More Than Two Double Bonds, E.g., Diene Polymerization, Etc. Patents (Class 585/507)
  • Patent number: 10723673
    Abstract: A process is provided for the selective oligomerisation of C5 to C20 alpha-olefins to produce polyalphaolefin oligomers with a molecular weight distribution that is suitable for use in lubricant base oils.
    Type: Grant
    Filed: April 9, 2014
    Date of Patent: July 28, 2020
    Assignee: PETROLIAM NASIONAL BERHAD (PETRONAS)
    Inventors: Martin Philip Atkins, Kenneth Richard Seddon, Malgorzata Swadzba-Kwasny, Fergal Coleman
  • Patent number: 8722952
    Abstract: Disclosed is a process for production of benzene lean gasoline by recovery of high purity benzene from a narrow boiling benzene concentrated unprocessed cracked gasoline fraction. The process involves subjecting the feed material to an extractive distillation (ED) operation using an aromatic selective solvent in combination with a co-solvent.
    Type: Grant
    Filed: August 9, 2013
    Date of Patent: May 13, 2014
    Assignees: Council of Scientific & Industrial Research, Reliance Industries Limited
    Inventors: Madhukar Onkarnath Garg, Shrikant Madhusudan Nanoti, Ram Bhagat Nautiyal, Kumar Sunil, Prasenjit Ghosh, Nisha, Pooja Yadav, Kumar Jagdish, Manish Tiwari, Meka Raja Rao, Nagarathinam Shengaga Murthy
  • Publication number: 20130289326
    Abstract: A catalyst comprising a NCN pincer ligand group VI complex is capable of being used as an olefin polymerization or isomerization catalyst that does not require an expensive cocatalyst. The complex has the NCN pincer ligand in a trianionic form with the group VI in the +3 oxidation state or the +4 oxidation state and complexed to an anionic hydrocarbon group, or the complex has the NCN pincer ligand in a dianionic form with the group VI in the +2 oxidation state. The complex is capable of initiating the polymerization of alkenes without an added activator. The presence of a water scavenger and activator or cocatalyst, such as triisobutylaluminum, increases the catalytic activity. The complex is capable of selectively isomerizing 1-alkenes to cis/trans 2-alkenes.
    Type: Application
    Filed: March 28, 2013
    Publication date: October 31, 2013
    Inventors: KEVIN P. MCGOWAN, ADAM S. VEIGE
  • Patent number: 8524930
    Abstract: This invention relates to a metathesis catalyst comprising a Group 8 metal complex represented by the formula: wherein: M is a Group 8 metal; each X is independently an anionic ligand; R1 and R2 are independently selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R3 and R4 are independently selected from the group consisting of hydrogen, C1 to C12 hydrocarbyl groups, substituted C1 to C12 hydrocarbyl groups, and halides; and L is a neutral donor ligand. This invention also relates to processes for performing a metathesis reaction, in particular ring opening cross metathesis reactions and ring opening metathesis polymerization reactions, using the Group 8 metal complexes.
    Type: Grant
    Filed: May 31, 2011
    Date of Patent: September 3, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Matthew W. Holtcamp, Matthew S. Bedoya
  • Publication number: 20130066103
    Abstract: This invention relates to a co-oligomer having an Mn of 300 to 30,000 g/mol comprising 10 to 90 mol % propylene and 10 to 90 mol % of ethylene, wherein the oligomer has at least X % allyl chain ends, where: 1) X=(?0.94(mole % ethylene incorporated)+100), when 10 to 60 mole % ethylene is present in the co-oligomer, and 2) X=45, when greater than 60 and less than 70 mole % ethylene is present in the co-oligomer, and 3) X=(1.83*(mole % ethylene incorporated)?83), when 70 to 90 mole % ethylene is present in the co-oligomer. This invention also relates to a homo-oligomer, comprising propylene, wherein the oligomer has: at least 93% allyl chain ends, an Mn of about 500 to about 20,000 g/mol, an isobutyl chain end to allylic vinyl group ratio of 0.8:1 to 1.2:1.0, and less than 100 ppm aluminum. This invention also relates to a process of making homo-oligomer, comprising propylene, wherein the productivity is greater than 4500 g/mmol Hf (or Zr)/hour.
