Chemical Treatment Or Color Modification Of Polymerized Rosin Or Derivative, Or Product Thereof (e.g., Hydrogenation Or Esterification Of Polymerized Rosin; Removal Of Color Bodies From Polymerized Rosin, Etc.) Patents (Class 530/212)
  • 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: 8080602
    Abstract: The invention relates to a rubber composition comprising a natural or synthetic rubber or a mixture of such rubbers, a tackifier, and optionally further additives, wherein the tackifier is prepared from a rosin and an alkylphenol aldehyde resin of the resol type, which rubber composition has a good building tack and tack retention.
    Type: Grant
    Filed: September 18, 2007
    Date of Patent: December 20, 2011
    Assignee: Arizona Chemical Company, LLC
    Inventors: Wolfgang Pille-Wolf, Mark Stanley Pavlin, Frederik Keijzer, Ronnie Zeeman
  • Patent number: 8071087
    Abstract: Methods for treating proliferative disorders, by administering reovirus to a Ras-mediated proliferative disorder, are disclosed. The reovirus is administered so that it ultimately directly contacts ras-mediated proliferating cells. Proliferative disorders include but are not limited to neoplasms. Human reovirus, non-human mammalian reovirus, and/or avian reovirus can be used. If the reovirus is human reovirus, serotype 1 (e.g., strain Lang), serotype 2 (e.g., strain Jones), serotype 3 (e.g., strain Dearing or strain Abney), as well as other serotypes or strains of reovirus can be used. Combinations of more than one type and/or strain of reovirus can be used, as can reovirus from different species of animal. Either solid neoplasms or hematopoietic neoplasms can be treated.
    Type: Grant
    Filed: July 22, 2010
    Date of Patent: December 6, 2011
    Assignee: Oncolytics Biotech Inc.
    Inventors: Patrick W. K. Lee, James Strong, Matthew C. Coffey
  • 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: 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: 6562888
    Abstract: Rosin esters that are both light-colored and color stable may be produced by reacting rosin with an organic compound containing two or more hydroxyl groups each separated from each other by at least four carbon atoms. With appropriate choices for the esterification catalyst and antioxidant(s), the rosin ester may be useful as a tackifier, and can be formulated into an adhesive composition. The adhesive compositions will further comprise an appropriate adhesive polymer.
    Type: Grant
    Filed: July 27, 1998
    Date of Patent: May 13, 2003
    Assignee: Arizona Chemical Company
    Inventors: Charles R. Frihart, Nelson E. Lawson, Brett A. Neumann
  • 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: 6096861
    Abstract: A chemical complex comprising divalent metal ions, preferably Ca.sup.+2 ions, and peptide-peptoid trimers in a fixed ratio and having a centrosymmetric crystalline structure wherein three divalent metal ions at the interior of the complex are coordinated with the peptide carboxylate and urethane oxygen atoms. The globular complex has a hydrophobic outer surface and is useful as an ionophore.
    Type: Grant
    Filed: March 12, 1998
    Date of Patent: August 1, 2000
    Assignee: The Regents of the University of California
    Inventors: Murray Goodman, Elizabeth Jefferson
  • Patent number: 6087318
    Abstract: A process for disproportionating rosins using iodide catalysts. In one embodiment, a tall oil rosin is heated in the presence of a lithium iodide catalyst. In another embodiment, a catalyst system is formed from a mixture of lithium iodide and ferrous iodide. The mixed catalyst system completes disproportionation of tall oil rosin in about three hours. Phosphoric acid may be added to remove iron colored impurities when using the mixed catalyst system. Another aspect of the invention involves preparing a soap from the disproportionated rosin by adding a defoamer and a base, such as potassium hydroxide.
    Type: Grant
    Filed: October 19, 1998
    Date of Patent: July 11, 2000
    Assignee: Georgia-Pacific Resins, Inc.
