Oxygen Or Nitrogen Attached Indirectly To One Of The Acyclic Sulfurs By Acyclic Nonionic Bonding Patents (Class 508/274)
  • Publication number: 20140051615
    Abstract: The present invention relates to a lubricating composition containing an oil of lubricating viscosity and a dimercaptothiadiazole salt of a copolymer comprising units derived from monomers (i) an ?-olefin and (ii) an ethylenically unsaturated carboxylic acid or derivatives thereof (typically carboxylic acid groups or an anhydride), are partially esterified with an alcohol, or mixtures thereof, and wherein at least a portion of carboxylic acid groups not esterified are reacted with an amine. The invention further provides for a lubricating composition containing said copolymer. The invention further provides a method and use of lubricating composition in a mechanical device.
    Type: Application
    Filed: December 16, 2011
    Publication date: February 20, 2014
    Applicant: THE LUBRIZOL CORPORATION
    Inventors: Mary F. Salomon, Julie Edgar, William R.S. Barton, Mark R. Baker, Michael E. Huston
  • Patent number: 8410032
    Abstract: A lubricant composition, a multi-vehicle transmission fluid, and a method for making a transmission fluid. The lubricant composition includes a) a base oil; b) 2,5-dimercapto-1,3,4-thiadiazole (DMTD), a derivative of DMTD, or mixtures thereof; and c) a friction modifier. The friction modifier is made by reacting an olefin containing at least 40% by weight C10-C36 vinylidene olefin with maleic acid, anhydride, or ester to provide a first reaction product, and aminating the first reaction product with an effective amount of a compound containing basic nitrogen to provide the friction modifier. The C10-C36 vinylidene olefin is represented by the following formula: wherein Rc and Rd are independently a (C3-C15) alkyl, cycloalkyl or cycloalkenyl.
    Type: Grant
    Filed: July 9, 2012
    Date of Patent: April 2, 2013
    Assignee: Afton Chemical Corporation
    Inventors: Joseph B. Carroll, Christopher S. Cleveland
  • Patent number: 8211839
    Abstract: The invention relates to an extreme pressure additive composition with excellent corrosion resistance properties for use in grease, as well as a lubricating grease composition containing the additive. The additive composition is based on (a) approximately equal amounts by mass of antimony diamyldithiocarbamate and zinc diamyldithiocarbamate, and (b) thiadiazole dimer poly(ether)glycol complex; at (a):(b) mass ratio of about 1.6:1 to about 9.6:1.
    Type: Grant
    Filed: May 27, 2010
    Date of Patent: July 3, 2012
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Ronald J. Tepper, Gaston A. Aguilar, Robert Heverly
  • Patent number: 8138132
    Abstract: A lubricant composition is provided as follows: At least 90% of a base grease; (a) a thiadiazole poly(ether)glycol complex in an amount which provides about 1500 to 3500 ppm sulfur; (b) molybdenum dihydrocarbyldithiophosphate in amount which provides about 77 to 450 ppm molybdenum; and (c) zinc dihydrocarbyldithiophosphate in an amount which provides about 600 to 1000 ppm zinc. An additive composition for grease, consisting of components (a), (b) and (c), is also provided.
    Type: Grant
    Filed: December 11, 2008
    Date of Patent: March 20, 2012
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Gaston A Aguilar, Ronald J Hiza
  • Patent number: 7763574
    Abstract: A lubrication composition providing excellent anti-wear protection for corrosion-resistant materials which comprises a major amount of a synthetic ester base oil, and a minor amount of a molybdenum compound and an anti-wear additive selected from the group consisting of 1,3,4-thiadiazole derivative as an anti-wear additive, the reaction products of 2,5-dimercapto-1,3,4-thiadiazole dimers and poly(ether)glycols, and 2,5-dimercapto-1,3,4-thiadiazole monomer and mixtures thereof. Also described is a method for imparting anti-wear properties to a corrosion resistant material, comprising using the lubricating composition of the invention.
