstract: Copolymerization of isoterpinolene with maleic anhydride, preferably in the presence of a free radical initiator such as AIBN, to form high molecular weight (weight average molecular weight over 1000) polymers is disclosed. The polymerization may be conducted at a temperature up to about 190.degree. C., preferably in the range of about 40.degree. to 130.degree. C., preferably in the presence of a polar solvent.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: December 4, 1990
    Assignee: Union Camp Corporation
    Inventor: David W. Parker
  • Patent number: 4963630
    Abstract: Copolymerization of maleic anhydride with the resin acids present in rosin, especially abietic-type resin acids (e.g., abietic acid and neoabietic acid), to form high molecular weight copolymers is disclosed. The polymerization is carried out in the presence of a free radical initiator such as AIBN. The temperature can range up to about 190.degree. C. and a solvent such as THF can also be present.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: October 16, 1990
    Assignee: Union Camp Corporation
    Inventor: David W. Parker