Chemical Treating Agent Contains Elemental Hydrogen Or An Elemental Hydrogen-liberating Compound, E.g., Hydrogenation, Etc. Patents (Class 525/338)
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Patent number: 5367034Abstract: A process for partially isomerized partially hydrogenated diene polishers containing unsaturation in endo and exo trisubstituted chain configurations while substantially eliminating the unsaturation in the 1,4-trans configuration remaining after hydrogenation, by isomerizing the unsaturation in the presence of a phosphine, borane, or alkali alkoxide isomerizing agent.Type: GrantFiled: February 14, 1994Date of Patent: November 22, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: William L. Hergenrother, John M. Doshak
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Patent number: 5356993Abstract: This invention provides a reactive conjugated diene polymer composition that forms a phase-separated adhesive, sealant, or coating. The composition comprises an epoxidized polymer of conjugated dienes, a second reactive component which is phase separated from the polymerized conjugated diene upon cure, and optionally a tackifying resin. The invention also encompasses adhesive, coating and sealant compositions made with the above composition.Type: GrantFiled: July 12, 1993Date of Patent: October 18, 1994Assignee: Shell Oil CompanyInventors: James R. Erickson, Michael A. Masse, Steven H. Dillman, Esther M. Zimmermann, Dale L. Handlin, Jr.
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Patent number: 5352744Abstract: This invention relates to a method for hydrogenation of poly(alkenyl aromatic) polymers or poly(alkenyl aromatic)/polydiene block copolymers that provides hydrogenated polymers with 99.5% or greater unsaturation and an MWD of less than about 3. Hydrogenated polymers and adhesives comprising the hydrogenated polymers and tackifier are also provided.Type: GrantFiled: March 15, 1993Date of Patent: October 4, 1994Assignee: University of MinnesotaInventors: Frank S. Bates, Mark D. Gehlsen, Vincent L. Hughes, Patrick Brant
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Patent number: 5328956Abstract: A propylene (co) polymer terminated with a reactive group and a process for the preparation of the same.A graft copolymer having a specific side chain and a process for the preparation of the same.The propylene (co) polymer is usable as a radial- or ion-polymerizable propylene macromonomer or as an intermediate for the preparation of a block polymer. Examples of the application thereof include compatibizing agent for polymers, light- or laser-curable plastic, viscosity index and surface modifier.The graft copolymer is useful as a surface modifier or compatibilizing agent for polypropylene or a dispersant for fillers.Type: GrantFiled: November 4, 1991Date of Patent: July 12, 1994Assignee: Kao CorporationInventors: Yoshihiro Hasebe, Takayuki Amiya, Yutaka Yasuda
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Patent number: 5314967Abstract: A process for producing isomerized partially hydrogenated diene polymers containing unsaturation in endo and exo trisubstituted chain configurations while substantially eliminating the unsaturation in the 1,4-trans configuration remaining after hydrogenation, by isomerizing the unsaturation in the presence of a phosphine, borane, or alkali alkoxide isomerizing agent.Type: GrantFiled: August 24, 1993Date of Patent: May 24, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: William L. Hergenrother, John M. Doshak
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Patent number: 5310817Abstract: A process for producing partially hydrogenated diene polymers containing unsaturation in the endo and exo configurations while substantially eliminating the unsaturation in the 1,4-trans configuration, by isomerizing the unsaturation during hydrogenation in the presence of an arylphosphine isomerizing agent.Type: GrantFiled: August 24, 1993Date of Patent: May 10, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: William L. Hergenrother, John M. Doshak
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Patent number: 5296515Abstract: A method is provided for hydrovisbreaking hydrocarbon polymers, particularly those derived from scrap articles, in which a mixture of at least one hydrocarbon polymer and a solvent is contacted with hydrogen under conditions sufficient to hydrovisbreak the polymer. The solvent comprises a combined weight percentage of C.sub.n H.sub.2n-8 and C.sub.n H.sub.2n-10 hydrocarbons of at least about 10 weight percent, where n is an integer of at least 8 in C.sub.n H.sub.2n-8 and n is an integer of at least 10 in C.sub.n H.sub.2n-10. The hydrovisbroken polymer can be fed to a catalytic cracker for cracking to cracked products.Type: GrantFiled: June 3, 1992Date of Patent: March 22, 1994Assignee: Phillips Petroleum CompanyInventors: Marvin M. Johnson, Fernando C. Vidaurri, Jr., William R. Coutant, Kenneth S. Wheelock