    Type: Application
    Filed: November 6, 2012
    Publication date: March 14, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Patrick BRANT, Donna J. CROWTHER, Andrew G. NARVAEZ
  • Publication number: 20120309998
    Abstract: This invention relates to a metathesis catalyst comprising a Group 8 metal complex represented by the formula: wherein: M is a Group 8 metal; each X is independently an anionic ligand; R1 and R2 are independently selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R3 and R4 are independently selected from the group consisting of hydrogen, C1 to C12 hydrocarbyl groups, substituted C1 to C12 hydrocarbyl groups, and halides; and L is a neutral donor ligand. This invention also relates to processes for performing a metathesis reaction, in particular ring opening cross metathesis reactions and ring opening metathesis polymerization reactions, using the Group 8 metal complexes.
    Type: Application
    Filed: May 31, 2011
    Publication date: December 6, 2012
    Inventors: Matthew W. HOLTCAMP, Matthew S. BEDOYA
  • Patent number: 7981990
    Abstract: A method comprising: (a) forming a living liquid polymer, wherein said living liquid polymer is anionically initiated and comprises a cation; (b) adding a functional initiator precursor of the formula FI-H, wherein H is hydrogen and FI is a functional group, said H terminates said living liquid polymer resulting in said liquid polymer having a number average molecular weight of about 20,000 (g/mole) to about 100,000 (g/mole), and said FI and said cation form a functional initiator; (c) adding monomer, wherein said functional initiator initiates anionic polymerization of said monomer; and (d) terminating the polymerization reaction initiated in step (c). Steps (a) through (c) may be conducted in a single reactor, allowing a liquid polymer to be dispersed in a functionalized polymer in a single polymerization step. Thus, the liquid polymer does not have to be handled separately and processing efficiency is improved.
    Type: Grant
    Filed: August 28, 2008
    Date of Patent: July 19, 2011
    Assignee: Bridgestone Corporation
    Inventor: Yuan-Yong Yan
  • Patent number: 7960474
    Abstract: A single-component high-temperature-curing reactive composition based on natural and/or synthetic elastomers having olefinic double bonds and on vulcanizing agents is provided. Such compositions contain at least one liquid polyene with a molecular weight between 400 and 80,000, preferably between 800 and 25,000; at least one block copolymer with at least one polyene block and at least one saturated block; and a vulcanizing system of sulfur and accelerators and/or quinone oximes, if applicable. Such high-temperature-curing reactive compositions are useful as single-component adhesives, sealant or coating compositions or sealing compounds in automobile body manufacture.
    Type: Grant
    Filed: August 19, 2008
    Date of Patent: June 14, 2011
    Assignee: Henkel AG & Co. KGaA
    Inventors: Klaus Rappmann, Rainer Kohlstrung
  • Patent number: 7928266
    Abstract: The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and ?-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and ?-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.
    Type: Grant
    Filed: May 23, 2007
    Date of Patent: April 19, 2011
    Assignee: Myongji University Industry and Academia Cooperation
    Inventors: Sang Ho Koo, Eun Ho Choi
  • Patent number: 7696370
    Abstract: The invention provides processes for converting a vegetable oil to a polymer. In particular, the processing steps comprise bodying, epoxidation, hydrolysis, and oligomerization. These processes provide new processing paths for the formation of polyols for use in rigid foam and other applications.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 13, 2010
    Assignee: The Curators of the University of Missouri
    Inventors: Galen Suppes, Fu-hung Hsieh, Yuan-Chan Tu, Pimphan Kiatsimkul
  • Patent number: 7645914
    Abstract: Process for telomerizing noncyclic olefins having at least two conjugated double bonds with at least one nucleophile using a catalyst containing a metal of group 8, 9 or 10 of the Periodic Table of the Elements, wherein hydrogen is added via a hydrogen source to the process in at least one process step in the overall telomerization process.
    Type: Grant
    Filed: August 23, 2005
    Date of Patent: January 12, 2010
    Assignee: Evonik Oxeno GmbH
    Inventors: Cornelia Borgmann, Dirk Roettger, Dagmara Ortmann, Reiner Bukohl, Stephan Houbrechts, Franz Nierlich
  • Publication number: 20090318732
    Abstract: The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and ?-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and ?-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.
    Type: Application
    Filed: May 23, 2007
    Publication date: December 24, 2009
    Inventors: Sang Ho Koo, Eun Ho Choi
  • Publication number: 20090299116
    Abstract: A catalyst composition comprising a zirconium complex of a polyvalent aryloxyether and a polymerization processes employing the same, especially a continuous, solution polymerization of ethylene and one or more C3-30 olefins or diolefins to prepare interpolymers having improved processing properties, are disclosed.
