Compound Containing Dicyclopentadiene Moiety Patents (Class 526/283)
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Patent number: 5439992Abstract: A continuous process for the solution polymerization of appropriate polycycloolefins in a ROMP zone to obtain a processable ROMP homo- or copolymer in solution, and subsequent hydrogenation of the ROMP (co)polymer without removing the residual ROMP catalyst and co-catalyst, provides an optical product having a mol wt M.sub.w in the range from 50,000-300,000 and polydispersity M.sub.w /M.sub.n in the range from 1.3-5.0, more preferably from 1.3-3, the lower the polydispersity the more desirable the physical properties of the (co)polymer.Type: GrantFiled: June 6, 1994Date of Patent: August 8, 1995Assignee: The B. F. Goodrich CompanyInventors: Kong S. Yi, Linwood P. Tenney, Parley C. Lane, Jr., John V. Wessel, Nancy S. Marchant
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Patent number: 5438093Abstract: Solution and RIM polymerization of cycloolefins containing at least one norbornene moiety is carried out in the presence of a methathesis catalyst system and an activator, particularly a chlorosilane activator, to obtain faster reaction with higher conversions at lower mold temperatures. The methathesis catalyst system includes an organoammonium molybdate or tungstate catalyst and an alkylaluminum or an alkylaluminum halide cocatalyst. The chlorosilane activator is used at a level of 0.05 to 10 millimoles per mole of the cycloolefin monomers. The polymers of cycloolefins can be impact modified and/or flame-retarded.Type: GrantFiled: June 26, 1992Date of Patent: August 1, 1995Assignee: B. F. Goodrich CompanyInventors: Paul T. Stricharczuk, Robert J. Minchak, Timothy J. Kettering, Dennis J. Janda, Glen R. Gribble, Jr.
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Patent number: 5428098Abstract: A fiber-reinforced cycloolefin polymer material comprises 1 to 99% by weight of reinforcing fibers, in particular glass fibers, and 99 to 1% by weight of a cycloolefin copolymer which is built up froma) at least one (polycyclo)olefin which is derived from norbornene, for example tetracyclododecene, and b) at least one olefin which is chosen from monocycloolefins having 4 to 12 C atoms (VII) and/or the group of acyclic olefins VIII ##STR1## in which R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are identical or different and are a hydrogen atom or a C.sub.1 -C.sub.8 -alkyl radical. VII is preferably ethylene. The monomer units of the (polycyclo)olefin in the cycloolefin copolymer molecule are in each case separated by monomer units of the cyclic olefins VII and/or of the acyclic olefins of the formula VIII.Type: GrantFiled: January 27, 1994Date of Patent: June 27, 1995Assignee: Hoechst AktiengesellschaftInventors: Michael-Joachim Brekner, Horst-Tore Land, Frank Osan
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Patent number: 5410004Abstract: The specification discloses a method for making DCPD based resins that have relatively narrow molecular weight distributions. The method comprises thermally polymerizing dicyclopentadiene monomer in the presence of one or more strong acids, preferably with an olefinic modifier, to provide a dicyclopentadiene oligomer. Optionally, an organic sulfur species can also be used to further effect molecular weight control. For end-use performance in inks, adhesives, coatings and other related areas, the invention provides dicyclopentadiene oligomer resins having weight average molecular weights less than 1000 and relatively narrow molecular weight distributions, as measured by a polydispersity index, of less than about 2.3. Among the strong acids that are effective for controlling molecular weight, hypophosphorous acid is preferred because it gives light colored resins.Type: GrantFiled: January 24, 1994Date of Patent: April 25, 1995Assignee: Arizona Chemical CompanyInventor: Theodore J. Williams