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Patent number: 5286439Abstract: Semiconductor chips are packaged by injection molding while continuously feeding a lead frame, characterized by using for the injection molding a hydrogenated polymer (A) obtained by the hydrogenation of a polymer obtained by ring-opening polymerization of a specific norbornene derivative or a monomer mixture comprising said norbornene derivative and other monomer copolymerizable therewith, wherein said injection molding for the packaging is carried out under the conditions of a resin temperature in the range of 280.degree. C. to 360.degree. C.; the molding temperature in the range of Tg -80.degree. C. to Tg +10.degree. C., wherein Tg is the glass transition temperature of the hydrogenated polymer (A) is Tg; and the injection pressure in the range of 10 to 200 kgf/cm.sup.2.Type: GrantFiled: December 15, 1992Date of Patent: February 15, 1994Assignee: Japan Synthetic Rubber Co., Ltd.Inventor: Hironobu Shinohara
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Patent number: 5280081Abstract: In a first embodiment of the present invention, poisoning or deactivation of conventional homogeneous catalysts to be used in hydrogenation of the backbone unsaturation in liquid monofunctional and difunctional-terminated conjugated diene polymers, is prevented by reacting a blocking agent compound with the functional end groups present in these polymers. More specifically, subsequent to formation of a selected starting material monofunctional or difunctional-terminated conjugated diene polymer, a suitable blocking agent is reacted with the functional end groups of the polymer enabling relatively inexpensive titanium, iron, cobalt, or nickel-based homogeneous catalysts to be used in hydrogenating the backbone unsaturation of the polymer to a high degree. Subsequent to hydrogenation, the polymer is subjected to conventional hydrolysis using a mineral acid or base to remove the blocking groups and return the hydrogenated conjugated diene polymer to its original functionality.Type: GrantFiled: January 10, 1992Date of Patent: January 18, 1994Assignee: The B. F. Goodrich CompanyInventor: Tonson Abraham
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Patent number: 5280058Abstract: The present invention is an improvement upon a process for hydrogenating a diene polymer by contacting the polymer in the presence of hydrogen with a titanium hydrogenation catalyst. The improvement comprises preventing discoloration of the hydrogenated polymer by treating it with water, a peroxide or alcohol in the absence of oxygen and adding a non-phenolic antioxidant to the polymer.Type: GrantFiled: April 16, 1993Date of Patent: January 18, 1994Assignee: Shell Oil CompanyInventors: Linda R. Chamberlain, Carma J. Gibler, Miguel Prado
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Patent number: 5280059Abstract: The present invention is an improvement upon a process for hydrogenating a diene polymer by contacting the polymer in the presence of hydrogen with a titanium hydrogenation catalyst. The improvement comprises preventing discoloration of the hydrogenated polymer by treating it with water, a peroxide or alcohol in the absence of oxygen and adding a non-phenolic antioxidant to the polymer.Type: GrantFiled: April 16, 1993Date of Patent: January 18, 1994Assignee: Shell Oil CompanyInventors: Linda R. Chamberlain, Carma J. Gibler, Miguel Prado
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Patent number: 5266653Abstract: Poisoning or deactivation of conventional homogeneous catalysts to be used in hydrogenation of the backbone unsaturation in liquid monofunctional and difunctional-terminated conjugated diene polymers, is prevented by reacting a blocking agent compound with the functional end groups present in these polymers. More specifically, subsequent to formation of a selected starting material monofunctional or difunctional-terminated conjugated diene polymer, a suitable blocking agent is reacted with the functional end groups of the polymer enabling relatively inexpensive titanium, iron, cobalt, or nickel-based homogeneous catalysts to be used in hydrogenating the backbone unsaturation of the polymer to a high degree. Subsequent to hydrogenation, the polymer is subjected to conventional hydrolysis using a mineral acid or base to remove the blocking groups and return the hydrogenated conjugated diene polymer to its original functionality.Type: GrantFiled: June 5, 1991Date of Patent: November 30, 1993Assignee: The B. F. Goodrich CompanyInventor: Tonson Abraham
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Patent number: 5264480Abstract: A process for making polymers of conjugated dienes which contain hydroxyl groups, including highly reactive primary hydroxyl groups, in the diene blocks which comprises(a) making a precursor polymer by polymerizing at least one conjugated diene which leaves 1,2 disubstituted, 1,1 disubstituted, 1,1,2 trisubstituted or tetrasubstituted olefinic unsaturation in the polymer,(b) optionally partially hydrogenating said precursor polymer,(c) epoxidizing said precursor polymer such that epoxy groups form at said substituted sites and the amount of epoxy functionality in the polymer is from at least 0.1 Meq/g polymer, and(d) reacting the epoxidized polymer with an alcohol having one unprotected hydroxyl group in a solvent in the presence of a Lewis acid selected from the group consisting of MX.sub.n where M is selected from the group consisting of boron, aluminum, iron and tin, and X is a halogen, and organic complexes of such acids.A diene polymer containing 0.Type: GrantFiled: April 16, 1993Date of Patent: November 23, 1993Assignee: Shell Oil CompanyInventors: Robert C. Bening, James R. Erickson, Charles J. Stark, David J. St. Clair
