Oxygen Or Nitrogen Attached Indirectly To One Of The Acyclic Sulfurs By Acyclic Nonionic Bonding Patents (Class 508/274)
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Publication number: 20140051615Abstract: 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: ApplicationFiled: December 16, 2011Publication date: February 20, 2014Applicant: THE LUBRIZOL CORPORATIONInventors: Mary F. Salomon, Julie Edgar, William R.S. Barton, Mark R. Baker, Michael E. Huston
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Patent number: 8410032Abstract: 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: GrantFiled: July 9, 2012Date of Patent: April 2, 2013Assignee: Afton Chemical CorporationInventors: Joseph B. Carroll, Christopher S. Cleveland
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Patent number: 8211839Abstract: 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: GrantFiled: May 27, 2010Date of Patent: July 3, 2012Assignee: R.T. Vanderbilt Company, Inc.Inventors: Ronald J. Tepper, Gaston A. Aguilar, Robert Heverly
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Patent number: 8138132Abstract: 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: GrantFiled: December 11, 2008Date of Patent: March 20, 2012Assignee: R.T. Vanderbilt Company, Inc.Inventors: Gaston A Aguilar, Ronald J Hiza
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Patent number: 7763574Abstract: 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: GrantFiled: October 8, 2004Date of Patent: July 27, 2010Assignee: R.T. Vanderbilt Company, Inc.Inventors: Steven G. Donnelly, Ronald J. Hiza
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Patent number: 7598211Abstract: 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: GrantFiled: October 2, 2003Date of Patent: October 6, 2009Assignee: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Steven G. Donnelly
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Publication number: 20090156444Abstract: 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: ApplicationFiled: December 11, 2008Publication date: June 18, 2009Applicant: R.T. VANDERBILT COMPANY, INC.Inventors: GASTON A. AGUILAR, RONALD J. HIZA
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Patent number: 7041825Abstract: 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: GrantFiled: February 11, 2004Date of Patent: May 9, 2006Assignee: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Francis S. Cheng, Ronald J. Tepper
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Patent number: 6806241Abstract: 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: GrantFiled: September 19, 2002Date of Patent: October 19, 2004Assignee: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Steven G. Donnelly, Ronald J. Hiza
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Publication number: 20040138073Abstract: 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: ApplicationFiled: October 2, 2003Publication date: July 15, 2004Applicant: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Steven G. Donnelly
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Publication number: 20040063820Abstract: 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: ApplicationFiled: July 11, 2003Publication date: April 1, 2004Applicant: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Francis S. Cheng
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Patent number: 6635696Abstract: 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: GrantFiled: December 1, 2000Date of Patent: October 21, 2003Assignee: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Francis S. Cheng
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Patent number: 6620771Abstract: 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: GrantFiled: November 14, 2001Date of Patent: September 16, 2003Assignee: R. T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Ronald J. Tepper
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Publication number: 20030158051Abstract: Disclosed are antioxidant compositions comprising of:Type: ApplicationFiled: September 19, 2002Publication date: August 21, 2003Inventors: Thomas J. Karol, Steven G. Donnelly, Ronald J. Hiza
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Patent number: 6489484Abstract: 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: GrantFiled: October 20, 2000Date of Patent: December 3, 2002Assignee: R. T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Ronald J. Tepper
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Publication number: 20020058594Abstract: 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: ApplicationFiled: November 14, 2001Publication date: May 16, 2002Applicant: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Ronald J. Tepper
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Patent number: 6365557Abstract: 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: GrantFiled: October 20, 2000Date of Patent: April 2, 2002Assignee: R.T. Vanderbilt Company, Inc.Inventors: Thomas J. Karol, Ronald J. Tepper
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Patent number: 6362138Abstract: 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: GrantFiled: September 15, 2000Date of Patent: March 26, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Hugo Camenzind, Samuel Evans, Alfred Dratva, Peter Hänggi
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Patent number: 6150307Abstract: 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: GrantFiled: August 3, 1998Date of Patent: November 21, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Hugo Camenzind, Samuel Evans, Alfred Dratva, Peter Hanggi
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Patent number: 6001783Abstract: 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: GrantFiled: March 24, 1997Date of Patent: December 14, 1999Assignee: The Lubrizol CorporationInventors: John S. Manka, William D. Abraham, Stephen H. Roby, James A. Supp, Richard Yodice
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Patent number: 5885942Abstract: 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: GrantFiled: September 23, 1997Date of Patent: March 23, 1999Assignee: NCH CorporationInventors: Ruiming Zhang, Robert M. Hooks
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Patent number: 5801130Abstract: 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: GrantFiled: March 7, 1997Date of Patent: September 1, 1998Assignee: Exxon Research and Engineering CompanyInventors: Manual A. Francisco, Paul Joseph Berlowitz, Jeenok T. Kim
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Patent number: 5696062Abstract: 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: GrantFiled: February 7, 1997Date of Patent: December 9, 1997Assignee: Institut Francais Du PetroleInventors: Bruno Delfort, Maurice Born, Bertrand Daoudal, Jacques Lallement
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Patent number: 5686397Abstract: 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: GrantFiled: February 3, 1997Date of Patent: November 11, 1997Assignee: Uniroyal Chemical Company, Inc.Inventors: John R. Baranski, Cyril A. Migdal
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Patent number: 5641730Abstract: 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: GrantFiled: November 29, 1995Date of Patent: June 24, 1997Assignee: Chevron Chemical CompanyInventor: Stuart H. Brown
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Patent number: 5622922Abstract: 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: GrantFiled: December 27, 1995Date of Patent: April 22, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Dean B. Clarke, Dale R. Carroll
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Patent number: 5618778Abstract: 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: GrantFiled: April 12, 1995Date of Patent: April 8, 1997Assignee: Ciba-Geigy CorporationInventors: Hermann O. Wirth, Hans-Helmut Friedrich
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Patent number: 5597785Abstract: 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: GrantFiled: June 26, 1995Date of Patent: January 28, 1997Assignee: R. T. Vanderbilt Company, Inc.Inventor: Thomas J. Karol
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Patent number: 5585029Abstract: 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: GrantFiled: December 22, 1995Date of Patent: December 17, 1996Assignee: Exxon Research and Engineering CompanyInventors: Jeenok T. Kim, Morton Beltzer