Polycarboxylic Acid Esterifies Polyhydroxy Alcohol Patents (Class 508/492)
  • Patent number: 11279897
    Abstract: Embodiments of the present disclosure are directed towards esterified oil soluble polyalkylene glycols of Formula (I): R1[O(R2O)n(R3O)m(C?O)R4]p, where R1 is a linear alkyl having 1 to 18 carbon atoms, a branched alkyl having 4 to 18 carbon atoms or an aryl with 6 to 30 carbon atoms; R2O is an oxypropylene moiety derived from 1, 2-propylene oxide; R3O is an oxybutylene moiety derived from butylene oxide, where R2O and R3O are in a block or a random distribution; R4 is a linear alkyl with to 18 carbon atoms, a branched alkyl with 4 to 18 carbon atoms or an aryl with 6 to 18 carbon atoms; n and m are each independently integers ranging from 0 to 20 wherein n+m is greater than 0, and p is an integer from 1 to 4.
    Type: Grant
    Filed: December 25, 2017
    Date of Patent: March 22, 2022
    Assignee: Dow Global Technologies LLC
    Inventors: Yaokun Han, Cheng Shen, Martin R. Greaves, Yong Zhao
  • Patent number: 11136521
    Abstract: The present application relates to the use, in a lubricant composition comprising at least one base oil, of 2 to 12% by weight, relative to the weight of said lubricant composition, of an ester that has a viscosity at 100° C. of between 200 and 1000 cSt, for the purpose of improving the cleanliness of an engine.
    Type: Grant
    Filed: September 18, 2018
    Date of Patent: October 5, 2021
    Assignee: TOTAL MARKETING SERVICES
    Inventor: Modestino De Feo
  • Patent number: 10829436
    Abstract: The invention relates to novel ester compounds of the general formula (I) to a process for preparation thereof and to the use thereof. These ester compounds may contain a mixture of at least two compounds of the general formula (I).
    Type: Grant
    Filed: April 11, 2018
    Date of Patent: November 10, 2020
    Assignees: Klüber Lubrication München SE & CO. KG, Universität Bielefeld
    Inventors: Tobias Betke, Carmen Plass, Harald Gröger, Dirk Loderer, Stefan Seemeyer, Thomas Kilthau, Ling Ma
  • Patent number: 10559403
    Abstract: A composition having an oil film retention function which an oil film can be stably retained on surfaces of various metals, an anticorrosive agent using same, and insulated terminated electric wire. A composition having oil film retention function for being added to base oil to be applied onto a metal surface and retaining base oil on metal surface, and composition contains a component that is an adduct of an azole compound and acidic alkyl phosphate ester including one or more compounds represented by General Formulae (1) (Chemical Formula 1) P(?O)(—OR1)(—OH)2 . . . (1) or General Formula (2) (Chemical Formula 2) P(?O)(—OR1)2(—OH) . . . (2) where R1 represents an organic group having four or more carbon atoms, and component that is an adduct of a metal and/or organic amine compound and acidic alkyl phosphate ester including one or more compounds represented by General Formulae (1) or (2).
    Type: Grant
    Filed: September 26, 2014
    Date of Patent: February 11, 2020
    Assignees: AUTONETWORKS TECHNOLOGIES, LTD., SUMITOMO WIRING SYSTEMS, LTD., SUMITOMO ELECTRIC INDUSTRIES, LTD., KYUSHU UNIVERSITY
    Inventors: Tatsuya Hase, Takehiro Hosokawa, Kazuo Nakashima, Kazuhiro Goto, Hiroki Hirai, Junichi Ono, Takuji Otsuka, Hideki Nomura, Makoto Mizoguchi
  • Patent number: 10131616
    Abstract: Ester polyol esters are a unique class of lubricants that have adjustable molecular weights, viscosities, and pour points based on the character of their reaction materials and relative ratios. There is provided a method for preparing at least one ester polyol ester, the method comprising esterifying an ester polyol reaction mixture to produce ester polyol, the reaction mixture comprising an ozone acid mixture and at least one primary polyol, wherein the ozone acid mixture comprises at least one dicarboxylic acid and at least one monocarboxylic acid; and capping the ester polyol with at least one capping carboxylic acid to produce ester polyol ester.