    Type: Grant
    Filed: October 8, 2004
    Date of Patent: July 27, 2010
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Steven G. Donnelly, Ronald J. Hiza
  • Patent number: 7598211
    Abstract: An additive for imparting antiwear properties to a lubricant composition is based on a combination of (1) an organo borate ester composition and (2) one or more sulfur- or phosphorus-containing compounds or a non-sulfur molybdenum compound. The sulfur- or phosphorus-containing compounds are dithiocarbamate, bisdithiocarbamate, 1,3,4-diathiazole, phosphorodithioate, phosphorodithioate esters, and the molybdenum compound is prepared by reacting (a) about 1.0 mole of fatty oil having 12 or more carbon atoms, (b) about 1.0 to 2.5 moles diethanolamine and (c) a molybdenum source.
    Type: Grant
    Filed: October 2, 2003
    Date of Patent: October 6, 2009
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Steven G. Donnelly
  • Publication number: 20090156444
    Abstract: A lubricant composition is provided as follows: At least 90% of a base grease; (a) a thiadiazole poly(ether)glycol complex in an amount which provides about 1500 to 3500 ppm sulfur; (b) molybdenum dihydrocarbyldithiophosphate in amount which provides about 77 to 450 ppm molybdenum; and (c) zinc dihydrocarbyldithiophosphate in an amount which provides about 600 to 1000 ppm zinc. An additive composition for grease, consisting of components (a), (b) and (c), is also provided.
    Type: Application
    Filed: December 11, 2008
    Publication date: June 18, 2009
    Applicant: R.T. VANDERBILT COMPANY, INC.
    Inventors: GASTON A. AGUILAR, RONALD J. HIZA
  • Patent number: 7041825
    Abstract: The present invention relates to 1,3,4-thiadiazole reaction products useful as accelerators and/or curing agents for halogenated polymers in rubber vulcanization processes, and to halogenated polymer compositions containing the thiadiazole derivatives, as well as a method of preparing the same. The additive is the reaction product of a 1,3,4-thiadiazole compound and a dithiocarbamic acid or an amine, or an isomer thereof.
    Type: Grant
    Filed: February 11, 2004
    Date of Patent: May 9, 2006
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Francis S. Cheng, Ronald J. Tepper
  • Patent number: 6806241
    Abstract: Disclosed are antioxidant compositions comprising of: (1) an organomolybdenum compound; (2) an alkylated diphenylamine; and (3) a sulfur compound selected from the group consisting of: (a) thiadiazole; (b) dithiocarbamate; and (c) mixtures of (a) and (b).
    Type: Grant
    Filed: September 19, 2002
    Date of Patent: October 19, 2004
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Steven G. Donnelly, Ronald J. Hiza
  • Publication number: 20040138073
    Abstract: An additive for imparting antiwear properties to a lubricant composition is based on a combination of (1) an organo borate ester composition and (2) one or more sulfur- or phosphorus-containing compounds or a non-sulfur molybdenum compound. The sulfur- or phosphorus-containing compounds are dithiocarbamate, bisdithiocarbamate, 1,3,4-diathiazole, phosphorodithioate, phosphorodithioate esters, and the molybdenum compound is prepared by reacting (a) about 1.0 mole of fatty oil having 12 or more carbon atoms, (b) about 1.0 to 2.5 moles diethanolamine and (c) a molybdenum source.
    Type: Application
    Filed: October 2, 2003
    Publication date: July 15, 2004
    Applicant: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Steven G. Donnelly
  • Publication number: 20040063820
    Abstract: Additives including dithiocarbamyl derivatives of 2,5-dimercapto-1,3,4-thiadiazole (DMTD) useful as curing agents and accelerators. Curable polymer compositions including at least one halogenated polymer and at least one additive including the dithiocarbamyl DMTD derivatives. A method is also disclosed for preparing a cured polymer by admixing at least one halogenated polymer with at least one additive including the dithiocarbamyl DMTD derivatives and subsequently curing the composition.