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Patent number: 5262496Abstract: A process for making polymers of conjugated dienes which contain hydroxyl groups, including highly reactive primary hydroxyl groups, in the diene blocks which comprises(a) making a precursor polymer by polymerizing at least one conjugated diene which leaves 1,2 disubstituted, 1,1 disubstituted, 1,1,2 trisubstituted or tetrasubstituted olefinic unsaturation in the polymer,(b) optionally partially hydrogenating said precursor polymer,(c) epoxidizing said precursor polymer such that epoxy groups form at said substituted sites and the amount of epoxy functionality in the polymer is from at least 0.1 Meq/g polymer, and(d) reacting the epoxidized polymer with an alcohol having one unprotected hydroxyl group in a solvent in the presence of a Lewis acid selected from the group consisting of MX.sub.n where M is selected from the group consisting of boron, aluminum, iron and tin, and X is a halogen, and organic complexes of such acids.A diene polymer containing 0.Type: GrantFiled: April 16, 1993Date of Patent: November 16, 1993Assignee: Shell Oil CompanyInventors: Robert C. Bening, James R. Erickson, Charles J. Stark, David J. St. Clair
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Patent number: 5258467Abstract: An improved process is provided for the catalytic hydrogenation of nitrile rubber in solution in an organic medium using a ruthenium catalyst, the improvement being that the hydrogenation is undertaken in the presence of water and a selected organic additive whereby the molecular weight increase in the hydrogenation process is minimized and controlled.Type: GrantFiled: September 2, 1992Date of Patent: November 2, 1993Assignee: Polysar Rubber CorporationInventors: Garry L. Rempel, Neil T. McManus, Xiang-Yao Guo
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Patent number: 5256750Abstract: A hydrogenated liquid petroleum resin obtained by hydrogenating an aromatic liquid petroleum resin having a structure in which aromatic rings are linked by the medium of a methylene group, and a hot melt pressure-sensitive adhesive composition containing the same.Type: GrantFiled: May 28, 1992Date of Patent: October 26, 1993Assignee: Mitsubishi Oil Co., Ltd.Inventors: Hajime Yoshida, Akira Uekusa, Takashi Satoh, Ryoji Ohnishi
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Patent number: 5244965Abstract: The present invention provides a process to remove phosphine residues from a hydrogenated polymer solution.Type: GrantFiled: June 14, 1989Date of Patent: September 14, 1993Assignee: Polysar LimitedInventors: Akhtar Osman, William G. Bradford
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Patent number: 5244980Abstract: This is a process for the hydrogenation of conjugated diolefin polymers which comprises polymerizing or copolymerizing at least one conjugated diolefin with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer, terminating the polymerization by the addition of hydrogen and effecting selective hydrogenation of the unsaturated double bonds in the conjugated diolefin units of the terminated polymer by contacting the polymer with hydrogen in the presence of an organo alkali metal promoter and Tebbe's reagent.Type: GrantFiled: December 7, 1992Date of Patent: September 14, 1993Assignee: Shell Oil CompanyInventors: Carma J. Gibler, Stanley E. Wilson
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Patent number: 5244943Abstract: A nitrile group-containing rubber latex comprising an aqueous dispersion of a nitrile group-containing highly saturated rubber having an iodine value of not more than 120. The said rubber latex can be produced by converting a solution of a nitrile group-containing highly saturated polymer rubber having an iodine value of not more than 120 in an inert solvent into an oil-in-water emulsion using water and an emulsifier, and removing the solvent from the resulting emulsion.Type: GrantFiled: May 6, 1992Date of Patent: September 14, 1993Assignee: Nippon Zeon Co., Ltd.Inventors: Motofumi Oyama, Osamu Mori, Nagatoshi Sugi
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Patent number: 5242986Abstract: This is a process for the partial hydrogenation of conjugated diolefin polymers which comprises polymerizing at least one conjugated diolefin with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer comprising (1) ethylenic unsaturation between backbone carbons wherein at least one of the doubly bound backbone carbons is substituted and (2) ethylenic unsaturation which is not between doubly bound backbone carbons wherein at least one is substituted, terminating the polymerization, and effecting selective hydrogenation of the ethylenic unsaturation in the conjugated diolefin units of the terminated polymer which is not between doubly bound backbone carbons wherein at least one is substituted, by contacting the polymer with hydrogen in the presence of no more than 0.02 mM of catalyst per gram of polymer of a bis(cyclopentadienyl)titanium catalyst.Type: GrantFiled: August 10, 1992Date of Patent: September 7, 1993Assignee: Shell Oil CompanyInventors: Carma J. Gibler, Linda R. Chamberlain, Ronald J. Hoxmeier
