Group Iva (ge, Sn, Pb) Or Group Va (as, Sb, Bi) Metal Is Bonded To Hydrogen Or Carbon Atom Patents (Class 526/166)
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Patent number: 8481659Abstract: The present invention relates to cure accelerators useful for anaerobic curable compositions, such as adhesives and sealants.Type: GrantFiled: October 7, 2011Date of Patent: July 9, 2013Assignees: Henkel Corporation, Henkel Ireland Ltd.Inventors: David P. Birkett, Martin Wyer, Andrew Messana, Philip Klemarczyk, Anthony F. Jacobine
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Patent number: 7863394Abstract: A method of polymerizing poly(cyclic)olefin monomers encompassing (a) combining a monomer composition containing the poly(cyclic)olefin monomers, a non-olefinic chain transfer agent and an activator compound to form a mixture; (b) heating the mixture; and (c) adding a polymerization catalyst containing Ni and/or Pd. The non-olefinic chain transfer agent includes one or more compounds selected from H2, alkylsilanes, alkylalkoxysilanes, alkylgermanes, alkylalkoxygermanes, alkylstannanes, and alkylalkoxystannanes. The activator is characterized as having an active hydrogen with a pKa of at least 5. The resulting poly(cyclic)olefin polymers can be used in photoresist compositions.Type: GrantFiled: September 7, 2006Date of Patent: January 4, 2011Assignee: Promerus LLCInventors: Larry F. Rhodes, Dennis A. Barnes, Andrew Bell, Brian K. Bennett, Chun Chang, John-Henry Lipian, Xiaoming Wu
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Publication number: 20090221773Abstract: A method for forming a polymer on a substrate is disclosed. The method may include providing a substrate having a substrate surface, the substrate surface being at least partially hydrogen-terminated and reacting the substrate surface in a solution comprising at least one radical initiator and at least one monomer to form a polymer on the substrate surface. The monomer may comprise at least one of a monofunctional monomer and a polyfunctional monomer. A stationary phase for use in separation applications such as chromatography and solid-phase extraction is also disclosed. The stationary phase may include a plurality of diamond bodies and a polymeric compound covalently bonded to at least a surface portion of the plurality of diamond particles.Type: ApplicationFiled: February 28, 2008Publication date: September 3, 2009Applicant: Brigham Young UniversityInventors: Matthew R. Linford, Li Yang
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Patent number: 7446073Abstract: The present invention relates to a cyclic germanium bridged bulky ligand metallocene-type catalyst compound, a catalyst system thereof, and to its use in a process for polymerizing olefin(s) to produce enhanced processability polymers.Type: GrantFiled: October 19, 2004Date of Patent: November 4, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Donna J. Crowther, Phillip T. Matsunaga
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Publication number: 20080207855Abstract: A robust, impurity tolerant method of making substantially linear polymers of acyclic aliphatic olefins using catalyst complexes comprising a single palladium metal center and a substituted tri-aryl ligand is disclosed.Type: ApplicationFiled: February 20, 2008Publication date: August 28, 2008Inventors: David M. Conner, Brian Leslie Goodall, Lester Howard McIntosh
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Patent number: 7323526Abstract: A supported catalyst composition having improved flow properties is disclosed comprising an alkylalumoxane, a metallocene-alkyl an inorganic oxide support having an average particle size of from 0.1 to 50 ?m and calcined at a temperature greater than 600° C., and optionally an antifoulant agent and. In one embodiment, the metallocene-alkyl is a Group 4, 5 or 6 metallocene-alkyl, and in another embodiment is a hafnocene-alkyl. Also disclosed is a method of polymerization using such a supported catalyst composition.Type: GrantFiled: July 29, 2005Date of Patent: January 29, 2008Assignee: Univation Technologies, LLCInventors: Agapios K. Agapiou, Phuong Anh Cao, Sun-Chueh Kao
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Patent number: 7202316Abstract: A modified particle obtained by a process containing contacting a Bi compound, a compound having an electron-withdrawing group and an active hydrogen and particle; and a catalyst component for addition polymerization containing the modified particle; a catalyst for addition polymerization prepared by a process containing contacting the modified particle (A) and a transition metal compound of Groups 3 to 11 or lantanide series (B); and a catalyst for addition polymerization prepared by a process containing contacting the modified particle (A) and a transition metal compound of Groups 3 to 11 or lantanide series (B) and an orbanoaluminum compound (C); and a process for producing an addition polymer with the catalyst.Type: GrantFiled: September 22, 2003Date of Patent: April 10, 2007Assignee: Sumitomo Chemical Company, LimitedInventor: Kazuo Takaoki
