Of Differing Carbon Content, More Than Three Or With Bridge Patents (Class 585/22)
  • 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: 5076813
    Abstract: A high-energy-content fuel composition, for controlled-ignition internal combustion engines, contains quadricyclane (tetracyclo-[2.2.1.0-(2,6).0-3,5]-heptane), for which a new synthesis method is proposed.The use of the quadricyclane-containing fuel composition makes it possible a larger amount of energy to be available per each fuel volume unit, and favorably modifies the combustion kinetics in controlled-ignition internal combustion engines.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: December 31, 1991
    Assignees: Enichem Synthesis S.p.A., Agip Petroli S.p.A.
    Inventors: Fausto Alberici, Luigi Cassar, Fabio Monti, Carlo Neri, Nereo Nodari
  • 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: 5053568
    Abstract: The present invention provides a lubricant additive and lubricant composition comprising the copolymer of 1-vinyladamantane and 1-alkene having from about 4 to about 16 carbon atoms, said copolymer having a Viscosity Index of at least 80 and a kinematic viscosity of at least 6 cS at 212.degree. F. The invention further provides a catalytic method for the preparation of such a copolymer useful as a lubricant stock. In a preferred embodiment of the composition, the 1-alkene is 1-decene. Suitable polymerization catalysts include both acid and coordination catalysts. Useful coordination catalysts include Group VIA metals on an inert support, for example, chromium oxide supported on silica, or Ziegler-Natta catalysts such as TiCl.sub.4 and aluminum alkyl, while useful acid catalysts include BF.sub.3 and AlCl.sub.3, and their appropriate co-catalysts.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: October 1, 1991
    Assignee: Mobil Oil Corp.
    Inventor: Catherine S. H. Chen
  • Patent number: 5019660
    Abstract: Polymeric compositions of matter and methods of making the same are disclosed, said polymeric compositions comprising at least one monomer having the structure of one selected from the group consisting of diamantane, triamantane and the higher adamantalogs, said monomer being bonded through at least one double bond extending through a methylene position of said monomer.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: May 28, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Orville L. Chapman, D. Duayne Whitehurst
  • Patent number: 5017734
    Abstract: 1,3-Diethynyl-5,7-dimethyladamantane; 1,3,5-triethynyladamantane; 3,3'-diethynyl-1,1'-biadamantane; 1-ethynyldiamantane; 1,4-diethynyldiamantane; 1,6-diethynyldiamantane and 4,9-diethynyldiamantane as new compositions of matter, and a method of forming them in which adamantane; 1,3-dimethyladamatane; 1-hydroxy-3,5-dimethyladamantane; 1,1'-biadamantane and diamantane are each brominated to form a bromo derivative thereof; the bromo derivative is reacted with vinyl bromide in the presence of a Friedel-Crafts catalyst to convert it to its corresponding 2,2-dibromoethyl derivative and the 2,2-dibromoethyl derivative is subjected to dehydrohalogenation to convert it to its final ethynyl form. The 1,3-diethynyl-5,7-dimethyladamantane; 1,3,5-triethynyladamantane; 3,3'-diethynyl-1,1'-biadamantane; 1,4-diethynyldiamantane; 1,6-diethynyldiamantane and 4,9-diethynyldiamantane can be heat cured to form homopolymers having useful commercial properties.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: May 21, 1991
    Inventors: Kurt Baum, Thomas G. Archibald, Aslam A. Malik
  • 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: 4942256
    Abstract: This invention relates to several novel intermediates useful in the manufacture of thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: July 17, 1990
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4906797
    Abstract: Liquid dicyclopentadiene feedstocks are provided for bulk polymerization by the addition of reactive norbornene function containing cycloolefin monomers to solid, high purity dicyclopentadiene compositions. These liquid dicyclopentadiene feedstocks provide a high degree of conversion to polymer under bulk polymerization conditions.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: March 6, 1990
    Assignee: The B.F. Goodrich Company