    Type: Application
    Filed: July 11, 2003
    Publication date: April 1, 2004
    Applicant: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Francis S. Cheng
  • Patent number: 6635696
    Abstract: Additives including dithiocarbamyl derivatives of 2,5-dimercapto-1,3,4-thiadiazole (DMTD) useful as curing agents and accelerators. Curable polymer compositions including at least one halogenated polymer and at least one additive including the dithiocarbamyl DMTD derivatives. A method is also disclosed for preparing a cured polymer by admixing at least one halogenated polymer with at least one additive including the dithiocarbamyl DMTD derivatives and subsequently curing the composition.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: October 21, 2003
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Francis S. Cheng
  • Patent number: 6620771
    Abstract: 2,5-dimercapto-1,3,4-thiadiazole dimer-poly(ether)glycol reaction products and adducts useful as extreme pressure additives. Lubricating compositions (e.g., greases) containing reaction products and adducts exhibit improved Timken Load properties.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: September 16, 2003
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Ronald J. Tepper
  • Publication number: 20030158051
    Abstract: Disclosed are antioxidant compositions comprising of:
    Type: Application
    Filed: September 19, 2002
    Publication date: August 21, 2003
    Inventors: Thomas J. Karol, Steven G. Donnelly, Ronald J. Hiza
  • Patent number: 6489484
    Abstract: Thiadiazole-poly(ether)glycol reaction products and adducts useful as extreme pressure additives. Lubricating compositions (e.g., greases) containing the reaction products and adducts exhibit improved Timken Load properties.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: December 3, 2002
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Ronald J. Tepper
  • Publication number: 20020058594
    Abstract: 2,5-dimercapto-1,3,4-thiadiazole dimer-poly(ether)glycol reaction products and adducts useful as extreme pressure additives. Lubricating compositions (e.g., greases) containing reaction products and adducts exhibit improved Timken Load properties.
    Type: Application
    Filed: November 14, 2001
    Publication date: May 16, 2002
    Applicant: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Ronald J. Tepper
  • Patent number: 6365557
    Abstract: 2,5-dimercapto-1,3,4-thiadiazole dimer-poly(ether)glycol reaction products and adducts useful as extreme pressure additives. Lubricating compositions (e.g., greases) containing reaction products and adducts exhibit improved Timken Load properties.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: April 2, 2002
    Assignee: R.T. Vanderbilt Company, Inc.
    Inventors: Thomas J. Karol, Ronald J. Tepper
  • Patent number: 6362138
    Abstract: This invention relates to compounds which are suitable as ash-free antiwear additives and antioxidants, to lubricant compositions comprising said compounds as well as to their use. are particularly preferred. In the preferred compounds I′, R2 is isooctyloxycarbonylmethyl, R3 is isooctyloxycarbonylmethylthiomethyl and R4 is hydrogen; or R2 is tert-nonyl and R3 is tert-nonylthiomethyl and R4 is hydrogen; or R2 is isooctyloxycarbonylmethyl, R3 is hydrogen and R4 is isooctyloxycarbonylmethylthiomethyl; or R2 is tert-nonyl, R3 is hydrogen and R4 I is tert-nonylthiomethyl.
    Type: Grant
    Filed: September 15, 2000
    Date of Patent: March 26, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hugo Camenzind, Samuel Evans, Alfred Dratva, Peter Hänggi
  • Patent number: 6150307
    Abstract: This invention relates to compounds which are suitable as ash-free antiwear additives and antioxidants, to lubricant compositions comprising said compounds as well as to their use. Compounds of formulae ##STR1## are particularly preferred. In the preferred compounds I',R.sub.2 is isooctyloxycarbonylmethyl, R.sub.3 is isooctyloxycarbonylmethylthiomethyl and R.sub.4 is hydrogen; orR.sub.2 is tert-nonyl and R.sub.3 is tert-nonylthiomethyl and R.sub.4 is hydrogen; orR.sub.2 is isooctyloxycarbonylmethyl, R.sub.3 is hydrogen and R.sub.4 is isooctyloxycarbonylmethylthiomethyl; orR.sub.2 is tert-nonyl, R.sub.3 is hydrogen and R.sub.4 I is tert-nonylthiomethyl.In the preferred compounds II',R.sub.2 and R.sub.2 ' are isooctyloxycarbonylmethyl, R.sub.3 and R.sub.3 ' are isooctyloxycarbonylmethylthiomethyl and R.sub.4 and R.sub.4 ' are hydrogen; orR.sub.2 and R.sub.2 ' are tert-nonyl, R.sub.3 and R.sub.3 ' are tert-nonylthiomethyl and R.sub.4 and R.sub.4 ' are hydrogen; orR.sub.2 and R.sub.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: November 21, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hugo Camenzind, Samuel Evans, Alfred Dratva, Peter Hanggi
