More Than Two Double Bonds, E.g., Diene Polymerization, Etc. Patents (Class 585/507)
  • Patent number: 5306856
    Abstract: A method of manufacturing methylidene-group-containing .alpha.,.omega.-unsaturated oligomers from .alpha.,.omega.-diolefins in the presence of a catalytic amount of organoaluminum compounds, wherein the .alpha.,.omega.-diolefins are reacted in the liquid phase, at 150.degree.-350.degree. C., and the organoaluminum compounds have formula AlX.sub.3 or AlX.sub.2 H, where X represents an aliphatic, alicyclic, or aromatic hydrocarbon group with 1-30 C atoms. The higher molecular weight hydrocarbons manufactured according to this method are substantially linear oligomers which contain reactive double bonds.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: April 26, 1994
    Assignee: Huels Aktiengesellschaft
    Inventors: Roland Streck, Jaroslaw Monkiewicz, Hans G. Wey
  • Patent number: 5300716
    Abstract: A process for the preparation of a polyunsaturated olefinic compound, i.e. undeca-1,3,5-triene, in its (3E,5Z) isomeric form, consisting of four consecutive steps starting from deca-1,4-diyne, is disclosed.Said process has the advantage of making it possible to obtain the desired isomer in its essentially pure form.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: April 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5288937
    Abstract: Block and random straight chain and star-branched liquid copolymers of two different conjugated dienes, the residual ethylenic unsaturation of the polymerized units of one of which, e.g. isoprene, is less readily hydrogenated than that of the other diene, e.g., butadiene. In the case of block copolymers, the terminal blocks of a straight chain copolymer or the blocks of the free ends of the branches of a star-branched copolymer are composed of the less readily hydrogenated diene polymer while the more readily hydrogenated diene polymer is in the form of central blocks of a straight chain copolymer or interior blocks of the branches of a star-branched copolymer.
    Type: Grant
    Filed: December 17, 1992
    Date of Patent: February 22, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5238998
    Abstract: A toner composition comprised of multiblock or liquid glass resin particles with a glass transition temperature of between from about 20.degree. C. to about 65.degree. C., and pigment particles.
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: August 24, 1993
    Assignee: Xerox Corporation
    Inventors: Timothy J. Fuller, Samuel Kaplan, Michael J. Levy, Joseph D. Geiser, Richard B. Lewis, William M. Prest, Jr.
  • Patent number: 5216181
    Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an organic alcohol.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: June 1, 1993
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
  • Patent number: 5210359
    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: August 6, 1992
    Date of Patent: May 11, 1993
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5186918
    Abstract: Molecular sieve compositions are prepared by extracting aluminum and substituting chromium and/or tin for extracted aluminum to give molecular sieve products containing framework chromium and/or tin atoms. The process of preparing the chromium and/or tin-containing molecular sieves invovles contacting a starting molecular sieve with a solution or slurry of at least one of a fluoro salt of chromium or a fluoro salt of tin under effective process conditions to provide for aluminum extraction and substitution of chromium and/or tin. These compositions are effective as hydrocarbon conversion catalysts and for separating mixtures of molecular species.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: February 16, 1993
    Assignee: UOP
    Inventors: Gary W. Skeels, Diane M. Chapman, Edith M. Flanigen
  • Patent number: 5149895
    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: January 16, 1990
    Date of Patent: September 22, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas S. Coolbaugh, Frederick C. Loveless, Demetreos N. Matthews, Leslie R. Rudnick
  • Patent number: 5004857
    Abstract: A method for continuously producing a liquid low molecular weight polymer of conjugated diolefin having a number average molecular weight of 300 to 10000. The method comprises the step of continuously polymerizing or copolymerizing conjugated diolefin in an inert hydrocarbon solvent at a temperature of 40.degree. to 70.degree. C. with maintaining the quantity of dissolved oxygen in the reaction system at 1 ppm or below and in the presence of a polymerization catalyst of an organic sodium compound and a chain transfer agent of an alkylaryl compound.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: April 2, 1991
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Shoji Iida, Kazuo Miyazaki, Nobuyuki Takizawa
  • Patent number: 4999409
    Abstract: 1,4-Addition polymers or copolymers of diolefins useful as a functional or active polymer is provided which comprises, in combination, the following recurring units (A) and (B): ##STR1## wherein n=4 to 6 and A/B mole ratio=0 to 98/100 to 2.
