Contains An Exterior Ethylenic Substituent Bonded To A Single Carbon Atom Of The Bridged Ring System Patents (Class 526/282)
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Patent number: 5204427Abstract: A reaction solution comprising a mixture of tricyclopentadiene, a norbornene monomer with at least 3 rings in its backbone, a 5-alkenyl-2-norbornene pot life adjusting agent along with a molybdenum type catalyst system gives prolonged pot life without extending time to exotherm (e.g., smoking time). By utilizing this reaction solution it is possible to bulk polymerize reinforced or unreinforced articles in a mold via ring-opening polymerization. Articles so obtained have good outward appearance and excellent physical properties.Type: GrantFiled: May 24, 1991Date of Patent: April 20, 1993Assignee: Nippon Zeon Co., Ltd.Inventors: Masao Torii, Tomoo Sugawara, Kin-ichi Okumura, Motoyuki Yamato
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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: 5191041Abstract: An inert hydrocarbon solvent-soluble catalyst for polymerization of olefinic hydrocarbons and a process for producing an olefinic polymer using the same are disclosed, the catalyst being composed of (A) a reaction product obtained by reacting (a) at least one vanadium compound represented by formula:VO(OR).sub.m X.sub.3-mwherein R represents a hydrocarbon group; X represents a halogen atom; and m represents a real number of from 0 to 3, and (b) a dihydroxy hydrocarbon compound constituted of a straight chain hydrocarbon skeleton containing from 2 to 12 carbon atoms and having a hydroxyl group at each of both terminals thereof and at least one hydrocarbon branch bonded to said hydrocarbon skeleton in an inert hydrocarbon solvent at an (a) to (b) molar ratio of from 1:0.5 to 1:1.4 and (B) at least one organoaluminum compound represented by formula:R'.sub.n AlX'.sub.3-nwherein R' represents a hydrocarbon group; X' represents a halogen atom; and n represents a real number more than 0 and less than 3.Type: GrantFiled: January 16, 1992Date of Patent: March 2, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hayato Saba, Keisaku Yamamoto, Akio Imai, Kiyoyuki Sugimori, Kizuku Wakatsuki
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Patent number: 5191042Abstract: The present invention is directed toward novel copolymers of ethylene and at least one other alpha-olefin monomer which copolymers have an intermolecular compositional distribution (CD), such that at least about 25% by weight of the polymer differs from the mean ethylene content of the polymer by at least plus or minus 5 wt % ethylene and a relatively narrow molecular weight distribution (MWD) such that the weight average molecular weight (Mw) of the polymer divided by the number average molecular weight (Mn) by the polymer is not greater than about 5.0.The polymers of this invention, which are characterized by exceptional green strength and good processing properties, may be prepared using a catalyst system comprising:a) a vanadium compound with a valence of 3 or more;b) a triorgano aluminum compound; andc) a specific halogenated organic promoter used in catalytic amounts.Type: GrantFiled: September 25, 1991Date of Patent: March 2, 1993Assignee: Exxon Chemical Patents Inc.Inventor: Charles Cozewith
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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: 5168111Abstract: The invention is a catalyst system including a Group IV B transition metal component and an alumoxane component which may be employed to polymerize olefins to produce a high molecular weight polymer.Type: GrantFiled: March 28, 1991Date of Patent: December 1, 1992Assignee: Exxon Chemical Patents Inc.Inventor: Jo Ann M. Canich
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Patent number: 5164464Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5159030Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.Type: GrantFiled: March 25, 1991Date of Patent: October 27, 1992Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5157072Abstract: Cycloaliphatic compounds, which have one or more ethylenically unsaturated substituents, are disclosed as components of borehole-filling masses, optionally together with other curable components.Type: GrantFiled: December 4, 1990Date of Patent: October 20, 1992Assignee: Hilti AktiengesellschaftInventors: Ulrich Hense, Rudolf Hinterwaldner, Peter Mauthe