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Patent number: 7037990Abstract: A method is provided for the polymerization of olefins substituted with a functional group using a transition metal catalyst that, by virtue of one or more stabilizing groups incorporated within the catalyst structure, “fixes” the stereoconfiguration of each olefinic monomer relative to the transition metal complex during each successive reaction in the polymerization process. The invention substantially reduces the likelihood of olefin rearrangement at the active site of the catalyst during polymerization. In one particular embodiment, the functional group is a polar, electron-donating group and the stabilizing group is a Lewis acid substituent; examples of polymers that can be prepared with such a system include poly(vinyl acetate), poly(vinyl alcohol), and poly(vinyl ethers). Novel complexes and catalyst systems useful in the polymerization method are also provided.Type: GrantFiled: January 3, 2003Date of Patent: May 2, 2006Assignee: Nippon Synthetic Chemical CompanyInventors: Christopher D. Tagge, Robert B. Wilson, Jr., Hiroyuki Ono
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Patent number: 6982306Abstract: This invention relates to the field of olefin polymerization catalyst compositions, and methods for the polymerization and copolymerization of olefins, including polymerization methods using a catalyst composition. One aspect of this invention is the formation and use of a catalyst composition comprising a stannoxy-substituted half-sandwich metallocene and an activator for olefin polymerization processes. For example, this invention encompasses the preparation of (?5-C5H5)Ti(OSnPh3)Cl2, its contact with an activator, for example, zinc-impregnated chlorided alumina, to form a catalyst composition, and the use of this catalyst composition for polymerizing olefins or acetylenes.Type: GrantFiled: November 26, 2003Date of Patent: January 3, 2006Assignee: Chevron Phillips Chemical Company, L.P.Inventors: Joel L. Martin, Michael D. Jensen, Max P. McDaniel
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Patent number: 6936393Abstract: A catalyst for preparing a polyester for a toner, comprising an inorganic tin(II) compound; a polyester resin composition comprising a polyester and the catalyst; and a toner comprising the polyester resin composition. The catalyst for preparing a polyester is suitably used for a toner which is used for developing electrostatic latent images formed in electrophotography, electrostatic recording method, electrostatic printing method, and the like.Type: GrantFiled: December 4, 2002Date of Patent: August 30, 2005Assignee: Kao CorporationInventors: Takashi Kubo, Katsutoshi Aoki, Eiji Shirai, Masayuki Maruta
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Patent number: 6870016Abstract: Olefin polymerization processes using catalyst systems based on metallocenes and olefin, in particular, propylene polymers obtainable thereby. The metallocenes may be represented by the formula: ? wherein M1 preferably is zirconium or hafnium; and R12 is different from hydrogen.Type: GrantFiled: June 29, 2001Date of Patent: March 22, 2005Assignee: ExxonMobil Chemical Patents Inc.Inventors: Terry J. Burkhardt, James R. Hart, William T. Haygood, Robert T. Li
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Patent number: 6818585Abstract: The present invention relates to a cyclic germanium bridged bulky ligand metallocene-type catalyst compound, a catalyst system thereof, and to its use in a process for polymerizing olefin(s) to produce enhanced processability polymers.Type: GrantFiled: September 18, 2001Date of Patent: November 16, 2004Assignee: Univation Technologies, LLCInventors: Donna J. Crowther, Phillip T. Matsunaga, Ching-Tai Lue
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Patent number: 6528596Abstract: A modified particles obtained by contacting particles(a) with a metal compound(b) selected from the group consisting of compounds of the Group VI, VII, XIV metal elements and compounds of the lanthanide series, and contacting the particles with a compound(c) having a functional group containing active hydrogen or a non-proton donative Lewis basic functional group and an electron-withdrawing group; a carrier composed of the modified particles; a catalyst component for olefin polymerization composed of said modified particles; a catalyst for olefin polymerization obtained by contacting the modified particles(A) and a transition metal compound(B), or further an organometallic compound(C); and a process for producing an olefin polymer with the catalyst.Type: GrantFiled: December 22, 2000Date of Patent: March 4, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuo Takaoki, Tatsuya Miyatake
