The Nitrogen Is Bonded Directly To The Carbon Of A -c(=x)x- Group, Wherein The Xs May Be The Same Or Diverse Chalcogens (e.g., Dithiocarbamates, Etc.) Patents (Class 508/363)
  • Patent number: 6117826
    Abstract: Dithiocarbamyl derivatives, useful as multifunctional additives for lubricating oils, of the formula ##STR1## wherein Q is ##STR2## R.sup.1 and R.sup.2 are each independently C.sub.1 -C.sub.30 n-alkyl, C.sub.3 -C.sub.30 branched alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 aryl, or C.sub.6 -C.sub.12 alkylaryl; R.sup.3 is C.sub.1 -C.sub.20 alkylene; R.sup.4 is --R.sup.3 --C(O)--O--; R.sup.5 and R.sup.6 are each independently hydrogen, C.sub.1 -C.sub.30 n-alkyl, C.sub.3 -C.sub.30 branched alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 aryl, or C.sub.6 -C.sub.12 alkylaryl; R.sup.7 is C.sub.1 -C.sub.20 alkylene, optionally substituted with --OR.sup.5 or --COOH; R.sup.8 is --R.sup.3 --C(O)--NR.sup.5 --; n is 0, 1, 2 or 3; and y is 0, 1, 2, or 3.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: September 12, 2000
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: John Robert Baranski, Cyril Andrew Migdal
  • Patent number: 6110877
    Abstract: The invention relates to an extreme pressure lubricant composition, in per cent by weight, which includes from about 25 to about 37 percent polyalphaolefin, from about 1 to about 5 percent pentaerythritol ester of a fatty acid, from about 20 to about 35 percent of said methyl ester, from about 1 to about 10 percent of said copolymer of ethylene and propylene, from about 22 to about 32 percent of said bismuth salt and from about 1 to about 10 percent antimony diakyldithiocarbamate.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: August 29, 2000
    Inventor: John W. Roberts
  • Patent number: 6110878
    Abstract: Oil-soluble or oil-dispersible trinuclear molybdenum-sulfur compounds are made by reacting less than three, such as 1.5 to 2.5, preferably two to 2.1, molar equivalents of a disulfide with one molar equivalent of a compound containing the [Mo.sub.3 S.sub.13 ].sup.2- ion. The trinuclear compounds include S-containing ligands that are derived from the disulfide reactant via cleavage of the disulfide bond; the ligands are bound to the core via the S atoms.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: August 29, 2000
    Assignee: Exxon Chemical Patents Inc
    Inventors: Jonathan M. McConnachie, Edward Ira Stiefel, Ian Alexander Weston Bell, Velautha-Cumaran Arunasalam
  • Patent number: 6096693
    Abstract: The present invention is directed to a zinc-molybdenum-based dithiocarbamate derivative which is a complex salt having the metallic components of zinc and molybdenum in the same molecule. When used as a lubricant additive, it imparts a notable friction-reducing effect to the lubricant composition in which it is incorporated, reducing its friction coefficient and improving its stability of friction coefficient at both low and high temperature, particularly at high temperature. In particular, it improves friction-related characteristics much more notably than a combination of a molybdenum and zinc compound.