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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: 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: 5135996Abstract: A method of making a VI improver is disclosed. The one-step method of this invention includes reacting ethylene, an olefin other than ethylene and N-phenylphenylene methacrylamide in the presence of a cocatalyst system including a combination of a first group and a second group, said first group consisting of triethylaluminum, ethylaluminum, sesquichloride, diethylaluminum chloride, diethylzinc, ethylzinc chloride, triisobutylaluminum and mixtures thereof, and said second group consisting of titanium trichloride, titanium tetrachloride, vanadium tetrachloride, vanadium oxychloride, tetrabutyl titanate and mixtures thereof.Type: GrantFiled: August 2, 1991Date of Patent: August 4, 1992Assignee: Texaco Inc.Inventors: Munmaya K. Mishra, Isaac D. Rubin, Thomas J. Mach
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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: 5106927Abstract: A process for the production of EPDM comprising reacting ethylene, propylene, ethylidene norbornene, and hydrogen, in the gas phase, in a fluidized bed, under polymerization conditions, in the presence of a catalyst system comprising:(a) a titanium based catalyst having the formula Mg.sub.a Ti(OR).sub.b X.sub.c (ED).sub.d whereinR is an aliphatic or aromatic hydrocarbon radical having 1 to 14 carbon atoms or COR' wherein R' is an aliphatic or aromatic hydrocarbon radical having 1 to 14 carbon atoms;each OR group is alike or different;each X is independently chlorine, bromine, or iodineED is an electron donora is 0.5 to 56;b is 0, 1, or 2;c is 2 to 116; andd is greater than 1.5 a+2;(b) at least one modifier having the formula BX.sub.3 or AlR.sub.(3-b) X.sub.Type: GrantFiled: September 11, 1989Date of Patent: April 21, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Mahmoud R. Rifi, Kiu H. Lee, Mark J. Kriss, Han-Tai Liu
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Patent number: 5106931Abstract: This invention is to provide a novel process for the isomerization of a cycloolefin having an endo form to a cycloolefin having an exo form. The resulting isomer mixture has a novel composition, and a random copolymer produced from the above compositionally novel isomer mixture and ethylene has an excellent heat resistance and mechanical strength.Type: GrantFiled: August 10, 1990Date of Patent: April 21, 1992Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Toshihiro Sagane, Hideaki Yamaguchi, Shuji Minami, Akira Mizuno, Hiroo Wamura
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Patent number: 5098973Abstract: The invention relates to a hardening resin composition including a monomer represented by the formulas (1) or (2), a monomer represented by the formula (3), and epoxyacrylate or epoxymethacrylate. This composition is easily hardened at low temperature, weak in odor, small in shrinkage in hardening, excellent during durability against water and hot water, and thus suitable as the flooring material for a food processing factory, refrigerated warehouse, and cold storage. ##STR1## where R.sup.1 to R.sup.6, p and r are as defined.Type: GrantFiled: May 23, 1990Date of Patent: March 24, 1992Assignees: Sumitomo Rubber Industries Ltd., Nippon Kayaku Kabushiki KaishaInventors: Soichiro Kozuka, Tetsuya Kojimoto, Minoru Yokoshima
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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: 5091492Abstract: A resin composition for use as a paint contains a copolymer prepared by copolymerizing a monomer (I) represented by the following formula (I): ##STR1## wherein either one of X.sub.1 and X.sub.2 stands for an acryloyloxy or methacryloyloxy group, the other being a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R.sub.1 to R.sub.10 each stand for a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and n is an integer of 1 to 4; with an .alpha.,.beta.-ethylenically unsaturated monomer having a reactive functional group and an .alpha.,.beta.-ethylenically unsaturated monomer having no reactive functional group. A monomer mixture for preparing the copolymer contains 5 to 95 wt % of the monomer (I).Type: GrantFiled: August 7, 1990Date of Patent: February 25, 1992Assignees: Nippon Oil and Fats Co., Ltd., Mitsui Petrochemical Industries, Ltd.Inventors: Masahiro Ishidoya, Kishio Shibato, Osamu Ohe, Masaaki Kawasaki
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Patent number: 5082910Abstract: Free radical polymerization of monomers in the presence of t-amylperoxy pivalate as the free radical initiator is described. Copolymers of maleic anhydride and a vinyl monomer, e.g. a C.sub.1 -C.sub.5 alkyl vinyl ether, and water soluble polyvinylpyrrolidone, are representative polymers prepared in accordance with the process of the invention.Type: GrantFiled: September 1, 1989Date of Patent: January 21, 1992Assignee: ISP Investments Inc.Inventor: Mohammed Tazi
