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: 5856412Abstract: A crosslinking system which includes a 1,2,4-trioxacycloheptane and a crosslink-promoting polyfunctional ethylenically unsaturated compound. This system is employed in a process of crosslinking a thermoplastic polymer. Preferred polymers, useful in this process, include ethylene homopolymers and copolymers.Type: GrantFiled: May 2, 1997Date of Patent: January 5, 1999Assignee: Witco CorporationInventors: Lawrence A. Bock, Roger N. Lewis
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Patent number: 5852130Abstract: A novel catalytic composition comprises at least one quaternary ammonium and/or phosphonium salt in which the anion is selected from the group formed by tetrafluoroborate, tetrachloroborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, trifluorosulphonate, fluorosulphonate, tetrachloroaluminate, dichlorocuprate, and trichlorozincate, and at least one complex of a transition metal from groups 8, 9 and 10, i.e., iron, ruthenium, cobalt, rhodium iridium, nickel, palladium and platinum. Application to total or selective hydrogenation of unsaturated compounds such as monoolefins, diolefins, acetylenic compounds, aromatic compounds, polynuclear aromatic compounds. Hydrogenation may be accompanied by isomerisation.Type: GrantFiled: June 17, 1996Date of Patent: December 22, 1998Assignee: Institut Francais du PetroleInventors: Lothar Mussmann, Yves Chauvin, Helene Olivier
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Patent number: 5849847Abstract: Polyalkenylaromatic-polyethylene copolymers are prepared using protected functional organolithium initiators. Polymerization of an alkenylsubstituted aromatic monomer followed by ethylene, results in a protected functional block polystyrene-co-polyethylenyllithium. Termination with a functionalizing agent followed by deprotection produces polymeric products with high functionalization at the initiating chain-end and at least partial functionalization at the terminal chain-end.Type: GrantFiled: July 29, 1996Date of Patent: December 15, 1998Assignee: FMC CorporationInventor: Roderic P. Quirk
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Patent number: 5827929Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Z--O--C(R.sup.1 R.sup.2 R.sup.3)wherein M is an alkali metal; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkoxy, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkoxy, lower alkylthio, and lower dialkylamino groups, and their employment as initiators in the anionic polymerization of olefin containing monomers in an inert, hydrocarbon solvent comprising reacting an omega-protected-1-haloalkyl with lithium metal dispersion having a particle size between 10 and 300 millimicrons in size, at a temperature between 35.degree. and 130.degree. C. in an alkane solvent containing 5 to 10 carbon atoms.Type: GrantFiled: April 12, 1996Date of Patent: October 27, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Eric J. Granger, John F. Engel, Conrad W. Kamienski
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Patent number: 5821307Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is an aromatic substituted saturated hydrocarbyl group produced by the incorporation of one or more alkenyl substituted aromatic hydrocarbons containing 8-25 carbon atoms into the M--Z linkage; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: May 23, 1996Date of Patent: October 13, 1998Assignee: FMC CorporationInventors: James Anthony Schwindeman, Conrad William Kamienski, Eric John Granger, Robert Charles Morrison
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Patent number: 5804644Abstract: A rubber composition comprising(A) 100 parts by weight of a raw material rubber which contains not less than 30% by weight of at least one partially hydrogenated rubber of a conjugated diene rubber, wherein 5 to 70% of the unsaturated double bonds of the conjugated diene portion thereof have been hydrogenated;(B) 10 to 150 parts by weight of a silica;(C) 0.1 to 20 parts by weight of an organo-silane coupling agent; and(D) 0.1 to 10 parts by weight of a vulcanizing agent. The rubber composition of the present invention has extremely excellent resilience, low exothermic property, and excellent wet skid resistance, and further improved processability, and therefore, by utilizing the characteristics, can be used to make industrial parts such as tires for various types of automobiles, rubber vibration insulators, belts, and the like.Type: GrantFiled: January 15, 1997Date of Patent: September 8, 1998Assignee: Asahi Kasei Kabushiki KaishaInventors: Yasunobu Nakafutami, Akira Saito, Tsuyoshi Sugiyama
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Patent number: 5792815Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Z--O--C(R.sup.1 R.sup.2 R.sup.3)wherein M is an alkali metal; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and their employment as initiators in the anionic polymerization of olefin containing monomers in an inert, hydrocarbon solvent comprising reacting an omega-protected-1-haloalkyl with lithium metal dispersion having a particle size between 10 and 300 millimicrons in size, at a temperature between 35.degree. and 130.degree. C. in an alkane solvent containing 5 to 10 carbon atoms.Type: GrantFiled: June 19, 1997Date of Patent: August 11, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Eric J. Granger, John F. Engel, Conrad W. Kamienski