    Type: Application
    Filed: April 24, 2007
    Publication date: December 3, 2009
    Inventors: Wayde V. Konze, Daniel D. Vanderlende
  • Patent number: 7541506
    Abstract: The invention relates to a process for the telomerization of acyclic olefins having at least two conjugated double bonds (I) or mixtures in which such olefins are present with nucleophiles (II) using a metal-carbene complex as catalyst.
    Type: Grant
    Filed: June 17, 2003
    Date of Patent: June 2, 2009
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Dirk Roettger, Ralf Jackstell, Holger Klein, Matthias Beller
  • Patent number: 6699813
    Abstract: A catalyst composition that is the combination of or the reaction product of ingredients comprising (a) an lanthanide compound, (b) an alkylating agent, (c) a nickel-containing compound, and optionally (d) a halogen-containing compound, with the proviso that the halogen-containing compound must be present where none of the lanthanide compound, the alkylating agent, and the nickel-containing compound contain a labile halogen atom.
    Type: Grant
    Filed: November 4, 2002
    Date of Patent: March 2, 2004
    Assignee: Bridgestone Corporation
    Inventors: Steven Luo, Yoichi Ozawa, Koji Masaki, David Lawson
  • Publication number: 20040034184
    Abstract: Butene oligomer derivatives having tert-butyl groups as one of the terminal groups, having a repeating unit of the main hydrocarbon chain consisting of 80% by mole or more of —CH2C(CH3)2—, and carrying the other terminal group consisting of 60% by mole or more of 1,4-butanediol type functional groups. These derivatives are useful as macromonomers which can be subjected to polycondensation, polyaddition, etc.
    Type: Application
    Filed: August 29, 2003
    Publication date: February 19, 2004
    Inventors: Tsutomu Takashima, Koji Fujimura, Yuichi Tokumoto
  • Patent number: 6593505
    Abstract: A catalyst comprising A) a stationary acid component selected from the group consisting of a perfluorinated ion exchange polymer on an inert support, a silane modified perfluorosulfonic acid, and a sulfated metal oxide; and B) a mobile acid component selected from the group consisting of chlorosulfonic acid, fluorosulfonic acid, a fluorinated monosulfonic acid, a fluorinated sulfonimide, a fluorinated disulfonic acid, and an adjunct acid mixture is disclosed.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: July 15, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark A. Harmer, Eugene F. Hartstein
  • Publication number: 20020137978
    Abstract: The invention is directed to the cross-metathesis and ring-closing metathesis reactions between geminal disubstituted olefins and terminal olefins, wherein the reaction employs a Ruthenium or Osmium metal carbene complex. Specifically, the invention relates to the synthesis of &agr;-functionalized or unfunctionalized olefins via intermolecular cross-metathesis and intramolecular ring-closing metathesis using a ruthenium alkylidene complex.
    Type: Application
    Filed: June 25, 2001
    Publication date: September 26, 2002
    Inventors: Robert H. Grubbs, Arnab K. Chatterjee, John P. Morgan, Matthias Scholl, Tae-Lim Choi
  • Patent number: 6448452
    Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: September 10, 2002
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Patent number: 6437205
    Abstract: A process for polymerizing 1,3-butadiene into a low molecular weight high-cis polybutadiene is described using a catalyst system comprising: (a) a neodymium-containing compound, (b) an aluminoxane or a trialkyl aluminum compound, (c) an organoaluminum hydride, and (d) a halogen source. A blend of a high molecular weight high-cis polybutadiene and the low molecular weight high-cis polybutadiene is also disclosed for use in pneumatic tire treads. Desirably both the high and the low molecular weight polymers have high cis contents, with the low molecular weight polymer being at least 70 percent cis and the high molecular weight polymer being at least 92 percent cis. Desirably both polymers are made with a neodymium catalyst system. The blends provide a balance of properties including good snow traction, wet traction, and rolling resistance while providing a balance of good physical properties including tension at break, modulus etc.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: August 20, 2002
    Assignee: Bridgestone Corporation
    Inventors: H. Jerrold Miller, Tatsuro Hamada, Yoichi Ozawa, Peyman Pakdel
  • Patent number: 6433237
    Abstract: A catalyst composition that is the combination of or the reaction product of ingredients comprising (a) (i) a halogen-containing iron compound or (ii) an iron-containing compound and a halogen-containing compound, (b) a silyl phosphonate, and (c) an organoaluminum compound.