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Patent number: 5071929Abstract: A thermoset resin composition comprises a compound (A) having one or more maleimido groups in its molecule and at least one vinylbenzyl ether compound (B) selected from the group consisting of compounds (B.sub.1) having at least two vinylbenzyl ether groups bonded to a naphthalene nucleus in its molecule and compounds (B.sub.2) having at least two vinylbenzyl ether groups bonded to a benzene nucleus having at least one substituent selected from the group consisting of hydroxyl groups, alkyl groups and alkoxy groups in its molecule.The composition exhibits excellent low-temperature curing properties, heat resistance and mechanical strength.Type: GrantFiled: September 26, 1989Date of Patent: December 10, 1991Assignee: Showa Highpolymer Co., Ltd.Inventors: Toshiaki Hanyuda, Kojiro Mori, Kazuo Ohtani, Norio Shinohara, Jouji Shibata
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Patent number: 5068296Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.Type: GrantFiled: February 25, 1991Date of Patent: November 26, 1991Assignee: Hercules IncorporatedInventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
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Patent number: 5066740Abstract: This invention pertains to the use of pyridinium isopoly and heteropoly molybdates and tungstates as catalysts in a metathesis catalyst system in polymerization of norbornene-type 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 monomers are selected from polycycloolefins containing at least on enorbornene group and mixtures thereof.Type: GrantFiled: December 26, 1989Date of Patent: November 19, 1991Assignee: The B. F. Goodrich CompanyInventor: Larry F. Rhodes
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Ring-opened polymer from norbornene type of polycyclic monomer and process for producing the polymer
Patent number: 5061771Abstract: (1) A solvent-soluble ring-opened polymer constituted of 100-50% by weight of a norbornene derivative of monomer (A) represented by the formula ##STR1## wherein, R.sub.1 and R.sub.2 are the same or different and each denote hydrogen or alkyl and m denotes an interger of 0 to 2, and 0-50% by weight of another norbornene derivative of monomer (B) capable of undergoing ring-opening copolymerization with the preceding monomer (A), the polymer having a number average molecular weight of 10,000 to 50,000, a weight average molecular weight-to-number average molecular weight ratio (Mw/Mn) of up to 3, and a glass transition temperature of at least 80.degree. C., and(2) a process for producing such ring-opened polymers as stated above.Type: GrantFiled: November 8, 1989Date of Patent: October 29, 1991Assignee: Nippon Zeon Co., Ltd.Inventors: Masayoshi Oshima, Teiji Kohara, Tohru Hosaka, Tadao Natsuume -
Patent number: 5051485Abstract: The present invention provides a method for the polymerization or copolymerization of a monomer or blend of monomers selected from the group consisting of C-10 terpenes, vinyl aromatics and C-5 dienes that comprises complexing a Lewis acid with an organic ketone to produce a catalyst complex. The monomer or blend of monomers is added to the catalyst complex producing the reaction mixture. The reaction mixture is maintained at a temperature of between 10.degree. C. and 60.degree. C. and, when the reaction is complete, is quenched with water. The polymerized or copolymerized resin is then recovered.Type: GrantFiled: December 18, 1989Date of Patent: September 24, 1991Assignee: Arizona Chemical CompanyInventors: John J. Schmid, James W. Booth
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Patent number: 5006616Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.Type: GrantFiled: February 16, 1988Date of Patent: April 9, 1991Assignee: Hercules IncorporatedInventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
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Patent number: 4992518Abstract: The present invention relates to amides of formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each independently hydrogen or methyl, m is 1 to 5 and n is 1 to 5 and R.sup.4 is --NH.sub.2 or is derived from a mono- to pentavalent amine.Intermediates of formula VIII ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and m are as defined above and X is a carboxylic acid or acid ester group, --COCl, --COBr, --CHO or --CN, are also described.The compounds of formula I can be polymerized thermally. They are suitable for the preparation of adhesives, matrix resins or electrical insulating materials.Type: GrantFiled: May 15, 1987Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Andreas Kramer, Roland Darms