    Type: Grant
    Filed: February 28, 2013
    Date of Patent: November 20, 2018
    Assignee: Petroliam Nasional Berhad
    Inventors: Herman Paul Benecke, Daniel B. Garbark
  • Patent number: 9157044
    Abstract: A bearing lubricant composition includes a base oil containing an ester compound (?) represent by the general formula (1), and has a pour point of ?30° C. or lower and a viscosity index of 150 or more. [wherein, A1 is a C3-8 linear or branched alkylene group; and at least one of Xa and Xb is a C2-20 linear or branched alkyl ether group, or when it is not an alkyl ether group, it is a C5-13 linear or branched alkyl group.
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: October 13, 2015
    Assignees: BALBIS CO., LTD., SATO SPECIAL OIL CO., LTD., KNC LABORATORIES CO., LTD.
    Inventor: Akihiro Oda
  • Publication number: 20150018260
    Abstract: Ester polyol esters are a unique class of lubricants that have adjustable molecular weights, viscosities, and pour points based on the character of their reaction materials and relative ratios. There is provided a method for preparing at least one ester polyol ester, the method comprising esterifying an ester polyol reaction mixture to produce ester polyol, the reaction mixture comprising an ozone acid mixture and at least one primary polyol, wherein the ozone acid mixture comprises at least one dicarboxylic acid and at least one monocarboxylic acid; and capping the ester polyol with at least one capping carboxylic acid to produce ester polyol ester.
    Type: Application
    Filed: February 28, 2013
    Publication date: January 15, 2015
    Inventors: Herman Paul Benecke, Daniel B. Garbark
  • Patent number: 8703677
    Abstract: Provided herein are lubricating oil compositions for high performance engines comprising a Group III base oil and a combination of ester base stocks, wherein the combination comprises (i) an ester base stock having a kinematic viscosity at 100° C. of about 2-10 cSt, (ii) an ester base stock having a kinematic viscosity at 100° C. of about 10 to 50 cSt, and (iii) an ester base stock having a kinematic viscosity at 100° C. of greater than about 100 cSt. The lubricating oil composition can further comprise at least one additive. Methods of making and using the lubricating oil compositions are also described.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: April 22, 2014
    Assignees: Chevron Japan Ltd, Chevron Oronite Company LLC
    Inventors: Alexander B. Boffa, Satoshi Hirano, Mark Louis Sztenderowicz, Kenji Takeoka
  • Publication number: 20140100149
    Abstract: Disclosed is a lubricant base stock, exhibiting a combination of high flash point, low evaporation loss, high viscosity and unexpectedly exceptionally low pour point and high viscosity index value. Said lubricant base stock comprises at least one ester between 2-propylheptanoic acid and at least one 2,2-substituted 1,3-propanediol and/or at least one dimer, trimer or polymer thereof and/or at least one alkoxylated species of a said 2,2-substituted 1,3-propanediol or a said dimer, trimer or polymer thereof.
    Type: Application
    Filed: December 9, 2013
    Publication date: April 10, 2014
    Applicant: PERSTORP SPECIALTY CHEMICALS AB
    Inventors: Robert JANSSON, Irma Auvinen
  • Patent number: 8486871
    Abstract: A lubricating oil for a compression-type refrigerator using a hydrofluorocarbon refrigerant including a polyvinyl ether-based compound containing in the molecule an alkylene glycol unit or a polyoxyalkylene glycol unit and a polyvinyl ether unit and having a molecular weight in the range of 300 to 3,000, and a refrigeration apparatus using the lubricating oil. The present invention can provide a lubricating oil for a compression-type refrigerator having good compatibility in the atmosphere of a hydrofluorocarbon and a high viscosity index, and a refrigeration apparatus using such a lubricating oil.