    Type: Grant
    Filed: February 23, 1999
    Date of Patent: August 1, 2000
    Assignee: Tonen Corporation
    Inventors: Hiroshi Nakanishi, Hiroyuki Iwasaki, Katsuya Koganei
  • Patent number: 6043200
    Abstract: The compatibility with nitrile ester seals of lubricating compositions containing active sulphur-containing additives may be enhanced bt treating the additives, or concentrates containing them, or the composition themselves, with one or more olefinically unsaturated compounds selected from:(a) acyclic compounds having at least two double bonds with adjacent double bonds separated by two saturated carbon atoms;(b) compounds containing an acyclic ring, which ring contains at least, eight carbon atoms and at least two double bonds, each double bond being separated from the closest adjacent double bond(s) by two saturated carbon atoms; and(c) compounds containing a saturated alicyclic ring and at least one exocyclic double bond.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: March 28, 2000
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Dale Robert Carroll, Brid Dilworth, Michele Anne Thornhill
  • Patent number: 6037314
    Abstract: A grease composition for constant velocity joints comprises (a) a base oil; (b) a urea thickener; (c) at least one organic molybdenum compound selected from the group consisting of molybdenum dithiocarbamate and molybdenum dithiophosphate; and (d) at least one calcium salt selected from the group consisting of calcium salts of petroleum sulfonates, calcium salts of alkyl aryl sulfonates, calcium salts of salicylate, calcium salts of phenates, calcium salts of oxidized waxes, overbasic calcium salts of petroleum sulfonates, overbasic calcium salts of alkyl aryl sulfonates, overbasic calcium salts of salicylate, overbasic calcium salts of phenates, and overbasic calcium salts of oxidized waxes. The grease composition exhibits good performance for reducing vibration and effectively lubricates the constant velocity joints to effectively reduce frictional wear and to eliminate vibration.
    Type: Grant
    Filed: June 5, 1997
    Date of Patent: March 14, 2000
    Assignees: Kyodo Yushi Co., Ltd., Toyota Jidosha Kabushiki Kaisha
    Inventors: Shinya Kondo, Junichi Imai, Takashi Okaniwa, Kenji Ueno, Hitoshi Ishii, Fumio Ueda
  • Patent number: 6010987
    Abstract: The invention is a method for improving the friction reduction and friction reduction retention performance of a lubricating oil comprising adding to the lubricating oil a trinuclear molybdenum sulfur compound selected from the group of trinuclear molybdenum compounds preferably those having the formulas Mo.sub.3 S.sub.7 (dtc).sub.4 and Mo.sub.3 S.sub.4 (dtc).sub.4 and mixtures thereof wherein dtc represents independently selected diorganodithiocarbamate ligands containing independently selected organo groups and wherein the ligands have a sufficient number of carbon atoms among all the organo groups of the compound's ligands are present to render the compound soluble or dispersible in the lubricating oil. Concentrates of the composition are also included in the invention.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: January 4, 2000
    Assignee: Exxon Research and Engineering Co.
    Inventors: Edward Ira Stiefel, Jonathan M. McConnachie, Daniel Paul Leta, Charles Frederick Pictroski
  • Patent number: 5939364
    Abstract: Multifunctional molybdenum compounds, which are the reactive product of molybdenum dithiocarbamates and (non-metal containing) dihydrocarbyl dithiophosphoric acids, and the oils that contain them are new compositions which are useful as lubricant additives. They impart to the lubricant formulations to which they are added low friction and excellent friction retention properties.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: August 17, 1999
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard Samuel Polizzotti, Elisavet P. Vrahopoulou, Stephen D. Cameron, Charles Frederick Pictroski
  • Patent number: 5916851
    Abstract: There is disclosed a lubricating oil for internal combustion engine which comprises:a mineral oil and/or a synthetic lubricating oil as a base oil, and oxymolybdenum dithiocarbamate sulfide expressed by the chemical formula (1): ##STR1## wherein R.sub.1 or R.sub.1 and R.sub.3 denote a branched aliphatic hydrocarbon group having not less than fourteen carbons, and R.sub.2 through R.sub.4 or R.sub.2 and R.sub.4 denote an aliphatic hydrocarbon group having not less than four carbons, in the amount of 0.005 to 0.2% by weight, when calculated as molybdenum (Mo).