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Patent number: 4986648Abstract: An optical resin material comprising a polymer containing as an essential component at least one norbornyl acrylate or methacrylate or a derivative thereof is excellent in properties, particularly in moisture resistance and can be used for molding optical elements such as lenses, optical discs, etc.Type: GrantFiled: December 21, 1988Date of Patent: January 22, 1991Assignee: Hitachi Chemical Company, Ltd.Inventors: Akihiro Kobayashi, Toshiyuki Fujita, Takayuki Saito, Hiromasa Kawai, Yutaka Hosoi, Hideaki Shibata
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Patent number: 4962163Abstract: Thermosettable vinyl ester compositions are prepared from an advanced epoxy resin containing a mesogenic or rodlike moiety and a monounsaturated monocarboxylic acid and, optionally, a monoepoxide compound. These vinyl ester compounds can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: January 17, 1989Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 4959395Abstract: This invention is directed to the use of microencapsulated blowing agents in the bulk polymerization of cycloolefin monomers by ring-opening polymerization. These microencapsulated blowing agents aid in filling molds during reaction injection molding procedures such that both surfaces of the article being molded remain in contact with their respective mold surfaces eliminating sink marks in these surfaces. In addition, the microencapsulants may be introduced at higher levels which provide structural foams with the polymers from cycloolefin monomers.Type: GrantFiled: February 21, 1990Date of Patent: September 25, 1990Assignee: The B. F. Goodrich CompanyInventor: Dennis J. Janda
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Patent number: 4957990Abstract: A polymer excellent in transparency, mechanical properties, moisture resistance suitable for optical use is obtained by copolymerizing a (meth)acrylate compound (I) and a (meth)acrylate compound (II).Type: GrantFiled: October 13, 1988Date of Patent: September 18, 1990Assignee: Hitachi, Ltd.Inventors: Ryoichi Sudo, Makoto Kobata, Hiroaki Miwa, Tetsuo Tajima
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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: 4923939Abstract: This invention pertains to the use of organophosphonium and organoarsonium molybdates and tungstates 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 polycycloolefins containing at least one norbornene group, and mixtures thereof.Type: GrantFiled: February 21, 1989Date of Patent: May 8, 1990Assignee: The B.F. Goodrich CompanyInventor: Brian L. Goodall
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Patent number: 4923942Abstract: An optical resin consisting essentially of a radical polymerization polymer of an ethylenically unsaturated monomer, characterized in that at least a major part of the ethlenically unsaturated monomer is an ester of 1 mole of tricyclo[5,2,1,0.sup.2,6 ]decanedimethanol with 2 moles of a mixture of acrylic acid and metharcylic acid. Because the resin is a polymer obtained from the restricted monomer as specified above, the resin possesses high thermal resistance and high heat stability as well as low hygroscopic property. Dimethanol compounds from higher Diels-Alder adducts of cyclopentadine are also used in place of the tricyclo [5,2,1,0.sup.2,6 ]decanedimthanol which is a Diels-Alder adduct of two moles of cyclopentadiene.Type: GrantFiled: September 30, 1988Date of Patent: May 8, 1990Assignee: Mitsubishi Petrochemical Company, Ltd.Inventors: Tadao Takeyama, Mitsutoshi Aritomi
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Patent number: 4918158Abstract: 1,3-Diethynyladamantane and a method of forming same by brominating adamantane to yield 1,3-dibromoadamantane, subjecting vinyl bromide to Friedel-Crafts alkylation with the 1,3-dibromoadamantane to form 1,3-bis(2,2-dibromoethyl)adamantane and subjecting the 1,3-bis(2,2-dibromoethyl)adamantane to dehydrohalogenation to yield the 1,3-diethynyladamantane. 1,3-Diethynyladamantane can be polymerized to produce strong, thermally stable resins suitable for advanced aerospace structural applications, as matrices for carbon-carbon systems and as electrical insulators. It can also be copolymerized with 1-ethynyladamantane to yield similarly useful resins.Type: GrantFiled: July 21, 1986Date of Patent: April 17, 1990Assignee: Fluorochem Inc.Inventors: Kurt Baum, Thomas G. Archibald