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Patent number: 6172168Abstract: In the case of Ziegler catalysts based on a metallocene as the transition metal component and an aluminoxane as the activator, preactivation of the metallocene with the aluminoxane results in a considerable increase in the activity of the catalyst system. Furthermore, 1-olefin polymers of a high degree of isotacticity and having compact, spherical particles, a very narrow particle size distribution and a high bulk density are obtained by means of a catalyst system of this type.Type: GrantFiled: December 14, 1999Date of Patent: January 9, 2001Assignee: Targor GmbHInventors: Andreas Winter, Walter Spaleck
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Patent number: 6143842Abstract: Disclosed herein are novel polymers and copolymers of alphaolefins produced using various Ziegler/Natta and Metallocene catalysts. Commercial production of these polymers is now possible for the first time owing to the polymer harvesting technology also disclosed herein.Type: GrantFiled: June 29, 1998Date of Patent: November 7, 2000Assignee: Huntsman Polymers CorporationInventors: Samuel J. Paton, Stephen C. McHaney, Steven L. Oetting, Karl L. Herzog
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Patent number: 6034192Abstract: This invention relates to a process for polymerizing ethylene comprising contacting ethylene and optional comonomers with a catalyst system comprising an activator and a transition metal compound represented by the formula: ##STR1## Wherein R.sub.1 and R2 are independently hydrogen or a group having up to 100 carbon atoms, Cp.sub.1 is a bulky ligand; Cp.sub.2 is a bulky ligand or a heteroatom optionally bound to a C.sub.1 to C.sub.50 hydrocarbyl group, n is the valence state of the transition metal, Tm is a Group 3 to 10 metal, and each X is independently an anionic leaving group.Type: GrantFiled: December 30, 1998Date of Patent: March 7, 2000Assignee: Univation Technologies, LLCInventors: Donna J. Crowther, Natalie A. Merrill, Ching-Tai Lue
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Patent number: 6017841Abstract: In the case of Ziegler catalysts based on a metallocene as the transition metal component and an aluminoxane as the activator, preactivation of the metallocene with the aluminoxane results in a considerable increase in the activity of the catalyst system. Furthermore, 1-olefin polymers of a high degree of isotacticity and having compact, spherical particles, a very narrow particle size distribution and a high bulk density are obtained by means of a catalyst system of this type.Type: GrantFiled: May 1, 1997Date of Patent: January 25, 2000Assignee: Targor GmbHInventors: Andreas Winter, Walter Spaleck
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Patent number: 5767210Abstract: This process is characterized by the fact that at least one of the said monomers is polymerized or copolymerized in bulk, solution, emulsion or suspension, at a temperature that can be as low as 0.degree. C., in the presence of an initiation system including: at least one compound generating radicals, other than bromofluorene, and at least one catalyst consisting of a complex of palladium in the 0 oxidation state, denoted by the following formula (I): Pd(0)L.sup.1 L.sup.2 L.sup.3 L.sup.4 in which each of L.sup.1, L.sup.2, L.sup.3 and L.sup.4, which are identical or different, denotes a ligand which may be a chiral ligand, which is chosen from PRR'R", P(OR)(OR')(OR"), NRR'R", ORR', SRR', SeRR', AsRR'R", SbRR'R", where each of R, R' and R" independently denotes a C.sub.1 -C.sub.14 alkyl group, optionally substituted, or an optionally substituted aromatic group, it being possible for at least two of these ligands to be joined to one another by one or more divalent radicals.Type: GrantFiled: March 27, 1997Date of Patent: June 16, 1998Assignee: Elf Atochem, S.A.Inventors: Philippe Lecomte, Philippe Dubois, Robert Jerome, Philippe Teyssie, Thierry Senninger
