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)
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Patent number: 8901245Abstract: 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: GrantFiled: December 10, 2013Date of Patent: December 2, 2014Assignee: University of South CarolinaInventors: Chuanbing Tang, Jifu Wang, Alan W. Decho, Yung Pin Chen
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Patent number: 8604128Abstract: 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: GrantFiled: February 15, 2012Date of Patent: December 10, 2013Assignee: University of South CarolinaInventors: Chuanbing Tang, Jifu Wang, Alan W. Decho, Yung Pin Chen
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Patent number: 8080602Abstract: 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: GrantFiled: September 18, 2007Date of Patent: December 20, 2011Assignee: Arizona Chemical Company, LLCInventors: Wolfgang Pille-Wolf, Mark Stanley Pavlin, Frederik Keijzer, Ronnie Zeeman
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Patent number: 8071087Abstract: 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: GrantFiled: July 22, 2010Date of Patent: December 6, 2011Assignee: Oncolytics Biotech Inc.Inventors: Patrick W. K. Lee, James Strong, Matthew C. Coffey
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Patent number: 7411036Abstract: 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: GrantFiled: November 23, 2005Date of Patent: August 12, 2008Assignee: Sun Chemical CorporationInventor: Kai-Uwe Gaudl
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Patent number: 7411035Abstract: 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: GrantFiled: November 23, 2005Date of Patent: August 12, 2008Assignee: Sun Chemical CorporationInventor: Kai-Uwe Gaudl
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Patent number: 7001981Abstract: 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: GrantFiled: April 25, 2003Date of Patent: February 21, 2006Assignee: Sun Chemical CorporationInventor: Kai-Uwe Gaudl
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Patent number: 6583263Abstract: 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: GrantFiled: January 5, 2001Date of Patent: June 24, 2003Assignee: Sun Chemical CorporationInventor: Kai-Uwe Gaudl
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Patent number: 6562888Abstract: 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: GrantFiled: July 27, 1998Date of Patent: May 13, 2003Assignee: Arizona Chemical CompanyInventors: Charles R. Frihart, Nelson E. Lawson, Brett A. Neumann
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Patent number: 6172174Abstract: 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: GrantFiled: March 26, 1999Date of Patent: January 9, 2001Assignee: Westvaco CorporationInventor: Michael D. Matzinger
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Patent number: 6096861Abstract: 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: GrantFiled: March 12, 1998Date of Patent: August 1, 2000Assignee: The Regents of the University of CaliforniaInventors: Murray Goodman, Elizabeth Jefferson
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Patent number: 6087318Abstract: 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: GrantFiled: October 19, 1998Date of Patent: July 11, 2000Assignee: Georgia-Pacific Resins, Inc.Inventor: Jalandar Y. Jadhav
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Patent number: 6022947Abstract: 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: GrantFiled: September 18, 1998Date of Patent: February 8, 2000Assignee: Union Camp CorporationInventors: Charles R. Frihart, Kenneth E. Krajca, Brett A. Neumann
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Patent number: 5969071Abstract: 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: GrantFiled: May 8, 1998Date of Patent: October 19, 1999Assignee: Westvaco CorporationInventor: Michael D. Matzinger
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Patent number: 5874507Abstract: 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: GrantFiled: September 15, 1997Date of Patent: February 23, 1999Assignee: Arizona Chemical CompanyInventors: Xinya Lu, Eric S. Gardiner
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Patent number: 5830992Abstract: 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: GrantFiled: December 12, 1996Date of Patent: November 3, 1998Assignee: Union Camp CorporationInventor: David Mayo Whalen
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Patent number: 5698668Abstract: 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: GrantFiled: June 3, 1996Date of Patent: December 16, 1997Assignee: Vianova Resins GmbHInventor: Albert Bender
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Patent number: 5559206Abstract: 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: GrantFiled: March 1, 1995Date of Patent: September 24, 1996Assignee: Arizona Chemical CompanyInventor: Theodore J. Williams
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Patent number: 5491215Abstract: 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: GrantFiled: April 11, 1995Date of Patent: February 13, 1996Assignee: Westvaco CorporationInventor: G. Frederick Hutter
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Patent number: 5395920Abstract: 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 theType: GrantFiled: July 26, 1994Date of Patent: March 7, 1995Assignee: Arakawa Kagaku Kogyp Kabushiki KaishaInventors: Masao Maeda, Yukiharu Yamada, Yutaka Koba
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Patent number: 5266682Abstract: 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: GrantFiled: May 14, 1992Date of Patent: November 30, 1993Assignee: Hoechst AktiengesellschaftInventors: Heinz Uhrig, Siegfried Schwerin, Dieter Schnaitmann, Hans-Joachim Metz
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Patent number: 5208319Abstract: 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: GrantFiled: June 25, 1992Date of Patent: May 4, 1993Assignee: Westvaco CorporationInventor: Peter Schilling
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Patent number: 5162496Abstract: 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: GrantFiled: May 30, 1990Date of Patent: November 10, 1992Assignee: Union Camp CorporationInventor: Robert W. Johnson, Jr.
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Patent number: 5084554Abstract: 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: GrantFiled: January 2, 1991Date of Patent: January 28, 1992Assignee: Hercules IncorporatedInventor: James Minn
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Patent number: 5023319Abstract: 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: GrantFiled: December 15, 1987Date of Patent: June 11, 1991Assignee: Union Camp CorporationInventors: Samuel D. Hollis, Robert W. Johnson, Jr.
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Patent number: 5021548Abstract: 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: GrantFiled: January 22, 1990Date of Patent: June 4, 1991Assignee: Hercules IncorporatedInventor: James Minn
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Patent number: 4939238Abstract: 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: GrantFiled: June 22, 1988Date of Patent: July 3, 1990Assignee: Hoechst AktiengesellschaftInventors: Heinz Uhrig, Siegfried Schwerin, Reinhold Deubel