    Inventor: Jalandar Y. Jadhav
  • Patent number: 6022947
    Abstract: Light-colored phenolic-modified rosin esters, suitable for use as, for example, tackifiers in adhesive compositions, are prepared by reacting together rosin, a phenolic compound, formaldehyde or a reactive equivalent thereof, and a non-phenolic hydroxyl-containing organic compound in the presence of at least one lightening agent selected from phenol sulfide compounds, phosphorous acid, esters of phosphorous acid, and hypophosphite salts. The formaldehyde or reactive equivalent is present in an amount ranging from about 1.1 to about 3.5 equivalents of --CHO moieties per 1 equivalent of Ar--OH moiety of the phenolic compound, in order to obtain rosin esters having desirably low color, and adequately low molecular weight to effectively function as tackifiers.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: February 8, 2000
    Assignee: Union Camp Corporation
    Inventors: Charles R. Frihart, Kenneth E. Krajca, Brett A. Neumann
  • 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: 5874507
    Abstract: The specification discloses a method and additive for increasing the surface activity of non-polar polymeric materials, and a non-polar polymeric material exhibiting increased surface activity. The invention employs an additive of the formulaA-B-A.sup.1wherein each of the A and A.sup.1 blocks which may be the same or different has a number molecular weight in the range of from about 200 to about 1000 daltons and is selected from the group substituted and unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and alkylaryl units derived from one or more esters, organic acids, organic halides or organic acid halides, and units derived from alkyl or aryl isocyanates or ester-amides. The B-block is a polyepichlorohydrin unit derived from a polyepichlorohydrin polyol having at least two terminal hydroxyl groups and having an average molecular weight in the range of from about 400 to about 4000 daltons.
    Type: Grant
    Filed: September 15, 1997
    Date of Patent: February 23, 1999
    Assignee: Arizona Chemical Company
    Inventors: Xinya Lu, Eric S. Gardiner
  • Patent number: 5830992
    Abstract: Rosin esters that are both light colored and color stable are produced by reacting polyhydric alcohol with an equivalent excess of rosin, in the presence of calcium bis(monoethyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate. When phosphinic acid is added to the reaction mixture, light colored and color stable rosin esters are produced regardless of whether the rosin or polyol are in equivalent excess, although preferably the rosin is in equivalent excess. It is preferred to include a phenol sulfide compound, such as Vultac.RTM. 2, with the calcium bis(monoethyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, and to add the phosphinic acid incrementally after the acid number of the rosin and polyhydric alcohol reaction mixture has dropped to about 100. Excess rosin is preferably stripped from the product mixture at about 275.degree. C.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: November 3, 1998
    Assignee: Union Camp Corporation
    Inventor: David Mayo Whalen
  • Patent number: 5698668
    Abstract: Toluene-soluble modified natural-resin acid esters which can be prepared by reacting at least one compound from each of the component groups: A) natural resins or natural-resin acids; B) .alpha.,.beta.-ethylenically unsaturated carboxylic acids or their anhydrides; C) phenols which are polyfunctional with respect to oxo compounds; D) aldehydes or aldehyde acetals; E) alcohols having at least two hydroxyl groups; and, if desired, further compounds from the substance groups: F) fatty acids or fatty acid esters; G) ethylenically unsaturated monomers; H) ethylenically unsaturated hydrocarbon resins in the presence of: I) monovalent or divalent metal compounds or mixtures thereof at a temperature of from 100.degree. to 300 .degree. C., with elimination of water, to an acid number of less than 100 mg of KOH/g of resin, and then reacting the resulting products with: J) carboxylic acids which contain at least two carboxyl groups and are not .alpha.,.beta.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: December 16, 1997
    Assignee: Vianova Resins GmbH
    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: 5395920
    Abstract: The present invention relates to a process for preparing a rosin ester, which comprises esterifying a purified product of a disproportionated rosin with an alcohol, and then subjecting the esterified rosin to dehydrogenation in the presence of a dehydrogenating catalyst, a process for preparing a rosin ester, which comprises heating a purified rosin and an alcohol in the presence of a disproportionating catalyst, simultaneously subjecting the resulting rosin to disproportionation and esterification, dehydrogenating the reactant in the presence of a dehydrogenating catalyst, and thereafter adding an organic phosphorus compound to the reaction system, a process for preparing a colorless rosin, which comprises simultaneously subjecting a purified rosin to disproportionation and dehydrogenation in the presence of a catalyst, and then adding an organic phosphorus compound to the reaction system and a process for preparing a colorless rosin, which comprises dehydrogenating a purified disproportionated rosin in the
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: March 7, 1995
    Assignee: Arakawa Kagaku Kogyp Kabushiki Kaisha
    Inventors: Masao Maeda, Yukiharu Yamada, Yutaka Koba
  • Patent number: 5266682
    Abstract: The invention relates to mixtures of nitrogen-containing surface-active agents which are obtained by esterification of oxyalkylates based on modified or nonmodified naturally occurring resin acids or resin amines or resin alcohols derived therefrom with dicarboxylic acids or anhydrides thereof and subsequent reaction with alkylenediamines or alkylenepolyamines. These nitrogen-containing surface-active agents are suitable as coupling auxiliaries, emulsifiers, dispersing agents, preparation agents for solids dispersions, corrosion protection and metal-working agents and as wetting agents and dyeing auxiliaries.
