Esterification Of Rosin Or Derivative Via Carboxyl Group, Or Product Thereof Patents (Class 530/215)
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Patent number: 10344164Abstract: 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, or low molecular weight copolymer having a relatively high melt index, derived from ethylene and vinyl acetate and/or a copolymer, or low molecular weight copolymer having a relatively high melt index, derived from ethylene and «-buty! acrylate) and a rosin ester. The rosin ester can have a low hydroxy! number (e.g., a hydroxy! number six or five or less), a low acid number (e.g., an acid number of ten or less), a relatively low PAN number (e.g., a PAN number less than twenty-two or in between eight and twenty), a relatively high third moment or third power average molecular weight (Mz), (e.g., an Mz value in between 2500 and 12000 g/mol), a low sulfur content (e.g., a sulfur content lower than 600 ppm prior to antioxidant addition) or combinations thereof. The compositions can exhibit a high heat stress resistance (e.g.Type: GrantFiled: March 24, 2016Date of Patent: July 9, 2019Assignee: Kraton Chemical, LLCInventors: Jos H. M. Lange, Mark C Schaapman, Justyna J. Hinc
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Patent number: 9822059Abstract: The invention relates to a method for separating a mixture containing at least one carboxylic acid vinyl ester of general formula R?—C(O)O—CH?CH2 and at least one carboxylic acid of general formula R?—COOH, wherein R? in either case can be an aliphatic group having 12 to 22 C atoms or a cycloaliphatic group having 12 to 22 C atoms, or an aromatic group having 12 to 22 C atoms, and R? can be identical or different, characterized in that the carboxylic acid is converted to its anhydride R?—C(O)—O—C(O)—R? and the carboxylic acid vinyl ester is subsequently separated.Type: GrantFiled: May 21, 2015Date of Patent: November 21, 2017Assignee: Wacker Chemie AGInventors: Peter Gigler, Jürgen Stohrer
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Patent number: 8383765Abstract: 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: GrantFiled: April 16, 2007Date of Patent: February 26, 2013Assignee: Kao CorporationInventors: Takashi Kubo, Yoshitomo Kimura, Yoshihiro Ueno, Yasunori Inagaki
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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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Publication number: 20110288208Abstract: The present invention provides a resin modifier comprising as an active ingredient a hydrogenated rosin ester in which a component having a molecular weight of 320 of a methylation product of a hydrolyzate of the hydrogenated rosin ester as measured by gas chromatography-mass spectrometry accounts for 95 wt % or greater of the total amount of the components having a molecular weight of 314 to 320; a modifier that is an optical embrittlement inhibitor for use in an adhesive polymer resin; an adhesive composition comprising the optical embrittlement inhibitor; a modifier that is a melt fluidity and adhesion improver for a thermoplastic resin; and a thermoplastic resin composition comprising the melt fluidity and adhesion improver.Type: ApplicationFiled: March 11, 2010Publication date: November 24, 2011Inventors: Takashi Nakatani, Takumi Okazaki
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Patent number: 7923531Abstract: 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-haloproprionate ester of the natural resin ester and dehydrohalogenated the 3-halopropionate ester by reacting it with an organic base.Type: GrantFiled: June 12, 2007Date of Patent: April 12, 2011Assignee: Sun Chemical CorporationInventor: Kai-Uwe Gaudl
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Patent number: 7799895Abstract: A one component adhesive composition is provided, which can be formulated from substantially or totally bio-based, renewable raw materials. Such adhesives can be formulated to have high strength and/or low or substantially no VOC emissions. This can be achieved by utilizing polymers that are derived or extracted from renewable plant materials such as soybeans, corn, sunflowers, wheat, etc. Adhesive compositions in accordance with the invention can include oils. The composition preferably contains bio-based oils only, but need not be completely free of fossil fuel or synthetic based oils. It should also include drying oils and/or similarly acting polymers, co-polymers, and fatty acids. Plasticizers, such as hydrogen oxide, derived from renewable sources are utilized to impart performance properties to the formulated adhesive. Metal napthanates can be used to catalyze the drying and/or curing speed when the adhesive composition is applied to a substrate.Type: GrantFiled: September 12, 2006Date of Patent: September 21, 2010Assignee: W.F. Taylor Co., Inc.Inventors: Robert Kintu Ddamulira, John Edmund Raidy, Jr., Barry Kenneth Wright