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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: 5391670Abstract: The alkylation resins of this invention comprise the alkylation reaction product of (a) at least one substituted or unsubstituted polycyclic aromatic compound and (b) at least one ethylenically unsaturated hydrocarbon monomer having at least two carbon-carbon double bonds that reacts with the polycyclic aromatic compound by alkylation in the presence of an acid catalyst, wherein the ratio of (a) to (b) in the resin is about 1:9 to about 3:1 by weight. The resins have a weight average molecular weight of less than 10,000 measured by size exclusion chromatography, and a Ring & Ball softening point of about 50.degree. to about 250.degree. C. Because of their high softening point and low molecular weight, the resins are useful in a variety of applications such as flow rate modifiers for engineering polymers, tackifiers for adhesives, and flushing agents for inks.Type: GrantFiled: August 9, 1993Date of Patent: February 21, 1995Assignee: Hercules IncorporatedInventors: Atanu Biswas, Daniel W. Klosiewicz
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Patent number: 5391658Abstract: A process for increasing the molecular weight of cycloolefin monomers is provided by this invention which can be incorporated into ring-opening polymerization methods. This method is particularly suited for bulk polymerization processes but can also be used for solution polymerization processes. By increasing the molecular weight of the cycloolefin monomers, polymers having higher glass transition temperatures are obtained.Type: GrantFiled: January 25, 1989Date of Patent: February 21, 1995Assignee: B. F. Goodrich CompanyInventors: Parley C. Lane, Linwood P. Tenney, George M. Benedikt, Paul T. Stricharczuk
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Patent number: 5387644Abstract: A hardenable monomer composition useful for flooring composition, grouts, mortars and the like comprises a mixture of crosslinkable acrylic monomer, carbon black and/or polyester- or polyether-methane oligomer having at least two polymerizable double bonds and a paraffin oil.The monomer is preferably of the formula I ##STR1## and there is preferably present other monomers, particularly hydroxypropyl methacrylate.Type: GrantFiled: December 14, 1993Date of Patent: February 7, 1995Assignee: Sandoz Ltd.Inventor: Karoly Discho
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Patent number: 5387661Abstract: Polymerizable compositions comprising (a) hydroxypropyl methacrylate; (b) a C.sub.8 to C.sub.10 alkyl ester of acrylic or methacrylic acid; (c) a crosslinking agent; (d) a promoter; and (e) a free-radical initiator.Type: GrantFiled: May 13, 1994Date of Patent: February 7, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: George W. Frost
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Patent number: 5378783Abstract: A highly polymerizable dicyclopentadiene (DCPD) monomer composition is obtained. The dicyclopentadiene so obtained is highly suitable for ring-opening polymerization by metathesis catalysts. The active DCPD yields articles with excellent physical properties upon in-mold polymerization.Type: GrantFiled: May 23, 1991Date of Patent: January 3, 1995Assignee: Nippon Zeon Co., Ltd.Inventors: Kin-ichi Okumura, Masao Torii, Hirotoshi Tanimoto, Motoyuji Yamato
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Patent number: 5369195Abstract: A catalyst and process for the polymerization of cyclic olefins, such as dicyclopentadiene, are disclosed. The catalyst includes a transition metal compound, a co-catalyst and a boron halide promoter. Polymerization can be carried out in a reaction injection molding process to prepare a thermoset molded article having high Tg and superior flexural strength.Type: GrantFiled: November 9, 1992Date of Patent: November 29, 1994Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5366812Abstract: The present invention provides a thermoplastic composition excellent in heat resistance and water resistance which comprises a thermoplastic saturated norbornene polymer which has a number-average molecular weight (Mn) of 50,000-500,000 and a weight-average molecular weight (Mw) of 100,000-2,000,000 which are measured by high performance liquid chromatography, and a molecular weight distribution (Mw/Mn) of 2.2 or more, and a volatile content of at most 0.3% by weight. The composition is suitable for optical materials, electroconductive composite materials and optical recording media.Type: GrantFiled: November 12, 1992Date of Patent: November 22, 1994Assignee: Nippon Zeon Co., Ltd.Inventors: Nobukazu Takahashi, Teiji Kohara, Tadao Natsuume