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Patent number: 5728784Abstract: Process for the preparation of crystalline vinylaromatic polymers with a predominantly syndiotactic structure which comprises polymerizing vinylaromatic monomers, alone or mixed with at least one other monomer, in the presence of a catalytic system essentially consisting of:a) a complex of titanium or zirconium selected from those having general formula:MR.sub.1 R.sub.2 R.sub.3 R.sub.4, A.sub.1 MR.sub.1 R.sub.2 R.sub.3, A.sub.1 A.sub.2 MR.sub.1 R.sub.2 (I)b) a co-catalyst selected from an alkylalumoxane and a compound of boron having formula (II):BX.sub.1 X.sub.2 X.sub.3 (II)or one of its salts;c) a derivative of tin having general formula:SnR.sub.5 R.sub.6 R.sub.7 R.sub.Type: GrantFiled: November 27, 1996Date of Patent: March 17, 1998Assignee: Enichem S.p.A.Inventors: Riccardo Po', Nicoletta Cardi, Roberto Santi
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Patent number: 5621047Abstract: This invention relates to a process for preparation of non-crosslinked linear monofunctional and telechelic difunctional unsaturated polymers wherein the functional groups are acrylate or methacrylate groups. The average functionality number of the monofunctional unsaturated polymers is at least 0.7, as determined by nuclear magnetic resonance spectroscopy (NMR). The average functionality number of the telechelic difunctional polymers is at least 1.7, as determined by NMR. Alkyl acrylates or alkyl methacrylates are reacted with cyclic olefinic non-conjugated compounds or unsaturated hydrocarbon polymers to prepare monofunctional and difunctional polymers. The process is substantially free of side reactions comprising double bond migration and cyclization.Type: GrantFiled: October 13, 1995Date of Patent: April 15, 1997Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson, Steven A. Cohen, William G. Bouslog
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Patent number: 5589548Abstract: This invention relates to difunctional telechelic linear non-crosslinked polyolefins without pendant chain branched groups. The polyolefin compounds of this invention are useful for preparing high molecular weight polyesters, polyamides, polyureas and polyurethanes of high density without branching of the polymer chains, and with low permeability to gases and solvents.Type: GrantFiled: June 2, 1995Date of Patent: December 31, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson
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Patent number: 5585509Abstract: Metallocene complexes of the general formula I ##STR1## where the substituents Y, M, x, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are as described in the disclosure, and ligand systems of the general formula II ##STR2## as intermediates.Type: GrantFiled: March 1, 1995Date of Patent: December 17, 1996Assignee: BASF AktiengesellschaftInventors: Franz Langhauser, David Fischer, J urgen Kerth, G unther Schweier, Hans-Herbert Brintzinger, Elke Barsties, Werner Roell
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Patent number: 5519101Abstract: A polymerization process for preparation of oligomers and polymers having at least one internal carbon-to-carbon double bond and containing functional groups comprising terminal carbon-to-carbon double bonds is disclosed. The polymerization process is substantially free of side reactions comprising double bond migration. The oligomers and polymers are prepared from acyclic polyenes of from 2 to about 30 carbon atoms. The catalyst system comprises a metathesis catalyst (A) comprising a transition metal compound, an activator (B) selected from the group consisting of organic tin compounds and organic aluminum halides and (C) an organic Lewis base. Yields are at least 60% of theoretical based on acyclic polyene reactant.Type: GrantFiled: May 27, 1993Date of Patent: May 21, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Vahid Bagheri
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Patent number: 5512635Abstract: This invention relates to a process for preparation of non-crosslinked linear monofunctional and telechelic difunctional unsaturated polymers wherein the functional groups are reactive terminal groups other than vinyl groups. The average functionality number of the monofunctional unsaturated polymers is at least 0.7, as determined by nuclear magnetic resonance spectroscopy (NMR). The average functionality number of the telechelic difunctional polymers is at least 1.7, as determined by NMR. Monofunctional olefins and difunctional olefins are reacted with cyclic olefins or unsaturated polymers to prepare difunctional polymers. The process is substantially free of side reactions comprising double bond migration and cyclization.Type: GrantFiled: December 15, 1993Date of Patent: April 30, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Howard B. Yokelson, Steven A. Cohen, Raymond T. Behrends, William G. Bouslog, James P. Nelson