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Patent number: 5780551Abstract: This invention concerns novel, unsymmetrically protected, telechelically functionalized linear and star or multi-arm polymers, their optionally hydrogenated analogues, the polymers produced by selective removal of the protecting groups, the segmented block polymers produced by further reaction of these selectively deprotected polymers with selected comonomers, and the processes to prepare these polymers.Type: GrantFiled: June 3, 1996Date of Patent: July 14, 1998Assignee: FMC CorporationInventors: John F. Engel, James A. Schwindeman, Roderic P. Quirk, Conrad W. Kamienski
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Patent number: 5777041Abstract: A saturated polymer having a terminal aldehyde or hydroxy substituent which may be used directly or in a derivative form as a dispersant for both fuel and lubricating oil compositions, wherein the saturated polymer has a M.sub.n of about 300 to 10,000, and is derived from a polyolefin which is derived from a monomer of the formula H.sub.2 C=CHR.sup.4, wherein R.sup.4 is hydrogen or a straight or branched chain alkyl radical, and wherein the polyolefin has at least about 30% terminal vinylidene unsaturation. Particularly desirable amine derivatives can be formed by either a single step aminomethylation process or a two step hydroformylation and reductive amination process.Type: GrantFiled: January 22, 1997Date of Patent: July 7, 1998Assignee: Exxon Chemical Patents IncInventors: Jacob Emert, Istvan T. Horvath, Richard H. Schlosberg, Warren A. Thaler, David A. Young, Stephen Zushma
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Patent number: 5763531Abstract: Preparation of storage stable, polybutadiene containing, unsaturated polyester resins by heating a mixture containing an unsaturated hydroxyl terminated polybutadiene resin, a saturated anhydride or dibasic acid, an unsaturated anhydride or dibasic acid, a polymerization inhibitor and, optionally, a saturated glycol, while removing water as it is formed, the molar ratio of the saturated anhydride or acid to the unsaturated anhydride or acid being at least equal to 2.Type: GrantFiled: April 22, 1997Date of Patent: June 9, 1998Assignee: Elf Atochem North America, Inc.Inventor: Robert H. Boutier
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Patent number: 5753778Abstract: There is provided a method for selectively hydrogenating living polymers having olefinic double bonds, in which the living polymers resulting from the polymerization initiated by alkyllithium compound are deactivated by contacting the polymerization terminators for a short time under a mild condition and hydrogenated in the presence of bis(cyclopentadienyl)titanium compound in high efficiency and high reproducibility without adjusting accurate molar ratio of the lithium compound to the titanium compound.Type: GrantFiled: October 29, 1996Date of Patent: May 19, 1998Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young-Hoon Ko, Hoo-Chae Kim, Seung-Duk Cho
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Patent number: 5750032Abstract: Process for removing an alkali metal compound from an acid solution also containing nickel and aluminum compounds, which requires contacting the acid solution first with an ion exchange resin functional to remove the nickel and aluminum compounds from the acid solution; and then contacting the acid solution with an ion exchange resin which is more selective to remove the alkali metal compound from the acid solution.Type: GrantFiled: May 23, 1996Date of Patent: May 12, 1998Assignee: Shell Oil CompanyInventors: Zaida Diaz, John David Wilkey
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Patent number: 5747620Abstract: Ethylene copolymers are disclosed herein which are each derived from ethylene and an olefin of C.sub.3 to C.sub.20 and in which any quaternary carbon atom is not present in a polymeric main chain; the activation energy (Ea) of melt flow is in the range of 8 to 20 kcal/mol; and (1) a ratio between a Huggins coefficient (k.sup.1) of the copolymer and a Huggins coefficient (k.sup.2) of a straight-chain ethylene polymer having the same intrinsic viscosity meets the equation 1.12<k.sup.1 /k.sup.2 .ltoreq.5, or (2) a molar ratio ?CH.sub.3 /CH.sub.2 ! of a methyl group to a methylene group in a molecular chain is in the range of 0.005 to 0.1, and the equation Tm.gtoreq.131-1,340 ?CH.sub.3 /CH.sub.2 ! is met, or (3) Mw and a die swell ratio (DR) meet the equation DR>0.5+0.125.times.log Mw.Type: GrantFiled: August 21, 1995Date of Patent: May 5, 1998Assignee: Idemitsu Kosan Co., Ltd.Inventors: Shuji Machida, Haruo Shikuma, Ayami Hoshino, Yutaka Takakura