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Patent number: 5344900Abstract: A process for producing a norbornene polymer consisting essentially of a repeating unit of the formula (I) ##STR1## wherein R.sup.1 to R.sup.12 are the same or different and are hydrogen, C.sub.1 -C.sub.20 hydrocarbon, or a group having a halogen, oxygen or nitrogen, R.sup.5 and R.sup.7 may combine to form a ring, and n is an integer of 0 or more; and having a weight average molecular weight as determined by GPC of 1.times.10.sup.5 to 1.times.10.sup.7. The process comprises polymerizing a norbornene monomer of the formula (II) ##STR2## wherein R.sup.1 to R.sup.12 are the same or different and are independently hydrogen, C.sub.1 -C.sub.20 hydrocarbon, or a substituent containing a halogen atom, an oxygen atom or a nitrogen atom; R.sup.5 and R.sup.Type: GrantFiled: April 30, 1993Date of Patent: September 6, 1994Assignee: Idemitsu Kosan Company LimitedInventors: Hiroshi Maezawa, Junichi Matsumoto, Hideki Aiura, Satoshi Asahi
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Patent number: 5342909Abstract: Processes for the synthesis of several new carbene compounds of ruthenium and osmium are provided. These novel complexes function as stable, well-defined catalysts for the metathesis polymerization of cyclic olefins.Type: GrantFiled: August 13, 1993Date of Patent: August 30, 1994Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Lynda K. Johnson, Sonbinh T. Nguyen
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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: 5288805Abstract: A copolymer of linseed oil and dicyclopentadiene provides a new polymeric vehicle and formulated coating composition which are low in volatile organic compounds (VOCs), yet provide low viscosities which facilitate application to a substrate with existing equipment.Type: GrantFiled: August 14, 1992Date of Patent: February 22, 1994Assignee: Cargill, IncorporatedInventor: Dharma R. Kodali
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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: 5276119Abstract: An improved olefin metathesis catalyst system is disclosed. The catalyst system comprises a transition metal halide metathesis catalyst and an organo transition metal hydride co-catalyst of the formulaL.sub.x --M--Hwherein M is a group IVB transition metal including zirconium, titanium or hafnium; L is a ligand selected independently from the group of hydrogen, halide and organic ligands such as an optionally substituted C.sub.1-20 alkyl or alkenyl, an optionally substituted C.sub.3-20 cycloalkyl or cycloalkenyl having 3 to 6 carbon atoms in the ring, an optionally substituted C.sub.5-20 cycloakadienyl having 5 carbon atoms in the cycloalkadienyl ring, or an optionally substituted C.sub.6-20 aryl or fused aryl, where at least one L is a cycloalkadienyl; and x is one less than the valence of M. The optional substitutions on the organic ligands include halogens, preferably chloride or flouride; C.sub.1-6 alkyl; C.sub.1-6 alkoxy; and C.sub.1-6 haloalkyl. The preferred ligand is a C.sub.Type: GrantFiled: December 29, 1992Date of Patent: January 4, 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: 5268232Abstract: A molded article comprising a cross-linked ring-opened polymer produced by the metathesis polymerization of a dicyclopentadiene (DCPD) monomer, which may be dicyclopentadiene (DCPD) or of a mixture of (DCPD) and norbornene group-containing cycloolefins, in the presence of an effective amount of a metathesis polymerization catalyst and a co catalyst that is capable of crosslinking the unsaturated double bonds of the polymer and thereby increasing the crosslink density of the polymer and its T.sub.g, a process for making it, a process for increasing the T.sub.g of the molded article, and uses of the molded article with a high T.sub.g.Type: GrantFiled: October 15, 1991Date of Patent: December 7, 1993Assignee: Hercules IncorporatedInventors: Nitya P. Khasat, John F. L. Newport