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: June 29, 1999
    Assignee: Japan Energy Corporation
    Inventors: Kunihiko Hosonuma, Yasushi Naitoh, Toru Imori, Kouichi Nakamura
  • Patent number: 5906968
    Abstract: A method of making an oil-soluble or oil-dispersible trinuclear molybdenum-sulfur compound, comprising: reacting two to less than three equivalents of a tetrahydrocarbyl thiuram disulfide and one equivalent of a compound containing the ?Mo.sub.3 S.sub.13 !.sup.2- ion to produce a trinuclear molybdenum compound of the formula Mo.sub.3 S.sub.x (L).sub.4 wherein x is from 4 to 10 and L is dihydrocarbyl-dithiocarbamate.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: May 25, 1999
    Assignee: Exxon Research & Engineering Company
    Inventors: Jonathan M. McConnachie, Edward I. Stiefel, Ian Alexander Weston Bell, Velautha-Cumaran Arunasalam
  • Patent number: 5888945
    Abstract: The invention is a method for enhancing and restoring the friction reduction effectiveness of a lubricating oil comprising adding to the lubricating oil a trinuclear molybdenum sulfur compound selected from the group of trinuclear molybdenum compounds preferably those having the formulas Mo.sub.3 S.sub.7 (dtc).sub.4 and Mo.sub.3 S.sub.4 (dtc).sub.4 and mixtures thereof wherein dtc represents independently selected diorganodithiocarbamate ligands containing independently selected organo groups and wherein the ligands have a sufficient number of carbon atoms among all the organo groups of the compound's ligands are present to render the compound soluble or dispersible in the lubricating oil. The oil may be a fresh or used oil. Concentrates of the composition are also included in the invention.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: March 30, 1999
    Assignee: Exxon Research and Engineering Company
    Inventors: Edward Ira Stiefel, Jonathan M. McConnachie, Daniel Paul Leta
  • Patent number: 5837657
    Abstract: The present invention is directed to a method for improving the performance of a sooted diesel oil and controlling soot induced viscosity increase by adding to a major amount of a diesel oil a minor amount of a composition comprising at least one compound having the formula Mo.sub.3 S.sub.k L.sub.n Q.sub.z and mixtures thereof wherein the L are independently selected ligands having organo groups with a sufficient number of carbon atoms to render the compound soluble or dispersible in the oil, n is from 1 to 4, k varies from 4 through 10, Q is selected from the group of neutral electron donating compounds such as water, amines, alcohols, phosphines, and ethers, and z ranges from 0 to 5 and includes nonstoichiometric values.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: November 17, 1998
    Inventors: Howard L. Fang, Jonathan M. McConnachie, Edward Ira Stiefel
  • Patent number: 5824627
    Abstract: The invention relates to lube oil compositions containing a major amount of a lube oil and a minor amount of at least one compound containing a heterometallic tetranuclear preferably cubane, more preferably thiocubane core having 1 to 3 molybdenum atoms and the remainder Co, Cr, Cu, Ni, W, Mn, and Fe. Preferred is Cu. Thiocubane cores are also preferred and these typically have the formula M.sub.4-y Mo.sub.y S.sub.4 L.sub.n Q.sub.z, wherein y is 1 to 3, n is 2 to 6 and z is 0 to 4. Additive concentrates of the compounds as well as the method of making the compositions are disclosed.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: October 20, 1998
    Assignee: Exxon Research and Engineering Company
    Inventors: Jonathan M. McConnachie, Catherine Louise Coyle, Mark Alan Greaney, Edward Ira Stiefel
  • Patent number: 5814587
    Abstract: Multifunctional molybdenum compounds, which are the reactive product of molybdenum dithiocarbamates and metal dihydrocarbyl dithiophosphates, are new compositions which are useful as lubricant additives. They impart to the lubricant formulations to which they are added low friction and excellent wear properties at reduced phosphorous concentrations.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: September 29, 1998
    Assignee: Exxon Research and Engineering Company
    Inventors: Elisavet P. Vrahopoulou, Richard S. Polizzotti, Daniel Paul Leta, Stephan D. Cameron
  • Patent number: 5807813