    Inventors: Parley C. Lane, Jr., George M. Benedikt, Linwood P. Tenney, Paul T. Stricharczuk
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4849565
    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-bidromoadamantane 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 co-polymerized with 1-ethynyladamantane to yield similarly useful resins.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: July 18, 1989
    Inventors: Kurt Baum, Thomas G. Archibald
  • Patent number: 4804795
    Abstract: The present invention provided a high-density fuel oil comprising an isomerized product prepared by isomerizing an alicyclic saturated hydrocarbon represented by the following formula in the presence of an acid catalyst: ##STR1## wherein each of m and n is 0 or 1, and each of R.sup.1 to R.sup.3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, but the number of the total carbons of R.sup.1 to R.sup.3 is within the range of 1 to 3.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: February 14, 1989
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
  • Patent number: 4774013
    Abstract: This invention provides a novel perhydrofluorene derivative which is represented by the following general formula and which is useful as a fluid for traction drive and a process for production of the derivative. ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each represents a hydrogen atom or an alkyl group of 1-4 carbon atoms, X represents (CH.sub.2).sub.p or ##STR2## wherein R.sup.4 represents a hydrogen atom or an alkyl group of 1-4 carbon atoms, p represents a real number of 2-6, q represents a real number of 1-4 and s represents 1 or 0 and k, m and n each represents a real number of 1-4.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: September 27, 1988
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4762092
    Abstract: The present invention provides a high-density fuel oil which is suitable for rockets and jet engines and which mainly comprises a tetracyclo (7. 3. 1. O.sup.2,7. 1.sup.7,11) tetradecane derivative represented by the general formula: ##STR1## wherein each of m and n is 0, 1 or 2, and the sum of m and n is 2 or less.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: August 9, 1988
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Tetsuo Satoh
  • Patent number: 4709061
    Abstract: Mixtures of new dimethyl-tricyclo[5.2.1.0.sup.2,6 ]decane derivatives, notably the primary isomers of the common formula A, whereinR.sup.1 and R.sup.2 mean either methyl group or hydrogen, one of the substituents being a methyl group and the other hydrogen,R.sup.3 and R.sup.4 mean either methyl group or hydrogen, one of the substituents being a methyl group and the other hydrogen, andX indicates the .pi.-system of a C-C double bond or an epoxide system, can advantageously be used as new acent- and flavor materials.The compounds of the common formula A, were prepared by hydrogenation of dimeric methylcyclopentadiene selectively in the norbornane part and when desired by epoxidation of the remaining double bond.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: November 24, 1987
    Assignee: DRAGOCO Gerberding & Co. GmbH
    Inventors: Ernst-Joachim Brunke, Hartmut Struwe
  • Patent number: 4705847
    Abstract: The invention relates to a process for preparing substituted polycyclo-alkylidene polycyclo-alkanes, such as substituted adamantylidene adamantanes, and the corresponding epidioxy compounds, in which polycyclo-alkylidene polycyclo-alkanes are halogenated with an N-halosuccinimide, tert.-butylhypohalite or sodium hypohalite/CH.sub.3 COOH, the halogenation product is optionally subjected to a substitution reaction, and the substituted polycycloalkylidene polycyclo-alkanes are converted to the corresponding epidioxy compounds in a way known per se.Further, the invention relates to compounds of formula 44 ##STR1## in which A and B represent alkylene radicals, which alkylene radicals may be attached to each other via an alkylene radical C, and R.sub.1 represents a substituent, which, in case of 4-eq.-R.sub.1 -2,2'-adamantylidene adamantane cannot be chloro, hydroxy, oxo, D or a group of formula 1: ##STR2## as well as to compounds of formula 45: ##STR3## in which A, B and C are as defined above, and R.sub.
    Type: Grant
    Filed: December 7, 1983
    Date of Patent: November 10, 1987
    Assignee: Akzo N.V.