    Type: Grant
    Filed: February 19, 2001
    Date of Patent: August 13, 2002
    Assignee: Bridgestone Corporation
    Inventor: Steven Luo
  • Patent number: 6388118
    Abstract: A process is disclosed for preparing bis-cyclopentadienyl compounds bridged by a single carbon atom by reacting a carbonyl compound with a cyclopentadienyl compound in the presence of a base and of an oxygen-containing solvent having an atomic ratio carbon/oxygen not higher than 3. The compounds obtainable in high yields with this simple single-step process can be used to prepare ansa-metallocenes which are active as catalyst components in the polymerization of olefins.
    Type: Grant
    Filed: March 27, 2000
    Date of Patent: May 14, 2002
    Assignee: Basell Technology Company bv
    Inventors: Ilya E. Nifant'ev, Pavel V. Ivchenko
  • Patent number: 6262172
    Abstract: A method for preparing a carbonized resin DNA immunoadsorbent, which uses styrene, acrylonitrile, divinylbenzene, toluene, liquid paraffin, benzoyl peroxide and water solution of polyvinyl alcohol as raw materials, produces a DNA immunoadsorbent with 0.3-0.5 mg DNA per milliliter of resin using two-staged procedures for preparation of first carbonized resin, and secondly carbonized resin DNA immunoadsorbent. The resultant immunoadsorbent is high in adsorbent capacity, low in production cost, and can be synthesized without pyrogens. It therefore satisfies the demands of medical application for the treatment of systemic lupus erythematosus by immunoadsorption.
    Type: Grant
    Filed: February 7, 2000
    Date of Patent: July 17, 2001
    Assignee: Nankai University
    Inventors: Yaoting Yu, Changzhi Chen, Deling Kong
  • Patent number: 6177603
    Abstract: The instant invention provides a process for substantially reducing the polymer cement viscosity or reducing the molecular weight distribution of the a conjugated diene polymer synthesized by using a charge of catalytically effective amounts of a rare earth catalyst and an organo magnesium component by adding an organo zinc component to the charge in an amount and under conditions sufficient to reduce the polymer cement viscosity. The invention also contemplates a catalyst compostion for substantially reducing the polymer cement viscosity of a polymer product as well the resultant polymer product.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: January 23, 2001
    Assignee: Bridgestone Corporation
    Inventor: Thomas J. Lynch
  • Patent number: 6153772
    Abstract: A cobalt catalytic system that makes it possible to obtain branched compounds from fatty substances by reacting simple olefins on polyunsaturated esters, which may or may not be conjugated, is described.The compounds that are obtained may be hydrogenated and used as lubricant bases.
    Type: Grant
    Filed: July 24, 1998
    Date of Patent: November 28, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Gerard Hillion, Helene Olivier, Katja Siepen, Robert Stern
  • Patent number: 6103676
    Abstract: The invention provides dispersants and dispersant viscosity index improvers which include polymers of conjugated dienes which have been hydrogenated, functionalized, optionally modified and post treated. The dispersant substances include a copolymer of two different conjugated dienes. The polymers are selectively hydrogenated to produce polymers which have highly controlled amounts of unsaturation, permitting highly selective functionalization. The polymers may be functionalized by hydroformylation followed by reductive amination. Also provided are lubricant fluids, such as mineral and synthetic oils, which have been modified in their dispersancy and/or viscometric properties by means of the dispersant substances of the invention. Also provided are methods of modifying the dispersancy and/or viscometric properties of lubricating fluids such as mineral and synthetic lubricating oils. The dispersant substances may also include a carrier fluid to provide dispersant concentrates.