    Abstract: A lubricating oil composition comprising a base oil, (A) at least one compound selected from the group consisting of molybdenum dithiocarbamate and molybdenum dithiophosphate, and (B) an aromatic compound having at least one functional group selected from the group consisting of hydroxyl group, carboxyl group, mercapto group, and thiocarboxyl group on the aromatic ring. The lubricating oil composition maintains the low friction property to achieve sustained low fuel consumption during the use and also enables using the organic molybdenum compound added as the friction modifier in a smaller amount than the amount required in conventional lubricating oil compositions.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: September 15, 1998
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventor: Ryou Yamada
  • Patent number: 5696063
    Abstract: The present invention provides novel basic metallic salts of dithiocarbamic acid, in which the content of the basic ingredient (=a.times.3.times.100) is 30-100 mol %, represented by general formula (1): ##STR1## wherein R.sup.1 to R.sup.4, which may be the same or different, are each a lipophilic group having 1-30 carbon atoms, M is a metal atom selected from the group consisting of zinc, copper, nickel, iron, cadmium, silver, lead, antimony, tin, and bismuth, and "a" is a coefficient of 1/3 to 1/10,said basic metallic salts of dithiocarbamic acid containing no phosphorus atoms and imparting low-wear properties when used as an additive for lubricating oils. The present invention also provides lubricating oil compositions containing in a lubricating base oil said basic metal salt of dithiocarbamic acid, which compositions are excellent in wear-resistant properties and frictional characteristics and suitable as a lubricating oil for automotive internal combustion engines.
    Type: Grant
    Filed: September 11, 1996
    Date of Patent: December 9, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Michihide Tokashiki, Hirotaka Tomizawa, Katsuya Arai
  • Patent number: 5688748
    Abstract: Providing a lubricating oil composition for internal combustion engines which has high resistance to oxidation by nitrogen oxides, excellent friction characteristics that is maintained for a prolonged period, and reduces the fuel consumption for a prolonged period. A lubricating oil composition for internal combustion engines is provided consisting of a base oil principally consisting of a hydrocarbon oil which has a dynamic viscosity of 2-20 mm.sup.2 /s at 100.degree. C. and contains 3 wt % or less aromatic components in total, 45 wt% or more one- and two-ring naphthenes in total, 50 wt ppm or less sulfur and 50 wt ppm or less nitrogen, to which are added, with respect to the total weight of the composition, 0.02-0.2 wt % as molybdenum of molybdenum dithiocarbamate, 0.02-0.15 wt % as phosphorus of zinc dithiophosphate, and 0.05-3 wt % of phenol-based antioxidant.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: November 18, 1997
    Assignee: Tonen Corporation
    Inventor: Hirotaka Tomizawa
  • Patent number: 5672571
    Abstract: A grease composition for constant velocity joints comprises (a) a base oil; (b) a lithium-containing thickener selected from the group consisting of lithium soap and lithium complex soap; (c) an organic molybdenum compound selected from the group consisting of molybdenum dithiophosphates and molybdenum dithiocarbamates; (d) a zinc dithiophosphate; (e) a sulfur-phosphorus extreme pressure agent free of any metal; and (f) a calcium salt selected from the group consisting of calcium salts of oxidized waxes, calcium salts of petroleum sulfonates and calcium salts of alkyl aromatic sulfonates. The grease composition for constant velocity joints exhibits a substantially improved effect of reducing friction coefficient and a substantially improved effect of reducing the axial force proportional to the third order component of rotation.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: September 30, 1997
    Assignee: Kyodo Yushi Co., Ltd.
    Inventors: Ko Hatakeyama, Shinya Kondo
  • Patent number: 5665684
    Abstract: A lubricating oil composition containing from 0.01 to 0.8% by weight, based on the whole composition, of a phosphoric ester and/or a phosphorous ester, from 50 to 2,000 ppm (in terms of molybdenum) of sulfurized oxymolybdenum dithiocarbamate having at least one hydrocarbyl group having 8 to 18 carbon atoms and from 0.3 to 2.5% by weight of a calcium salicylate having a total base number of 10 to 100.