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Patent number: 7750105Abstract: A process for producing rosin resins comprising reacting together rosin and phenolic compound and/or terpene-phenol resin, in the presence of a Brønsted acid. These resins may be used as tackifiers in adhesive formulations, including chloroprene contact cements.Type: GrantFiled: May 31, 2006Date of Patent: July 6, 2010Assignee: Arizona Chemical CompanyInventors: George A Locko, Abhay K Deshpande
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Publication number: 20090145329Abstract: The present invention provides a tackifier that is a raw material of an adherence adhesive having good adhesion performance (in particular, holding power) for all members and can be used for various adherence adhesives, and a tackifier emulsion capable of being used for various aqueous adherence adhesives. The tackifier and the tackifier emulsion including a rosin resin wherein a ratio of the content of a component with a molecular weight of at most 300 comprised in the rosin resin to the softening point of the rosin resin (the content (% by weight) of a component with a molecular weight of at most 300/softening point (K)) is at most 0.004; and the adherence adhesive composition including the tackifier; and the aqueous adherence adhesive composition including the tackifier emulsion.Type: ApplicationFiled: March 20, 2006Publication date: June 11, 2009Applicant: ARAKAWA CHEMICAL INDUSTRIES, LTD.Inventor: Takuro Miyamoto
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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: 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: 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: 6939944Abstract: The invention relates to the inhibition of crystallization in rosin and rosin-based materials through the use of crystallization inhibitors. More specifically, the crystallization inhibitor is selected from the group consisting of carboxylic acids and the salts of carboxylic acids. The invention also relates to the process of inhibiting crystallization in rosin and rosin-based materials.Type: GrantFiled: December 30, 2002Date of Patent: September 6, 2005Assignee: Eastman Chemical CompanyInventor: George Joseph Kutsek
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Publication number: 20040214987Abstract: 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: ApplicationFiled: April 25, 2003Publication date: October 28, 2004Inventor: Kai-Uwe Gaudl
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Publication number: 20040181026Abstract: The present invention provides a rosin modified phenolic resin having a weight average molecular weight of 3,000 to 400,000, which is obtained by reacting a monoester with a polyhydric alcohol and a phenol formaldehyde initial condensate, said monoester being prepared by partially esterifying a rosin and an animal and vegetable oil fatty acid with a monoalcohol, and a method for producing the same. Also the present invention provides a gel varnish comprising the resin, an animal and vegetable oil component, and a gelling agent, and a printing ink comprising the gel varnish. Printing is conducted using the printing ink.Type: ApplicationFiled: March 9, 2004Publication date: September 16, 2004Applicant: HARIMA CHEMICALS, INC.Inventors: Hiroshi Toyoda, Tadahisa Chiyoda
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Patent number: 6590070Abstract: This invention provides thermosetting adhesives which have properties advantageous for bonding electronic parts that are capable of being cured using a low dose of radiation such as electron beam. The thermosetting adhesive of the invention comprises (a) ethylene-glycidyl (meth)acrylate copolymer; (b) rosin having a carboxyl group; and (c) (meth)acrylate having a carboxyl group.Type: GrantFiled: September 19, 2000Date of Patent: July 8, 2003Assignee: 3M Innovative Properties CompanyInventors: Naoyuki Toriumi, Koichiro Kawate, Masaaki Takeda, Shigeyoshi Ishii, Koji Itoh
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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: 6525162Abstract: A new polyol family for the manufacture of novel polyurethane systems, preferably of polyurethane reactive hot melt adhesives is disclosed. The polyol(s) are reactive modifiers that enhance the properties of polyurethane systems. The inventive polyols are the reaction product of a monocarboxylic acid, a polycarboxylic acid and a polyhydric alcohol. The polyol of the present invention is used to produce urethane polymers, preferably polyurethane reactive hot melt adhesives by reacting the polyol with polyfunctional isocyanates. A method for producing the polyol, the urethane polymer as well as the polyurethane reactive hot melt adhesives is also provided.Type: GrantFiled: June 12, 2000Date of Patent: February 25, 2003Assignee: Eastman Chemical Resins, Inc.Inventor: Georges Napoleon Altounian