    Inventors: Jan C. Hummelen, Egbert W. Meijer, Hans Wynberg
  • Patent number: 4675459
    Abstract: A traction drive fluid comprising as a base stock at least one hydrocarbon selected from the group consisting of compounds of the following general formulae (I) to (V) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10, independently from each other, represent a hydrogen atom or a methyl group.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: June 23, 1987
    Assignee: Nippon Oil Company, Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno
  • Patent number: 4622430
    Abstract: Pentacyclo[6.3.0.0..sup.2,6.0.sup.3,10.0.sup.5,9 ]undecane and its derivatives are prepared. The compounds find use as antiviral agents.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: November 11, 1986
    Assignee: Noristan Limited
    Inventors: Theodor G. Dekker, Douglas W. Oliver, Friedrich O. Snyckers, Cornelis J. van der Schyf
  • Patent number: 4604492
    Abstract: The invention provides a novel class of compounds dicyclohexylcyclopentanes or, in particular, 1,3-dicyclohexyl-1-methyl cyclopentane which is synthesized by the hydrogenation of 1-methyl-1,3-diphenyl cyclopentane which in turn is obtained by the dimerization reaction of .alpha.-methylstyrene in the presence of metallic sodium as the catalyst. The compound is useful as a fluid for traction drive.
    Type: Grant
    Filed: October 8, 1985
    Date of Patent: August 5, 1986
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4604493
    Abstract: The invention provides a novel compound 1-cyclohexyl-1,4-dimethyl decahydronaphthalene which is useful as fluids for traction drive. The compound can be synthesized by the hydrogenation of 1,4-dimethyl-4-phenyl-1,2,3,4-tetrahydronaphthalene and analytical results for the identification of the compound are given.
    Type: Grant
    Filed: October 8, 1985
    Date of Patent: August 5, 1986
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4570024
    Abstract: An aromatic hydrocarbon in which at least one hydrogen atom on the ring is substituted by a group selected from the class consisting of unsubstituted or lower alkyl-substituted tricyclo[5.2.1.0.sup.2,6 ]dec-3-yl, tricyclo[5.2.1.0.sup.2,6 ]dec-4-yl, tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-4-yl and tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-5-yl groups, or its hydrogenation product.The compound is prepared by reacting an aromatic hydrocarbon having at least one hydrogen atom on the ring with a compound selected from the group consisting of unsubstituted or lower alkyl-substituted tricyclo[5.2.1.0.sup.2,6 ]dec-3-ene and tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-4-ene in the presence of a Friedel-Crafts catalyst, or hydrogenating the thus-obtained compound in the presence of a hydrogenation catalyst.The compound is useful as an additive for adhesives.
    Type: Grant
    Filed: May 7, 1985
    Date of Patent: February 11, 1986
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kinya Mizui, Masami Takeda, Yoshimi Ozaki, Ryosuke Tomita
  • Patent number: 4556745
    Abstract: A liquid crystal composition includes at least one compound of Formula (I) as follows:A--CH.sub.2.CH.sub.2 --B Formula (I)where A and B are substituted ring structures which include terminal alkyl groups, A being selected from: ##STR1## where R'.sub.1 is an alkyl group R.sub.1, an alkoxy group R.sub.1 O, an alkylcarbonyloxy group R.sub.1 CO.O or an alkoxycarbonyloxy group R.sub.1 OCO.O; ##STR2## where R.sub.1 is an alkyl group; or ##STR3## where R.sub.1 is an alkyl group; and B being selected from: ##STR4## where R'.sub.2 is an alkyl group R.sub.2, an alkoxy group OR.sub.2, an alkylcarbonyloxy group OCO.R.sub.2 or an alkoxycarbonyloxy group OCO.OR'.sub.2 ; and X is hydrogen or a cyano group or a methyl group or a halogen; ##STR5## where R.sub.2 is an alkyl group; or ##STR6## where R.sub.2 is an alkyl group; ##STR7## being a trans-1,4-disubstituted cyclohexane ring and ##STR8## a 1,4-disubstituted bicyclo(2,2,2)octane ring.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: December 3, 1985
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Neil Carr, George W. Gray
  • Patent number: 4544497
    Abstract: Liquid crystal compositions are described which comprise a mixture of compounds and which includes at least one additive compound characterized in that the composition includes one or more additive compounds of Formula I as follows: ##STR1## wherein R.sub.1 represents an alkyl group, R.sub.2 represents an alkyl or alkoxy group or hydrogen and ##STR2## represents a 1,4-disubstituted bicyclo(2,2,2)octane ring. The preparation and properties of novel compounds of Formula I are also described. These liquid crystal compositions are useful in display devices such as digital calculators and word displays.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: October 1, 1985