    Type: Grant
    Filed: June 23, 1998
    Date of Patent: August 15, 2000
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, John E. Marlin, II, Demetreos N. Matthews
  • Patent number: 6103814
    Abstract: Disclosed are hot-melt adhesive compositions suitable for the manufacture of soft goods. They have a melt viscosity of 60,000 mPa.s or less at a temperature of 120.degree. C. and include: (a) 50 to 150 parts by weight of a styrenic block copolymer or mixtures and/or modified and/or hydrogenated derivatives thereof; (b) 20 to 450 parts by weight of a tackifying resin which, when incorporated into a reference composition, leads to the following properties:a tan .delta. value of 3.5 or less, wherein tan .delta. is defined as the ratio between the loss modulus and the storage modulus of said composition andan elastic retention on spandex fibers (300%) or natural latex rubber (200%) after 4 h at 40.degree. C. of 70% or more; anda crossover temperature of 95.degree. C. or less.Further disclosed are novel partially hydrogenated hydrocarbon resins which are useful as tackifying resins and have the following properties: (a) a R&B softening point (R&B) of 50.degree. C. to 150.degree. C.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: August 15, 2000
    Assignee: Hercules Incorporated
    Inventors: Jan vanDrongelen, Johannes Cornelis M. Simons
  • Patent number: 6080826
    Abstract: Functionalized cyclic olefins and methods for making the same are disclosed. Methods include template-directed ring-closing metathesis ("RCM") of functionalized acyclic dienes and template-directed depolymerization of functionalized polymers possessing regularly spaced sites of unsaturation. Although the template species may be any anion, cation, or dipolar compound, cationic species, especially alkali metals, are preferred. Functionalized polymers with regularly spaced sites of unsaturation and methods for making the same are also disclosed. One method for synthesizing these polymers is by ring-opening metathesis polymerization ("ROMP") of functionalized cyclic olefins. The metathesis catalysts for both RCM and ROMP reaction are ruthenium or osmium carbene complex catalysts of the formula ##STR1## where M is Os or Ru; R and R.sup.1 each may be hydrogen, C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: June 27, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Michael J. Marsella, Heather D. Maynard
  • Patent number: 6043403
    Abstract: A process is disclosed for preparing bis-cyclopentadienyl compounds bridged by a single carbon atom by reacting a carbonyl compound with a cyclopentadienyl compound in the presence of a base and of an oxygen-containing solvent having an atomic ratio carbon/oxygen not higher than 3. The compounds obtainable in high yields with this simple single-step process can be used to prepare ansa-metallocenes which are active as catalyst components in the polymerization of olefins.
    Type: Grant
    Filed: January 23, 1996
    Date of Patent: March 28, 2000
    Assignee: Montell Technology Company bv
    Inventors: Ilya E. Nifant'ev, Pavel V. Ivchenko
  • Patent number: 5929185
    Abstract: Copolymers have a viscosity index VI of more than 160 and compriseA) from 99.0 to 99.99 % by weight of C.sub.2 -C.sub.20 -alk-1-enes andB) from 0.01 to 1.0% by weight of C.sub.5 -C.sub.20 -.alpha.,.omega.-dienes having isolated double bonds.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: July 27, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Rosch, Helmut Mach, Freddy Gruber
  • Patent number: 5859280
    Abstract: An alpha-tocopherol is disclosed as a polymerization inhibitor effective against vinyl monomer polymerization. Alpha-tocopherol was found to inhibit polymerization of acrylonitrile and diolefines such as isoprene and butadiene. Alpha-tocopherol was found to interact synergistically with hydroquinone in inhibiting polymerization of acrylonitrile.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: January 12, 1999
    Assignee: BetzDearborn Inc.
    Inventor: Graciela B. Arhancet
  • Patent number: 5744675
    Abstract: The process of the invention, using a plurality of passes, divides the crude product of each pass into a part which contains tetramers and higher oligomers and represents the desired product of a pass and at least one further part which contains the major part of the monomers, dimers and trimers and which serves at least in part as part of the starting materials in a subsequent reaction pass. At the same time, the catalyst concentration is increased. In all reaction passes, only a moderate starting material conversion is sought.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: April 28, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Emmanuel Fiolitakis, Hans Guenther Wey, Jaroslaw Monkiewicz
  • Patent number: 5728911
    Abstract: A copolymer having an RSV less than 0.6 and a process for its preparation in which ethylene, at least one other 1-alkene and, optionally, an aliphatic or alicyclic polyunsaturated monomer are polymerized in the presence of a catalyst system containing (1) a compound of vanadium, (2) at least one alkyl aluminum halide, (3) an .alpha.-halo, ketoaromatic promoter and (4) a chain transfer agent in which the molar ratio of alkyl groups of the alkyl aluminum halide to halogen atoms is at least 1.5.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: March 17, 1998
    Assignee: DSM Copolymer, Inc.
