Contains An Exterior Ethylenic Substituent Bonded To A Single Carbon Atom Of The Bridged Ring System Patents (Class 526/282)
  • Patent number: 5204427
    Abstract: 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: Grant
    Filed: May 24, 1991
    Date of Patent: April 20, 1993
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masao Torii, Tomoo Sugawara, Kin-ichi Okumura, Motoyuki Yamato
  • Patent number: 5194534
    Abstract: 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: Grant
    Filed: September 24, 1991
    Date of Patent: March 16, 1993
    Assignee: Hercules Incorporated
    Inventor: Andrew Bell
  • Patent number: 5191041
    Abstract: 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: Grant
    Filed: January 16, 1992
    Date of Patent: March 2, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hayato Saba, Keisaku Yamamoto, Akio Imai, Kiyoyuki Sugimori, Kizuku Wakatsuki
  • Patent number: 5191042
    Abstract: 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: Grant
    Filed: September 25, 1991
    Date of Patent: March 2, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Charles Cozewith
  • Patent number: 5191027
    Abstract: 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: Grant
    Filed: May 11, 1990
    Date of Patent: March 2, 1993
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Ikuo Takahashi, Hiroyuki Oshima
  • Patent number: 5187012
    Abstract: 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: Grant
    Filed: December 20, 1990
    Date of Patent: February 16, 1993
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Nobukazu Takahashi, Teiji Kohara, Tadao Natsuume
  • Patent number: 5168111
    Abstract: 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: Grant
    Filed: March 28, 1991
    Date of Patent: December 1, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Jo Ann M. Canich
  • Patent number: 5164464
    Abstract: 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: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5159030
    Abstract: 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: Grant
    Filed: March 25, 1991
    Date of Patent: October 27, 1992
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5157072
    Abstract: 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: Grant
    Filed: December 4, 1990
    Date of Patent: October 20, 1992
    Assignee: Hilti Aktiengesellschaft
    Inventors: Ulrich Hense, Rudolf Hinterwaldner, Peter Mauthe
  • Patent number: 5155188
    Abstract: 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: Grant
    Filed: January 12, 1990
    Date of Patent: October 13, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: Brian L. Goodall
  • Patent number: 5143992
    Abstract: 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: Grant
    Filed: July 12, 1991
    Date of Patent: September 1, 1992
    Assignee: Shell Oil Company
    Inventor: Donald R. Kelsey
  • Patent number: 5135996
    Abstract: 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: Grant
    Filed: August 2, 1991
    Date of Patent: August 4, 1992
    Assignee: Texaco Inc.
    Inventors: Munmaya K. Mishra, Isaac D. Rubin, Thomas J. Mach
  • Patent number: 5118773
    Abstract: 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: Grant
    Filed: October 30, 1991
    Date of Patent: June 2, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroyoshi Takao, Hiroyuki Harada, Kiyoyuki Sugimori, Nobuyuki Yoshida, Masahiro Fukuyama, Hideaki Yamada, Junichi Koshiba
  • Patent number: 5106927
    Abstract: 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: Grant
    Filed: September 11, 1989
    Date of Patent: April 21, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Mahmoud R. Rifi, Kiu H. Lee, Mark J. Kriss, Han-Tai Liu
  • Patent number: 5106931
    Abstract: 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: Grant
    Filed: August 10, 1990
    Date of Patent: April 21, 1992
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Toshihiro Sagane, Hideaki Yamaguchi, Shuji Minami, Akira Mizuno, Hiroo Wamura
  • Patent number: 5098973
    Abstract: 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: Grant
    Filed: May 23, 1990
    Date of Patent: March 24, 1992
    Assignees: Sumitomo Rubber Industries Ltd., Nippon Kayaku Kabushiki Kaisha
    Inventors: Soichiro Kozuka, Tetsuya Kojimoto, Minoru Yokoshima
  • Patent number: 5095082
    Abstract: 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: Grant
    Filed: June 10, 1991
    Date of Patent: March 10, 1992
    Assignee: Shell Oil Company
    Inventor: Donald R. Kelsey
  • Patent number: 5091492
    Abstract: 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: Grant
    Filed: August 7, 1990
    Date of Patent: February 25, 1992
    Assignees: Nippon Oil and Fats Co., Ltd., Mitsui Petrochemical Industries, Ltd.
    Inventors: Masahiro Ishidoya, Kishio Shibato, Osamu Ohe, Masaaki Kawasaki
  • Patent number: 5082910
    Abstract: 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: Grant
    Filed: September 1, 1989
    Date of Patent: January 21, 1992
    Assignee: ISP Investments Inc.
    Inventor: Mohammed Tazi
  • Patent number: 5071929
    Abstract: 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: Grant
    Filed: September 26, 1989
    Date of Patent: December 10, 1991
    Assignee: Showa Highpolymer Co., Ltd.