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Patent number: 5266665Abstract: Cyclic olefin metathesis polymerization catalyst comprising metal compounds wherein said metals consist essentially of a minor amount of a transition metal which Will initiate ring-opening metathesis polymerization of a cyclic olefin and a major amount of at least one second metal which will propagate the polymerization, wherein said catalyst is essentially devoid of pyrophoric metal compounds, e.g. metal alkyls, and preformed metal carbenes. A preferred transition metal is ruthenium. Said second metal can comprise aluminum, copper, hafnium, iron (III), iridium, manganese, molybdenum, nickel, niobium, rhenium, rhodium, tantalum, titanium, tungsten, yttrium, a Lanthanide, zinc or zirconium or a mixture thereof. Using such catalyst cyclic olefin, e.g. norbornene derivatives, can be polymerized, e.g. in an extruder, even in the presence of water.Type: GrantFiled: June 1, 1990Date of Patent: November 30, 1993Assignee: Monsanto CompanyInventor: Christopher J. Hardiman
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Patent number: 5262501Abstract: Mixtures essentially comprising compounds of formula I or II ##STR1## wherein X is a hydrogen atom or vinyl, A is a divalent aromatic radical which is unsubstituted or substituted by one or more C.sub.1 -C.sub.20 alkyl groups, halogen atoms or halogen-substituted C.sub.1 -C.sub.20 alkyl groups, R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are each a hydrogen atom, or R.sub.1 and R.sub.1 ', R.sub.2 and R.sub.2 ' and R.sub.3 and R.sub.3 ' are each together ethylene, R.sub.4 is C.sub.1 -C.sub.6 alkyl, phenylalkyl containing 1 to 6 carbon atoms in the alkyl moiety or is trialkylsilyl containing 1 to 6 carbon atoms in each alkyl moiety, m is 0, 1 or 2, n is 0 or an average number from 1 to 200, p is an average number from 1 to 100 and q is 0 or an average number from 1 to 100, can be cured by heating and are suitable for making laminates, especially for fabricating copper-clad circuit boards.Type: GrantFiled: May 12, 1992Date of Patent: November 16, 1993Assignee: Ciga-Geigy CorporationInventors: Sheik Abdul-Cader Zahir, Cecile Pasquier, Wolfgang Scharf, Maurice Dupre
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Patent number: 5254629Abstract: A catalyst and process for the polymerization of cyclic olefins, such as dicyclopentadiene, in the presence of an elastomer polymer, are disclosed. The catalyst includes a transition metal compound, a co-catalyst and a boron halide promoter. Polymerization can be carried out at fast reaction times in a reaction injection molding process to prepare a thermoset molded article having high Tg and superior toughness.Type: GrantFiled: April 29, 1992Date of Patent: October 19, 1993Assignee: Shell Oil CompanyInventors: Donald R. Kelsey, Dale L. Handlin, Jr.
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Patent number: 5248745Abstract: 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: September 23, 1992Date of Patent: September 28, 1993Assignee: Shell Oil CompanyInventors: Willem Sjardijn, Johannes J. M. Snel
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Patent number: 5241031Abstract: Disclosed is a process for improving the unload power of a precursor elastic film comprising orienting the film to a draw ratio in the range of about 2:1 to about 20:1 followed by annealing. Further disclosed is an elastic film oriented to a draw ratio in the range of about 2:1 to about 20:1 and comprising a copolymer of ethylene polymerized with at least one comonomer selected from the group consisting of C.sub.3 to C.sub.20 alpha-olefins and C.sub.3 to C.sub.20 polyenes, wherein the copolymer has a density in the range of about 0.855 g/cm.sup.3 to about 0.9 g/cm.sup.3, a melt index in the range of about 0.5 to about 50, with a composition distribution index at least about 45 percent.Type: GrantFiled: February 19, 1992Date of Patent: August 31, 1993Assignee: Exxon Chemical Patents Inc.Inventor: Aspy K. Mehta
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Patent number: 5229478Abstract: A process for producing a high molecular weight EPDM elastomer having low crystallinity using a bridged bis-metallocene-alumoxane catalyst wherein the metallocene component of the catalyst has the formula: ##STR1## wherein "M" is titanium, zirconium or hafnium; each "R.sup.1 " independently is a C.sub.1 to C.sub.20 linear, branched or cyclic alkyl group or a C.sub.2 to C.sub.4 alkylene which forms a fused ring system; "R.sup.2 " is a C.sub.1 to C.sub.6 linear, branched or cyclic alkylene group, an alkyl substituted silanylene group or an alkyl substituted silaalkylene group; each "X" independently is a halogen, hydride, alkyl, aryl or chelating group, and "y" is an integer of 2 to 4.Type: GrantFiled: October 9, 1990Date of Patent: July 20, 1993Assignee: Exxon Chemical Patents Inc.Inventors: Sigmund Floyd, Elvin L. Hoel