  • Patent number: 6001783
    Abstract: This invention relates to a composition, comprising:(A) at least one compound selected from the group consisting of(A-1) a compound represented by the formulaT.sup.1 T.sup.2 --P(X.sup.1)--(S).sub.n --S--C (X.sup.2)--L.sup.1(A-I)(A-2) a compound represented by the formulaT.sup.3 T.sup.4 --P(X.sup.3)--(S).sub.n --S--(DMTD)--S--J (A-II)(A-3) a compound represented by the formulaL.sup.2 --C(X.sup.4)--(S).sub.n --S--(DMTD)--S--G (A-III)and(A-4) mixture of two or more of (A-1), (A-2) and (A-3);wherein in Formulae (A-I), (A-II) and (A-III): (DMTD) is a dimercaptothiadiazole nucleus; J is H, SR, --S--P(X.sup.5)--T.sup.5 T.sup.6 or --S--C(X.sup.6)-L.sup.3G is H, SR or --S--C(X.sup.7)--L.sup.4T.sup.1, T.sup.2, T.sup.3, T.sup.4, T.sup.5 and T.sup.6 are independently R, SR or OR; L.sup.1, L.sup.2, L.sup.3 and L.sup.4 are independently R, SR, OR or NRR; X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6 and X.sup.7 are independently O or S; each R is independently a hydrocarbyl group; and n is 1 to 4.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: December 14, 1999
    Assignee: The Lubrizol Corporation
    Inventors: John S. Manka, William D. Abraham, Stephen H. Roby, James A. Supp, Richard Yodice
  • Patent number: 5885942
    Abstract: The multifunctional lubricant additive compositions of the invention preferably contain a methylene bis(dibutyldithiocarbamate) as an antiwear and extreme pressure additive, a 2,5-dimercapto-1,3,4-thiadiazole derivative as an antioxidant and antiwear additive, a tolutriazole compound as an antioxidant and corrosion inhibitor, a glycerol monooleate as a friction modifier, a calcium sulfonate as a detergent and extreme pressure additive, a zinc dialkyl dithiophosphate as an antiwear and antioxidant additive, a polymethylacrylate as a dispersant, a polyol ester as a carrier and friction modifier, a red dye for leak detection, and optionally, solvent neutral oil and a pour point depressant.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: March 23, 1999
    Assignee: NCH Corporation
    Inventors: Ruiming Zhang, Robert M. Hooks
  • Patent number: 5801130
    Abstract: This invention relates to synthetic based turbo oils, preferably polyol ester-based turbo oils which exhibit exceptional load-carrying capacity by use of a synergistic combination of sulfur (S)-based and phosphorous (P)-based load additives. The S-containing additives of the present invention are DMTD and its derivative including the capped DMTD and the DMTD dimer, and the P-containing component is one or more amine phosphates. The turbo oil composition consisting of the dual P/S additives of the present invention achieves an excellent load-carrying capacity, which is better than that obtained when each additive was used alone at a treat rate higher than or comparable to the total combination additive treat rate, and the lower concentration requirement of the P-based additive allows the turbo oil composition to meet US Navy MIL-L-23699 requirement on the Si seal compatibility.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: September 1, 1998
    Assignee: Exxon Research and Engineering Company
    Inventors: Manual A. Francisco, Paul Joseph Berlowitz, Jeenok T. Kim
  • Patent number: 5696062
    Abstract: Colloidal products are obtained by a process which comprises at least partial neutralization of an overbased colloidal bismuth sulphonate type product containing a basicity reserve in the form of micellized calcium, barium or magnesium carbonate, using at least one carboxylic acid containing sulphur and optionally containing nitrogen. These products can be used as antiwear and extreme-pressure additives in lubricating oils and greases.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: December 9, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Bruno Delfort, Maurice Born, Bertrand Daoudal, Jacques Lallement
  • Patent number: 5686397
