Patents Represented by Attorney, Agent or Law Firm Donald F. Haas
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Patent number: 6660892Abstract: This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.Type: GrantFiled: February 7, 2003Date of Patent: December 9, 2003Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, John Frederick Knifton, Kevin Dale Allen, Lynn Henry Slaugh, Juan Pedro Arhancet
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Patent number: 6657044Abstract: An improved process for the polymerization of polytrimethylene terephthalate by esterification of terephthalic acid or dimethylterephthalate with 1,3-propanediol (PDO), precondensation of the esterification product to produce a precondensation product, and polycondensation of the precondensation product to produce polytrimethylene terephthalate wherein excess PDO is removed from the esterification and/or polycondensation stages and PDO vapor is separated from the high boiling fraction (solid byproduct). The improvement comprises: (a) heating the solid byproduct in the presence of about 5 ppm to about 5000 ppm, based on metal, of a metal catalyst selected from the group consisting of one or more 3rd, 4th, or 5th row metal compounds from Groups 3-12 and Groups 14-15 of the Periodic Table (IUPAC 1989) at a temperature of from about 100° C. to about 240° C.Type: GrantFiled: October 18, 2002Date of Patent: December 2, 2003Assignee: Shell Oil CompanyInventors: Donald Ross Kelsey, Kathleen Suzanne Kiibler, Wen Tzung Tang
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Patent number: 6610819Abstract: The friability of crystallized PTT and solid stated PTT can be effectively reduced by lowering the temperature of the quenching water used in the pelletizing of the melt polycondensation polymer to between 32° F. (0° C.) and 65° F. (18° C.). In addition, the robustness of solid stated PTT pellets is effectively increased by using a prepolymer with a lower intrinsic viscosity (IV) or by increasing the IV of the solid stated product.Type: GrantFiled: May 30, 2002Date of Patent: August 26, 2003Assignee: Shell Oil CompanyInventors: Ben Duh, Robert Lawrence Blackbourn, Kathleen Suzanne Kiibler, Cecilia Zuqi Tse
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Patent number: 6576774Abstract: This invention is an improvement upon the known process for polymerization of polytrimethylene terephthalate by esterification of terephthalic acid or dimethyl terephthalate with 1,3-propane diol, precondensation of the esterification product to produce a precondensation product, and polycondensation of the precondensation product to produce polytrimethylene terephthalate and, optionally, solid stating of this product to produce higher intrinsic viscosity polytrimethylene terephthalate. The cyclic dimer of terephthalic acid and 1,3-propane diol is produced as a byproduct of the above process and the improvement comprises (a) recovering the cyclic dimer from the polymerization, (b) reacting from 0.5 to 25 percent by weight of the cyclic dimer in 1,3-propane diol in the presence of from 0.1 to 10 percent by weight of the cyclic dimer of a basic catalyst for five minutes to 24 hours at 50 to 210° C.Type: GrantFiled: June 26, 2001Date of Patent: June 10, 2003Assignee: Shell Oil CompanyInventors: Betty Marrou Scardino, Donald Ross Kelsey
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Patent number: 6576802Abstract: Disclosed is a novel class of modified ruthenium catalysts useful in the one step synthesis of 1,3-PDO comprising (a) a cobalt component comprising one or more non-ligated cobalt compounds; and (b) a ruthenium component comprising in major part a ruthenium carbonyl compound ligated with a phospholanoalkane ligand, solubilized in an ether solvent, that provides potential improvements in cost and performance in one step hydroformylation/hydrogenation. For example, cobalt-ruthenium-bidentate, bis(phospholano)alkane catalyst precursors in ether solvents provide good yields of 1,3-PDO in a one step synthesis.Type: GrantFiled: May 30, 2002Date of Patent: June 10, 2003Assignee: Shell Oil CompanyInventors: John Frederick Knifton, Talmadge Gail James, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell, Lynn Henry Slaugh