    Inventors: Toshiaki Hanyuda, Kojiro Mori, Kazuo Ohtani, Norio Shinohara, Jouji Shibata
  • Patent number: 5068296
    Abstract: 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: Grant
    Filed: February 25, 1991
    Date of Patent: November 26, 1991
    Assignee: Hercules Incorporated
    Inventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
  • Patent number: 5066740
    Abstract: 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: Grant
    Filed: December 26, 1989
    Date of Patent: November 19, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: Larry F. Rhodes
  • Patent number: 5061771
    Abstract: (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: Grant
    Filed: November 8, 1989
    Date of Patent: October 29, 1991
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayoshi Oshima, Teiji Kohara, Tohru Hosaka, Tadao Natsuume
  • Patent number: 5051485
    Abstract: 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: Grant
    Filed: December 18, 1989
    Date of Patent: September 24, 1991
    Assignee: Arizona Chemical Company
    Inventors: John J. Schmid, James W. Booth
  • Patent number: 5006616
    Abstract: 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: Grant
    Filed: February 16, 1988
    Date of Patent: April 9, 1991
    Assignee: Hercules Incorporated
    Inventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
  • Patent number: 4992518
    Abstract: 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: Grant
    Filed: May 15, 1987
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Kramer, Roland Darms
  • Patent number: 4986648
    Abstract: 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: Grant
    Filed: December 21, 1988
    Date of Patent: January 22, 1991
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akihiro Kobayashi, Toshiyuki Fujita, Takayuki Saito, Hiromasa Kawai, Yutaka Hosoi, Hideaki Shibata
  • Patent number: 4962163
    Abstract: 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: Grant
    Filed: January 17, 1989
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 4959395
    Abstract: 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: Grant
    Filed: February 21, 1990
    Date of Patent: September 25, 1990
    Assignee: The B. F. Goodrich Company
    Inventor: Dennis J. Janda
  • Patent number: 4957990
    Abstract: 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: Grant
    Filed: October 13, 1988
    Date of Patent: September 18, 1990
    Assignee: Hitachi, Ltd.
    Inventors: Ryoichi Sudo, Makoto Kobata, Hiroaki Miwa, Tetsuo Tajima
  • Patent number: 4943621
    Abstract: 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: Grant
    Filed: August 4, 1988
    Date of Patent: July 24, 1990
    Assignee: The B. F. Goodrich Company
    Inventors: Dennis J. Janda, Paul T. Stricharczuk, Robert J. Minchak
  • Patent number: 4933402
    Abstract: 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: Grant
    Filed: December 30, 1988
    Date of Patent: June 12, 1990
    Assignee: Hercules Incorporated
    Inventor: Albert S. Matlack
  • Patent number: 4923936
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: May 8, 1990
    Assignee: The BFGoodrich Company
    Inventors: Brian L. Goodall, Larry F. Rhodes
  • Patent number: 4923939
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: May 8, 1990
    Assignee: The B.F. Goodrich Company
    Inventor: Brian L. Goodall
  • Patent number: 4923942
    Abstract: 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: Grant
    Filed: September 30, 1988
    Date of Patent: May 8, 1990
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Tadao Takeyama, Mitsutoshi Aritomi
  • Patent number: 4918158
    Abstract: 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: Grant
    Filed: July 21, 1986
    Date of Patent: April 17, 1990
    Assignee: Fluorochem Inc.
    Inventors: Kurt Baum, Thomas G. Archibald
  • Patent number: 4910080
    Abstract: 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: Grant
    Filed: May 10, 1989
    Date of Patent: March 20, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: George W. Frost
  • Patent number: 4910295
    Abstract: 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: Grant
    Filed: April 28, 1989
    Date of Patent: March 20, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Robert J. Bernier, George E. Keller, II
  • Patent number: 4908420
    Abstract: 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: Grant
    Filed: July 21, 1989
    Date of Patent: March 13, 1990
    Assignee: Nippon Oil Company, Ltd.
    Inventors: Makoto Sasaki, Yukio Kobayashi, Shozo Tsuchiya
  • Patent number: 4906675
    Abstract: 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: Grant
    Filed: February 10, 1987
    Date of Patent: March 6, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hajime Inagaki, Kenji Yamane
  • Patent number: 4900799
    Abstract: 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: Grant
    Filed: June 24, 1987
    Date of Patent: February 13, 1990
    Assignee: Teijin Limited
    Inventors: Shigeyoshi Hara, Zen-ichiro Endo
  • Patent number: 4897456
    Abstract: 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: Grant
    Filed: January 13, 1989
    Date of Patent: January 30, 1990
    Assignee: Hercules Incorporated
    Inventor: Lawrence L. Nelson
  • Patent number: 4883849
    Abstract: 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: Grant
    Filed: December 30, 1988
    Date of Patent: November 28, 1989
    Assignee: Hercules Incorporated
    Inventor: Albert S. Matlack
  • Patent number: 4882401
    Abstract: 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: Grant
    Filed: September 28, 1988
    Date of Patent: November 21, 1989
    Assignee: Hercules Incorporated
    Inventor: Andrew Bell
  • Patent number: 4868261
    Abstract: 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: Grant
    Filed: June 18, 1987
    Date of Patent: September 19, 1989
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akihiro Kobayashi, Toshiyuki Fujita, Takayuki Saito, Hiromasa Kawai, Yutaka Hosoi, Hideaki Shibata
  • Patent number: 4859730
    Abstract: 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: Grant
    Filed: January 11, 1989
    Date of Patent: August 22, 1989
    Assignee: Societe Chimique des Charbonnages Sa Tour Aurore
    Inventor: Didier Lozachmeur
  • Patent number: 4841005
    Abstract: 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: Grant
    Filed: February 12, 1988
    Date of Patent: June 20, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo
  • Patent number: 4835230
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: May 30, 1989
    Assignee: Hercules Incorporated
    Inventors: Nitya P. Khasat, Birendra K. Patnaik
  • Patent number: RE34061
    Abstract: 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: Grant
    Filed: May 27, 1988
    Date of Patent: September 8, 1992
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Hiromasa Kawai, Takashi Morinaga, Hiromu Miyajima, Toshio Akima, Mitsuharu Kato, Yutaka Hosoi