Polycyclo, I.e., Fused Patents (Class 585/21)
  • Patent number: 6593363
    Abstract: The present invention relates to diterpene derivatives prepared from the components which are extracted from Acanthopanax Koreanum and represented by Chemical Formula (1).
    Type: Grant
    Filed: September 15, 2000
    Date of Patent: July 15, 2003
    Assignees: Sae Han Pharm. Co., Ltd.
    Inventors: Young Ger Suh, Young Hoon Choi, Hye Kyung Lee, Young Ho Kim, Hyoung Sup Park
  • Patent number: 6512152
    Abstract: The present invention is drawn to a tetracyclododecene composition having a regulated cyclopentadiene trimer content, whereby addition polymerization with the aid of a Ziegler catalyst can be carried out while preventing gelation caused by a cross-linking reaction. A tetracyclododecene composition regulated with respect to the content of a specific ingredient having a molecular weight of 188 is disclosed, whereby polymers having high glass transition temperatures can be obtained through various polymerizations. Further, the present invention is drawn to a method for producing tetracyclododecene in the presence of an aliphatic solvent having a boiling point close to that of norbornene, which solvent is effective in inhibiting the recovered norbornene from solidifying.
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: January 28, 2003
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Masaki Hashizume, Tomonobu Uchida, Fuyuki Aida, Takashi Suzuki, Yoshihisa Inomata, Yasuo Matsumura
  • Publication number: 20030004090
    Abstract: The compound according to the formula set forth below 1
    Type: Application
    Filed: May 17, 2001
    Publication date: January 2, 2003
    Inventors: Anthony T. Levorse, Anubahv P.S. Narula, Edward Mark Arruda, Charles E.J. Beck
  • Publication number: 20020193648
    Abstract: Disclosed are processes for the recovery and purification of higher diamondoids from a hydrocarbonaceous feedstock. Specifically disclosed is a multi-step recovery process for obtaining diamondoid compositions enhanced in tetramantane components and higher diamondoid components. Also disclosed are compositions comprising at least about 10 weight percent of non-ionized tetramantane components and higher diamondoid components and at least about 0.5 weight percent of non-ionized pentamantane components and higher diamondoid components based on the total weight of diamondoid components present.
    Type: Application
    Filed: December 12, 2001
    Publication date: December 19, 2002
    Inventors: Jeremy E. Dahl, Robert M. Carlson
  • Patent number: 6482966
    Abstract: A process for producing a crosslink-cyclized cyclopentadiene, comprising the steps of reacting a cyclopentenone with an alkali metal hydride to thereby reduce the cyclopentenone (reduction step A) into a cyclopentenol; and reacting the cyclopentenol with a dehydrating agent to thereby dehydrate the cyclopentenol (dehydration step B) into a crosslink-cyclized cyclopentadiene of the general formula (III): wherein each of R1 and R2 independently represents a hydrogen atom or a linear or branched saturated alkyl group having 1 to 6 carbon atoms, n is an integer of 3 to 10, and the broken line in the 5-membered ring denotes that the 5-membered ring has two double bonds.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: November 19, 2002
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventor: Keiichi Yokoyama
  • Patent number: 6323315
    Abstract: The present invention provides compounds of the formula where R1-R5 are each, independently, a hydrogen atom or a normal or branched C1-C6-alkyl group; A is a methionyl, phenylalanyl or phenylglycyl residue; n is 0 or 1; R6 is a hydrogen atom; and R7 is a carbocylic group, an aromatic group, a C1-C4-alkyl group, a pyridylalkyl group or a heterocyclic group. In another embodiment, R6 is benzyl or —C(O)OR8, where R8 is a C1-C6-alkyl group, and R7 is a heteroaromatic group, such as a 2-thiazolyl group.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: November 27, 2001
    Assignees: BASF Aktiengesellschaft, Arizona Board of Regents
    Inventors: George R. Pettit, Jayaram K. Srirangam, Michael D. Williams, Kieran P. M. Durkin, Teresa Barlozzari, Andreas Kling, Bernd Janssen, Andreas Haupt
  • Patent number: 6320088
    Abstract: Traction drive fluids comprise a saturated polycyclic hydrocarbon compound obtained by hydrogenating a trimeric compound of a cyclopentadiene-based condensed hydrocarbon compound resulting from the Diels-Alder reaction of cyclopentadiene and then isomerizing the resulting compound so as to have a pour point of −10° C. or below. The traction drive fluids can be used not only in driving force transmitting mechanisms but also in hydraulic pressure controlling mechanism and friction properties controlling mechanisms of wet clutches.