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Patent number: 6171385Abstract: A method of mounting and demounting a semiconductor wafer, in which a temperature dependent adhesive and curable joint is provided by an adhesive mixture between the semiconductor wafer and a carrier plate. The adhesive mixture contains a colophonium resin which is chemically modified and esterified. The cured joint is released with water again after polishing the semiconductor wafer. The adhesive mixture suitable for carrying out the method is this resin with an amine which saponifies the resin.Type: GrantFiled: December 8, 1998Date of Patent: January 9, 2001Assignee: Wacker Siltronic Gesellschaft f{umlaut over (u)}r Halbleitermaterialien AGInventors: Robert Rurlaender, Norbert Franze, Franz Mangs, Anton Schnegg
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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: 6153693Abstract: 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: GrantFiled: February 11, 1999Date of Patent: November 28, 2000Assignee: Westvaco CorporationInventors: Michael D. Matzinger, G. Frederick Hutter
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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: 5969092Abstract: The invention relates to a process for the preparation of a tall oil rosin ester with a low odor level, which process comprises an esterification step wherein a tall oil rosin is esterified with a polyol in order to form a product which contains a tall oil rosin ester, and evaporation is carried out on this product in order to remove odor components and other volatile components from the product, which evaporation is carried out in a short-path evaporator which has an evaporation surface and, in the vicinity of this surface, a condenser on which the vaporized components to be removed condense, whereupon a tall oil rosin ester with a low odor level is recovered from the evaporator.Type: GrantFiled: April 21, 1998Date of Patent: October 19, 1999Assignee: Arizona Chemical OyInventor: Mikko Kalevi Karvo
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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: 5922420Abstract: A granulate of wood or some other cellulose-containing material, pieces or particles of said material being at least partially esterified with 10-50% of a dicarboxylic acid anhydride and then impregnated with 2-25% of a polyol, the granulate being stable in storage and being possible to hot press or hot form later. A method for preparing the granulate by esterification at 80-160.degree. C. and, subsequently, impregnation at 150.degree. C. at most. A method for manufacturing formed articles by hot pressing or hot forming of the granulate, without the presence of a formaldehyde-containing adhesive and preferably without the presence of any other type of adhesive.Type: GrantFiled: February 13, 1997Date of Patent: July 13, 1999Assignee: Stora Kopparbergs Bergslags ABInventors: Jorgen Dahlin, Ulf Nyberg
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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: 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: 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: 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: 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: 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: 5246998Abstract: The present invention relates to dicyclopentadiene alcohol resin acid derivatives which are useful as a rubber additive. In one embodiment, the ester linked rosin acid derivative may serve as a total or partial replacement for oil and/or wax. The dicyclopentadiene alcohol rosin acid derivatives are prepared by reacting abietic acid and/or dehydroabietic acid with dicyclopentadiene alcohol under esterification conditions.Type: GrantFiled: April 24, 1992Date of Patent: September 21, 1993Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Paul H. Sandstrom, Denise J. Keith
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Patent number: 5177133Abstract: An improved, stable rosin ester tackifier consisting essentially of an adduct of rosin and a polyhydric alcohol selected from the group consisting of trimethylolpropane, trimethylolethane, and mixtures thereof, and hot melt adhesive compositions consisting essentially of said tackifier and a polymer component, said compositions containing a mixture of antioxidants containing a higher alkyl diester of thiopropionic acid, a hindered phenolic compound and a phenol sulfide compound, preferably an alkyl phenol disulfide oligomer.Type: GrantFiled: October 10, 1990Date of Patent: January 5, 1993Assignee: Georgia-Pacific Resins, Inc.Inventors: Michael C. Peck, Alan H. Deitch, Susan L. Whitfield