    Inventor: James R. Hall
  • Patent number: 5717042
    Abstract: A process and catalyst system for the preparation of diene oligomers and copolymeric oligomers is disclosed. The oligomers and copolymers are prepared in an alkane solvent from one or more 1,3-diene monomers using a secondary amine transfer agent and an anionic initiator. A catalyst system including a secondary amine transfer agent and an anionic initiator is also provided.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: February 10, 1998
    Assignee: Bridgestone/Firestone, Inc.
    Inventor: James E. Hall
  • Patent number: 5698751
    Abstract: A branched polyene compound represented by the formula ##STR1## wherein f is an integer of 1-5; R.sup.1 and R.sup.2 represent hydrogen atoms or alkyl groups of 1-5 carbons; R.sup.3 represents a hydrogen atom or an alkyl group of 1-5 carbons or an alkenyl group represented by the formula ##STR2## wherein n is an integer of 1-5; R.sup.4, R.sup.5 and R.sup.6 represent hydrogen atoms or alkyl groups of 1-5 carbons; all of R.sup.1, R.sup.2, R.sup.3 are not simultaneously hydrogen atoms; and all of R.sup.4, R.sup.5 and R.sup.6 are not simultaneously hydrogen atoms.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: December 16, 1997
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tatsuyoshi Ishida, Masaaki Yasuda, Hitoshi Ohnishi, Noriaki Kihara, Toshihiro Sagane, Toshiyuki Tsutsui
  • Patent number: 5686371
    Abstract: A process for the polymerization of one or more conjugated dienes by means of a rare earth based catalyst in which the catalyst is formed by bringing together in liquid hydrocarbon medium in the presence of a small portion of conjugated diene: a) a rare earth salt, b) an organo aluminum and c) a silicon halide or organosilicon halide and aging the catalyst before contact with the conjugated diene(s) to be polymerized. This catalyst formation procedure offers the possibility of producing a diene polymer of high cis content with a narrower molecular weight distribution and/or smaller high molecular weight fraction which is reflected in improved processing characteristics and reduced viscosity in styrene.
    Type: Grant
    Filed: August 10, 1994
    Date of Patent: November 11, 1997
    Assignee: Enichem Elastomers Ltd.
    Inventors: Peter John Ansell, Hugh David Williams
  • Patent number: 5686535
    Abstract: 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: Grant
    Filed: December 20, 1996
    Date of Patent: November 11, 1997
    Assignee: Shell Oil Company
    Inventors: James Robert Erickson, David John St. Clair
  • Patent number: 5637783
    Abstract: The invention provides dispersants and dispersant viscosity index improvers which include polymers of conjugated dienes which have been hydrogenated and functionalized. The dispersant substances include compositions including a copolymer of a ring substituted styrene and a conjugated diene. The polymers are selectively hydrogenated to produce polymers which have highly controlled residual amounts of aromatic unsaturation, permitting highly selective functionalization. Also provided are lubricant fluids, such as mineral and synthetic oils, which have been modified in their dispersancy and/or viscometric properties by means of the dispersant substances of the invention. Also provided are methods of modifying the dispersancy and/or viscometric properties of lubricating fluids such as mineral and synthetic lubricating oils. The dispersant substances may also include a carrier fluid to provide dispersant concentrates.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 10, 1997
    Assignee: Mobil Oil Corporation
    Inventors: Ellen B. Brandes, Frederick C. Loveless
  • Patent number: 5637661
    Abstract: The subject invention discloses a technique for controlling the molecular weight of synthetic polymers which are made by anionic polymerization. This invention is based upon the discovery that the molecular weight of diene polymers made by anionic polymerization utilizing organolithium initiators can be reduced by conducting the polymerization in the presence of bis(1,5-cyclooctadiene) nickel. The present invention more specifically discloses a process for producing a polymer of controlled molecular weight by anionic polymerization, said process comprising initiating the anionic polymerization of at least one conjugated diolefin monomer with an organolithium compound, wherein the polymerization is conducted in the presence of bis(1,5-cyclooctadiene) nickel. This technique is particularly useful in synthesizing liquid polymers but can also be used to reduce the molecular weight of rubbery polymers.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: June 10, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Kenneth F. Castner, Jean S. Clites
  • Patent number: 5633415