    Abstract: A composition of matter is disclosed having the structure: ##STR1## wherein R and R.sup.1 are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl; R.sup.2 is an alkylene moiety; R.sup.3 is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl, or 2-hydroxyalkyl; X is sulfur; and y is 0 or 1. Lubricants and lubricant additives comprising the composition are also disclosed. The lubricants are preferably lubricating oils.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: November 11, 1997
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: John R. Baranski, Cyril A. Migdal
  • Patent number: 5641730
    Abstract: An antiwear additive has an alkali metal borate; and a thiadiazole compound. That thiadiazole compound may be a 2,5-dimercapto-1,3,4-thiadiazole, a 2-alkylpolythio-5-mercapto-1,3,4-thiadiazole, or a 2-alkylestermercapto-5-mercapto-1,3,4-thiadiazole. If the thiadiazole compound is a 2-alkylpolythio-5-mercapto-1,3,4-thiadiazole or a 2-alkylestermercapto-5-mercapto-1,3,4-thiadiazole, the alkyl group has from one to twenty carbon atoms. If the thiadiazole compound is a 2-alkylpolythio-5-mercapto-1,3,4-thiadiazole, the polythio group has from two to eight sulfur atoms. This antiwear additive can be used with a base grease in a grease composition.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: June 24, 1997
    Assignee: Chevron Chemical Company
    Inventor: Stuart H. Brown
  • Patent number: 5622922
    Abstract: A homogenous product is formed by heating at a temperature in the range of from 50.degree. to 150.degree. C. a mixture of a benzotriazole and a 2,5-dihydrocarbyldithio-1,3,4-thiadiazole.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: April 22, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Dean B. Clarke, Dale R. Carroll
  • Patent number: 5618778
    Abstract: The present invention relates to a composition containing a lubricant or hydraulic fluid and in an effective amount to improve extreme pressure and anti-wear properties of said lubricant or hydraulic fluid of at least one compound of the formula II ##STR1## R.sup.1, R.sup.2, and R.sup.3 together with the C atom to which they are bound are tert-C.sub.4 -C.sub.14 -alkyl. R.sup.4 is phenyl, --CH.sub.2 --CH.sub.2 --NH.sub.2, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH(OH)--CH.sub.2 --OH, tert-C.sub.4 -C.sub.14 alkyl, --(CH.sub.2).sub.2 --S--CH(OH)--CH.sub.2 --S-(tert-C.sub.8 -C.sub.12 alkyl), --CH.sub.2 --COOH, --CH.sub.2 --COO--(i-C.sub.8 H.sub.17), --CH.sub.2 --CO--OH.H.sub.2 N-(tert-C.sub.10 -C.sub.16 -alkyl), --P(S)--[O--(i-C.sub.3 H.sub.7)].sub.2, --P(S)--[O--(i-C.sub.8 H.sub.17)].sub.2, .alpha.-naphthyl, benzothiazolyl, benzimidazolyl, thiazolyl, --CH.sub.2 --CH--(OH)--CH.sub.2 --S--R.sup.10 wherein R.sup.10 is tertiary C.sub.4 -C.sub.14 -alkyl, or R.sup.4 is radical ##STR2## R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: April 8, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 5597785
    Abstract: Disclosed the novel compounds prepared by reacting 2,5-dimercapto-1,3,4,-thiadiazole with maleic anhydride and N-polyethylene amine-substituted succinimide. The compounds are dispersants or detergents, antiwear agents and antioxidants when incorporated into lubricating compositions.
    Type: Grant
    Filed: June 26, 1995
    Date of Patent: January 28, 1997
    Assignee: R. T. Vanderbilt Company, Inc.
    Inventor: Thomas J. Karol
  • Patent number: 5585029
    Abstract: This invention relates to synthetic based turbo oils, preferably polyol ester-based turbo oils which exhibit exceptional load-carrying capacity by use of a synergistic combination of sulfur (S)-based and phosphorous (P)-based load additives. The S-containing additive of the present invention is 2-alkylthio-1,3,4-thiadiazole-5 alkanoic acid (ATAA) obtained by reacting 2,5-dimercapto-1,3,4-thiadiazole (DMTD) with alkyl bromide and subsequently reacting the intermediate with haloalkanoic acid. The P-containing additive is one or more amine phosphate(s). The turbo oil composition consisting of the dual P/S additives of the present invention achieves a superior load-carrying capacity over that obtained when each additive was used alone at individual treat rates higher than the total additive combination treatrate, and also meets or exceeds US Navy MIL-L-23699 requirements including Oxidation and Corrosion Stability and Si seal compatibility.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: December 17, 1996
    Assignee: Exxon Research and Engineering Company
    Inventors: Jeenok T. Kim, Morton Beltzer