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Hilal M. Abdullah, Jennifer Constant, George W. Gray, Damien G. McDonnell, Kenneth J. Toyne
  • Patent number: 4521324
    Abstract: A fluid for traction drive is described, containing a liquid material as a base stock wherein the liquid material is prepared by bringing naphthalene or tetralin into contact with a Friedel-Crafts catalyst and then hydrogenating the resulting compounds. This traction drive fluid exhibits a superior traction coefficient from low temperature to elevated temperature and further has a low viscosity. Thus the fluid contributes to the production of small-sized drive mechanisms and can be widely used in various machines.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: June 4, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4507516
    Abstract: A fuel composition comprising a hydrogenated material obtained by hydrogenating a reaction mixture ranging from C.sub.11 to C.sub.16 containing mainly compounds which comprise butadiene and cyclopentadiene as basic structural units, produced by reacting an acyclic conjugated diene with cyclopentadiene, dicyclopentadiene, an alkyl-substituted cyclopentadiene, or an alkyl-substituted dicyclopentadiene in accordance with Diels-Alder reaction an isomeric material prepared by isomerizing the hydrogenated material or the mixture of the hydrogenated material and the isomeric material.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: March 26, 1985
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Seiji Hirooka, Michiaki Torii
  • Patent number: 4446041
    Abstract: This invention relates to a solar energy system wherein chemical A is converted into chemical B in the presence of a photo-sensitizer with the absorption of considerable heat, which heat can be redelivered at will by placing chemical B in contact with a catalyst. The catalyst is stable at high temperatures permitting operation through the phase change from liquid to vapor with consequent use of chemical B for performing work in engines, heat pumps and the like.
    Type: Grant
    Filed: March 10, 1981
    Date of Patent: May 1, 1984
    Inventor: Michael P. Neary
  • Patent number: 4427467
    Abstract: An improved ramjet fuel consisting of hydrogenated hydrocarbons uses a mium weight percentage of 50% tetrahydromethylcyclopentadiene dimer (TH-dimer) with about 50% by wt. exo-tetrahydrodicyclopentadiene (Exo-THDC). The mixture exceeds U.S. Navy flash point requirements of 60.degree. C. while yielding a lower viscosity than TH-dimer alone. Volumetric heating properties of the mixture make it an excellent ramjet fuel.
    Type: Grant
    Filed: April 29, 1982
    Date of Patent: January 24, 1984
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: George W. Burdette, Lewis Hall
  • Patent number: 4410749
    Abstract: A high energy, high density synthetic liquid hydrocarbon fuel, RJ-6, is pared by blending 60 weight percent perhydrodinorbornadiene, a synthetic fuel known as RJ-5, and 40 weight percent exo-tetrahydrocyclopentadiene, a synthetic fuel known as JP-10. This fuel is particularly suitable for use in air launched ramjet engine applications such as aircraft missile systems. This new fuel substantially meets the desirable viscosity, energy content, and flash point of the previously employed synthetic fuel blend while exhibiting superior storage characteristics in elastomeric fuel systems used in missile applications.
    Type: Grant
    Filed: October 13, 1981
    Date of Patent: October 18, 1983
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George W. Burdette
  • Patent number: 4394528
    Abstract: A high density liquid hydrocarbon fuel composition singularly suited for propelling turbojet limited volume missile systems designed for shipborne deployment. The contemplated fuels are basically composed of the saturated analogues of dimers of methyl cyclopentadiene and of dicyclopentadiene and optionally include the saturated analogues of the co-trimers of said dienes or the trimers of cyclopentadiene. The various dimers and trimers are combined in a relative relationship to provide optimal performing fuels for the indicated purpose.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: July 19, 1983
    Assignee: Ashland Oil, Inc.