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Patent number: 5717035Abstract: There is disclosed a linear block copolymer comprising at least one triblock I-B-I, wherein I is a block of a polymerized conjugated diene of at least 5 carbon atoms, such as isoprene, and B is a block of a polymer of a conjugated diene, different from that of formula (1), of at least 4 carbon atoms, such as 1,3-butadiene. The B block is selectively hydrogenated, while each of the I blocks retains a sufficient amount of its original unsaturation to vulcanize the copolymer. There is also disclosed an alternative linear block copolymer containing at least one triblock of the first polymer block made from an aryl-substituted olefin, such as styrene, and the conjugated diene used to polymerize the block I, the second middle polymer block of the diene used to polymerize the block B, and the third polymer block which is the same as the first polymer block.Type: GrantFiled: October 22, 1996Date of Patent: February 10, 1998Assignee: Mobil Oil CorporationInventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews
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Patent number: 5708092Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: April 12, 1996Date of Patent: January 13, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
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Patent number: 5705571Abstract: The present invention provides a process for selective hydrogenation of a conjugated diene polymer. The process includes bringing the conjugated diene polymer in an inert organic solvent into contact with hydrogen in the presence of a specific hydrogenation catalyst combination including (A) a substituted or unsubstituted bis(cyclopentadienyl) Group VIII transition metal compound and (B) an organic lithium compound. The hydrogenation can be carried out in the presence of a small amount of the hydrogenation catalyst combination under mild conditions, and both the hydrogenation conversion and selectivity to conjugated diene units are high.Type: GrantFiled: June 25, 1996Date of Patent: January 6, 1998Assignee: Taiwan Synthetic Rubber CorporationInventors: Raymond Chien-Chao Tsiang, Henry Chi-Chen Hsieh, Wen-Shien Yang
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Patent number: 5705572Abstract: A continuous process for the solution polymerization of appropriate polycycloolefins in a ROMP zone to obtain a processable ROMP homo- or copolymer in solution, and subsequent hydrogenation of the ROMP (co)polymer without removing the residual ROMP catalyst and co-catalyst, provides an optical product having a mol wt M.sub.w in the range from 50,000-300,000 and polydispersity M.sub.w /M.sub.n in the range from 1.3-5.0, more preferably from 1.3-3, the lower the polydispersity the more desirable the physical properties of the (co)polymer.Type: GrantFiled: August 8, 1995Date of Patent: January 6, 1998Assignee: The B.F. Goodrich CompanyInventors: Kong Sung Yi, Linwood Powers Tenney, Parley Clive Lane, Jr., John Victor Wessel, Nancy Susan Marchant
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Patent number: 5693721Abstract: The invention comprises a hydrogenated hydrocarbon resin suitable as tackifier for acrylic adhesive polymers, having greater than 20% aromatic protons after hydrogenation, a z-average molecular weight of less than about 1800, a narrow molecular weight distribution, typically of less than or equal to 2.1, and a softening point of from 40.degree. C. to about 120.degree. C. It additionally comprises a method for preparing a hydrogenated aromatic tackifier resin suitable as tackifier for acrylic adhesive polymers comprising the steps of: a) polymerizing under Friedel-Crafts polymerization conditions steam-cracked petroleum distillates, or fractions thereof; having boiling points between about 135.degree. C. and 220.degree. C. and containing at least 40% of by weight vinyl aromatic monomer contents, in the presence of a chain transfer agent; and b) catalytically hydrogenating the results of a) such that at least 75% of the aromaticity is retained.Type: GrantFiled: February 14, 1997Date of Patent: December 2, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Steven George Hentges, Frank Carl Jagisch, Edward Francis Smith
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Patent number: 5691422Abstract: A saturated polymer having a terminal aldehyde or hydroxy substituent which may be used directly or in a derivative form as a dispersant for both fuel and lubricating oil compositions, wherein the saturated polymer has a M.sub.n of about 300 to 10,000, and is derived from a polyolefin which is derived from a monomer of the formula H.sub.2 C.dbd.CHR.sup.4, wherein R.sup.4 is hydrogen or a straight or branched chain alkyl radical, and wherein the polyolefin has at least about 30% terminal vinylidene unsaturation. Particularly desirable amine derivatives can be formed by either a single step aminomethylation process or a two step hydroformylation and reductive amination process.Type: GrantFiled: June 12, 1996Date of Patent: November 25, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Jacob Emert, Istvan T. Horvath, Richard H. Schlosberg, Warren A. Thaler, David A. Young, Stephen Zushma
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Patent number: 5681900Abstract: A resin obtained by subjecting a norbornene type monomer having an aromatic ring structure (e.g. 5-phenyl-2-norbornene) to ring-opening polymerization and hydrogenating 95% or more of the unsaturated bonds in the backbone structure of the resulting polymer by the use of a catalyst composed of a combination of a transition metal compound and an alkyl metal compound, while leaving 80% or more of the aromatic ring structures, which resin has not only a high refractive index but also characteristics of a hydrogenated norbornene ring-opening polymerization product, i.e., excellent heat resistance, transparency, low birefringent properties, weather resistance, light resistance, low water absorption properties, moisture resistance, small dielectric constant, small dielectric loss, chemical resistance, etc., said resin being usable in optical materials, medical tools and materials, tools and materials for treating electronic parts, etc.Type: GrantFiled: January 22, 1996Date of Patent: October 28, 1997Assignee: Nippon Zeon Co., Ltd.Inventors: Toshihide Murakami, Teiji Kohara, Tadao Natsuume