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Patent number: 5241013Abstract: An improved process is provided for the catalytic hydrogenation of nitrile rubber in solution in an organic medium using a ruthenium catalyst, the improvement being that the hydrogenation is undertaken in the presence of water and a selected inorganic additive whereby the molecular weight increase in the hydrogenation process is minimized and controlled.Type: GrantFiled: September 2, 1992Date of Patent: August 31, 1993Assignee: Polysar Rubber CorporationInventors: Garry L. Rempel, Neil T. McManus, Xiang-Yao Guo
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Patent number: 5231143Abstract: High-temperature oil-resistant elastomers are prepared from butadiene alkenylpyridine copolymers, butadiene-acrylate copolymers, and copolymers of butadiene with 1,3-dienes containing fluorine. The unsaturated olefinic backbone and pendant unsaturation derived from the hydrocarbon diene of each of the copolymers is hydrogenated to a high degree by a catalyst which improves the heat resistance of the copolymer without hydrogenation of the polar groups thereof which would lower the oil-resistance of the copolymer. A complexing agent for the hydrogenation catalyst prevents poisoning of the catalyst by the polar groups of the copolymers thereby enabling the catalyst to complex with unsaturated sites along the olefinic copolymer backbone to achieve high levels of hydrogenation thereof.Type: GrantFiled: May 27, 1992Date of Patent: July 27, 1993Assignee: The B. F. Goodrich CompanyInventor: Tonson Abraham
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Patent number: 5229464Abstract: A viscous block copolymer of the formula(A--B--A).sub.n --Y.sub.r --(A.sub.q --B).sub.mwherein Y is a coupling agent or coupling monomers, andwherein A and B are polymer blocks which may be homopolymer blocks of conjugated diolefin monomers, copolymer blocks of conjugated diolefin monomer or copolymer blocks of conjugated diolefin monomers and monoalkenyl aromatic hydrocarbon monomers, andwherein the A blocks have a higher number of aliphatic double bonds between a tertiary carbon atom and either a primary or secondary carbon atom per unit of block mass than do the B blocks, andwherein the A blocks have a molecular weight from about 100 to about 3000 and the B blocks have a molecular weight from about 1000 to about 15,000, andwherein p and q are 0 or 1 and n>0, r is 0 or 1, m.gtoreq.0 and n+m ranges from 1 to 100.This block copolymer is preferably partially hydrogenated, epoxidized and crosslinked through at least some of the epoxy functionality to form an adhesive, coating or sealant composition.Type: GrantFiled: April 29, 1991Date of Patent: July 20, 1993Assignee: Shell Oil CompanyInventors: James R. Erickson, David J. St. Clair
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Patent number: 5210151Abstract: An improved process is provided for the catalytic hydrogenation of nitrile rubber using a ruthenium catalyst wherein the improvement is that the nitrile rubber is provided as an aqueous emulsion and a solvent and a selected inorganic additive are present during the hydrogenation, whereby the molecular weight increase in the hydrogenation process is minimized and controlled.Type: GrantFiled: September 2, 1992Date of Patent: May 11, 1993Assignee: Polysar Rubber CorporationInventors: Garry L. Rempel, Xiang-Yao Guo
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Patent number: 5208296Abstract: An improved process is provided for the catalytic hydrogenation of nitrile rubber using a ruthenium catalyst wherein the improvement is that the nitrile rubber is provided as an aqueous emulsion and a solvent and a selected organic additive are present during the hydrogenation, whereby the molecular weight increase in the hydrogenation process is minimized and controlled.Type: GrantFiled: September 2, 1992Date of Patent: May 4, 1993Assignee: Polysar Rubber CorporationInventors: Garry L. Rempel, Xiang-Yao Guo
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Patent number: 5206307Abstract: This is an improved process for the hydrogenation of conjugated diolefin polymers which comprises polymerizing or copolymerizing at least one conjugated diolefin with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer, terminating the polymerization by the addition of hydrogen and effecting selective hydrogenation of the unsaturated double bonds in the conjugated diolefin units of the terminated polymer by contacting the polymer, in the absence of hydrocarbon lithium and alkoxy lithium compounds, with hydrogen in the presence of at least one bis(cyclopentadienyl)titanium compound. The improvement is the use of an alkyl benzoate as a promoter in the hydrogenation step.Type: GrantFiled: July 1, 1992Date of Patent: April 27, 1993Assignee: Shell Oil CompanyInventors: Linda Rae Chamberlain, Carma J. Gibler