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Patent number: 6539596Abstract: This invention relates to making high quality, soft and relatively elastic nonwoven fiber webs from polytrimethylene terephthalate (PTT). Staple PTT fibers are first manufactured. Usually, this involves spinning the polymer into fibers and then cutting them to a length of from 10 to 200 millimeters. Thereafter, the fibers are carded and hydroentangled. This combination of steps produces high quality PTT nonwoven fabrics, i.e., which are softer than fabrics from other materials, require less energy to hydroentangle, can be manufactured at higher carding rates, and have a higher dye yield. The staple polymers are first carded. This can be carried out in conventional carding machines such as roller top carding machines, layered carding machines, and flat top carding machines. The web is crosslapped to from 5 to 500 g/m2 basis weight web. Next, the webs are hydroentangled.Type: GrantFiled: September 21, 2001Date of Patent: April 1, 2003Assignee: Shell Oil CompanyInventors: Charles Chiu-Hsiung Hwo, Donald Albert Shiffler
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Patent number: 6534178Abstract: In accordance with the foregoing, the present invention comprises a polyester epoxy resin powder coating exhibiting improved impact resistance and flexibility, without the loss of other key properties and where the 1,3-PDO modified polyester has lower melt viscosity than polyesters made with 100% neopentyl glycol, which is formed by reacting: a) A carboxyl functional polyester resin formed by reacting one or more aliphatic glycols and one or more polycarboxylic acids and/or anhydrides, wherein 5 to 90% (on a molar basis) of the aliphatic glycol is 1,3-propanediol, in the presence of an esterification catalyst and then endcapping the polyester with an endcapping agent to ensure that the polyester has carboxyl chain ends; and b) An epoxy resin crosslinking agent.Type: GrantFiled: March 15, 2001Date of Patent: March 18, 2003Assignee: Shell Oil CompanyInventors: Lichang Zhou, Shelby F. Thames, Oliver Wendell Smith, Wyndham Henry Boon, Thomas Clayton Forschner
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Patent number: 6534573Abstract: The present invention provides a method for reducing bleeding number in wax compositions comprising wax and oil, wherein said waxes are selected from petroleum and synthetic waxes and said oil is present in the range of 1 to 45% w/w, by incorporating in the composition an effective amount of an oil retention agent in the form of an elastomeric polymer. The invention has particularly useful application to wax compositions used for wax candles. The invention further provides the use of elastomeric polymers for reducing bleeding number in wax compositions.Type: GrantFiled: March 29, 2000Date of Patent: March 18, 2003Assignee: Shell Oil CompanyInventors: Jean-Michel Mace, Olivier Roumache
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Patent number: 6528579Abstract: The invention relates to a process for the preparation of polyesters of a glycol and a dicarboxylic acid which comprises the following steps: a) introducing a feedstock comprising one or more glycols and one or more dicarboxylic acids or monoalcohol esters thereof into a reactor vessel, b) heating the feedstock to an elevated temperature to cause the glycols and the acids or monoalcohol esters thereof to polycondense into a polyester, c) removing all of the polyester from the reactor vessel, wherein step b) is carried out in the absence of a preformed polyester (“zero heel” process). A condensation catalyst is added in step a) or b) or both.Type: GrantFiled: February 6, 2001Date of Patent: March 4, 2003Assignee: Shell Oil CompanyInventors: Kevin Dale Allen, Emery Don Johnson, Cecilia Zuqi Tse, Samuel Martin Moats
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Patent number: 6509438Abstract: According to the invention, a polytrimethylene terephthalate is provided having 0.6 to less than 2 mole percent dipropylene glycol. Such compositions have a reduced tendency to generate acrolein when heated in air. These PTT polymer compositions exhibit improved and enhanced dyeability as compared to conventional PTT made by the DMT process and the TPA polycondensation/solid state polymerization processes.Type: GrantFiled: April 23, 2001Date of Patent: January 21, 2003Assignee: Shell Oil CompanyInventors: Donald Ross Kelsey, Betty Marrou Scardino, Kailash Dangayach, Houston Slade Brown, Hans Reitz, Eckhard Seidel, Fritz Wilhelm