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Patent number: 5663250Abstract: Protected functional initiator initiated elastomer solutions are deprotected and optionally ionic impurities removed by contact with a molten component such as sodium bisulphate monohydrate. This allows deprotection and removal of metal contaminants such as the initiator or residue from hydrogenation catalysts without the introduction of significant amounts of additional water which cause emulsion formation. In accordance with this invention, better metal removal is achieved and the process of metal removal operates more smoothly because of the absence of emulsion formation. Separation of the molten component containing the extracted metal contaminants can easily be carried out by simple liquid-liquid phase separation on either a continuous or batch basis.Type: GrantFiled: May 16, 1996Date of Patent: September 2, 1997Assignee: Shell Oil CompanyInventors: Michael Wayne Potter, William Charles Malven, Cary Alan Veith
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Patent number: 5656698Abstract: The invention comprises a hydrogenated hydrocarbon resin suitable as tackifier for acrylic adhesive polymers, having greater than 20% aromatic protons after hydrogenation, a z-average molecular weight of less than about 1800, a narrow molecular weight distribution, typically of less than or equal to 2.1, and a softening point of from 40.degree. C. to about 120.degree. C. It additionally comprises a method for preparing a hydrogenated aromatic tackifier resin suitable as tackifier for acrylic adhesive polymers comprising the steps of: a) polymerizing under Friedel-Crafts polymerization conditions stem-cracked petroleum distillates, or fractions thereof, having boiling points between about 135.degree. C. and 220.degree. C. and containing at least 40% of by weight vinyl aromatic monomer contents, in the presence of a chain transfer agent; and b) catalytically hydrogenating the results of a) such that at least 75% of the aromaticity is retained.Type: GrantFiled: November 3, 1994Date of Patent: August 12, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Steven George Hentges, Frank Carl Jagisch, Edward Francis Smith
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Patent number: 5654371Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3) (II)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is defined as a branched or straight chain hydrocarbon tether or connecting group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and n is an integer from 1 to 5.Type: GrantFiled: June 2, 1995Date of Patent: August 5, 1997Assignee: FMC CorporationInventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
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Patent number: 5651995Abstract: A nitrile group-containing highly saturated copolymer rubber which is a product obtained by hydrogenating the conjugated diene portion of an unsaturated nitrile-conjugated diene copolymer. The highly saturated copolymer rubber has an alkylthio group having 12 to 16 carbon atoms, which include at least three tertiary carbon atoms, and having a sulfur atom which is directly bound to at least one of the tertiary carbon atom, and the highly saturated copolymer rubber further has a Mooney viscosity of 15 to 200 and an iodine value not larger than 80. The highly saturated copolymer rubber is produced copolymerizing an unsaturated nitrile, a conjugated diene and an optional copolymerizable monomer by using as a molecular weight modifier an alkylthiol compound having 12 to 16 carbon atoms, which include at least three tertiary carbon atoms, and having a sulfur atom which is directly bound to at least one of the tertiary carbon atoms; and then, hydrogenating the thus-obtained copolymer.Type: GrantFiled: June 7, 1995Date of Patent: July 29, 1997Assignee: Nippon Zeon Co., Ltd.Inventors: Motofumi Oyama, Yoshiaki Aimura, Kazuyoshi Nakajima, Osamu Mori, Mitsugu Ishihara
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Patent number: 5614595Abstract: Polymers Ia and Ib carrying functional groups and obtainable byA) 1. hydrogenation of the olefinic double bonds of a polymer IIa comprisinga) from 20 to 100% by weight of a conjugated diene,b) from 0 to 80% by weight of an aromatic vinyl compound, andc) from 0 to 20% by weight of further comonomers,to give the hydrogenated polymer IIb,2. metallation of IIb using an organoalkali metal compound to give IIc,3. reaction of IIc with a diaziridine III to give IId, and4. hydrolysis or alcoholysis of IId to give Ia, or byB) 1. partial hydrogenation of IIa to give a partially hydrogenated polymer IIb',2. epoxidation of the double bonds of IIb' to give IIe, and3. reaction of IIe with a compound IV carrying functional groups, to give Ib,are suitable as viscosity index improvers for engine oils.Type: GrantFiled: October 16, 1995Date of Patent: March 25, 1997Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert, Helmut Mach, Martin Fischer