    Type: Grant
    Filed: May 14, 1992
    Date of Patent: November 30, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Uhrig, Siegfried Schwerin, Dieter Schnaitmann, Hans-Joachim Metz
  • 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: 5162496
    Abstract: The catalytic combination of a phosphite ester and a phenol sulfide is disclosed. The catalyst combination accelerates and mediates the esterification reaction of rosin with a polyhydric alcohol, resulting in esterified rosins having numerous advantageous characteristics and particular utility as tackifiers in hot melt adhesives.
    Type: Grant
    Filed: May 30, 1990
    Date of Patent: November 10, 1992
    Assignee: Union Camp Corporation
    Inventor: Robert W. Johnson, Jr.
  • Patent number: 5084554
    Abstract: The color stability of polymerized rosin is improved by heating the polymerized rosin at a temperature of 250.degree.-290.degree. C. in the presence of 0.05% to 5% sodium hydroxymethane sulfonate.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: January 28, 1992
    Assignee: Hercules Incorporated
    Inventor: James Minn
  • Patent number: 5023319
    Abstract: This invention relates to a method for treating polymerized rosin to decrease its tendency to oxidize comprising heating the polymerized rosin to an elevated temperature in the presence of an effective amount of one or more disproportionating agents. This invention also relates to the novel products of such disproportionation treatments.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: June 11, 1991
    Assignee: Union Camp Corporation
    Inventors: Samuel D. Hollis, Robert W. Johnson, Jr.
  • Patent number: 5021548
    Abstract: The color stability of rosin esters is improved by carrying out the esterification reaction in the presence of 0.05% to 5% sodium hydroxymethane sulfonate (SHS). The color stability of polymerized rosin is improved by heating at a temperature of 250.degree.-290.degree. C. in the presence of SHS.
    Type: Grant
    Filed: January 22, 1990
    Date of Patent: June 4, 1991
    Assignee: Hercules Incorporated
    Inventor: James Minn
  • Patent number: 4939238
    Abstract: Nitrogen-containing condensation products based on unmodified or modified natural resins, process for the preparation thereof and the use thereof.The invention relates to surface-active agents of the general formulaA--[(X--O).sub.n --Y--Z].sub.min which A is a radical of an unmodified or modified natural resin or esterification product thereof with a polyhydric alcohol, X is 1,2-ethylene or -propylene, Y is as defined for X or is --CH.sub.2 CHOHCH.sub.2 --, Z is OH or (Ia)(--NH--Q).sub.a --NR--(Q--NH--).sub.b H (Ia)in which R is H or C.sub.1 -C.sub.24 --alkyl or (--CH.sub.2 CH.sub.2 O).sub.p --H, with p being 1 to 100, or (--Q--NH).sub.c --H, Q is C.sub.1 -C.sub.24 ---alkylene which can be interrupted by oxygen atoms, a is 0-5 and c is 0-5,at least one Z being other than OH,n is 0 to 150 andm is 1 to 5.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: July 3, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Uhrig, Siegfried Schwerin, Reinhold Deubel