    Abstract: The invention provides dispersants and dispersant viscosity index improvers which include polymers of conjugated dienes which have been hydrogenated and functionalized. The dispersant substances include compositions including a copolymer of two different conjugated dienes, a copolymer of a p-alkylstyrene and a conjugated diene, or a homopolymer of a conjugated diene. The polymers are selectively hydrogenated to produce polymers which have highly controlled amounts of unsaturation, permitting highly selective functionalization. Also provided are lubricant fluids, such as mineral and synthetic oils, which have been modified in their dispersancy and/or viscometric properties by means of the dispersant substances of the invention. Also provided are methods of modifying the dispersancy and/or viscometric properties of lubricating fluids such as mineral and synthetic lubricating oils. The dispersant substances may also include a carrier fluid to provide dispersant concentrates.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 27, 1997
    Assignee: Mobil Oil Corporation
    Inventors: Ellen B. Brandes, Frederick C. Loveless
  • Patent number: 5625100
    Abstract: There is disclosed a linear block copolymer comprising at least one triblock I--B--I, wherein I is a block of at least one polymerized conjugated diene of at least five (5) carbon atoms, such as isoprene, and B is a block of a polymer of at least one conjugated diene, different from that used to polymerize the block I, of at least four (4) carbon atoms, such as 1,3-butadiene. The B block is selectively hydrogenated, while each of the I blocks is unhydrogenated and therefore 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 a minor proportion of at least one aryl-substituted olefin, such as styrene, and a major proportion of at least one conjugated diene used to polymerize the block I, the second middle polymer block of at least one diene used to polymerize the block B, and the third polymer block which is the same as the first polymer block.
    Type: Grant
    Filed: December 26, 1995
    Date of Patent: April 29, 1997
    Assignee: Mobil Oil Company
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5556932
    Abstract: Chlorine-free, non-drying copolymer of isobutene with C.sub.4 -C.sub.10 -dienes having isolated or conjugated double bonds and containing at least 60 mol % of terminal double bonds, and a process for their preparation.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: September 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans P. Rath, Konrad Knoll, Helmut Mach
  • Patent number: 5548045
    Abstract: A process for producing a polybutadiene, which comprises polymerizing 1,3-butadiene in an inert organic solvent with a catalyst comprising (A) a cobalt compound, (B) an organoaluminum compound consisting essentially of an aluminoxane and, if necessary, (C) a tertiary phosphine compound, (D) at least one compound selected from the group consisting of an ester compound, an alcohol compound, a phenolic compound, a sulfoxide compound, a nitrogen-containing heterocyclic compound, water and a tertiary amine compound and (E) at least one compound selected from the group consisting of carbon disulfide, a xanthogen compound and a thioisocyanide. By this process, there can be produced, as desired, a cis-1,4-polybutadiene, a 1,2-polybutadiene having a desired vinyl content, a crystalline 1,2-polybutadiene or a polybutadiene containing crystalline 1,2-polybutadiene segments.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: August 20, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Kohei Goto, Iwakazu Hattori, Shoji Ogasahara, Masahiro Shibata, Yoshiyuki Michino, Kazuo Soga, Takeshi Shiono
  • Patent number: 5545783
    Abstract: There is disclosed a linear block copolymer comprising at least one triblock I-B-I, wherein I is a block of at least one polymerized conjugated diene of at least five (5) carbon atoms, such as isoprene, and B is a block of a polymer of at least one conjugated diene, different from that used to polymerize the block I, of at least four (4) carbon atoms, such as 1,3-butadiene. The B block is selectively hydrogenated, while each of the I blocks is unhydrogenated and therefore 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 a minor proportion of at least one aryl-substituted olefin, such as styrene, and a major proportion of at least one conjugated diene used to polymerize the block I, the second middle polymer block of at least one diene used to polymerize the block B, and the third polymer block which is the same as the first polymer block.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: August 13, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5510548
    Abstract: There is disclosed a linear block copolymer comprising at least one triblock I-B-I, wherein I is a block of at least one polymerized conjugated diene of at least five (5) carbon atoms, such as isoprene, and B is a block of a polymer of at least one conjugated diene, different from that used to polymerize the block I, of at least four (4) carbon atoms, such as 1,3-butadiene. The B block is selectively hydrogenated, while each of the I blocks is unhydrogenated and therefore 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 a minor proportion of at least one aryl-substituted olefin, such as styrene, and a major proportion of at least one conjugated diene used to polymerize the block I, the second middle polymer block of at least one diene used to polymerize the block B, and the third polymer block which is the same as the first polymer block.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 23, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5476956