    Type: Grant
    Filed: March 4, 2008
    Date of Patent: July 16, 2013
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Satoshi Nagao, Izumi Terada, Nobuaki Shimizu, Masato Kaneko
  • Patent number: 8299004
    Abstract: A hydraulic fluid of the present invention contains, as a base oil, an ester having two or more ring structures, the two or more ring structures being at least one selected from an aromatic ring and a saturated naphthenic ring. Particularly, the hydraulic fluid contains an ester having two or more aromatic rings as the base oil. The hydraulic fluid has low energy loss due to compression and exhibits excellent responsiveness when being used in a hydraulic circuit. Consequently, the hydraulic fluid realizes energy-saving, high-speed operation and high precision of control in the hydraulic circuit.
    Type: Grant
    Filed: April 21, 2008
    Date of Patent: October 30, 2012
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventor: Toshiyuki Tsubouchi
  • Patent number: 8183190
    Abstract: A biodegradable lubricant composition containing a complex polyol ester having a polyfunctional alcohol residue and a saturated or unsaturated dicarboxylic acid residue having from about 9 to about 22 carbon atoms.
    Type: Grant
    Filed: July 29, 2004
    Date of Patent: May 22, 2012
    Assignee: Cognis IP Management GmbH
    Inventors: Eugene Zehler, Christopher Costello
  • Patent number: 8129320
    Abstract: The present disclosure relates to lubricant oil compositions formed from base stock oils to optimize internal combustion engine performance. Base stock oils are identified that have selected cetane number characteristics and relatively reduced reactivity to improve their associated combustion characteristics and reduce engine knock without the need to modify the engine fuel or engine parameters such as compression ratio and/or ignition timing. The base stocks may specifically include esters of dicarboxylic acids, esters of trimellitic anhydride and/or alklyated naphthalene compounds.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: March 6, 2012
    Assignee: Southwest Research Institute
    Inventors: Manfred Amann, Terrence Francis Alger, II, Thomas W. Ryan, III
  • Patent number: 8071519
    Abstract: A composition comprising a blend of first and second esters: the first ester comprising a reaction product of first reactants comprising trimer acid, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C8-18 monohydric alcohols; the second ester comprising a reaction product of second reactants comprising trimer acid, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C6-10 monohydric alcohols; the first and second monohydric alcohols being non-identical. This blend of esters, in combination with silica, is useful as a sealant composition, e.g., as a cable-protectant composition.
    Type: Grant
    Filed: April 25, 2002
    Date of Patent: December 6, 2011
    Assignee: Arizona Chemical Company, LLC
    Inventors: Lloyd A. Nelson, Nancy D. Mosby
  • Patent number: 7875580
    Abstract: An automotive engine oil comprising a base oil and an antiwear additive system comprising an ester. The antiwear additive system preferably further comprises a phosphorus-containing and/or sulphur-containing antiwear additive. The antiwear additive system of the invention has superior antiwear properties and also reduced metal, phosphorus and sulphur levels compared to current commercial antiwear agents such as ZDDP.
    Type: Grant
    Filed: February 25, 2005
    Date of Patent: January 25, 2011
    Assignee: Croda Internatonal PLC
    Inventor: Andrew S Oldfield
  • Patent number: 7339003
    Abstract: An antioxidant which comprises a primary aliphatic hydroxyl group linked to an organic backbone such that upon oxidation a hydroperoxyl moiety capable of boosting the efficacy of free radical scavengers and hydroperoxide decomposer type antioxidants is generated in situ. The antioxidant is preferably a high hydroxyl polyol ester having a hydroxyl number ranging from about 30 to about 180 which ester is the reaction product of polyol and an acid which is at least fifty percent branched carboxylic acid, wherein the unconverted hydroxyl group is reacted with a facile leaving group, thereby producing free —CH2OH groups upon hydrolysis or oxidation.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: March 4, 2008
    Assignee: Exxonmobil Research and Engineering Company
    Inventors: Haven S. Aldrich, Richard H. Schlosberg, Stanley J. Brois
  • Patent number: 7045490
    Abstract: A refrigerating machine oil composition according to the invention comprises an alicyclic polycarboxylic acid ester compound obtained from the following compounds (a) to (c): (a) an alicyclic polycarboxylic acid having an alicyclic ring and two or more carboxyl groups, or its derivative, wherein at least two of the carboxyl groups are bonded to mutually adjacent carbon atoms on the alicyclic ring; (b) a compound with two or more hydroxyl groups or its derivative; and (c) a compound with one hydroxyl group or its derivative. It can be used together with HFC refrigerants and natural refrigerants such as carbon dioxide and hydrocarbons, to provide a satisfactory balance between all of the properties of lubricity, miscibility with refrigerants, heat and hydrolytic stability and electric insulating property.