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Patent number: 5219968Abstract: A substantially syndiotactic propylene copolymer which comprises propylene and at least one cyclic diolefin having 6 to 25 carbon atoms or an alkadiene having 6 to 25 carbon atoms and at least one terminal double bond, in the .sup.13 C-NMR spectrum of the copolymer measured in a 1,2,4-trichlorobenzene solution, a peak intensity observed at about 20.2 ppm as the reference of tetramethylsilane at 0.0 ppm being 0.5 or more of the total peak intensity attributed to methyl groups of propylene; the content of the cyclic diolefin or the alkadiene being from 0.01 to 20 mol %; the intrinsic viscosity [.eta.] of the copolymer measured in a tetralin solution at 135.degree. C. being from 0.1 to 10 dl/g.This copolymer can contain an .alpha.-olefin other than propylene, particularly ethylene.Type: GrantFiled: November 12, 1991Date of Patent: June 15, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tetsunosuke Shiomura, Tadashi Asanuma, Masashiro Kouno, Norihide Inoue, Satoshi Fukushima, Yoshiho Sonobe, Kazumi Mizutani, Tutomu Iwatani, Ryuichi Sugimoto
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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: 5212043Abstract: A photoresist composition comprising:a resin soluble in an aqueous alkaline solution, having units of an aliphatic cyclic hydrocarbon main frame and units derived from maleic anhydride and/or units derived from a maleimide; anda photosensitive agent in a sufficient amount to promote or hinder the solubility of said resin in an aqueous alkaline solution upon exposure to active radiation so as to create a substantial difference in the solubility as between an exposed portion and a non-exposed portion and to form a positive or negative image by subsequent development with an aqueous alkaline solution.Type: GrantFiled: October 17, 1990Date of Patent: May 18, 1993Assignee: Tosho CorporationInventors: Takashi Yamamoto, Masaaki Todoko, Toru Seita, Kyoko Nagaoka, Kosaburo Matsumura
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Patent number: 5204420Abstract: A Grignard reagent having the formula RMgX where R is a cycloalkyl or cycloalkenyl group and X is Cl, Br or I, is used as the catalyst activator for the metathesis polymerization of dicyclopentadiene and other polycyclic cycloolefins.Type: GrantFiled: December 23, 1991Date of Patent: April 20, 1993Assignee: Hercules IncorporatedInventor: Tim J. Coffy
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Patent number: 5194534Abstract: This invention relates to a two component catalyst system for the polymerization of metathesis polymerizable cycloolefins, comprising(a) a pure tungsten-imido compound (procatalyst) of the formulaW(NR.sup.1)X.sub.4-x (OR.sup.2).sub.x.L.sub.ywherein x=0, 1, 2, 3 or 4; y=0 or 1; R.sup.1 and R.sup.2 are alkyl, phenyl, phenyl-substituted phenyl, phenylalkyl or halogen substituted derivatives of alkyl, phenyl, phenyl-substituted phenyl or phenylalkyl; X=Br or Cl; where alkyl has 1 to 8 carbon atoms, phenyl-substituted phenyl has 12-18 carbon atoms and phenylalkyl has 7 to 20 carbon atoms; L is a donor ligand; and(b) an activator compound selected from organometals and organometal hydrides with tri-n-butyltin hydride and tri-octyltin hydride the most preferred.Type: GrantFiled: September 24, 1991Date of Patent: March 16, 1993Assignee: Hercules IncorporatedInventor: Andrew Bell
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Patent number: 5191027Abstract: A novel composition is disclosed comprising an alicyclic epoxy compound formed by an epoxidation reaction of a polymerized cyclo olefin compound having double bonds with an epoxidating agent.A cured epoxy resin according to the present invention has excellent heat resistance, outdoor durability, and water resistance, attributable to the absence of ether units derived from the ring-opening of epoxy groups and hydroxyl groups derived from an initiating agent.Type: GrantFiled: May 11, 1990Date of Patent: March 2, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Ikuo Takahashi, Hiroyuki Oshima