    Type: Grant
    Filed: February 27, 2001
    Date of Patent: November 20, 2001
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Mitsuo Matsuno, Shinichi Shirahama, Tetsuo Okawa
  • Publication number: 20010012902
    Abstract: A process for producing a crosslink-cyclized cyclopentadiene, comprising the steps of reacting a cyclopentenone with an alkali metal hydride to thereby reduce the cyclopentenone (reduction step A) into a cyclopentenol; and reacting the cyclopentenol with a dehydrating agent to thereby dehydrate the cyclopentenol (dehydration step B) into a crosslink-cyclized cyclopentadiene of the general formula (III): 1
    Type: Application
    Filed: January 31, 2001
    Publication date: August 9, 2001
    Inventor: Keiichi Yokoyama
  • Patent number: 6242393
    Abstract: A traction drive fluid comprises a tractant selected from the specific types of hydrocarbons, carboxylates and carbonate, optionally an effective amount of a base oil selected from a mineral oil and a synthetic oil and additives selected from a viscosity index improver, a ashless dispersant, a phosphorus-containing additive, a friction adjusting agent, a metallic detergent, an oxidation inhibitor, a polar additive, a corrosion inhibitor, a rubber swelling agent, a antifoamer and a colorant.
    Type: Grant
    Filed: April 8, 1999
    Date of Patent: June 5, 2001
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Noboru Ishida, Junya Kohno, Shinichi Shirahama, Tetsuo Okawa
  • Patent number: 6191330
    Abstract: Disclosed is a traction drive fluid which comprises (A) one or more than two compounds selected from the group consisting of saturated polycyclic hydrocarbon compounds represented by the formulae: wherein R1 and R2 are each independently hydrogen or a methyl group, provided that the case where both R1 and R2 are a methyl group at the same time is excluded, and R3 and R4 are each independently hydrogen or a methyl group; wherein R5 and R6 are each independently hydrogen or a methyl group, provided that the case where both R5 and R6 are a methyl group at the same time is excluded, R7 and R8 are each independently hydrogen or a methyl group; and wherein R9, R10 and R11 are each independently hydrogen or a methyl group.
    Type: Grant
    Filed: September 16, 1999
    Date of Patent: February 20, 2001
    Assignees: Nippon Mitsubishi Oil Corporation, San-Petrochemical Co., Ltd.
    Inventors: Mitsuo Matsuno, Shinichi Shirahama, Tetsuo Okawa, Takashi Kiyota
  • Patent number: 6139484
    Abstract: Bridged cyclopentadienyl derivatives having general formula (I)A--X--B (I)wherein:1) A is a monofunctional hydrocarbyl radical having general formula (II) ##STR1## 2) --X-- is the bridge between A and B and consists of a bifunctional radical selected from an alkylene group, a silanylene group, an alkyl substituted silaalkylene group, a siloxasilanylene group;3) B is a monofunctional hydrocarbyl radical selected from:e) any of the A radicals defined above,f) a cyclopentadienyl radical.
    Type: Grant
    Filed: October 10, 1996
    Date of Patent: October 31, 2000
    Assignee: Enichem S.p.A.
    Inventors: Paolo Biagini, Gabriele Lugli, Roberto Santi, Giampiero Borsotti, Viviano Banzi
  • Patent number: 5939595
    Abstract: A process for preparing diarylethanes of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each hydrogen or C.sub.1 -C.sub.8 -alkyl, by reacting aromatic compounds of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the abovementioned meanings, with styrenes of the general formula III ##STR3## where R.sup.1 has the abovementioned meanings, at from -20 to 300.degree. C. under from 1 to 100 bar in the presence of heterogeneous catalysts, wherein beta-zeolites or mordenites are used as heterogeneous catalysts.