    Inventor: Dennis H. Fisher
  • Patent number: 4367351
    Abstract: A high density specialty fuel for propelling limited volume ramjet and turbojet missile systems comprising a blend of at least 70 weight percent of exotetrahydrodicyclopentadiene and a correspondingly minor amount of a combination of a mixture of C.sub.5 -C.sub.7 alkanes and/or cycloalkanes and hydrogenated dimers of norbornadiene.
    Type: Grant
    Filed: July 1, 1981
    Date of Patent: January 4, 1983
    Assignee: Ashland Oil, Inc.
    Inventors: Dennis H. Fisher, Steven C. Howe, Richard L. Linard
  • Patent number: 4355194
    Abstract: A method for catalytically isomerizing a mixture of hexacyclic dimers obtained by dimerizing norbornadiene in the presence of a zero valent iron complex whereby the hydrogenated derivatives of the resultant isomerization product exhibits substantially lower freeze point than that associated with the hydrogenated derivatives of said precursor dimer mixture, the latter representing the highest energy liquid hydrocarbon fuel commercially available.
    Type: Grant
    Filed: November 6, 1980
    Date of Patent: October 19, 1982
    Assignee: Ashland Oil, Inc.
    Inventors: Richard V. Norton, Dennis H. Fisher, Garry M. Graham, Peter J. Frank
  • Patent number: 4351977
    Abstract: New polyunsaturated compounds, their preparation and their use as starting materials for preparing monounsaturated bicyclic compounds useful as intermediates in the preparation of macrocyclic ketones.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: September 28, 1982
    Assignee: Firmenich SA
    Inventor: Charles Fehr
  • Patent number: 4320238
    Abstract: A high density fuel composition having low temperature operational capability for propelling turbo-jet, limited volume missile systems consisting essentially of at least 95 weight percent exo-tetrahydrodicyclopentadiene (JP-10) and a correspondingly minor amount of a C.sub.3 -C.sub.7 saturated hydrocarbon.
    Type: Grant
    Filed: August 21, 1980
    Date of Patent: March 16, 1982
    Assignee: Ashland Oil, Inc.
    Inventors: Richard V. Norton, Steven C. Howe
  • Patent number: 4288644
    Abstract: Tetrahydrodimethyldicyclopentadiene is catalytically isomerized to a liquid isomeric mixture having a suitable low temperature viscosity making it suitable as a missile fuel. The catalyst comprises an acidic alumina. Hydrogen is also present and in an amount sufficient to maintain the isomerization activity of the alumina. The elevated temperature is sufficient to cause isomerization.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: September 8, 1981
    Assignee: Suntech, Inc.
    Inventors: Edward J. Janoski, Abraham Schneider, Richard E. Ware
  • Patent number: 4286109
    Abstract: A high density specialty fuel for propelling limited volume ramjet and turbojet missile systems comprising a blend of at least 70 weight percent of exotetrahydrodicyclopentadiene and a correspondingly minor amount of a combination of a C.sub.5 -C.sub.7 alkane or cycloalkane and a tetrahydro derivative of the trimer and/or co-trimer of cyclopentadiene and methylcyclopentadiene.
    Type: Grant
    Filed: July 31, 1980
    Date of Patent: August 25, 1981
    Assignee: Ashland Oil, Inc.