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Patent number: 5612435Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved by selecting A' from the structures --CH.sub.2 --CH.sub.2 --CH.sub.2 -- (1,3-propyl), --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 -- (2-methyl-1,3-propyl), --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --(2,2-dimethyl-1,3-propyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,8-octyl). This narrow class of polymerization initiators operate at surprisingly higher polymerization temperatures with surprisingly lower amounts of dead initiator than similar initiators wherein A' is --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,4-butyl), --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,5-pentyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,6-hexyl).Type: GrantFiled: October 5, 1995Date of Patent: March 18, 1997Assignee: Shell Oil CompanyInventors: Robert C. Bening, Carl L. Willis
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Patent number: 5612422Abstract: The present invention is a process of hydrogenating high molecular weight aromatic polymers comprising hydrogenating the high molecular weight aromatic polymer in the presence of a silica supported metal hydrogenation catalyst, characterized in that the silica has a pore size distribution such that at least 98 percent of the pore volume is defined by pores having diameter of greater than 600 angstroms.Type: GrantFiled: May 4, 1995Date of Patent: March 18, 1997Assignee: The Dow Chemical CompanyInventors: Dennis A. Hucul, Stephen F. Hahn
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Patent number: 5599882Abstract: The present invention discloses a polycyclic norbornene-based ring-opening polymer which comprises(A) 90-5% by mol of a repeating unit represented by the following formula [I] or the alkyl-substituted derivative thereof, and(B) 10-95% by mol of at least one repeating unit selected from a repeating unit represented by the following formula [II], the alkyl-substituted derivative thereof, a repeating unit represented by the following formula [III], the alkyl-substituted derivative thereof, or the alkylidene-substituted derivative thereof, and which has an intrinsic viscosity [.eta.] of 0.01-20 dl/g as determined in toluene at 25.degree. C., the hydrogenation products thereof, and a process for production thereof ##STR1## wherein ------ denotes a single bond or a double bond.Type: GrantFiled: February 13, 1990Date of Patent: February 4, 1997Assignee: Nippon Zeon Co., Ltd.Inventors: Yoshikatsu Nishi, Masayoshi Ohshima, Teiji Kohara, Toshiyasu Matsui, Tadao Natsuume
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Patent number: 5583185Abstract: A process of hydrogenation in solution of polymers of conjugated dienes in the presence of homogeneous catalysts which contain, as an essential component, a titanium compound of the type Cp.sub.2 Ti(PhOR).sub.2, where Cp is a cylopentadienyl group, ph a phenyl group, and OR an alkoxide group containing 1 to 4 carbon atoms; or a titanium compound of the type Cp.sub.2 TiR.sub.2, where R is a Ch.sub.2 PPh.sub.2 group.These catalysts are very active in the selective hydrogenation of the double bonds of the diene units of polymers or copolymers of conjugated dienes having number-averaged molecular weights or between approximately 500 and 1,000,000 and, in particular, of random and block copolymers of styrene and butadiene or isoprene, the latter containing at least one styrene block and one polybutadiene and/or polyisoprene block.Type: GrantFiled: February 23, 1995Date of Patent: December 10, 1996Assignee: Repsol Quimica S.A.Inventors: Maria D. Parellada Ferrer, Juan A. Barrio Calle
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Patent number: 5580934Abstract: There are disclosed a polycyclic norbornene or its derivative hydrogenated copolymer which containsa repeating unit represented by the following formula [I] or the alkyl-substituted derivative thereof (A),a repeating unit represented by the following formula [II] or the alkyl-substituted derivative thereof (B) and, as desired,5-85% by mole of at least one repeating unit (C) selected from a repeating unit represented by the following formula [III], the alkyl-substituted derivative thereof, a repeating unit represented by the following formula [IV], the alkyl-substituted derivative and the alkylidene-substituted derivative thereof, and a process for producing the polycyclic norbornene or its derivative ring-opening hydrogenated copolymer ##STR1## wherein ------ represents either a single bond or a double bond.Type: GrantFiled: June 7, 1990Date of Patent: December 3, 1996Assignee: Nippon Zeon Co., Ltd.Inventors: Yoshikatsu Nishi, Masayoshi Oshima, Teiji Kohara, Tadao Natsuume
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Patent number: 5580935Abstract: This invention relates to functionalized polymers and a method to obtain them comprising combing a living polymer or a polymer having a terminal halide with an alkylsilylpseudohalide.Type: GrantFiled: January 13, 1995Date of Patent: December 3, 1996Assignee: Exxon Chemical Patents Inc.Inventor: Timothy D. Shaffer