    Type: Grant
    Filed: July 18, 2001
    Date of Patent: May 16, 2006
    Assignee: Nippon Oil Corporation
    Inventors: Yuji Shimomura, Katsuya Takigawa
  • Patent number: 6713438
    Abstract: High performance engine oils and other liquid lubricants comprise a liquid lubricant basestock of low viscosity from 1.5 to 12 cSt (100C) with two dissolved polymer components of differing molecular weights. The basestock is preferably a single PAO or blend of PAOs with a co-basestock component which is preferably an ester or an alkylated aromatic of comparable viscosity. The lower molecular weight polymer is highly viscoelastic in character and is preferably an HVI-PAO; this component in the lubricant which provides unexpectedly high film thickness and unexpectedly good wear protection under conditions where the second, higher molecular weight polymer may lose some or all of its thickening power. The use of the highly viscoelastic low molecular weight polymer in combination with the higher molecular weight thickener enables the production of very widely cross-graded engine oils, especially oils with a low temperature grading of 0W or better.
    Type: Grant
    Filed: March 24, 1999
    Date of Patent: March 30, 2004
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Raymond J. Bergstra, Andrew Jackson, William L. Maxwell, G. James Johnston, Robert A. Pache
  • Publication number: 20040002429
    Abstract: Novel oil-in-oil emulsions and methods of lubrication using the same are provided. The lubricants are stable emulsions of carrier fluid and high viscosity fluid that display superior properties related to lubricating film thickness and reduced shear strength.
    Type: Application
    Filed: June 28, 2002
    Publication date: January 1, 2004
    Inventor: Thomas R. Forbus
  • Patent number: 6649574
    Abstract: A biodegradable lubricating oil composition especially useful as a gear oil employs a synthetic alcohol ester basestock formed from mono- and dipentaerythritol with certain mono- and dicarboxylic acids or dicarboxylic acid anhydrides and an effective amount of a polyoxyalkylene alcohol demulsifying agent, a combination of alkylated organic acid and ashless succinimide rust inhibitors and an ashless dithiocarbamate antiwear and extreme pressure agent.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: November 18, 2003
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Angeline Baird Cardis, Susan Ardito
  • Publication number: 20030166478
    Abstract: A refrigerating machine oil composition according to the invention comprises an alicyclic polycarboxylic acid ester compound obtained from the following compounds (a) to (c):
    Type: Application
    Filed: January 23, 2003
    Publication date: September 4, 2003
    Inventors: Yuji Shimomura, Katsuya Takigawa
  • Publication number: 20030125218
    Abstract: A biodegradable lubricating oil composition especially useful as a gear oil employs a synthetic alcohol ester basestock formed from mono- and dipentaerythritol with certain mono- and dicarboxylic acids or dicarboxylic acid anhydrides and an effective amount of a polyoxyalkylene alcohol demulsifying agent, a combination of alkylated organic acid and ashless succinimide rust inhibitors and an ashless dithiocarbamate antiwear and extreme pressure agent.
    Type: Application
    Filed: October 8, 2002
    Publication date: July 3, 2003
    Inventors: Angeline Baird Cardis, Susan Ardito
  • Patent number: 6544937
    Abstract: A lubricating composition containing naphthenic basestocks has demulsification properties improved by the addition of a demulsification additive selected from oxyalkylated glycols, esters of oxyalkylated glycols and mixtures thereof.
    Type: Grant
    Filed: March 22, 2002
    Date of Patent: April 8, 2003
    Assignee: ExxonMobile Research and Engineering Company
    Inventors: William Donald Hewson, Terrence Edward Addley
  • Publication number: 20020193262
    Abstract: The present invention relates to a refrigeration oil for a refrigerating machine using Flon as a refrigerant. In particular, the present invention relates to a lubricating oil composition for a refrigerating machine using hydrofluorocarbon (HFC) containing no chlorine as a refrigerant, also relates to a working fluid and a refrigerating machine.