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Patent number: 5206306Abstract: Substantially optically clear molding compositions comprising polymerized cycloolefin monomers (e.g., norbornene-type polymers) which, subsequent to polymerization have been hydrogenated are provided. The polymers have a weight average molecular weight of from about 37-47.times.10.sup.3.Type: GrantFiled: March 3, 1992Date of Patent: April 27, 1993Assignee: The B. F. Goodrich CompanyInventor: Dennis C. Shen
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Patent number: 5202388Abstract: A process for producing a hydrogenation product of ring-opening polymer by hydrogenating, in the presence of a hydrogenation catalyst, the non-aromatic carbon-to-carbon double bond present in a ring-opening polymer obtained by subjecting to ring-opening polymerization at least one norbornene derivative represented by general formula (I): ##STR1## wherein A and B independently represent hydrogen atoms or hydrocarbon groups having 1-10 carbon atoms, X and Y independently represent hydrogen atoms, halogen atoms or monovalent organic groups, and m is 0 or 1, alone or in combination with a monomer copolymerizable with said norbronene derivative, characterized by using, as the hydrogenation catalyst, a ruthenium compound represented by general formula (II):RuH.sub.k Q.sub.n T.sub.p Z.sub.q (11)wherein Q represents a halogen atom, T represents at least one atomic group selected from the group consisting of CO, NO and CH.sub.3 COCH.sub.2 COCH.sub.3, Z represents PR.sup.1 R.sup.2 R.sup.3 (R.sup.1, R.sub.2 and R.sup.Type: GrantFiled: November 29, 1991Date of Patent: April 13, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Akira Iio, Noboru Oshima, Yosihiro Ohira, Masao Sakamoto, Hiroshi Oka
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Patent number: 5200470Abstract: High Tg polymers prepared by metathesis ring-opening polymerization of N-aryl norbornene dicarboximide and one or more other norbornene derivative monomers, wherein said N-aryl group is substituted with a halo, cyano, alkyl or halogenated alkyl substituting group which is ortho or meta to the imide nitrogen. Preferred polymers with exceptionally high Tg are prepared from N-ortho substituted phenyl norbornene dicarboximide monomer. Mixtures of N-ortho substituted phenyl norbornene dicarboximide and N-meta substituted phenyl norbornene dicarboximide can exhibit eutectic melting points which facilitates melt polymerization.Type: GrantFiled: December 18, 1991Date of Patent: April 6, 1993Assignee: Monsanto CompanyInventor: Jawed Asrar
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Patent number: 5177155Abstract: This invention provides a catalyst and a process for the hydrogenation of conjugated diolefin polymers which first involves the polymerization or copolymerization of such monomers with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer. The living polymer can be terminated by the addition of hydrogen. Finally, selective hydrogenation of the unsaturable double bonds in the conjugated diolefin units of the terminated polymer is carried out in the presence of an initiator and at least one rare earth compound of the formula*Cp.sub. MRwhere *Cp is pentamethylcyclopentadiene, M is a rare earth element and R is alkyl, aryl, aralkyl or hydrogen.Type: GrantFiled: May 13, 1991Date of Patent: January 5, 1993Assignee: Shell Oil CompanyInventors: Linda R. Chamberlain, Carma J. Gibler, Richard A. Kemp, Stanley E. Wilson, Thomas F. Brownscombe
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Patent number: 5173537Abstract: This is an improvement in a process for the hydrogenation of conjugated diolefin polymers which comprises polymerizing or copolymerizing at least one conjugated diolefin with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer, terminating the polymerization by the addition of hydrogen, thereby generating an alkali metal hydride, and effecting selective hydrogenation of the unsaturated double bonds in the conjugated diolefin units of the terminated polymer by contacting the polymer, in the absence of hydrocarbon lithium and alkoxy lithium compounds, with hydrogen in the presence of at least one bis(cyclopentadienyl)titanium compound. The improvement comprises treating the polymer, before hydrogenation, with a reagent to increase catalyst activity, the reagent being such that it will react with the alkali metal hydride present in the polymer.Type: GrantFiled: December 20, 1991Date of Patent: December 22, 1992Assignee: Shell Oil CompanyInventors: Linda Rae Chamberlain, Carma J. Gibler
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Patent number: 5171793Abstract: A thermally polymerized hydrogenated hydrocarbon resin and a novel process for hydrogenating a hydrocarbon resin. The resin is a copolymer of a feed which is a mixture of styrene and indene and derivatives thereof and cyclodiene monomers and dimers and optionally acyclic dienes. The process for hydrogenation of hydrocarbon resins is a process in which the resins are hydrogenated in the presence of an olefinic diluent which increases the hydrogenation reaction temperature to improve hydrogenation efficiency. The resin is useful in block copolymer and ethylene-unsaturated ester copolymer adhesive systems.Type: GrantFiled: February 22, 1990Date of Patent: December 15, 1992Assignee: Exxon Chemical Patents Inc.Inventors: Carlton B. Johnson, Steve G. Hentges, Serge Maroie, Ronald J. Litz