    Inventors: Richard V. Norton, Dennis H. Fisher
  • Patent number: 4282354
    Abstract: In general, materials having the structure ##STR1## wherein A represents phenylene, napthylene, anthracenediyl, and dibenzothien-diyl;R.sub.1 and R.sub.2, which may be the same or different when taken alone represent hydrogen, cyano, alkylcarbonyl and arylcarbamoyl, arylcarbonyl, cyanoaryl;R.sub.1 and R.sub.2, when taken together, represent sufficient atoms to form substituted and unsubstituted radicals selected from the group consisting of furanylidene, fluorenylidene, pyrimidinylidene, thiazolidinylidene, pyrrolinyl, and indenyl, isoxazolinylidene, pyrazolinylidene and indanylidene, wherein said substituents are selected from the group consisting of hydrogen, cyano, aryl, oxo, thioxo, nitro, alkyl, nitroaryl, carbamoyl and cyanoalkyl; andalkyl represents an alkyl group having from one to six carbon atoms; aryl represents an aromatic nucleus selected from the group consisting of benzene, napthalene or anthracene, are useful in electrophoretic migration imaging processes.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: August 4, 1981
    Assignee: Eastman Kodak Company
    Inventors: James A. Van Allan, Louis J. Rossi, Melvin S. Bloom, Michael T. Regan, Hal E. Wright, Joseph Y. Kaukeinen
  • Patent number: 4278823
    Abstract: Hydrogenolysis of a saturated endo-endo dihydronorbornadiene hexacyclic dimer involves the use of a catalytic amount of a Group VIII metal and the presence of hydrogen. The resulting pentacyclic isomers can be used as a diluent for depressing the freezing point of the saturated hexacyclic dimer which is a component of a high density missile fuel.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: July 14, 1981
    Assignee: Suntech, Inc.
    Inventors: Abraham Schneider, Harry K. Myers, Jr.
  • Patent number: 4277636
    Abstract: Method for effecting the formation of co-trimers of cyclopentadiene and methylcyclopentadiene whereby a mixture of the dimers of said dienes is heated in the presence of an inert solvent. The foregoing method is implemented to provide a high energy fuel by substantially completely hydrogenating the resultant trimerization product.
    Type: Grant
    Filed: August 11, 1980
    Date of Patent: July 7, 1981
    Assignee: Ashland Oil, Inc.
    Inventors: Richard V. Norton, Peter J. Frank, Dennis H. Fisher, Steven C. Howe
  • Patent number: 4270014
    Abstract: A method for converting endo-tetrahydrodicyclopentadiene to the corresponding exo isomeric form which is advantageously carried out in the presence of aluminum chloride catalyst and the spent nickel hydrogenation catalyst utilized in hydrogenating an endo dimer of cyclopentadiene to provide said tetrahydro derivative thereof.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: May 26, 1981
    Assignee: Ashland Oil, Inc.
    Inventors: Richard V. Norton, Steven C. Howe
  • Patent number: 4213901
    Abstract: Compounds of the formula ##STR1## and a process for their preparation by reacting azabutadienes with dienes, especially 1,3-butadiene, in the presence of catalysts are described. In the formula I, R.sub.1 and R.sub.3 independently of one another are hydrogen or alkyl having 1-8 C atoms and R.sub.2 and R.sub.4 independently of one another are alkyl having 1-8 C atoms, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together with the bonding C atom form a cycloaliphatic ring having 4-8 C atoms, and R.sub.5 and R.sub.6 independently of one another are hydrogen or alkyl having 1-4 C atoms. The compounds of the formula I are valuable intermediates for the preparation of active compounds for combating plant pests.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Reinehr
  • Patent number: 4207080
    Abstract: Norbornadiene [bicyclo(2.2.1)heptadiene-2,5] is dimerized to the exo-exo stereoisomer of the hexacyclic dimer of norbornadiene at both an excellent selectivity and conversion using an effective amount of a three component catalytic system of diethylaluminum chloride, ferric or ferrous or cobaltic or cobaltous acetylacetonate and bis(1,2-diphenylphosphino)ethane. The reaction rate is rapid. After hydrogenation the exo-exo hexacyclic dimer can be used as a component of high energy fuel for either jet or rocket propulsion.
    Type: Grant
    Filed: December 11, 1975
    Date of Patent: June 10, 1980
    Assignee: Suntech, Inc.
    Inventors: George Suld, Abraham Schneider, Harry K. Myers, Jr.