    Type: Grant
    Filed: April 26, 1996
    Date of Patent: August 17, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Eugen Gehrer, Klemens Massonne, Hermann Gausepohl, Martin Fischer, Christopher William Rieker, Lorenz Siggel
  • Patent number: 5900517
    Abstract: Cyclopentadienyl derivatives are described having general formula (I) ##STR1## where R, R.sub.1, R.sub.2, R.sub.4, equivalent to or different from one another, are selected from: --H, alkyl radicals having a number of carbon atoms from 1 to 5, cycloalkyl radicals having a number of carbon atoms from 5 to 8, aryl and alkylaryl radicals having a number of carbon atoms from 6 to 8, aralkyl radicals having a number of carbon atoms from 7 to 9; n is an integer from 2 to 18; with the proviso that the number of R different from H does not exceed 2; with the exclusion of the compound having n=3, R.dbd.R.sub.1 .dbd.R.sub.2 .dbd.R.sub.4 .dbd.H. The invention a-so describes the process for the preparation of the above-mentioned cyclopentadienyl derivatives.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: May 4, 1999
    Assignee: Enichem S.p.A.
    Inventors: Paolo Biagini, Roberto Santi, Giampiero Borsotti, Gabriele Lugli, Viviano Banzi
  • Patent number: 5866733
    Abstract: Diarylethanes of the formula I ##STR1## where R.sup.1 is hydrogen or C.sub.1 -C.sub.8 -alkyl, are prepared by reacting benzene with a styrene of the formula III ##STR2## where R.sup.1 has the abovementioned meanings, by a process in which the reaction is carried out batchwise or continuously in the liquid or supercritical phase at from 150.degree. to 350.degree. C. and from 5 to 200 bar in the presence of a strongly acidic large-pore zeolite.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: February 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Eugen Gehrer, Klemens Massonne, Wolfgang Harder
  • Patent number: 5847247
    Abstract: The specification discloses terpene-based solvent compositions which comprise diterpenes as a major component and a minor amount of monoterpenes. The mixtures exhibit solvent properties similar to monoterpenes but have flash points high enough to be classified as combustible rather than flammable materials.
    Type: Grant
    Filed: March 18, 1996
    Date of Patent: December 8, 1998
    Assignee: Arizona Chemical Company
    Inventors: Alexander J. Conte, Bobby G. Johnson, Raymond H. Jones, Claude F. Phillips, Jr.
  • Patent number: 5807477
    Abstract: A process for treating a light cracked naphtha to be used as an etherification or alkylation feedstock in which the mercaptans and diolefins reacted in a single pass fixed bed reactor and are removed in a distillation column reactor which hydrogenate the unreacted diolefins. The mercaptans are reacted with the diolefins to form sulfides which are higher boiling than that portion of the naphtha which is used as feed to the etherification or alkylation unit. The higher boiling sulfides are removed as bottoms along with any C.sub.6 and heavier materials. Any diolefins not converted to sulfides are selectively hydrogenated to mono-olefins for use in the etherification process. Certain C.sub.5 olefins, for example pentene-1 and 3-methyl butene-1 are isomerized during the process to more beneficial isomers.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: September 15, 1998
    Assignee: Catalytic Distillation Technologies
    Inventors: Dennis Hearn, Gary R. Gildert
  • Patent number: 5723709
    Abstract: Terpene dimer compositions are provided which dry into a hard, tack free film upon exposure to air. The compositions include a terpene dimer having the molecular formula C.sub.20 H.sub.32 and contain at least one double bond. The terpene dimer is derived from a naturally occurring monoterpene, or mixtures thereof, having the molecular formula C.sub.10 H.sub.16. In an another embodiment the compositions, in addition to the terpene dimer, include isomers of the monoterpenes. The compositions are substantially free of higher terpene oligomers having molecular formulas greater than C.sub.20 H.sub.32. Processes for making the terpene dimer compositions are also provided. Advantageous utilization of these compositions is as a diluent, solvent or component in coating, adhesive, alkyd or ink formulations, as an environmentally safe non-toxic material.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: March 3, 1998
    Assignee: Arizona Chemical Company
    Inventors: Claude Frank Phillips, Jr., James William Booth
  • Patent number: 5662830