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Patent number: 5169901Abstract: A catalyst comprising a high-molecular complex formed from a palladium compound and a nitrile group-containing polymer, and a method for hydrogenating a conjugated diene polymer which comprises selectively hydrogenating only a carbon-carbon double bond of the conjugated diene polymer using same.Type: GrantFiled: December 13, 1991Date of Patent: December 8, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Kazuhiro Takahashi, Yoichiro Kubo
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Patent number: 5169905Abstract: A hydrogenation catalyst composition comprising, as essential components, (a) at least one bis(cyclopentadienyl)transition metal compound represented by general formula (i): ##STR1## and (b) at least one member selected from the group consisting of complex compounds represented by general formulas (ii) and (iii): ##STR2## and further comprising, if necessary, (c) at least one polar compound selected from the group consisting of ether compounds, thioether compounds, ketone compounds, sulfoxide compounds, carboxylic acid ester compounds, lactone compounds, amine compounds, amide compounds, nitrile compounds and oxime compounds and/or (d) an alkali compound represented by general formula (iv):M.sup.2 OR.sup.7 (iv)The contact of an olefinically unsaturated polymer with hydrogen in the presence of said catalyst composition enables the selective hydrogenation of the olefinic double bonds in said polymer.Type: GrantFiled: December 14, 1990Date of Patent: December 8, 1992Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshiharu Hashiguchi, Hideo Katsumata, Kunio Goshima, Toshio Teramoto, Yasuhiko Takemura
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Patent number: 5166277Abstract: Complete hydrogenation of residual unsaturation in low molecular weight polymers containing conjugated dienes is enhanced by removal of strong lithium bases by filtering or decanting the polymer solution prior to hydrogenation.Type: GrantFiled: October 31, 1991Date of Patent: November 24, 1992Assignee: Shell Oil CompanyInventors: Daniel E. Goodwin, Carl L. Willis
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Patent number: 5164469Abstract: A transparent resin material consisting of a hydrogenation product of a (co)polymer obtained by subjecting at least one compound represented by general formula (I) or a combination of at least 5% by weight of said compound and 95% by weight or less of other copolymerizable cyclic olefin monomer to metathesis polymerization: ##STR1## wherein A and B are independently hydrogen atoms or C.sub.1-10 hydrocarbon groups; and X and Y are independently hydrogen atoms, C.sub.1-10 hydrocarbon groups, --C(CH.sub.2).sub.n COOR.sup.1 groups or --(CH.sub.2).sub.n OCOR.sup.1 groups [R.sup.1 is a C.sub.1-20 hydrocarbon group and n is 0 or an integer of 1-10] with the proviso that at least one of X and Y is selected from the above --(CH.sub.2).sub.n COOR.sup.1 and --(CH.sub.2).sub.n OCOR.sup.1 groups. Said transparent resin material is moldable and has sufficient optical properties, low hygroscopicity, good heat resistance and excellent adhesion to recording layer.Type: GrantFiled: January 31, 1991Date of Patent: November 17, 1992Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Kohei Goto, Zen Komiya, Noboru Yamahara, Akira Iio, Masao Hisatomi, Hiroshi Oka
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Patent number: 5164457Abstract: In a method for hydrogenating a nitrile group-containing unsaturated copolymer which comprises selectively hydrogenating only a carbon-carbon double bond of the nitrile group-containing unsaturated copolymer in solution, the improvement wherein a palladium complex represented by formulaPd(Y).sub.n (X).sub.mwherein Y denotes at least one neutral ligand, X denotes an anion, n is an integer of 1 to 4 and m is 0, 2 or 4,is used as a hydrogenation catalyst.Type: GrantFiled: March 1, 1991Date of Patent: November 17, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Yoichiro Kubo, Kazuhiro Takahashi
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Patent number: 5162446Abstract: This is a process for the depolymerization of conjugated diene polymers which comprises contacting the polymers with hydrogen in the presence of at least one bis(cyclopentadienyl)zirconium compound.Type: GrantFiled: October 30, 1991Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Carma J. Gibler, Linda R. Chamberlain, Richard A. Kemp, Stanley E. Wilson