  • Patent number: 4203930
    Abstract: Novel codimer (I) of norbornadiene and 1,3-cyclohexadiene and its hydrogenated derivative (II), having the following structures: ##STR1## and processes for preparing both are disclosed. Product (II) can be used as a high energy fuel. Process for codimer I involves use of three component homogeneous catalytic system of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphino ethane and one of three alkyl aluminum chlorides.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: May 20, 1980
    Assignee: Sun Oil Company of Pennsylvania
    Inventor: Harry K. Myers, Jr.
  • Patent number: 4190610
    Abstract: Catalytic codimerization of norbornadiene and 1,3-pentadiene yields an olefinic codimer which, after hydrogenation, has utility as a high energy missile fuel or a diluent for a higher viscous missile fuel. Used is a three-component homogeneous catalytic system, consisting of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphina ethane and an alkyl aluminum chloride.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: February 26, 1980
    Assignee: Sun Oil Company of Pennsylvania
    Inventors: Harry K. Myers, Jr., James E. Lyons, Abraham Schneider
  • Patent number: 4190611
    Abstract: Norbornadiene and nobornene are catalytically codimerized to the saturated exo-exo hexacyclic dimer of norbornadiene. Used is a three-component homogeneous catalytic system consisting of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphino ethane and an alkyl aluminum chloride. Resulting dimer can be used as a component of high energy fuel.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: February 26, 1980
    Assignee: Sun Oil Company of Pennsylvania
    Inventors: James E. Lyons, Harry K. Myers, Jr., Abraham Schneider
  • Patent number: 4170576
    Abstract: A process is described for providing clear extended compositions of essential oils which comprises a composition of an essential oil and an extender material miscible with said essential oil which does not appreciably alter the aroma of the essential oil insofar as its quality or strength is concerned, the proportion of essential oil in extender material being from about 70% up to about 99%, said extender material being a mixture of (A) a dimerization product of an alpha methyl styrene or a methyl or other C.sub.2 -C.sub.4 lower alkyl homologue thereof or mixture of same, and (B) one or more "dimerization" (or "coupling") products of one or more terpenes which are monocyclic and have two carbon-carbon double bonds or which are bicyclic and have one carbon-carbon double bond or one or more hydrogenated derivatives thereof or mixtures of same.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: October 9, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Wilhelmus J. Wiegers, Ira D. Hill, Robert M. Novak, Frederick L. Schmitt
  • Patent number: 4169863
    Abstract: Norbornadiene and an alkyne are catalytically codimerized in the presence of a homogeneous catalytic system of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphino ethane and an alkyl alluminum chloride. Also, novel codimers of norbornadiene and an alkyne containing at least three carbons are disclosed. After hydrogenation, resulting codimers can be used as high energy fuels or diluents for such fuels.
    Type: Grant
    Filed: March 22, 1978
    Date of Patent: October 2, 1979
    Assignee: Suntech, Inc.
    Inventors: Harry K. Myers, Jr., James E. Lyons, Abraham Schneider
  • Patent number: 4169864
    Abstract: Novel codimers (I) of norbornadiene and phenylacetylenes and their hydrogenated derivatives (II), having the following structures ##STR1## wherein R is a hydrogen, a phenyl, or a phenyl having alkyl substitutents and R.sub.1 is a phenyl or a phenyl having alkyl substituents and processes for preparing both are disclosed. Codimer (II) can be used as a high energy fuel or a diluent for such a fuel. Process for making codimer (I) involves reacting norbornadiene and phenylacetylene or diphenylacetylene with a catalyst system of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphino ethane and an alkyl aluminum chloride.
    Type: Grant
    Filed: March 22, 1978
    Date of Patent: October 2, 1979
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, Abraham Schneider, Harry K. Myers, Jr.
  • Patent number: 4168282
    Abstract: Mono or dialkyl substituted norbornenes or cyclic norbornene derivatives are prepared by condensing an appropriate olefin or an ethylenically unsaturated alicyclic compound with dicyclopentadiene or cyclopentadiene at an elevated temperature and pressure in the presence of a chlorinated hydrocarbon solvent.
    Type: Grant
    Filed: May 15, 1978
    Date of Patent: September 18, 1979
    Assignee: The B. F. Goodrich Company
    Inventor: Wolfgang Schneider