    Abstract: A novel liquid crystal material having a carbon chain containing a conjugated diene as a terminal substituent of the molecule and exhibiting superior characteristics is provided, which is a diene derivative expressed by the formula (I) ##STR1## wherein R and R' each independently represent 1-5C alkyl; A and B each independently represent 1,4-cyclohexylene or 1,4-phenylene; n is 0 or 1; m is an integer of 0 to 2; X and X' each independently represent H atom or F atom when A is 1,4-phenylene or represent H atom when A is 1,4-cyclohexylene; Y is alkyl, halogen or CN, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-phenylene, or represent alkyl, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-cyclohexylene; and R and R' are not simultaneously alkyl chain of 4 or more carbon atoms.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: September 2, 1997
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
  • Patent number: 5455265
    Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 3, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5446222
    Abstract: The invention provides a two-step process for converting cyclopentadiene dimer to a high density fuel mixture comprising the steps of:(a) reacting said cyclopentadiene dimer in the presence of a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under oligomerization/isomerization conditions to convert at least a portion of said cyclopentadiene dimer to a normally liquid intermediate product containing cyclopentadiene trimer, cyclopentadiene tetramer, and the isomerized and oligomerized products derived from the reaction of at least three cyclopentadiene monomer units;(b) hydrogenating said normally liquid intermediate product of step (a) in the presence of a hydrogenation catalyst to form a normally liquid high energy density fuel.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 29, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James R. Boulton, Ross A. Kremer
  • Patent number: 5422027
    Abstract: A process for improving the traction coefficient between at least two relatively rotatable elements having tractive surfaces in a torque transmitting relationship which comprises introducing between the tractive surfaces of the elements a traction drive fluid comprising, as the active component, a hydrocarbon compound having a bicylo octane skeleton.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: June 6, 1995
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 5399647
    Abstract: New copolymers are disclosed which are copolymers of 1-(1'-cyanoethenyl)adamantane or 2-norbornene-2-carbonitrile monomer with an acrylate or methacrylate monomer. Resist compositions are also disclosed which comprise one of the disclosed new copolymers and an acid generator. The resist compositions advantageously form thinner resist films on substrates and, on the exposure to light having a short wavelength, such as KrF and ArF excimer laser light, provide finer resist pattern required in the production of advanced, highly integrated semiconductor devices. Novel 1-(1'-cyanoethenyl)adamantane is also disclosed.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: March 21, 1995
    Assignee: Fujitsu Limited
    Inventor: Koji Nozaki
  • Patent number: 5384059
    Abstract: Mixtures consisting essentially of cyclohexylbiphenyls, dicyclohexylbenzenes, phenylbicyclohexyls and tercyclohexyls are outstandingly suitable as heat transfer media. The mixtures can be prepared from biphenyl and cyclohexanol in the presence of bleaching earths and subsequent hydrogenation.
    Type: Grant
    Filed: August 20, 1993
    Date of Patent: January 24, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alfons Klein, Rudolf Kron, Helmut Fiege, Klaus-Christian Paetz
  • Patent number: 5344582
    Abstract: A traction fluid lubricant is disclosed which contains a naphthenic ingredient having a weight average molecular weight of 200-300 and obtained by hydrogenating oligomers of cyclopentadiene having a ratio of the number of norbornenic double bond to that of cyclopentenic double bond of smaller than 0.9 but not smaller than 0.1. The naphthenic ingredient is suitably used in conjunction with an auxiliary ingredient selected from a polybutene having a viscosity of 5-60 cSt at 40.degree. C. and a bicyclohexyl compound.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: September 6, 1994
    Assignee: Tonen Corporation
    Inventors: Noboru Umemoto, Takeshi Nomura, Toshiaki Kuribayashi, Takehisa Sato, Hirotaka Tomizawa
  • Patent number: 5306851
    Abstract: The invention provides a composition comprising at least about 10 different diamondoid compounds selected from the group consisting of methyl-substituted and ethyl-substituted adamantane, diamantane, and triamantane, wherein each of said selected diamondoid compounds comprises no more than about 10 weight percent of said composition. The composition is useful as high quality lubricating fluid and exhibits the unusual combination of high Viscosity Index and very low pour point.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: April 26, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Margaret M. Wu, Dong-Ming Shen, Catherine S. H. Chen