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Patent number: 5159010Abstract: An adhesive composition for adhering an organic synthetic fiber to a nitrile group-containing highly saturated copolymer rubber, said composition comprising a nitrile group-containing highly saturated copolymer rubber latex having an iodine value of not more than 120 and a resorcinol-formaldehyde resin, characterized in that the nitrile group-containing highly saturated copolymer rubber latex is obtained by treating a nitrile group-containing unsaturated copolymer rubber latex resulting from emulsion polymerization with hydrogen in the presence of a hydrogenation catalyst to selectively hydrogenate a carbon-carbon double bond of the nitrile group-containing unsaturated copolymer constituting said latex.Type: GrantFiled: November 28, 1990Date of Patent: October 27, 1992Assignee: Zeon Co., Ltd.Inventors: Osamu Mori, Hiroshi Hisaki, Motofumi Oyama, Kiyomori Ohura
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Patent number: 5141997Abstract: This invention provides a catalyst and a process for the hydrogenation of conjugated diolefin polymers which first involves the polymerization or copolymerization of such monomers with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer. The living polymer is preferably terminated by the addition of hydrogen. Finally, selective hydrogenation of the unsaturated double bonds in the conjugated diolefin units of the terminated polymer is carried out in the presence of at least one bis(cyclopentadienyl)titanium (+3) compound of the formula:(C.sub.5 R".sub.5).sub.2 --Ti--Rwhere R is selected from the group consisting of alkyl, aralkyl, allyl, aryl, alkoxy, halogen, silyl or amine and R", which may be the same or different, is selected from the group consisting of hydrogen, alkyl, aralkyl or aryl.Type: GrantFiled: August 15, 1990Date of Patent: August 25, 1992Assignee: Shell Oil CompanyInventors: Linda R. Chamberlain, Carma J. Gibler, Richard A. Kemp, Stanley E. Wilson
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Patent number: 5134200Abstract: There is disclosed a polymer consisting essentially of segmeric units, a portion of said units consisting of at least one segmeric unit having the structural formula: ##STR1## wherein X is selected from the group of monovalent radicals, consisting of: ##STR2## wherein R is hydrogen or methyl; R.sup.1 is hydrogen or methyl; R.sup.2 is selected from the group of radicals consisting of hydrogen, hydroxy, --NH.sub.2 ; R.sup.3 and R.sup.4 are independently selected from the group of radicals consisting of alkyls having 3 to 12 carbon atoms, cycloaliphatics having 6 carbon atoms, aryls having 6 to 12 carbon atoms and aralkyls having 7 to 12 carbon atoms; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are independently selected from the group of radicals consisting of hydrogen, hydroxy, alkyls having 1 to 20 carbon atoms and aralkyls having 7 to 12 carbon atoms.Type: GrantFiled: October 9, 1990Date of Patent: July 28, 1992Assignee: The Goodyear Tire & Rubber CompanyInventor: Lawson G. Wideman
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Patent number: 5132372Abstract: This is an improved process for the hydrogenation of conjugated diolefin polymers which comprises polymerizing or copolymerizing at least one conjugated diolefin with an organo alkali metal polymerization initiator in a suitable solvent thereby creating a living polymer, terminating the polymerization by the addition of hydrogen and effecting selective hydrogenation of the unsaturated double bonds in the conjugated diolefin units of the terminated polymer by contacting the polymer, in the absence of hydrocarbon lithium and alkoxy lithium compounds, with hydrogen in the presence of at least one bis(cyclopentadienyl)titanium compound. The improvement is the use of methyl benzoate as a promoter in the hydrogenation step.Type: GrantFiled: September 9, 1991Date of Patent: July 21, 1992Assignee: Shell Oil CompanyInventors: Linda R. Chamberlain, Carma J. Gibler
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Patent number: 5115041Abstract: Substantially optically clear molding compositions comprising polymerized cycloolefin monomers (e.g., norbornene-type polymers) which, subsequent to polymerization have been hydrogenated are provided. The polymers have a weight average molecular weight of from about 37-47.times.10.sup.3.Type: GrantFiled: March 31, 1989Date of Patent: May 19, 1992Assignee: The B. F. Goodrich CompanyInventors: Linwood P. Tenney, Dennis C. Shen
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Patent number: 5115037Abstract: Polyethylene cyclopentanedicarboximides, e.g. having an imide group which is alkyl, cycloalkyl or aryl, prepared by hydrogenation of a presursor polymer having olefinic unsaturation in the polymer backbone and derived from norbornene dicarboximide units. Such polyethylene cyclopentanedicarboximides exhibit a substantially higher thermo-oxidative stability then the unsaturated precursor polymer.Type: GrantFiled: December 19, 1990Date of Patent: May 19, 1992Assignee: Monsanto CompanyInventor: Jawed Asrar