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Patent number: 5187012Abstract: The present invention provides a thermoplastic composition excellent in heat resistance and water resistance which includes a thermoplastic saturated norbornene polymer which has a number-average molecular weight (Mn) of 50,000-500,000 and a weight-average molecular weight (Mw) of 100,000-2,000,000 which are measured by high performance liquid chromatography, and a molecular weight distribution (Mw/Mn) of 2.2 or more, and a volatile content of at most 0.3% by weight higher. The composition is suitable for optical materials, electroconductive composite materials and optical recording media.Type: GrantFiled: December 20, 1990Date of Patent: February 16, 1993Assignee: Nippon Zeon Co., Ltd.Inventors: Nobukazu Takahashi, Teiji Kohara, Tadao Natsuume
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Patent number: 5182320Abstract: The present invention provides a material for light-heat energy accumulation and conversion comprising a composition of a high-molecular compound having norbonadien derivative group as side chain with a catalytic matter converting a quadrycylan derivative group of high-molecular side chain into the norbonadien derivative group.The invention also provides a material for light-heat energy accumulation and conversion, characterized by putting to an esterification reaction high-molecular compounds having an epoxy group as side chain with norbonadien carbonic acid or its derivative.Type: GrantFiled: April 1, 1991Date of Patent: January 26, 1993Assignee: Research Development Corporation of JapanInventor: Tadaomi Nishikubo
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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: 5179171Abstract: A random copolymer characterized in that (A) the copolymer comprises polymerized units from ethylene and polymerized units from at least one cycloolefin, (B) the mole ratio of the polymerized units from the cycloolefin to the polymerized units from ethylene is from 3:97 to 60:40, (C) the cycloolefin is incorporated in the polymer chain without ring opening, (D) the copolymer has an intrinsic viscosity of 0.01 to 20 dl/g, (E) the copolymer has a molecular weight distribution (Mw/Mn) of not more than 4, and (F) the copolymer has a crystallinity of 0 to 10%. The random copolymer may be grafted by (a) alpha, beta-unsaturated carboxylic acids and/or their derivatives, (b) styrenes, (c) organic silicon compounds having an olefinically unsaturated bond and a hydrolyzable group, or (d) unsaturated epoxy monomers.Type: GrantFiled: February 10, 1992Date of Patent: January 12, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Syuji Minami, Hirokazu Kajiura, Hidekuni Oda, Hideaki Yamaguchi
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Patent number: 5171811Abstract: A protective coating material comprising polyfunctional (meth)acrylate derivatives of the following formulas 1, 2, 3, 4 and 5 within the following ranges of a, b, c, d and e % by weight, respectively: ##STR1## wherein each of R.sub.1 to R.sub.3 is H or CH.sub.3, and R.sub.4 is CH.sub.2 CH.sub.3 or CH.sub.2 OH, ##STR2## wherein each of R.sub.5 to R.sub.10 is H or CH.sub.3,CH.sub.2 .dbd.C(R.sub.11)COO(CH.sub.2 CH.sub.2 O).sub.n COC(R.sub.12).dbd.CH.sub.2 3wherein each of R.sub.11 and R.sub.12 is H or CH.sub.3, and n is an integer of from 3 to 14, ##STR3## wherein each of R.sub.13 and R.sub.14 is H or CH.sub.3, and R.sub.15 is H or CH.sub.2 OCOC(R.sub.19).dbd.CH.sub.2 wherein R.sub.19 is H or CH.sub.3,CH.sub.2 .dbd.C(R.sub.16)COO(CH.sub.2).sub.n OCOC(R.sub.17).dbd.CH.sub.25wherein each of R.sub.16 and R.sub.17 is H or CH.sub.3, and n is an integer of from 2 to 10.Type: GrantFiled: October 18, 1991Date of Patent: December 15, 1992Assignee: Tosoh CorporationInventors: Yosuke Takahashi, Noriaki Oshima, Yasuhiko Shida