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Patent number: 4910080Abstract: Impregnating compositions are described comprising dicyclopentenyl acrylate or methacrylate together with a C.sub.5 to C.sub.8 alkyl ester of acrylic or methacrylic acid.Type: GrantFiled: May 10, 1989Date of Patent: March 20, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventor: George W. Frost
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Patent number: 4910295Abstract: A process for reducing the odor of ethylidene norbornene present in EPDM resin which comprises introducing a crystalline siliceous molecular sieve into said EPDM resin in an amount sufficient to reduce the odor produced by ethylidene norbornene present in said EPDM resin.Type: GrantFiled: April 28, 1989Date of Patent: March 20, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Robert J. Bernier, George E. Keller, II
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Patent number: 4908420Abstract: A method for preparing a resin having light color comprises the steps of: hydrogenating a compound represented by the formula (1) ##STR1## wherein l, m and n are integers of 0.ltoreq.l.ltoreq.3, 0.ltoreq.m.ltoreq.8 and l.ltoreq.n.ltoreq.3, respectively, and R.sup.1 and R.sup.6 each represent a hydrogen atom or a hydrocarbon residue having 1 to 3 carbon atoms, with or without R.sup.5 and R.sup.6 forming a ring, in the presence of a Ziegler catalyst containing a transition metal compound of the groups IV to VI of the Periodic Table and an organometallic compound of the groups I to III of the Periodic Table in combination to obtain a norbornene compound represented by the formula (2) ##STR2## wherein l, m, n and R.sup.1 and R.sup.6 are the same as above; and polymerizing the norbornene compound to give the resin having light color.Type: GrantFiled: July 21, 1989Date of Patent: March 13, 1990Assignee: Nippon Oil Company, Ltd.Inventors: Makoto Sasaki, Yukio Kobayashi, Shozo Tsuchiya
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Patent number: 4906675Abstract: An active energy ray-curable composition substantially comprising at least one of (meth)acrylates and oligomers thereof represented by the following general formula (I) ##STR1## wherein R represents a hydrogen atom or a methyl group, X represents an alkylene group in which at least one hydrogen atom may be replaced by a hydroxyl group, m is 0 or an integer of 1 to 4, Y represents a hydrocarbon group having a cyclic hydrocarbon moiety therein, and n is 1 or 2. The composition is useful as an adhesive, particularly as one in the production of optical discs.Type: GrantFiled: February 10, 1987Date of Patent: March 6, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hajime Inagaki, Kenji Yamane
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Patent number: 4900799Abstract: A polymer prepared by metathesis polymerizing at least one compound represented by the formula ##STR1## wherein m is 0 or 1 and R.sub.1 and R.sub.2 respectively represent hydrogen atom or an alkyl group containing up to three carbon atoms provided that both R.sub.1 and R.sub.2 are not hydrogen atom at the same time, or a mixture of said compound with at least one other metathesis polymerizable comonomer, a useful molded article, processes for preparing the polymer and a polymerizable composition therefor.Type: GrantFiled: June 24, 1987Date of Patent: February 13, 1990Assignee: Teijin LimitedInventors: Shigeyoshi Hara, Zen-ichiro Endo
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Patent number: 4897456Abstract: Disclosed is a method of reducing the activation rate of an alkyl aluminum activator in the metathesis polymerization of polycyclic cycloolefins. Activation rate is reduced by use of a bidentate Lewis base as the reaction rate moderator.Type: GrantFiled: January 13, 1989Date of Patent: January 30, 1990Assignee: Hercules IncorporatedInventor: Lawrence L. Nelson
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Patent number: 4883849Abstract: Disclosed is a method of delaying the metathesis polymerization of strained ring cycloolefins by addition of certain nitrogen-containing compounds including various aromatic amines or mixtures thereof.Type: GrantFiled: December 30, 1988Date of Patent: November 28, 1989Assignee: Hercules IncorporatedInventor: Albert S. Matlack