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Patent number: 5405924Abstract: An olefin metathesis catalyst system and process for the metathesis polymerization of cyclic olefins, such as dicyclopentadiene, are disclosed. The catalyst system comprises the reaction product of:(a) an imido transition metal halide complex of formula: ##STR1## wherein Ar is C.sub.6-20 aryl, preferably phenyl; M is a transition metal selected from the second and third rows of Groups 5, 6, 7 and 8 of the Periodic Table (IUPAC 1989 convention) and including for example niobium, tantalum, molybdenum, tungsten, rhenium, ruthenium or osmium, preferably tungsten or molybdenum; R is independently halide, C.sub.1-20 alkyl, C.sub.1-12 alkoxy, C.sub.1-12 haloalkyl, C.sub.6-20 aryl, C.sub.6-20 aryloxy, cyano or combinations thereof; L is independently a complexing ligand selected from carbonyl, C.sub.1-12 alkoxy, C.sub.1-12 haloalkoxy, C.sub.1-12 alkyl ethers, including mono-, di- and higher ethers, C.sub.12 alkylnitriles, C.sub.5-20 pyridines, C.sub.Type: GrantFiled: June 22, 1994Date of Patent: April 11, 1995Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5403904Abstract: 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: GrantFiled: May 27, 1993Date of Patent: April 4, 1995Assignee: Amoco CorporationInventors: Philip O. Nubel, Robert B. Morland, Howard B. Yokelson
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Patent number: 5391661Abstract: There are disclosed a catalyst well suited for producing a styrenic polymer having a high degree of syndiotactic configuration which comprises a transition-metal compound such as pentamethylcyclopentadienyltrimethyltitanium and a coordination complex compound comprising an anion in which a plurality of radicals are bonded to a metal and a quaternary ammonium salt, the compound being exemplified by orthocyano-N-methylpyridinium tetra(pentafluorophenyl)borate, or comprises an alkylating agent such as triisobutylaluminum in addition to the above two compounds; and a process for producing a styrenic polymer having a high degree of syndiotactic configuration by polymerizing a styrenic monomer using the aforementioned catalyst. Consequently, a styrenic polymer having a high degree of syndiotactic configuration can be produced effectively without the use of an expensive aluminoxane required in a large amount if used.Type: GrantFiled: February 2, 1993Date of Patent: February 21, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Shoji Naganuma, Masami Watanabe, Norio Tomotsu
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Patent number: 5374753Abstract: An organometal complex is provided which is represented by the general formula (1) below: ##STR1## wherein Cp.sup.1 and Cp.sup.2 are respectively a substituted or unsubstituted cyclopentadienyl group; R.sup.1 is a group selected from alkylene groups or arylalkylene groups having 1 to 20 carbons, dialkylsilylene groups, dialkylgermanylene groups, alkylphosphinediyl groups, or alkylimino groups and R.sup.1 crosslinking Cp.sup.1 and Cp.sup.2 together; m is 0 or 1; M is selected from titanium, zirconium, and hafnium; R.sup.2, R.sup.3, and R.sup.4 are independently hydrogen, a hydrocarbon group of 1 to 12 carbons, an alkoxyl group, or an aryloxy group; and MAO is a methylalumoxane group. This organometal complex is capable of producing selectively an olefin polymer without use of any other additional catalyst component.Type: GrantFiled: September 7, 1993Date of Patent: December 20, 1994Assignee: Tosoh CorporationInventors: Satoru Yamada, Akihiro Yano
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Patent number: 5319042Abstract: This invention relates to a two component catalyst system for the polymerization of metathesis polymerizable cycloolefins, comprising (a) a tungsten compound of the formula WOX.sub.4-x (OAr).sub.x where X is chlorine, bromine or fluorine, Ar is a hindered phenyl ring having 1-5 specified substituents and x = 1, 2 or 3; and (b) an activator compound.Among the preferred molecules or groups that are substituted on the phenyl ring of the tungsten compound are phenyl, chlorine, bromine, methoxy and isopropyl groups. Ar can also represent a multi-substituted phenyl group such as 2,4-dichloro-6-methylphenyl.Type: GrantFiled: October 18, 1991Date of Patent: June 7, 1994Assignee: Hercules IncorporatedInventor: Andrew Bell
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Patent number: 5300605Abstract: Poly(1-hydro-1-R-1-silapent-3-ene) homopolymers and copolymers contain silane segments with reactive silicon-hydride bonds and contain hydrocarbon segments with cis and trans carbon-carbon double bonds.Type: GrantFiled: March 19, 1993Date of Patent: April 5, 1994Assignee: University of Southern CaliforniaInventors: William P. Weber, Xiugao Liao