  • Patent number: 5283384
    Abstract: A traction drive fluid composition comprising a hydrocarbon having a bicyclo octane skeleton, such as a bicyclo(3,2,1) octane skeleton, a bicyclo(2,2,2)octane skeleton or a bicyclo(3,3,0)octane skeleton. The traction drive fluid has a low viscosity and has a high traction coefficient over a wide temperature range.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: February 1, 1994
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 5262501
    Abstract: Mixtures essentially comprising compounds of formula I or II ##STR1## wherein X is a hydrogen atom or vinyl, A is a divalent aromatic radical which is unsubstituted or substituted by one or more C.sub.1 -C.sub.20 alkyl groups, halogen atoms or halogen-substituted C.sub.1 -C.sub.20 alkyl groups, R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are each a hydrogen atom, or R.sub.1 and R.sub.1 ', R.sub.2 and R.sub.2 ' and R.sub.3 and R.sub.3 ' are each together ethylene, R.sub.4 is C.sub.1 -C.sub.6 alkyl, phenylalkyl containing 1 to 6 carbon atoms in the alkyl moiety or is trialkylsilyl containing 1 to 6 carbon atoms in each alkyl moiety, m is 0, 1 or 2, n is 0 or an average number from 1 to 200, p is an average number from 1 to 100 and q is 0 or an average number from 1 to 100, can be cured by heating and are suitable for making laminates, especially for fabricating copper-clad circuit boards.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: November 16, 1993
    Assignee: Ciga-Geigy Corporation
    Inventors: Sheik Abdul-Cader Zahir, Cecile Pasquier, Wolfgang Scharf, Maurice Dupre
  • Patent number: 5107041
    Abstract: The invention provides a novel compound 1,1-dicyclohexyl cycloalkane derivative represented by the general formula ##STR1## in which R.sup.1 and R.sup.2 are each a hydrogen atom or lower alkyl group, R.sup.3 to R.sup.6 are each a hydrogen atom, lower alkyl group or alkylene group forming a ring structure together with either one of the others and the carbon atom in the cycloalkane ring, and m and n are each zero or a positive integer not exceeding 6 with the proviso that m+n is 4-6, such as 1,1-dicyclohexyl cyclohexane. The compound has a relatively low viscosity and high traction coefficient even at elevated temperatures so that it is useful as a constituent of a traction-drive fluid usable in a compact and light-weight traction-drive apparatus. The compound can be synthesized by subjecting a corresponding 1,1-di(hydroxyphenyl) cycloalkane compound to a hydrogenation reaction and dehydration reaction in combination in the simultaneous presence of a hydrogenation catalyst and a dehydration catalyst.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: April 21, 1992
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 5064642
    Abstract: A composition for external application comprising a tricyclic saturated hydrocarbon represented by formula (I) is disclosed. ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and independently represents a hydrogen atom or a methyl group and R.sup.3 represents an alkyl group having 2-3 carbon atoms. The compositions for external application of the present invention exhibit an excellent moisture-retention effect and impart moistened feel without sliminess and irritation to the skin. They are thus useful as skin cosmetics, hair cosmetics, medical compositions for external application, and the like.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: November 12, 1991
    Assignee: Kao Corporation
    Inventors: Yoko Kikuchi, Yukihiro Ohashi, Yuji Suzuki, Toshiyuki Suzuki
  • 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: 5043497
    Abstract: A lubricating oil is disclosed, which mainly is composed of a naphthenic hydrocarbon having 19 carbon atoms comprising two cyclohexane rings which have methyl-substitution at the 1, 2 and 4 positions thereof, the two cyclohexane rings being linked by a methylene group.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: August 27, 1991
    Assignee: Mitsubishi Oil Co., Ltd.
    Inventors: Masayoshi Muraki, Hajime Yoshida, Koji Tsuchimoto
  • 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: 4943302
    Abstract: A fuel composition with a high energy content, for direct-ignition internal combustion engines contains a gasoline from petroleum and an amount of up to 90% by volume, as referred to the same fuel composition, of hydrocarbon "cubane" or of its alkyl-derivatives, to be defined by means of the formula: ##STR1## wherein R' and R" represent, independently from each other, a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: July 24, 1990
    Assignees: Enichem Synthesis S.p.A., AGIP Petroli S.p.A.