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Patent number: 5561197Abstract: A process is provided for the hydrogenation of carbon-carbon double bonds in polymers by treatment of the polymer in solution with hydrogen in the presence of osmium-based catalysts.Type: GrantFiled: June 27, 1995Date of Patent: October 1, 1996Assignee: University of WaterlooInventors: Garry L. Rempel, Neil T. McManus, John S. Parent
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Patent number: 5552493Abstract: The present invention is a process for producing predominately four-armed asymmetric radial block copolymers which contain predominately, on average, two arms which are copolymers of at least one conjugated diene and at least one vinyl aromatic hydrocarbon and two conjugated diene homopolymer or copolymer arms, said process comprising:(a) anionically polymerizing at least one conjugated diene monomer and at least one vinylaromatic hydrocarbon monomer to form a set of living polymer arms,(b) anionically polymerizing at least one conjugated diene monomer to form another set of living polymer arms,(c) coupling the one set of living polymer arms with a coupling agent which is selected from the group consisting of tetramethoxysilane and .gamma.Type: GrantFiled: May 30, 1995Date of Patent: September 3, 1996Assignee: Shell Oil CompanyInventors: Bridget A. Spence, Ronald J. Hoxmeier, Glenn R. Himes
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Patent number: 5550203Abstract: A process for the preparation of hydrocarbon solutions of monofunctional amine initiators of the following general structures:M--Q.sub.n --Z--N(A(R.sup.1 R.sup.2 R.sup.3)).sub.2or ##STR1## wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenyl substituted aromatic hydrocarbons; Z is a hydrocarbon tether group which contains 3-25 carbon atoms; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, substituted alkyl, cycloalkyl, aryl or substituted aryl groups, m is an integer from 0 to 7, and n is an integer from 1 to 5, monofunctional amine initiators produced by the process, use of the initiators in a polymerization process and polymers produced by the polymerization process.Type: GrantFiled: June 2, 1995Date of Patent: August 27, 1996Assignee: FMC CorporationInventors: John F. Engel, Conrad W. Kamienski, James A. Schwindeman, Randy W. Hall, Robert C. Morrison, B. Troy Dover
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Patent number: 5539060Abstract: The present invention provides a method for hydrogenating a metathesis polymer solution obtained by polymerization in the presence of a metathesis polymerization catalyst comprising (a) the catalyst component of a transition metal compound and (b) the co-catalyst component of a metal compound by bringing the above solution into contact with hydrogen, without adding an inactivating agent for the metathesis polymerization catalyst, that is, with the solution left to contain the catalyst, in the presence of a hydrogenation catalyst comprising a transition metal compound (c) and a reductive metal compound (d) and if necessary by adding an acid-binding compound.Type: GrantFiled: October 13, 1995Date of Patent: July 23, 1996Assignee: Nippon Zeon Co., Ltd.Inventors: Yasuo Tsunogae, Hideharu Mizuno, Teiji Kohara, Tadao Natsuume
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Patent number: 5523364Abstract: A process for the preparation of hydrocarbon solutions of monofunctional amine initiators of the following general structures: ##STR1## wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenyl substituted aromatic hydrocarbons; Z is a hydrocarbon tether group which contains 3-25 carbon atoms; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl groups, m is an integer from 0 to 7, and n is an integer from 1 to 5, monofunctional amine initiators produced by the process, use of the initiators in a polymerization process and polymers produced by the polymerization process.Type: GrantFiled: June 2, 1995Date of Patent: June 4, 1996Assignee: FMC CorporationInventors: John F. Engel, Conrad W. Kamienski, James A. Schwindeman, Randy W. Hall, Robert C. Morrison, B. Troy Dover
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Patent number: 5521255Abstract: A method for preparing a telechelic polydiene having at least 70% 1,4-microstructure and at least 70% of its end groups capped by reactive silyl functionality is disclosed, said method comprising:(I) reacting, in a non-polar solvent solution,(A) at least one diene monomer,(B) a dianionic initiator which is soluble in said non-polar solvent and, optionally,(C) a polymerization adjuvant to form a dianionically active polydiene; and(II) capping both ends of said dianionically active polydiene from step (I) with(D) a silane, said capping being carried out in the presence of(E) a promoter selected from the group consisting of a tertiary amine and a crown ether based on 12-crown-4.Type: GrantFiled: May 30, 1995Date of Patent: May 28, 1996Assignee: Dow Corning CorporationInventor: Aroop K. Roy