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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: 5100989Abstract: The invention relates to surface-active compounds of the general formula (I) ##STR1## in which Ar is an aromatic system which is optionally substituted by C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.18 -alkoxy, C.sub.2 -C.sub.5 -alkanoyl, C.sub.6 -C.sub.10 -aryl, (C.sub.6 -C.sub.10 -aryl)-C.sub.1 -C.sub.4 -alkyl, A has the formula --(X--O).sub.n --Y, wherein n denotes 1 to 50, X denotes ethylene or methylethylene and all or some of Y denote an acyl radical of a non-modified or modified natural resin acid and the other radicals Y denote radicals from the group comprising hydrogen, acyl radicals of saturated C.sub.1-24 -carboxylic acids, unsaturated C.sub.3-24 -carboxylic acids, C.sub.2-24 -hydroxy-fatty acids or C.sub.8-18 -alkyl-, -alkenyl- and -alkylidene-succinic acids, maleic acid, fumaric acid, sulfosuccinic acid, sulfuric acid, benzodicarboxylic acids and C.sub.1-16 -n-alkanedicarboxylic acids, W is a group --CHR-- or --CHR--N(R*)--T--N(R*)--CHR--, wherein R*is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.Type: GrantFiled: September 1, 1988Date of Patent: March 31, 1992Assignee: Hoechst AktiengesellschaftInventors: Heinz Uhrig, Erich Ackermann, Reinhold Deubel
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Patent number: 5073623Abstract: 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: GrantFiled: September 6, 1989Date of Patent: December 17, 1991Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Bernhard Prantl, Rolf Walz, Erwin Stark
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Patent number: 5049652Abstract: Rosin esters having improved viscosity stability are prepared by heating a mixture of rosin and a polyol in the presence of a catalyst mixture of 0.1% to 0.6% by weight calcium bis(ethyl 3,5-di-t-butyl-4-hydroxybenzyl phosphonate) and 0.02 to 1.0% by weight of a second calcium compound selected from calcium carbonate, calcium oxide and a calcium salt of an aliphatic carboxylic acid, all percentages being based on the weight of rosin.Type: GrantFiled: November 30, 1990Date of Patent: September 17, 1991Assignee: Hercules IncorporatedInventor: James Minn
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Patent number: 5049607Abstract: The present invention relates to alkyl (C.sub.6 -C.sub.22) amides of rosin acids which are useful as a total or partial replacement for extender or processing oil in rubber formulations. Addition of the alkyl (C.sub.6 -C.sub.22) amides of rosin acid also significantly reduce rheometer t25 and t90 values.Type: GrantFiled: September 25, 1989Date of Patent: September 17, 1991Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Paul H. Sandstrom
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Patent number: 5039726Abstract: The present invention relates to alkyl (C.sub.12 -C.sub.22) esters of rosin acids which are useful as a total or partial replacement for extender or processing oil in rubber formulations. Addition of the alkyl (C.sub.12 -C.sub.22) esters of rosin acid improve the tear of the vulcanizate.Type: GrantFiled: September 25, 1989Date of Patent: August 13, 1991Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Paul H. Sandstrom
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Patent number: 5037956Abstract: The present invention relates to the preparation of the p-hydroxydiphenylamine ester of rosin acid. The process involves first reacting hydroquinone and aniline in the presence of a bentonite catalyst to form a reaction mixture containing p-hydroxydiphenylamine. To this reaction mixture is added rosin acid under esterification conditions to form the p-hydroxydiphenylamine ester.Type: GrantFiled: September 5, 1989Date of Patent: August 6, 1991Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Denise J. Keith
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Patent number: 4962186Abstract: A method of improving the color of tall oil rosin esters comprising the sequential steps of (a) recrystallizing a tall oil rosin from a solvent, (b) purifying the crystalline portion by distillation, and (c) esterifying the resultant rosin with a polyol.Type: GrantFiled: July 10, 1989Date of Patent: October 9, 1990Assignee: Union Camp CorporationInventor: Robert W. Johnson, Jr.
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Patent number: 4946879Abstract: There is disclosed a reaction product of a rosin acid and a polyfunctional compound having at least one functional group capable of reacting with a carboxylic acid functionality and another functional group having antidegradant properties.The reaction products of this invention can be used as antidegradants in polymeric compositions and lubricating oil compositions.Type: GrantFiled: August 11, 1988Date of Patent: August 7, 1990Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Paul H. Sandstrom