    Type: Grant
    Filed: September 29, 1988
    Date of Patent: March 12, 1991
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Doi, Kazuo Soga, Satoshi Ueki
  • Patent number: 4950826
    Abstract: Process for adjusting the cis-trans-double bond configuration in polyalkenamers produced by ring-opening polymerization of cis,cis-1,5-cyclooctadiene or 2-norbornene wherein the polymerization is performed in the presence of isoprene and/or a cyclic olefin with a double-bond pair in the 1,3-position.
    Type: Grant
    Filed: August 22, 1986
    Date of Patent: August 21, 1990
    Assignee: Huels Aktiengesellschaft
    Inventors: Dieter Zerpner, Roland Streck
  • Patent number: 4899013
    Abstract: A process is disclosed for the preparation of copolymers of a diene and isobutylene wherein the copolymer has a degree of unsaturation greater than 100% and average molecular weight range is from 400 to 10,000.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: February 6, 1990
    Assignee: Amoco Corporation
    Inventor: Kelley R. Lane
  • Patent number: 4762635
    Abstract: Highly branched synthetic hydrocarbon fluids produced by anionically oligomerizing selected dienes in the presence of organoalkali compounds and complexing reagents provide fluids having high traction coefficients and excellent elastohydrodynamic lubricating characteristics.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: August 9, 1988
    Assignee: Mobil Oil Corporation
    Inventor: Thomas R. Forbus
  • Patent number: 4486614
    Abstract: 1,3-pentadiene is polymerized from a mixture of saturated and unsaturated hydrocarbon compounds, the compounds having primarily 5 carbon atoms per molecule, with an anionic polymerization initiator. The mixture of saturated and unsaturated hydrocarbon compounds is contacted, in an inert atmosphere, with an anionic polymerization initiator to form a reaction mixture. The anionic polymerization initiator is present in an amount sufficient to inactivate polymerization-terminating compounds present in the mixture and to initiate polymerization of 1,3-pentadiene from the mixture. The reaction mixture is heated with stirring to a temperature sufficient to inactivate the polymerization terminating compounds. After inactivation of the polymerization terminating compounds, the reaction mixture is then heated with stirring to a temperature sufficient to initiate polymerization of 1,3-pentadiene from the reaction mixture. Polymer recovery and subsequent functionalization, if any, follow thereafter.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 4, 1984
    Assignee: The Dow Chemical Company
    Inventors: Felipe A. Donate, John W. Bozzelli, Kent S. Dennis
  • Patent number: 4482771
    Abstract: 1,3-Pentadiene is polymerized in an inert gaseous atmosphere from a mixture of saturated and unsaturated hydrocarbon molecules. At least 50 percent by weight of said molecules have 5 carbon atoms. An anionic polymerization initiator in conjunction with an organic polar solvent is used to effect polymerization. Cyclopentadiene, active hydrogen compounds and other polymerization-terminating compounds may be inactivated and separated from the mixture of hydrocarbon compounds before starting polymerization. As an alternative, inactivation and separation of cyclopentadiene, active hydrogen compounds and polymerization-terminating compounds may be omitted provided the anionic polymerization initiator is employed in an amount to (a) inactivate such compounds and (b) initiate polymerization of 1,3-pentadiene.The polymer of 1,3-pentadiene so prepared is then hydrogenated or functionalized by further reaction.
    Type: Grant
    Filed: December 8, 1983
    Date of Patent: November 13, 1984
    Assignee: The Dow Chemical Company
    Inventors: John W. Bozzelli, Kent S. Dennis, Felipe A. Donate
  • Patent number: 4373074
    Abstract: A process for preparing copolymers of acetylene and conjugated diene compounds by copolymerization of acetylene with at least one conjugated diene compound in the presence of a catalyst composition in a reactor, characterized in that the catalyst composition comprises a dialkyl aluminum halide, an organic nickel compound and an active hydrogen compound, of which the molar concentrations have the following relationships:[Al]=2[Ni]+[H][Al]/[Ni]>4wherein [Al], [Ni] and [H] represent respectively the molar concentrations of the dialkyl aluminum halide, of the organic nickel compound and of the active hydrogen compound, whereby the copolymer was obtained in a good yield without by-production of any gel material.