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Patent number: 5278305Abstract: A catalyst and process for the polymerization of cyclic olefins, such as dicyclopentadiene, are disclosed. The catalyst comprises the reaction product of a transition metal halide and a 1,4-hydroquinone of the general formula: ##STR1## wherein R is independently selected from the group of hydrogen, C.sub.1-12 alkyl, C.sub.6-20 aryl, halide, and C.sub.1-6 haloalkyl. Optional co-catalysts include borohydrides, organo tin hydrides and organo aluminum compounds. Polymerization can be carried out in a reaction injection molding process to prepare a molded article.Type: GrantFiled: December 31, 1992Date of Patent: January 11, 1994Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5276118Abstract: A catalyst and process for the metathesis polymerization of cyclic olefins, such as dicyclopentadiene, are disclosed. The catalyst comprises the reaction product of a transition metal halide preferably tungsten, molybdenum, or tantalum halides and a diaryl carbinol of the formula ##STR1## wherein G is independently C.sub.1-12 alkyl, C.sub.1-12 alkoxy, C.sub.1-12 alkylamino, C.sub.6-20 aryl, halide, or C.sub.1-6 haloalkyl; g is independently 0 to 4; R is independently hydrogen or G or the R's are combined as a single bond or as a bridging group X, where X is CH.sub.2, CH.sub.2 CH.sub.2, O, S, SO, SO.sub.2 or NR.sup.1, and R.sup.1 is H or C.sub.1-6 alkyl. Optional co-catalysts include borohydrides, organo tin hydrides and organo aluminum compounds. Polymerization can be carried out in a reaction injection molding process to prepare a molded article.Type: GrantFiled: December 31, 1992Date of Patent: January 4, 1994Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5260498Abstract: An improved process for the production of 1:1 molar adducts of 4-vinylcyclohexene and cyclopentadiene, primarily 5-(3-cyclohexen-1-yl)-2-norbornene, comprises contacting 4-vinylcyclohexene and dicyclopentadiene at elevated temperature in a suitable reactor, separating the resulting mixture of adducts into light product comprising predominately the 1:1 molar adduct and a heavy product comprising higher adducts and cyclopentadiene oligomers, and recycling the bottoms product to the reactor.Type: GrantFiled: December 7, 1992Date of Patent: November 9, 1993Assignee: Shell Oil CompanyInventor: Robert H. Ellison
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Patent number: 5218065Abstract: An improved olefin metathesis catalyst system comprises a tungsten halide having an average of no more than about one halide substituent and no more than one oxygen substituent per tungsten with the remaining tungsten valences satisfied with phenolic substituents incorporating at least one meta or para electron withdrawing group and a triorganotin hydride and, optionally, a boron halide promoter. The catalyst system forms a relatively stable polymerization mixture with polycycloolefins and effectively polymerizes dicyclopentadiene in the presence of water.Type: GrantFiled: August 30, 1991Date of Patent: June 8, 1993Assignee: Shell Oil CompanyInventors: Donald R. Kelsey, Betty M. Scardino, Dale L. Handlin, Jr.
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Patent number: 5180867Abstract: A process for the production of thermoset copolymers having tailored product properties such as high glass transition temperature and/or increased cross-linking, the process comprising contacting a comonomer mixture with a methathesis catalyst system obtainable by combining at least a catalyst component and an activator component, wherein the comonomer is selected from compounds according to the formulae: ##STR1##Type: GrantFiled: November 20, 1989Date of Patent: January 19, 1993Assignee: Shell Oil CompanyInventors: Willem Sjardijn, Johannes J. M. Snel
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Patent number: 5143992Abstract: An improved thermoset polymer having good mechanical properties and no detectable dicyclopentadiene odor is obtained by the ring-opening polymerization of a novel mixture of adducts comprising divinyl cyclohydrocarbon compound, such as 3,5-divinylcyclopentene and cyclopentadiene, optionally with added cycloolefinic compound, such as dicyclopentadiene, at polymerization conditions in the presence of an olefin metathesis catalyst.Type: GrantFiled: July 12, 1991Date of Patent: September 1, 1992Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5095082Abstract: A hard, infusible, crosslinked polymeric product free from detectable cyclopentadiene odor is obtained by contacting, under polymerization conditions, a mixture of Diels-Alder adducts of 4-vinylcyclohexene and cyclopentadiene and Diels-Alder oligomers of cyclopentadiene of at least 3 cyclopentadiene units with an olefin methathesis catalyst.Type: GrantFiled: June 10, 1991Date of Patent: March 10, 1992Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5082909Abstract: This invention relates to a two component catalyst system for polymerization of metathesis polymerizable cycloolefins, comprising(a) a tungsten compound of the formula WOCl.sub.4-x (OAr).sub.x wherein Ar represents a hindered phenyl ring having bulky alkyl, alkoxyl halogen or aryl groups in the 2,6 position, i.e., diisopropyl or phenyl group and x=1, 2 or 3; and(b) an activator compound that is triphenyl tin hydride or trialkyl tin hydride, preferably a tributyltin hydride.Among the preferred molecules or groups that are substituted on the phenyl ring of the tungsten compound include chlorine, bromine, phenyl, methoxy and isopropyl. Ar may also represent a multisubstituted phenyl group such as 2,4-dichloro-6-methyl phenyl.Type: GrantFiled: October 12, 1990Date of Patent: January 21, 1992Assignee: Hercules IncorporatedInventor: Andrew Bell
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Patent number: 5081208Abstract: A process is described for the polymerization of dicyclopentadiene using a novel catalyst system comprising (a) a tungsten compound which is the reaction product of a tungsten halide with a phenol which is not substituted with a bulky alkyl group at positions ortho with respect to the hydroxyl group, and (b) a trihydrocarbyl tin hydride.Type: GrantFiled: October 9, 1990Date of Patent: January 14, 1992Assignee: Shell Oil CompanyInventor: Willem Sjardijn
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Patent number: 5019544Abstract: This invention is a process for preparing a polymer which comprises contacting pure dicyclopentadiene with a pure tungsten catalyst complex, such as WCl.sub.3 (2,6-diisopropylphenoxy).sub.3, when tributyl tin hydride or triphenyl tin hydride is used as the activator for the polymerization. This process affords a method of polymerization of dicyclopentadiene in which the mixture gels slowly without the use of a rate moderator at 80.degree. C. (in from about 15 seconds to as much as two minutes or more) and furthermore cures quite slowly (in about 3-6 minutes). This delay makes these compositions particularly applicable to reaction injection molding processes. Moreover, both the tungsten complexes and the tin activator compounds employed in this invention are relatively insensitive to oxygen and water.Type: GrantFiled: August 9, 1990Date of Patent: May 28, 1991Assignee: Hercules IncorporatedInventor: Andrew Bell
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Patent number: 5011730Abstract: Dielectric supports for electronic components, such as circuit boards, are provided which are comprised of two or more bulk polymerized norbornene-type monomers. The monomers may be easily processed into circuit boards, etc. by reaction injection molding. The copolymers obtained exhibit high heat distortion temperatures and good dielectric properties and a balance of properties that make them, for example, well suited for molded wire board materials.Type: GrantFiled: April 11, 1989Date of Patent: April 30, 1991Assignee: The B. F. Goodrich CompanyInventors: Lindwood P. Tenney, David J. Smith, Dennis J. Janda, Dennis A. Barnes
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Patent number: 4981931Abstract: This invention is a process for preparing a polymer which comprises contacting pure dicyclopentadiene with a pure tungsten catalyst complex, such as WCl.sub.3 (2,6-diisopropylphenoxy).sub.3, when tributyl tin hydride or triphenyl tin hydride is used as the activator for the polymerization. This process affords a method of polymerization of dicyclopentadiene in which the mixture gels slowly without the use of a rate moderator at 80.degree. C. (in from about 15 seconds to as much as two minutes or more) and furthermore cures quite slowly (in about 3-6 minutes). This delay makes these compositions particularly applicable to reaction injection molding processes. Moreover, both the tungsten complexes and the tin activator compounds employed in this invention are relatively insensitive to oxygen and water.Type: GrantFiled: February 24, 1989Date of Patent: January 1, 1991Assignee: Hercules IncoporatedInventor: Andrew Bell
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Patent number: 4943621Abstract: Methods of preparing storage stable components useful for metathesis bulk polymerization of cycloolefin monomers are provided. These components contain cycloolefins with norbornene-functional groups and cocatalysts activated with a halometal compound. In these methods, the cocatalyst is completely formed before the halometal activator is added to prevent the formation of unwanted hydrogen halides, which catalyze undesired crosslinking reactions which destabilize the cocatalyst component. Bulk polymerization systems are provided wherein these storage stable cocatalyst components are paired with catalyst components that together form the complete metathesis catalyst system. For some embodiments, storage stability is aided by the removal of water.Type: GrantFiled: August 4, 1988Date of Patent: July 24, 1990Assignee: The B. F. Goodrich CompanyInventors: Dennis J. Janda, Paul T. Stricharczuk, Robert J. Minchak