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Patent number: 5093426Abstract: A hydrogenated copolymer rubber which is a hydrogenation product of a random copolymer rubber consisting of:(A) 30-70 mole % of a unit derived from at least one monomer selected from the group consisting of alkyl acrylates and alkoxy-substituted alkyl acrylates,(B) 20-70 mole % of a unit derived from at least one conjugated diene, and(C) 0-10 mole % of a unit derived from at least one other ethylenically unsaturated compound copolymerizable with the components (A) and (B) [(A)+(B)+(C)=100 mole %] wherein at least 90% of the double bonds of the conjugated diene unit is hydrogenated; a crosslinkable rubber composition comprising said hydrogenated copolymer rubber and a crosslinking agent; and a thermoplastic polymer comprising said hydrogenated copolymer rubber and a thermoplastic resin. These rubbers and compositions are superior in low-temperature resistance, heat resistance, ozone resistance, mechanical strengths, compression set, impact resilience and oil resistance.Type: GrantFiled: October 19, 1989Date of Patent: March 3, 1992Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Nobuyuki Sakabe, Toshio Ohhara, Toshio Miyabayashi, Hiroshi Ise
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Patent number: 5075388Abstract: An improved process is provided for the hydrogenation of nitrile rubber wherein the molecular weight increase during the hydrogenation process is minimized and controlled, the improvement being that the hydrogenation is undertaken in the presence in the solution of an NH.sub.2 -containing compound selected from ammonia and a C.sub.1 to C.sub.20 primary amine.Type: GrantFiled: December 13, 1990Date of Patent: December 24, 1991Inventors: Garry L. Rempel, Neil T. McMannus
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Patent number: 5071920Abstract: Tapered block copolymers of monovinylidene aromatic monomers and conjugated diene monomers having an isolated polymerized monovinylidene aromatic content of from 30 to 75 percent, hydrogenated derivatives thereof and a process for their preparation.Type: GrantFiled: March 27, 1991Date of Patent: December 10, 1991Assignee: The Dow Chemical CompanyInventor: Lu Ho Tung
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Patent number: 5057581Abstract: Selective hydrogenation of the carbon-carbon double bonds of conjugated diene copolymers is effected in homogeneous solution in an organic solvent in the presence of certain divalent ruthenium carbonyl complex catalysts containing phosphine ligands having bulky alkyl substituents. The ruthenium catalysts have the general formula:RuXY(CO)ZL.sub.2 (1)orRuX(NO)(CO)L.sub.2 (2)wherein X is a halogen atom, most preferably chlorine, or a carboxylate group, Y is a halogen atom, more preferably chlorine, a hydrogen atom, a phenyl group, a carboxylate group or phenylvinyl group, Z is carbonyl, pyridine, benzontrile, trimethylphosphite or no ligand and L is a phosphine ligand having at least one bulky alkyl substituent, preferably tricyclohexyl or triisopropyl.Type: GrantFiled: May 2, 1990Date of Patent: October 15, 1991Assignee: University of WaterlooInventors: Garry L. Rempel, Neil T. McManus, Narvoz Mohammadi
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Patent number: 5057582Abstract: A hydrogenation catalyst prepared by combining a Group VIIIA metal compound and an alkylalumoxane and a hydrogenation process wherein said catalyst is used to hydrogenate compounds or materials containing ethylenic and/or aromatic unsaturation. The Group VIIIA metal compound is selected from the group of compounds consisting of carboxylates, chelates, alkoxides, salts of acids containing sulfur, salts of partial half esters of acids containing sulfur and salts of aliphatic and aromatic sulfonic acids. Nickel and cobalt compounds are preferred for use in preparing the hydrogenation catalyst. Hydrogenation catalysts prepared with methylalumoxane initially exhibit less hydrogenation activity than catalysts known heretofore in the prior art and prepared with a metal alkyl of a metal selected from Groups I, II and III. These catalysts, then, permit or enable greater control over the extent of hydrogenation, particularly when partial hydrogenation is a desired end result.Type: GrantFiled: December 23, 1988Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Ronald J. Hoxmeier, Lynn H. Slaugh
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Patent number: 5053471Abstract: A transparent resin material consisting of a (co)polymer obtained by subjecting at least one compound represented by the general formula (I) or a combination of said compound and other copolymerizable monomer to metathesis polymerization, or a hydrogenation product of the (co)polymer: ##STR1## wherein A and B are independently hydrogen atoms or C.sub.1-10 hydrocarbon groups; X and Y are independently hydrogen atoms, C.sub.1-10 hydrocarbon groups, halogen atoms, halogen-substituted C.sub.1-10 hydrocarbon groups, --(CH.sub.2).sub.n COOR.sup.1, --(CH.sub.2).sub.n OCOR.sup.1, --(CH.sub.2).sub.n OR.sup.1, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.2 R.sup.3, --(CH.sub.2).sub.n COOZ, --(CH.sub.2).sub.n OCOZ, --(CH.sub.2).sub.n OZ or --(CH.sub.2).sub.n W [R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently C.sub.1-20 hydrocarbon groups, Z is a halogen-substituted hydrocarbon group, W is SiR.sub.p.sup.5 D.sub.3-p (R.sup.5 is a C.sub.1-10 hydrocarbon group, D is a halogen atom, --OCOR.sup.5 or --OR.sup.Type: GrantFiled: November 13, 1990Date of Patent: October 1, 1991Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Kohei Goto, Zen Komiya, Noboru Yamahara, Akira Iio