    Inventors: Philip Eaton, Nereo Nodari, Carlo Neri, Luigi Cassar, Fabio Monti, Fausto Alberici
  • 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: 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: 4755317
    Abstract: The working fluid for traction drive use has a particularly high traction coefficient at high temperatures and the principal ingredient thereof is a decahydronaphthalene compound substituted, on either one or both of the decahydronaphthalene rings, with two or three substituent groups which may be cyclohexyl groups, cyclohexyl alkyl groups, e.g. cyclohexyl methyl, cyclohexyl ethyl, 1-methyl-1-cyclohexyl ethyl and 1-methyl-1-(methylcyclohexyl) ethyl groups, or a combination thereof. The working fluid can be a mixture of a base oil of various types and the above mentioned decahydronaphthalene compound in an amount of 5 to 250 parts by weight per 100 parts by weight of the base oil.
    Type: Grant
    Filed: March 18, 1987
    Date of Patent: July 5, 1988
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Tomiyasu Minokami, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4707295
    Abstract: Bicyclooctane derivatives of the formula IR.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 being also --A.sup.3 --R.sup.3,A.sup.1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH.dbd.CH--, --S--, --SO-- or --SO.sub.2 --, or is substituted by F, Cl, Br, CN and/or CHO,A.sup.2 is a 1,4-bicyclo[2.2.2] octylene group,--A.sup.3 --R.sup.3 is --Cy--R.sup.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: November 17, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
  • Patent number: 4684754
    Abstract: The working fluid for traction drive comprises (A) a compound having, in a molecule, two decahydronaphthalene rings bonded either directly to each other or to the same or different carbon atoms in an alkane molecule or a compound having, in a molecule, one decahydronaphthalene ring and one cyclohexane ring bonded either directly to each other or to the same carbon atom in an alkane molecule and (B) a compound having two cyclohexane rings bonded either to the terminal carbon atoms of a C.sub.2-3 alkane molecule or to the carbon atoms of cyclopentane. The working fluid has a high traction coefficient with stability over a wide range of temperature, especially, in low temperatures.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: August 4, 1987
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • 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: 4627933
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4609481
    Abstract: A traction drive fluid composition comprising the principal component of at least one component represented by the general formula (I): ##STR1## wherein R.sup.1 to R.sup.5 are each a hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and 1, m and n are each 1 to 3, said compound (I) comprising a mixture of 70% or less of the cis-form and 30% or more of the trans-form.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: September 2, 1986
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • 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: 4604490
    Abstract: The present invention is connected with a high-density liquid fuel for rockets and jet engines which mainly comprises a compound represented by the general formula ##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 a sum of R.sup.1 to R.sup.3 is an integer of 1 to 3.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: August 5, 1986
    Assignee: Nippon Oil Company Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
  • 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: 4556503
    Abstract: A traction drive fluid is described, containing as the base stock a compound represented by the general formula (I): ##STR1## wherein all the symbols are as defined in the appended claims. This traction drive fluid has a high traction coefficient, has a good thermal stability, is of low viscosity, is of low volatility and further is reduced in temperature dependency of viscosity. Thus it is suitable for use in continuously variable transmission of cars or industrial machines.
    Type: Grant
    Filed: September 4, 1984
    Date of Patent: December 3, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • 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: 4525290
    Abstract: A process for improving traction coefficient of traction drive fluid at high temperatures by using a compound represented by the general formulae (I), (II) or (III) as a base stock of traction drive fluid, ##STR1## (All the symbols are as defined in the appended claims). This process is helpful for reducing the change of traction coefficients over a wide range of from low temperature to high temperature.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: June 25, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • 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: 4434073
    Abstract: Perhydrophenanthrene derivatives of formula I ##STR1## wherein R.sub.1 is alkyl of 1-10 C atoms and R.sub.2 is alkyl, alkoxy or alkanoyloxy each of 1-10 C atoms, H, Br, Cl or CN, have an extremely low optical anisotropy and are particularly suitable as components of liquid-crystalline dielectrics.
    Type: Grant
    Filed: December 8, 1982
    Date of Patent: February 28, 1984
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Hans-R/u/ diger Murawski, Hermann Minas, Horst Stegemeyer