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Patent number: 5171776Abstract: A crosslinked polymer composition obtained by the metathesis polymerization of a dicyclopentadiene monomer in which a chlorinated polymer such as a chlorinated elastomer or chlorinated polypropylene is dissolved; a crosslinked dicyclopentadiene polymer composition comprising a ring-opened dicyclopentadiene polymer and a dicyclopentadiene-soluble chlorinated polymer; and a method for preparing a crosslinked polymer composition comprising adding the chlorinated polymer to one of two reactant liquid streams, one of which contains dicyclopentadiene and a ring-opening metathesis catalyst and the other contains a catalyst activator, combining the two streams, and charging them to a mold or similar forming container in which the dicyclopentadiene polymerizes.Type: GrantFiled: June 19, 1991Date of Patent: December 15, 1992Assignee: Hercules IncorporatedInventor: Nitya P. Khasat
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Patent number: 5155188Abstract: This invention pertains to the use of a novel cocatalyst in ring opening polymerization of a cycloolefin containing a norbornene moiety in conjunction with a metathesis catalyst, said cocatalyst is selected from aluminum-siloxalanes, aluminum-stannoxalanes, aluminum-germoxalanes, aluminum-plumboxalanes, dialuminoxanes, and mixtures thereof.Type: GrantFiled: January 12, 1990Date of Patent: October 13, 1992Assignee: The B. F. Goodrich CompanyInventor: Brian L. Goodall
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Patent number: 5147950Abstract: A catalyst and process for the polymerization of cyclic olefins, such as dicyclopentadiene, are disclosed. The catalyst includes a transition metal compound and a borohydride co-catalyst, with optional boron halide promoter. Polymerization can be carried out in a reaction injection molding process to prepare a thermoset molded article.Type: GrantFiled: August 8, 1991Date of Patent: September 15, 1992Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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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: 5143979Abstract: A molding material suitable as an optical material and an optical recording medium formed of the molding material are disclosed. The molding material comprises a hydrogenated product of a polymer formed by ring-opening polymerization of a norbornene-type monomer, the hydrogenated product having a number average molecular weight (Mn) of 20,000 to 50,000, a weight average molecular weight (Mw) of 40,000 to 80,000 and a molecular distribution (Mw/Mn) of not more than 2.5 and having a volatile content of not more than 0.3% by weight.Type: GrantFiled: June 20, 1990Date of Patent: September 1, 1992Assignee: Nippon Zeon Co., LtdInventors: Yoshikatsu Nishi, Masayoshi Oshima, Tadao Natsuume, Teiji Kohara
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Patent number: 5142006Abstract: 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 biphenol. Polymerization can be carried out in a reaction injection molding process to prepare a thermoset molded article.Type: GrantFiled: January 29, 1990Date of Patent: August 25, 1992Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5140053Abstract: A foamable polymer composition comprising[A] at least one cyclo-olefin resin selected from the group consisting of(A-1) ring-opened polymers derived from cyclo-olefins represented by the following general formula [I],(A-2) ring-opened copolymers derived from the cyclo-olefins of general formula [I],(A-3) hydrogenation products of the ring-opened polymers (A-1),(A-4) hydrogenation products of the ring-opened copolyers (A-2), and(A-5) addition polymers of the cycloolefins of general formula [I] with ethylene, and[B] a blowing agent, ##STR1## wherein n is 0 or a positive integer; R.sup.1 to R.sup.12, independently from each other, represent an atom or a group selected from the class consisting of a hydrogen atom, halogen atoms and hydrocarbon groups; R.sup.9 to R.sup.12 may be linked to each other to form a monocyclic or polycyclic hydrocarbon group; and R.sup.9 and R.sup.10, or R.sup.11 and R.sup.12 may each form an alkylidene group.Type: GrantFiled: February 20, 1990Date of Patent: August 18, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yohzoh Yamamoto, Takasi Nakagawa
