Polyhydroxy Material Used In The Esterification, Or Product Thereof (e.g., Forming Ester Gum, Etc.) Patents (Class 530/218)
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Patent number: 11634584Abstract: Disclosed are compositions which include an ethylene polymer derived from at least one polar monomer with one or more ester groups, and a rosin ester. The rosin ester can have a low hydroxyl number (e.g., a hydroxyl number seven 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-five), 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., a heat stress pass temperature value higher than 52° C. or in between 48° C. and 60° C.) and/or improved viscosity stability and/or color stability upon thermal aging and/or improved compatibility.Type: GrantFiled: March 22, 2021Date of Patent: April 25, 2023Assignee: KRATON CORPORATIONInventors: Jos H. M. Lange, Mark C. Schaapman, Justyna J. Hinc
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Publication number: 20130197187Abstract: Rosin esters having suitable color, color stability and/or odor to make them useful for non-woven applications, to non-woven products made from and/or comprising rosin esters, and to methods of making and using such rosin esters and products.Type: ApplicationFiled: December 27, 2012Publication date: August 1, 2013Applicant: Arizona Chemical Company, LLCInventor: Arizona Chemical Company, LLC
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Publication number: 20110213120Abstract: Rosin esters having suitable color, color stability and/or odor to make them useful for non-woven applications, to non-woven products made from and/or comprising rosin esters, and to methods of making and using such rosin esters and products.Type: ApplicationFiled: March 1, 2010Publication date: September 1, 2011Inventors: Gary W. Astrologes, George A. Locko, Abhay Deshpande, Steven C. Gailbreath
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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: 6274657Abstract: A surfactant for forming stable dispersions of rosin esters compatible with elastomeric latexes, the surfactant having the formula R1—R2—R3. R1 and R3 are each rosin (i.e., rosin, rosin dimer or a mixture of rosin and rosin dimer). R2 is selected from the group consisting of polyethylene glycol and polyethylene glycol-R4-polyethylene glycol wherein R4 is rosin (i.e., rosin, rosin dimer or a mixture of rosin and rosin dimer). The surfactant is prepared by esterifying the rosin material with polyethylene glycol.Type: GrantFiled: January 27, 1994Date of Patent: August 14, 2001Assignee: Arizona Chemical CompanyInventors: John T. Geoghegan, Long S. Wang
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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: 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: 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: 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: 5594099Abstract: A modified resinate prepared by reactingA) rosins or rosin acids withB) aldehyde components and optionallyC) .alpha.,.beta.-olefinically unsaturated carboxylic acids or anhydrides thereof, subsequently reacting the resultant adduction products withD) phenols and optionallyE) alcohols containing at least two hydroxyl groups and subsequently forming resinates withF) basic compounds of divalent metals, useful as resin binders of high viscosity in low solid printing inks for intaglio printing of illustrations.Type: GrantFiled: March 31, 1995Date of Patent: January 14, 1997Assignee: Hoechst AktiengesellschaftInventor: 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: 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: 5543110Abstract: A process for deodorizing tall oil rosin and tall oil fatty acids and their derivatives by treating same with an ammonium hydroxide solution under conditions of a steam sparge.Type: GrantFiled: January 26, 1995Date of Patent: August 6, 1996Assignee: Westvaco CorporationInventors: Fredricke S. Starr, Joseph M. Wong, Norman L. Kennedy
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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: 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: 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: 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: 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: 4981939Abstract: This binder for toner preparation comprises as the main constituent thereof a polyester (X) composed of a polybasic acid component and a polyhydric alcohol component with a rosin-modified polyhydric alcohol (ab) introduced as part of the polyhydric alcohol component. The rosin-modified polyhydric alcohol is prepared in advance by reacting a polyhydric alcohol (a) having three or more hydroxyl groups with a rosin type compound (b).Type: GrantFiled: August 23, 1989Date of Patent: January 1, 1991Assignee: Nippon Gohsei Kagaku Kogyo KabushikiInventors: Akira Matsumura, Sadao Shigematsu, Tomiji Itou
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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