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Patent number: 5494976Abstract: Polymers Ia and Ib carrying functional groups and obtainable byA)1. hydrogenation of the olefinic double bonds of a polymer IIa comprisinga) from 20 to 100% by weight of a conjugated diene,b) from 0 to 80% by weight of an aromatic vinyl compound, andc) from 0 to 20% by weight of further comonomers,to give the hydrogenated polymer IIb,2. metallation of IIb using an organoalkali metal compound to give IIc,3. reaction of IIc with a diaziridine III to give IId, and4. hydrolysis or alcoholysis of IId to give Ia, or byB)1. partial hydrogenation of IIa to give a partially hydrogenated polymer IIb',2. epoxidation of the double bonds of IIb' to give IIe, and3. reaction of IIe with a compound IV carrying functional groups, to give Ib,are suitable as viscosity index improvers for engine oils.Type: GrantFiled: August 23, 1993Date of Patent: February 27, 1996Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert, Helmut Mach, Martin Fischer
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Patent number: 5491197Abstract: A description follows of epoxydated block copolymers, either linear or branched, which can be defined with the following formulae:1) [A--(E--B--EPOX)].sub.n X2) A.sub.1 --(E.sub.1 --B.sub.1 --EPOX.sub.1)--A--HT--(E.sub.2 --B.sub.2 --EPOX.sub.2)3) [(E.sub.1 --B.sub.1 --EPOX.sub.1)--HT--A(E.sub.2 --B.sub.2 --EPOX.sub.2)].sub.x Xwhere A is a polyvinylaromatic block in a percentage ranging from 10 to 50% by weight, E--B--EPOX is a block composed of ethylene units, epoxydated butene and diene units in which the percentage by weight of the epoxy group ranges from 1% to 40%, HT is a tapered copolymer segment made up of hydrogenated and epoxydated diene monomeric units and vinylaromatic units whose content ranges from 0 to 20%, x is a radical having a valence ranging from 1 to 20.The block copolymers have an average molecular weight ranging from 30,000 to 400,000, a content of polyvinylaromatic blocks of between 10 and 50% by weight and a content of (E.sub.1 --B.sub.1 --EPOX.sub.1)+(E.sub.2 --B.sub.2 --EPOX.sub.Type: GrantFiled: March 31, 1995Date of Patent: February 13, 1996Assignee: Enichem Elastomeri S.r.l.Inventors: Sergio Custro, Gian I. Viola
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Patent number: 5462995Abstract: The present invention provides the hydrogenated product of a thermoplastic norbornene polymer excellent in characteristics as optical materials by reducing the residual amounts of the transition metal atoms originating from the polymerization catalyst used at the polymerization to 1 ppm or less of the hydrogenated product.Reduction of the residual amounts to below the desired level is attained by treating the reaction solution with the adsorbent during or after production of the hydrogenated product from the thermoplastic norbornene polymer.The hydrogenated product of the thermoplastic norbornene polymer thus obtained in which the residual amounts of the transition metal atoms are 1 ppm or less, has a wide utilization field, including a material for optical articles having excellent utilization characteristics such as substrates for optical elements, lenses and the like.Type: GrantFiled: November 16, 1993Date of Patent: October 31, 1995Assignee: Nippon Zeon Co., Ltd.Inventors: Tohru Hosaka, Hideharu Mizuno, Yuji Koushima, Teiji Kohara, Tadao Natsuume
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Patent number: 5449718Abstract: A viscous block copolymer of the formula(A--B--A.sub.p).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 monomers or copolymer blocks of conjugated diolefin monomers and monoalkenyl aromatic hydrocarbon monomers, andwherein the A blocks have a higher number of more highly substituted aliphatic double bonds 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: September 30, 1993Date of Patent: September 12, 1995Assignee: Shell Oil CompanyInventors: James R. Erickson, David J. St. Clair
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Patent number: 5439992Abstract: A continuous process for the solution polymerization of appropriate polycycloolefins in a ROMP zone to obtain a processable ROMP homo- or copolymer in solution, and subsequent hydrogenation of the ROMP (co)polymer without removing the residual ROMP catalyst and co-catalyst, provides an optical product having a mol wt M.sub.w in the range from 50,000-300,000 and polydispersity M.sub.w /M.sub.n in the range from 1.3-5.0, more preferably from 1.3-3, the lower the polydispersity the more desirable the physical properties of the (co)polymer.Type: GrantFiled: June 6, 1994Date of Patent: August 8, 1995Assignee: The B. F. Goodrich CompanyInventors: Kong S. Yi, Linwood P. Tenney, Parley C. Lane, Jr., John V. Wessel, Nancy S. Marchant
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Patent number: 5416168Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved when each R is methyl and A' is --CH.sub.2 --C.sub.6 H.sub.10 --CH.sub.2 -- or --CH.sub.2 --CR'R"--CH.sub.2 -- wherein R' is a linear alkyl having from 1 to 10 carbon atoms and R" is hydrogen or a linear alkyl having from 1 to 10 carbon atoms. This initiator provides process and product advantages over all other known initiators of the same type.Type: GrantFiled: March 31, 1994Date of Patent: May 16, 1995Assignee: Shell Oil CompanyInventors: Carl L. Willis, Robert C. Bening