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Patent number: 5138003Abstract: Described herein is an oily, transparent reaction product which is prepared by heat treating at 110.degree.-220.degree. C. a dicyclopentadiene and a vinyl aromatic compound. This reaction product can be polymerized by ring-opening in presence or absence of a norbornene monomer to produce a thermoset polymer. Freezing point of the reaction product is below 10.degree. C.Type: GrantFiled: September 23, 1991Date of Patent: August 11, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Kin-ichi Okumura, Munetoshi Nakano, Hirotoshi Tanimoto, Motoyuki Yamato
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Patent number: 5120806Abstract: A metathesis catalyst activator composition consisting essentially of an alkoxyalkylaluminum halide and a tin compound in a molar ratio of about 0.15 to 2 moles of the alkoxyalkylaluminum halide per mole of tin compound.Type: GrantFiled: August 22, 1991Date of Patent: June 9, 1992Assignee: Hercules IncorporatedInventor: Andrea E. Martin
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Patent number: 5118773Abstract: Herein is disclosed a vulcanizable rubber composition comprising a copolymer rubber constituted of ethylene, propylene and nonconjugated polyene, wherein ethylene/propylene molar ratio is 78/22 to 97/3 and the total content of propylene and nonconjugated polyene is 6 to 30% by mole in said copolymer rubber. By the use of the rubber composition of the present invention, a vulcanized product excellent in tensile strength, heat resistance, oil resistance, compression set resistance and flex behavior can be obtained. The vulcanized product can be used as automobile parts and other innumerable articles such as socket cover, heat resistant hose, electric wire, condenser cap, heat resistant belt, vibration-proof rubber, hoses weather strip, seal sponge, black side wall of tire, etc.Type: GrantFiled: October 30, 1991Date of Patent: June 2, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroyoshi Takao, Hiroyuki Harada, Kiyoyuki Sugimori, Nobuyuki Yoshida, Masahiro Fukuyama, Hideaki Yamada, Junichi Koshiba
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Patent number: 5109081Abstract: A continuous thermal polymerization process for the manufacture of cyclic hydrocarbon resins. The molecular weight of polymerized cyclic hydrocarbon resins is controlled with selected process temperatures for the feed, selected times in the reactor, and recycle of thermal polymerized product.Type: GrantFiled: December 28, 1990Date of Patent: April 28, 1992Assignee: Exxon Chemical Patents, Inc.Inventors: Richard B. Pannell, Gerhardt E. Wissler
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Patent number: 5102589Abstract: A method of producing a pore-free polynorbornene article having thick-walled portions is provided. The method comprises providing a monomer charge containing at least one norbornene monomer having a tricyclic or higher cyclic structure; introducing the monomer charge into a mold at a temperature greater than the inside mold temperature; polymerizing the monomer charge under pressure via a ring-opening catalyst system; cooling the molded article; and removing the molded article from the mold.Type: GrantFiled: March 12, 1990Date of Patent: April 7, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Koji Chono, Hiroshi Ozeki, Kazunori Toshima, Motoyuki Yamato
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Patent number: H1388Abstract: A polyolefin composition comprises repeating units of a metathesis polymerizable olefin monomer, a metathesis polymerization procatalyst, a metathesis polymerization procatalyst activator, and at least one member selected from the group consisting of: (i) a Lewis acid catalyst and a Lewis acid cocatalyst, effective to obtain a residual metathesis polymerizable olefin monomer level of from 0 to 0.25 weight percent, based on the weight of the polyolefin; (ii) an anionic polymerization catalyst; (iii) a free radical polymerization initiator; and (iv) a hydrosilation polymerization catalyst. The method for making the composition is also disclosed. The use of metathesis polymerization in conjunction with another type of polymerization can achieve a variety of beneficial effects, including a very low level of residual metathesis polymerizable monomer.Type: GrantFiled: December 23, 1992Date of Patent: December 6, 1994Assignee: Hercules IncorporatedInventor: Albert S. Matlack