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Patent number: 4933402Abstract: Disclosed is a method of delaying the metathesis polymerization of strained ring cycloolefins by addition of certain phosphorus-containing compounds including various aryl phosphates, aliphatic phosphates, aliphatic phosphites, aryl phosphites, aryl phosphines and alkyl phosphines.Type: GrantFiled: December 30, 1988Date of Patent: June 12, 1990Assignee: Hercules IncorporatedInventor: Albert S. Matlack
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Patent number: 4923936Abstract: This invention pertains to the use of organoammonium, organophosphonium, organoarsonium heteropolymolybdates and heteropolytungstates, and mixtures thereof, as catalysts in a metathesis catalyst system in polymerization of cycloolefin monomers by ring opening polymerization. Polymerization can be by reaction injection molding in absence of a solvent whereby a thermoset polymer is produced or by solution polymerization in presence of a suitable solvent whereby a thermosetting or a thermoplastic polymer is produced. The cycloolefin monomers are selected from monocycloolefins except cyclohexane, polycycloolefins containing at least one norbornene group, and mixtures thereof.Type: GrantFiled: February 21, 1989Date of Patent: May 8, 1990Assignee: The BFGoodrich CompanyInventors: Brian L. Goodall, Larry F. Rhodes
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Patent number: 4886861Abstract: Free radical polymerization processes employing cobalt(II) chelates of vicinal iminohydroxyimino- and dihydroxyiminoalkanes, N,N'-bis(salicylidene)ethylenediamines and porphyrins as catalytic chain transfer agents, in admixture with certain Lewis bases, for controlling the molecular weight of the homopolymers and copolymers produced.Type: GrantFiled: April 16, 1987Date of Patent: December 12, 1989Assignee: E. I. DuPont de Nemours and CompanyInventor: Andrew H. Janowicz
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Patent number: 4810762Abstract: The invention is a process for preparing a polymer which comprises contacting dicyclopentadiene with a catalyst comprising a phenolic substituted tungsten halide and a trialkyltin hydride or triphenyltin hydride and recovering said polymer. The invention is also a polymer of dicyclopentadiene as prepared in the process of the invention and a catalyst used in the process of the invention to prepare said polymer.Type: GrantFiled: September 24, 1987Date of Patent: March 7, 1989Assignee: Shell Oil CompanyInventors: Willem Sjardijn, Arris H. Kramer
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Patent number: 4729976Abstract: The invention is a process for preparing a polymer which comprises contacting dicyclopentadiene with a catalyst comprising a phenolic substituted tungsten halide and a trialkyltin hydride or triphenyltin hydride and recovering said polymer. The invention is also a polymer of dicyclopentadiene as prepared in the process of the invention and a catalyst used in the process of the invention to prepare said polymer.Type: GrantFiled: October 27, 1986Date of Patent: March 8, 1988Assignee: Shell Oil CompanyInventors: Willem Sjardijn, Arris H. Kramer
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Patent number: 4701510Abstract: Thermoset polycycloolefins are obtained by polymerzing at an elevated temperature a cycloolefin containing at least one norbornene group in the presence of a metathesis catalyst system and also in the presence of an effective amount of a polyfunctional cycloolefin crosslinker containing at least one norbornene group, but preferably two or more, with two or more unsaturated sites, preferably two or more double bonds.Type: GrantFiled: December 16, 1985Date of Patent: October 20, 1987Assignee: The B.F. Goodrich CompanyInventors: Robert J. Minchak, Parley C. Lane, Jr.
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Patent number: RE35717Abstract: A cycloolefin copolymerization method, feed composition and product made from the feed which includes: a nonpolar cycloolefin, a polar cycloolefin and a catalyst. Preferably, the nonpolar cycloolefin is dicyclopentadiene, the catalyst comprises WCl.sub.6, the polar cycloolefin is an ester, and the composition also includes an activator.Type: GrantFiled: September 17, 1993Date of Patent: January 20, 1998Assignee: Metton America, Inc.Inventor: Steven H. Nahm