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Patent number: 5412040Abstract: A description follows of epoxydated block copolymers, either linear or branched, which can be defined with the following formulae:1) [A-(E-B-EPOX)].sub.n X2) A.sub.1 -(E.sub.1 -B.sub.1 -EPOX.sub.1)-A-HT-(E.sub.2 -B.sub.2 -EPOX.sub.2)3) [(E.sub.1 -B.sub.1 -EPOX.sub.1)-HT-A(E.sub.2 -B.sub.2 -EPOX.sub.2)].sub.n Xwhere A is a polyvinylaromatic block in a percentage ranging from 10 to 50% by weight, E-B-EPOX is a block composed of ethylene units, epoxydated butene and diene units in which the percentage by weight of the epoxy group ranges from 1% to 40%, HT is a tapered copolymer segment made up of hydrogenated and epoxydated diene monomeric units and vinylaromatic units whose content ranges from 0 to 20%, x is a radical having a valence ranging from 1 to 20.The block copolymers have an average molecular weight ranging from 30,000 to 400,000, a content of polyvinylaromatic blocks of between 10 and 50% by weight and a content of (E.sub.1 -B.sub.1 -EPOX.sub.1)+(E.sub.2 -B.sub.2 -EPOX.sub.Type: GrantFiled: February 5, 1992Date of Patent: May 2, 1995Assignee: Enichem Elastomeri S.R.L.Inventors: Sergio Custro, Gian T. Viola
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Patent number: 5405914Abstract: A process for improving the color of selectively hydrogenated block copolymers modified with acid compound or derivatives thereof which comprises:(a) anionically polymerizing at least one conjugated diene, and, optionally, at least one vinyl aromatic hydrocarbon, to produce a block copolymer,(b) selectively hydrogenating the block copolymer,(c) subjecting the block copolymer to an acid wash,(d) subjecting the acid washed block copolymer to high efficiency water washing at a residence time of not less than 50 minutes and a water to polymer cement weight ratio of more than 0.2, and(e) grafting an acid compound or a derivative thereof onto the block copolymer.Type: GrantFiled: July 29, 1993Date of Patent: April 11, 1995Assignee: Shell Oil CompanyInventor: Miguel Prado
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Patent number: 5399632Abstract: It has now been discovered that the hydrogenation of unsaturated homo and copolymers can be effectively carried out in the absence of added gaseous hydrogen by contacting the unsaturated polymer with a hydrogen donor compound in the presence of a Group VIII metal catalyst, especially a supported palladium catalyst, for a time and at a temperature sufficient to bring about the hydrogenation of the unsaturated polymer.Type: GrantFiled: September 30, 1992Date of Patent: March 21, 1995Assignee: Exxon Research & Engineering Co.Inventors: Christine A. Costello, Pamela J. Wright, Donald N. Schulz, Joseph A. Sissano
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Patent number: 5391663Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved by selecting A' from the structures --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,3-propyl), --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 --(2-methyl-1,3-propyl), --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --(2,2-dimethyl-1,3-propyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,8-octyl). This narrow class of polymerization initiators operate at surprisingly higher polymerization temperatures with surprisingly lower amounts of dead initiator than similar initiators wherein A' is --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,4-butyl), --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,5-pentyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 13 CH.sub.2 --(1,6-hexyl).Type: GrantFiled: November 22, 1993Date of Patent: February 21, 1995Assignee: Shell Oil CompanyInventors: Robert C. Bening, Carl L. Willis
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Patent number: 5391627Abstract: A rubber composition comprising 100 parts by weight of an ethylenically unsaturated nitrile-conjugated diene high-saturation copolymer rubber containing 20 weight % or less of conjugated diene units, and 1-100 parts by weight of an unsaturated carboxylic acid metal salt having the general formula: ##STR1## wherein R and R' represent aliphatic or aromatic hydrocarbon groups or a hydrogen atom, which may be the same or different from each other, Me represents a metal selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ti, Cr, Mo, Mn, Fe, Co, Ni, Cu, Ag, Zn, Cd, Hg, Al, Sn, Pb and Sb, and n is an integer of 2-4.Type: GrantFiled: August 27, 1993Date of Patent: February 21, 1995Assignees: Honda Giken Kogyo Kabushiki Kaisha, Yamashita Rubber Co., Ltd, Nippon Zeon Co., Ltd.Inventors: Junichi Araki, Masayuki Tamura, Takahiro Naka, Nobuhiro Saito, Hiroshi Kitagawa, Takeyoshi Usui, Shigeru Sato
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Patent number: 5378767Abstract: A method for hydrogenating unsaturated low molecular weight polymers, preferably polydiene monool, diol and polyol polymers, which comprises contacting the polymers under hydrogenation conditions with hydrogen in the presence of a fixed bed heterogeneous catalyst which is comprised of platinum, palladium or a mixture of the two supported on an alpha alumina support.Type: GrantFiled: June 18, 1993Date of Patent: January 3, 1995Assignee: Shell Oil CompanyInventor: Stephen N. Massie
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Patent number: 5373063Abstract: A process for producing partially hydrogenated diene pollers 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: February 14, 1994Date of Patent: December 13, 1994Assignee: Bridgestone/Firestone, Inc.Inventors: William L. Hergenrother, John M. Doshak