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Patent number: 6461993Abstract: This invention concerns a method for preparing a hydrogenation catalyst system involving the reaction of a group 4 metallocene (A) with a metal hydride or an organometallic compound (B) at a (B)/(A) molar ratio that is larger than 10 followed by the activation of the resulting catalyst mixture with hydrogen at a hydrogen pressure p (in MPa) and at a temperature T (in ° C.), wherein a neutralising agent (C) that is capable of reacting with the compound (B) is added to the catalyst mixture a) either prior to the activation, or b) within t hours from the activation wherein t equals x divided by (p*T*(B)/(A)), and x=10,000, and a process for the hydrogenation of an olefinically unsaturated compound with hydrogen in the presence of a hydrogenation catalyst system obtained by the method of the invention.Type: GrantFiled: October 8, 1999Date of Patent: October 8, 2002Assignee: Shell Oil CompanyInventors: Harry Van Der Heijden, Hendrik Van De Weg
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Patent number: 6451949Abstract: Disclosed is a process for the production of poly(trimethylene carbonate) which comprises reacting trimethylene carbonate, a catalyst, and an alcohol, preferably a polyhydric alcohol, under nitrogen at atmospheric pressure and a moderate temperature, in a stoichiometric ratio to give the desired molecular weight of poly(trimethylene carbonate) in the presence of a catalyst selected from the group consisting of a salt, preferably an acetate, of an element of Group IA or IIA of the Periodic Table. In an alternative embodiment, high molecular weight poly(trimethylene carbonate) is produced without the use of an initiator, using the same catalyst and longer reaction times.Type: GrantFiled: February 9, 2001Date of Patent: September 17, 2002Assignee: Shell Oil CompanyInventors: Wyndham Henry Boon, Roy Frank Smith, David Eric Gwyn, Thomas Clayton Forschner
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Patent number: 6441129Abstract: The present invention is a process for producing poly(trimethylene terephthalate) (PTT) at an increased solid state polymerization rate, wherein 1,3-propane diol and an aromatic acid or a dialkyl ester thereof are esterified or transesterified, the esterification or transesterification product is polycondensed, and the polycondensation product is pelletized and then subjected to continuous solid state polymerization at a temperature of 200 to 225° C., preferably 210 to 225° C. In one embodiment of the present invention, the temperature range is 200 to 220° C., and the pellet size of the polymer to be solid state polymerized is from 1.0 to 1.5 g/100. In another embodiment of the present invention, the solid state polymerization is carried out at 210 to 225° C. for from 1 to 20 hours and then the temperature is increased to above the initial melting point of the polymer to produce a PTT polymer with an intrinsic viscosity of 1.3 dl/g or greater.Type: GrantFiled: May 15, 2001Date of Patent: August 27, 2002Assignee: Shell Oil CompanyInventors: Ben Duh, Ann Marie Corey
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Patent number: 6433131Abstract: Disclosed is a modified acrylic coating composition cured with melamine characterized by improved impact resistance which comprises: An acrylic polyol dissolved in a suitable solvent to 40-90% solids; 2 to 50% by weight of said acrylic polyol substituted with a polytrimethylene carbonate polyol selected from a polytrimethylene carbonate diol, a polytrimethylene carbonate triol, or a higher functionality polytrimethylene carbonate polyol; a melamine crosslinking agent; optionally a catalyst; and optionally pigments and other additives commonly used in coatings. Also disclosed in a related embodiment is a melamine/urea formaldehyde polytrimethylene carbonate coating composition that is prepared without acrylic.Type: GrantFiled: February 15, 2001Date of Patent: August 13, 2002Assignee: Shell Oil CompanyInventors: Lichang Zhou, Shelby F. Thames, Oliver W. Smith, Thomas Clayton Forschner, Roy Frank Smith, David Eric Gwyn, Wyndham Henry Boon, Abdulai Mobolaji Dawodu
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Patent number: 6403762Abstract: The present invention is an improvement upon the process for producing poly(trimethylene terephthalate) (PTT) wherein 1,3-propanediol (PDO), and optionally other diols, and an aromatic diacid or diester thereof, and optionally other diacids or diesters, are esterified or transesterified and the esterification or transesterification product is polycondensed to produce a prepolymer which is solid state polymerized to produce a polymer with a desired intrinsic viscosity (IV). The prior art process includes the SSP prereaction steps of crystallization, drying/annealing, and preheating. The improvement in the present invention comprises crystallizing and preheating the PTT polymer in one step, without a drying/annealing step in between. Thus, the prepolymer still has a substantial moisture content when it is first exposed to the SSP reaction temperature inside the crystallizer/preheater.Type: GrantFiled: June 26, 2001Date of Patent: June 11, 2002Assignee: Shell Oil CompanyInventor: Ben Duh