    Abstract: Co dimerization is conducted of at least one monoolefin, for example a monoolefinic hydrocarbon such as ethylene, propylene or 1-butene, a halogenated monoolefin such as vinyl chloride, or an olefinic functional compound such as methyl acrylate, acrylonitrile, allyl acetate or vinyl acetate, with at least one polyolefin containing at least two conjugated or unconjugated ethylene bonds, for example a diene hydrocarbon such as 1,3-butadiene, piperylene, or isoprene or a polyolefin containing a carboxylic function, such as a fatty acid or a fatty acid ester having 14 to 24 carbon atoms in the fatty chain derived, for example, from a natural oil. The reaction is carried out in the presence of a catalytic system having general formula [RhX.sub.4 ][YR.sub.4 ] where X represents a halogen ion or a SO.sub.4.sup.--, SO.sub.3.sup.-, OH.sup.-, OR.sup.- or R.sup.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: December 19, 1995
    Assignee: Institut Francais Du Petrole
    Inventors: Gerard Hillion, Robert Stern, Abakar Kotoko, Yves Chauvin
  • Patent number: 5446222
    Abstract: The invention provides a two-step process for converting cyclopentadiene dimer to a high density fuel mixture comprising the steps of:(a) reacting said cyclopentadiene dimer in the presence of a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under oligomerization/isomerization conditions to convert at least a portion of said cyclopentadiene dimer to a normally liquid intermediate product containing cyclopentadiene trimer, cyclopentadiene tetramer, and the isomerized and oligomerized products derived from the reaction of at least three cyclopentadiene monomer units;(b) hydrogenating said normally liquid intermediate product of step (a) in the presence of a hydrogenation catalyst to form a normally liquid high energy density fuel.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 29, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James R. Boulton, Ross A. Kremer
  • Patent number: 5403904
    Abstract: A process is disclosed for preparation of telechelic difunctional unsaturated oligomers and polymers having at least one internal carbon-to-carbon double bond wherein the functional groups are terminal reactive groups. The reactants are acyclic polyenes with terminal carbon-to-carbon double bonds and olefins with at least one functional group. The polymerization process is substantially free of side reactions comprising double bond migration and cyclization. The telechelic difunctional unsaturated oligomers and polymers have a functionality of about 2 and are suitable for preparation of block copolymers, ion exchange resins, adhesives, and flocculants and for further functionalization.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: April 4, 1995
    Assignee: Amoco Corporation
    Inventors: Philip O. Nubel, Robert B. Morland, Howard B. Yokelson
  • Patent number: 5387730
    Abstract: There is disclosed a linear block copolymer comprising at least one triblock I-B-I, wherein I is a block of at least one polymerized conjugated diene of at least five (5) carbon atoms, such as isoprene, and B is a block of a polymer of at least one conjugated diene, different from that used to polymerize the block I, of at least four (4) carbon atoms, such as butadiene. The B block is selectively hydrogenated, while each of the I blocks is unhydrogenated and therefore 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 a minor proportion of at least one aryl-substituted olefin, such as styrene, and a major proportion of at least one conjugated diene used to polymerize the block I, the second middle polymer block of at least one diene used to polymerize the block B, and the third polymer block which is the same as the first polymer block.
    Type: Grant
    Filed: January 7, 1994
    Date of Patent: February 7, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5334678
    Abstract: Polymers of olefins such as ethylene and propylene, having functional groups introduced into both the ends thereof, can be provided which are useful as macromonomers for polycondensation. This new polymer comprises a recurring unit represented by the general formula --(--CH.sub.2.CHR--)-- and having functional groups bonded to both the ends of the polymer and a number average molecular weight of 300 to 500,000, the functional groups being selected from the group consisting of H.sub.2 C.dbd.CH-- group and ##STR1## wherein X is --OH, --OR.sup.1, a halogen atom or --SO.sub.3 R.sup.2, R.sup.1 is a hydrocarbon group of 1 to 5 carbon atoms and R.sup.2 is a halogen-substituted or non-substituted hydrocarbon group of 1 to 20 carbon atoms.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: August 2, 1994
    Assignee: Tonen Corporation
    Inventors: Hiroyuki Furuhashi, Naomi Koyama, Satoshi Ueki