    Type: Grant
    Filed: January 3, 1996
    Date of Patent: September 9, 1997
    Assignee: Exxon Research and Engineering Company
    Inventors: Katsuya Arai, Satoshi Asano, Sadao Wada
  • Patent number: 5631213
    Abstract: A process for producing molybdenum oxysulfide dithiocarbamate (MoDTC) by reacting [A] an aqueous solution or suspension prepared by reacting (a) a compound having hexavalent molybdenum, with (b) an alkali hydrogensulfide or an alkali sulfide, [B] a carbon disulfide, [C] a secondary amine and [D] a mineral acid, wherein [E] a reducing agent is added and reacted at any stage, and a lubricating oil composition containing the compound obtained according to said process. MoDTC can be efficiently produced in high yields by using a hexavalent molybdenum compound as a starting material, and the produced MoDTC has low corrosive action, excellent wear characteristics and excellent lubricating properties.
    Type: Grant
    Filed: February 6, 1996
    Date of Patent: May 20, 1997
    Assignee: Asahi Denka Kogyo K. K.
    Inventors: Noriyoshi Tanaka, Aritoshi Fukushima, Yukio Tatsumi, Kazuhisa Morita, Yoko Saito
  • Patent number: 5627146
    Abstract: The present invention is directed to providing a lubricating oil composition which contains an alkyl group asymmetric type molydbdenum dithiocarbamate (MoDTC) as an essential component thereof and which exhibits far more excellent lubrication performance than a conventional lubricating oil composition containing an alkyl group symmetric type MoDTC conventional used in the field of lubricating oils. The lubricating oil composition according to the present invention comprises a base oil for a lubricating oil consisting of a mineral oil and/or a synthetic oil and having a viscosity index of at least 115 and a viscosity at 100.degree. C. falling within the range of 2 to 50 cSt, and a specific alkyl group asymmetric type MoDTC as an essential component.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: May 6, 1997
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Noriyoshi Tanaka, Aritoshi Fukushima, Yukio Tatsumi, Yoko Saito
  • Patent number: 5612297
    Abstract: A grease composition comprising 0.1 to 10 parts by weight of a powdered molybdenum oxysulfide dithiocarbamate composition which comprises a compound represented by the following formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independent hydrocarbyl groups and may be the same or different groups, and the total number of carbon atoms contained in R.sup.1 to R.sup.4 is 4 to 36; and wherein X is sulfur or oxygen and the composition of the total of all Xs is given as S.sub.m and O.sub.n in which m and n satisfy the ranges of 1.7.ltoreq.m.ltoreq.3.5 and 0.5.ltoreq.n.ltoreq.2.3, respectively, in which the constituent particles have diameters of not larger than 50 .mu.m, based on 100 parts by weight of a base grease.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: March 18, 1997
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Tamiji Kamakura, Noriyoshi Tanaka, Aritoshi Fukushima, Yukio Tatsumi, Kazuhisa Morita
  • Patent number: 5607906
    Abstract: A grease composition for constant velocity joints which consists essentially of: (a) a base oil; (b) an urea thickener; (c) molybdenum disulfide; and (d) a metal salt or an overbasic metal salt selected from the group consisting of metal salts or overbasic metal salts of oxidized waxes, petroleum sulfonates, alkyl aryl sulfonates, salicylate, and phenates. In addition to (a) to (d), it may further contain, (e) an extreme pressure agent selected from the group consisting of a metal-free sulfur-phosphorus extreme pressure agent and molybdenum dithiophosphate, or (f) molybdenum dithiocarbamate. The grease composition exhibits excellent wear-resistance and pitting-inhibitory effect.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: March 4, 1997
    Assignee: Kyodo Yushi Co., Ltd.
    Inventors: Takashi Okaniwa, Hisayuki Osawa