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Patent number: 6326456Abstract: Process of producing polytrimethylene terephthalate (PTT) by esterification of terephthalic acid (TPA) with trimethylene glycol (TMG) in the presence of a catalytic titanium compound, precondensation and polycondensation. The sterification is effected in at least two stages, where in the first stage a molar ratio of TMG to TPA of 1.15 to 2.5, a content of titanium of 0 to 40 ppm, a temperature of 240 to 275° C., and a pressure of 1 to 3.5 bar are used. In the at least one subsequent stage a content of titanium is adjusted which is higher than in the initial stage by 35 to 110 ppm.Type: GrantFiled: May 18, 2001Date of Patent: December 4, 2001Assignee: Shell Oil CompanyInventors: Donald Ross Kelsey, Robert Lawrence Blackbourn, Robert Stephen Tomaskovic, Hans Reitz, Eckhard Seidel, Fritz Wilhelm
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Patent number: 6277947Abstract: Process of producing polytrimethylene terephthalate (PTT) by esterification of terephthalic acid (TPA) with trimethylene glycol (TMG) in the presence of a catalytic titanium compound, precondensation and polycondensation. The esterification is effected in at least two stages, where in the first stage a molar ratio of TMG to TPA of 1.15 to 2.5, a content of titanium of 0 to 40 ppm, a temperature of 240 to 275° C., and a pressure of 1 to 3.5 bar are used. In the at least one subsequent stage a content of titanium is adjusted which is higher than in the initial stage by 35 to 110 ppm.Type: GrantFiled: April 21, 2000Date of Patent: August 21, 2001Assignee: Shell Oil CompanyInventors: Donald Ross Kelsey, Robert Lawrence Blackbourn, Robert Stephen Tomaskovic, Hans Reitz, Eckhard Seidel, Fritz Wilhelm
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Patent number: 6258892Abstract: This invention is a toughened alpha-polyamide composition which has been admixed at a maximum shear rate of at least 400 sec−1 and which comprises: (a) 10 to 30, preferably 15 to 25, percent by weight (%wt) of a maleic anyhydride or acid functionalized polydiene polymer, (b) 60 to 89% wt of an alpha-polyamide, and (c) 1 to 10% wt of a polyamide prepared by copolymerizing a diamine and a dicarboxylic acid.Type: GrantFiled: April 27, 1999Date of Patent: July 10, 2001Assignee: Shell Oil CompanyInventor: Michael John Modic
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Patent number: 6258891Abstract: This invention is a solventless process for anionically polymerizing polysiloxane polymers. No volatile hydrocarbon solvent is used. A cyclic siloxane monomer and any comonomer are introduced into a molten polymer phase of a low molecular weight polymer that has a melting point within the polymerization temperature range for the cyclic siloxanes and the comonomer, for example, 30 to 80° C. which is the melting point range for polyethylene wax which is preferred. A non-volatile hydrocarbon oil with a melting point in this range may also be used, especially if a final polymer containing oil is desired. The cyclic siloxane monomer is anionically polymerized in the molten polymer phase or the oil at 30 to 150° C. Ethylene and styrene are preferred comonomers. The low molecular polymer or non-volatile oil is not separated from the polysiloxane after termination of the polymerization.Type: GrantFiled: November 16, 1999Date of Patent: July 10, 2001Assignee: Shell Oil CompanyInventor: Ronald James Hoxmeier
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Patent number: H2030Abstract: Random copolymers of a conjugated diene and at least 50% by weight of a vinyl aromatic compound are prepared by slowly reacting the monomers in a non-polar solvent in the presence of a chelating modifier such as ethylene glycol diethyl ether which results in at least 50% 1,2-polymerization of the conjugated diene.Type: GrantFiled: June 29, 1993Date of Patent: June 4, 2002Assignee: Shell Oil CompanyInventor: Ronald James Hoxmeier