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Patent number: 4882401Abstract: A process for preparing molded objects wherein a liquid reaction mass comprised of a metathesis polymerizable cycloolefin, a metathesis polymerization catalyst, a catalyst activator and a reaction rate moderator are charged to a mold wherein polymerization will take place, the improvement wherein said catalyst activator comprises a dialkylzinc compound. Significantly increased gel and cure times are obtained with the dialkylzinc compounds as compared to the use of aluminum alkyl activator compounds. The gel and cure times may be further controlled by the addition of a phenolic compound to the tungsten or molybdenum compound or by the addition of a Lewis base.Type: GrantFiled: September 28, 1988Date of Patent: November 21, 1989Assignee: Hercules IncorporatedInventor: Andrew Bell
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Patent number: 4868261Abstract: An optical resin material comprising a polymer containing as an essential component at least one norbornyl acrylate or methacrylate or a derivative thereof is excellent in properties, particularly in moisture resistance and can be used for molding optical elements such as lenses, optical discs, etc.Type: GrantFiled: June 18, 1987Date of Patent: September 19, 1989Assignee: Hitachi Chemical Company, Ltd.Inventors: Akihiro Kobayashi, Toshiyuki Fujita, Takayuki Saito, Hiromasa Kawai, Yutaka Hosoi, Hideaki Shibata
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Patent number: 4859730Abstract: The polymerization of compositions containing styrene by an aqueous suspension process in which is used a suspending agents system constituted by a mineral agent and, an extending agent which is at least a rosin acid derivative (abietic acid, neoabietic acid, dextropimaric acid) or their salts of a metal belonging to Group IIa of the Periodic Classification of elements. The use of this extending agent has the advantage of ameliorate the surface aspect of moulded articles obtained from expanded polymer pearls prepared with the above polymerization process.Type: GrantFiled: January 11, 1989Date of Patent: August 22, 1989Assignee: Societe Chimique des Charbonnages Sa Tour AuroreInventor: Didier Lozachmeur
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Patent number: 4841005Abstract: A tricyclodecane derivative represented by formula (I): ##STR1## wherein R.sup.1 represents a group X.sup.1 O-- or a hydrogen atom;R.sup.2 represents a hydrogen atom when R.sup.1 represents a group X.sup.1 O--, or R.sup.2 represents a group X.sup.1 O-- when R.sup.1 represents a hydrogen atom;wherein X.sup.1 represents a group ##STR2## or a hydrogen atom, wherein X.sup.2 represents a hydrogen atom, a methyl group, or a trifluoromethyl group;R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, an iodine atom, or a hydrogen atom; andR.sup.4 represents an iodine atom or a hydrogen atom when R.sup.3 represents a fluoroalkyl group containing from 1 to 21 carbon atoms, or R.sup.4 represents a fluoroalkyl group containing from 1 to 21 carbon atoms when R.sup.3 represents an iodine atom or a hydrogen atom.Type: GrantFiled: February 12, 1988Date of Patent: June 20, 1989Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo
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Patent number: 4835230Abstract: Disclosed is an improved method for making a thermoset polymer wherein a plurality of reactant streams, one of which contains the activator of a metathesis catalyst system combined with a moderator, and a second of which contains the catalyst of the metathesis catalyst system and at least one of which contains dicyclopentadiene are combined to form a reaction mixture, and the reaction mixture is then injected into a mold where polymerization occurs. The improvement comprises adding to the reaction mixture 1-25 mols of a cationic polymerization initiator per 1000 mols of dicyclopentadiene.Type: GrantFiled: October 17, 1988Date of Patent: May 30, 1989Assignee: Hercules IncorporatedInventors: Nitya P. Khasat, Birendra K. Patnaik
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Patent number: RE34061Abstract: A polymer obtained by polymerizing tricyclo[5.2.1.0.sup.2,6 ]deca-8-yl acrylate or methacrylate in an amount of 100-5% by weight with one or more copolymerizable unsaturated monomers in an amount of 0 to 95% by weight is excellent in transparency, moisture resistance, and heat resistance and is suitable as a material for optical elements.Type: GrantFiled: May 27, 1988Date of Patent: September 8, 1992Assignee: Hitachi Chemical Co., Ltd.Inventors: Hiromasa Kawai, Takashi Morinaga, Hiromu Miyajima, Toshio Akima, Mitsuharu Kato, Yutaka Hosoi