    Type: Grant
    Filed: June 3, 1981
    Date of Patent: February 8, 1983
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Junji Furukawa, Nobuo Furuno, Akira Matsumura, Teruaki Kuwajima
  • Patent number: 4331823
    Abstract: A catalyst comprising:(a) an organometallic compound corresponding to the following general formula: RMe wherein R represents a saturated aliphatic or aromatic hydrocarbon radical having from 2 to 8 carbon atoms; and Me represents an alkali metal;(b) a compound corresponding to the following general formula: R'OMe' wherein R' represents a saturated aliphatic or aromatic hydrocarbon radical having from 2 to 8 carbon atoms; and Me' represents an alkali metal; and(c) a tertiary aliphatic triamine.A process for the preparation of said catalyst wherein components (a), (b) and (c) are dissolved, in any order, in an aliphatic or aromatic hydrocarbon and reacted at temperatures of from 0.degree. to 100.degree. C., and its use in the preparation of telomeric polybutadiene homo- or co-polymers.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: May 25, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Wieder, Josef Witte
  • Patent number: 4323698
    Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: April 6, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4313019
    Abstract: In a method for producing a low molecular weight polymer or copolymer by introducing metallic sodium or an organic sodium compound as a polymerization initiator, an alkyl aryl compound as a chain transfer agent, an inert hydrocarbon as a solvent and a conjugated diolefin or both a conjugated diolefin and a vinyl compound having anionic copolymerization activity with diolefins as a monomer or monomers, into a polymerization vessel and polymerizing or copolymerizing therein successively at a temperature of 0.degree. to 100.degree. C., the improvement in the method for producing a low molecular weight polymer or copolymer having a number average molecular weight of 300 to 10,000 with good reproducibility is characterized in that 0.05 to 10 mole % per 1 mole of the said polymerization initiator, of oxygen is fed into said polymerization vessel.
    Type: Grant
    Filed: December 2, 1977
    Date of Patent: January 26, 1982
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hajime Hara, Atsushi Kaiya, Yoshihiko Araki
  • Patent number: 4242481
    Abstract: Novel organoaluminum compounds having the formula XYA1 ##STR1## in which X is a halogen, Y is an alkyl group having from 1 to 10 carbon atoms, a phenyl group or a halogen, R is an alkyl group having from 2 to 9 carbon atoms, and n is an integer from 1 to 20. These compounds are less viscous and more soluble in hydrocarbon solvents than are corresponding ethylene-based or butadiene-based compounds. The novel compounds are prepared by the reaction of alkylaluminum dihalides or aluminum trihalides with a terminal olefin having from 3 to 10 carbon atoms in the presence of aluminum metal.
    Type: Grant
    Filed: May 7, 1979
    Date of Patent: December 30, 1980
    Assignee: Texas Alkyls, Inc.
    Inventor: Loyd W. Fannin
  • Patent number: 4205193
    Abstract: A process of the production of isoprene cyclic trimers, i.e., 1, 5, 9- and 1, 6, 9-trimethylcyclododecatriene-(1, 5, 9) through a catalytic oligomerization of isoprene by employing a catalyst prepared by a combination of a tri-valent titanium compound, an organoaluminum compound, an oxygen-containing compound such as carbonyl and ether compounds, and a compound such as a sulfur-containing compound and a nitrile compound.
    Type: Grant
    Filed: July 26, 1978
    Date of Patent: May 27, 1980
    Assignee: Mitsubishi Petrochemical Company Limited
    Inventors: Hiroyuki Morikawa, Shooji Kitazume
  • Patent number: 4170603
    Abstract: Novel organoaluminum compounds having the formula ##STR1## in which X is a halogen, Y is an alkyl group having from 1 to 10 carbon atoms, a phenyl group or a halogen, R is an alkyl group having from 2 to 9 carbon atoms, and n is an integer from 1 to 20. These compounds are less viscous and more soluble in hydrocarbon solvents than are corresponding ethylene-based or butadiene-based compounds.The novel compounds are prepared by the reaction of alkylaluminum dihalides or aluminum trihalides with a terminal olefin having from 3 to 10 carbon atoms in the presence of aluminum metal.
    Type: Grant
    Filed: March 3, 1977
    Date of Patent: October 9, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Loyd W. Fannin