Chemical Treatment Or Color Modification Of Esterified Rosin Or Derivative, Or Product Thereof (e.g., Partial Saponification Of Rosin Triglycerides; Removal Of Color Bodies From Rosin Esters, Etc.) Patents (Class 530/216)
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Patent number: 10336922Abstract: Disclosed are compositions which include an ethylene polymer derived from at least one polar monomer with one or more ester groups, which polymerize with ethylene, (e.g., a copolymer derived from ethylene and vinyl acetate or a copolymer derived from ethylene and n-butyl acrylate) and a rosin ester. The rosin ester can have a low hydroxyl number (e.g., a hydroxyl number six or five or less), a low acid number (e.g., an acid number of ten or less), a low PAN number (e.g., a PAN number of eight or less), or combinations thereof. The compositions can exhibit improved viscosity stability and/or color stability and/or a decreased amount of char particle formation upon thermal aging.Type: GrantFiled: April 6, 2018Date of Patent: July 2, 2019Assignee: Kraton Chemical, LLCInventors: Josephus Hubertus Maria Lange, Mark c Schaapman, Erik Kelderman
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Publication number: 20110034669Abstract: A process for producing light color rosins ester resin, preferably based on tall rosin, is described. The process is conducted in the presence of less than 10 weight % of an acid functional organic compound and avoids the need for use of a stoichiometric excess of rosin acid, or a stoichiometric excess of polyol hydroxyl groups. The process allows for the use of lower colored or darker tall oil rosin in the production of low color rosin esters.Type: ApplicationFiled: October 14, 2010Publication date: February 10, 2011Inventor: Anthony J. Dallavia
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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: 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: 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: 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: 5606016Abstract: A process for preparing colorless rosins characterized by dehydrogenating purified hydrogenated rosins in the presence of a dehydrogenating catalyst. The colorless rosins obtained according to the process of the present invention are nearly colorless in appearance, odorless and excellent in stabilities, particularly are excellent in various properties such as odor, stabilities and compatibility in a heated state. Accordingly the above-mentioned colorless rosins are suitably used not only as modifiers for soap-type cleaning compositions, but also as emulsifiers for synthetic rubbers and emulsion polymerization in the form of alkali metal salts thereof.Type: GrantFiled: January 18, 1995Date of Patent: February 25, 1997Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Masao Maeda, Yukiharu Yamada, Yutaka Koba
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Patent number: 5552519Abstract: Surfactant obtainable by and method for the production thereof comprising (1) esterifying a rosin with an alcohol to an acid value of less than 30, (2a) grafting the rosin ester with an unsaturated carboxylic acid or anhydride, the mole ratio carboxylic acid or anhydride/rosin (calculated as each rosin associated with a rosin ester) being from 0.05:1-1.5:1, (3a) esterifying the grafted rosin ester with a polyethylene glycol with an Mw of 1000-20000 the mole ratio glycol/free carboxylic acid group being from 0.2:1-1:1 to an acid value of less than 30, alternatively (2b) esterifying an unsaturated carboxylic acid or anhydride with a polyethylene glycol with a Mw of 1000-20000 the mole ratio glycol/free carboxylic acid group or anhydride being from 0.2:1-1:1 to an acid value less than 30, (3b) grafting the rosin ester from (1) with the ester from (2b), the mole ratio ester from (2b)/rosin ester (calculated as in (2a)) being from 0.05:1-1.5:1.Type: GrantFiled: May 16, 1995Date of Patent: September 3, 1996Assignee: EKA Nobel, ABInventors: Paul N. Hemmings, Long Wang
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Patent number: 5387669Abstract: 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: August 17, 1993Date of Patent: February 7, 1995Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Masao Maeda, Yukiharu Yamada, Yutaka Koba
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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: 5116945Abstract: A resinous substance obtained by reacting a rosin compound containing 1 to 10 equivalents of carboxylic groups per kilogram with triglycidyl isocyanurate. A process for producing it is also disclosed.Type: GrantFiled: February 12, 1990Date of Patent: May 26, 1992Assignee: Nissan Chemical Industries, Ltd.Inventors: Ken'ichi Osawa, Hisao Ikeda, Fumio Mizuochi, Hiroyuki Uehara
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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: 4906733Abstract: A process for preparing a colorless rosin comprising a step for purifying a disproportionated rosin and hydrogenating the rosin. According to the process, a rosin having a color nearly equal to colorless and is excellent in various properties such as odorless at heating and stability is prepared.Type: GrantFiled: September 23, 1988Date of Patent: March 6, 1990Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Yoshihiro Kodama, Masao Maeda, Kiyoshi Kanagawa
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Patent number: 4847010Abstract: A process for preparing a rosin ester which comprises purifying a rosin and/or a disproportionated rosin, esterifying the resulting purified rosin and/or purified disproportionated rosin with an alcohol and subjecting the esterified rosin and/or esterified disproportionated rosin to hydrogenating. The resulting rosin ester has superior color nearly equal to colorless and is excellent in various properties such as odor at heating, stability and compatibility with organic polymers.Type: GrantFiled: January 28, 1988Date of Patent: July 11, 1989Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventors: Masao Maeda, Yoshihiro Kodama