    Type: Application
    Filed: May 14, 2002
    Publication date: December 19, 2002
    Inventors: Takashi Kaimai, Hitoshi Takahashi
  • Patent number: 6462001
    Abstract: An ester resulting from an esterification reaction between at least one polyfunctional alcohol and at least one polyfunctional carboxylic acid using a chain stopping agent to form ester bonds with the remaining hydroxyl or carboxyl groups is disclosed. The polyfunctional carboxylic acid comprises an aliphatic dicarboxylic acid containing from 9 to 18 carbon atoms, dimerised and/or trimerised fatty acids or mixtures thereof, with the proviso that dimerised and trimerised fatty acids do not constitute more than 80% by weight of the total amount of polyfunctional carboxylic acid used. The chain stopping agent may be a monocarboxylic acid or a monofuntional alcohol having at least 14 carbon atoms. The complex esters have a kinematic viscosity at 100 C of from 30 to 1000 cSt, preferably from 30 to 200 cSt.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: October 8, 2002
    Assignee: Unichema Chemie BV
    Inventors: Dirk Kenbeek, Cornelis Verboom, Gijsbert Van der Waal
  • Patent number: 6376435
    Abstract: A binary two phase engine oil composition having two substantially immiscible liquid phases exhibits improved fuel economy which is maintained over an extended period. The first liquid phase comprises a base oil, natural or synthetic. The second liquid phase is a polar organic liquid, preferably a complex alcohol ester, preferably derived from a polyol, a polybasic acid, and a monohydric alcohol.
    Type: Grant
    Filed: April 21, 2000
    Date of Patent: April 23, 2002
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Mahmoud Mostafa Hafez, Ulrich Witten, Paul Simon Woolley, Hiroki Kurosawa
  • Patent number: 6310012
    Abstract: An extreme pressure agent and a friction coefficient modifier which comprises a compound having, in a molecule, a group represented by general formula (I): wherein R1, R2, and R3 each represents hydrogen atom or methyl group, and at least one of R2 and R3 represents hydrogen atom; a fluid resistant to seizure under load and a wear resistant fluid which each comprises the above additive or the above modifier; and a flame resistant fluid which comprises a thermally polymerizable substance, preferably the above compound. The extreme pressure agent and the friction coefficient modifier have excellent properties and are advantageously used for lubricating oil, metal working oil, and hydraulic oil. The flame resistant fluid suppresses vaporization of flammable substances by thermal polymerization to prevent fire when the fluid is exposed to a high temperature and is advantageously used as lubricating oil, metal working oil, hydraulic oil, heat treatment oil, and grease.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: October 30, 2001
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Fumiaki Takagi, Kazuaki Abe
  • Patent number: 6267906
    Abstract: A high quality lubricant for heavy duty service air conditioner and refrigerator compressors, especially those using chlorine free hydrofluorocarbon refrigerant working fluids, is provided by mixed esters of hindered polyols, most desirably di-pentaerythritol, usually mixed with some pentaerythritol, with a mixture of carboxylic acids including at least some of each of iso-pentanoic acid and iso-nonanoic acid.
    Type: Grant
    Filed: April 9, 1999
    Date of Patent: July 31, 2001
    Assignee: Henkel Corporation
    Inventors: Nicholas E. Schnur, Eugene R. Zehler
  • Patent number: 6268319
    Abstract: A slide way lubricant composition includes at least (a) a hydrotreated petroleum having a viscosity of from about 10 cSt to about 250 cSt as measured at 40° C. and consisting predominately of hydrocarbons having from about 15 to about 50 carbon atoms per molecule and (b) a polymeric synthetic ester having an average molecular weight of at least about 200,000. The hydrotreated petroleum may be employed in an amount of from about 97.8 to about 99.4 weight percent and the ester may be employed in the composition in an amount of from about 0.6 to about 2.2 weight percent. The ester may be derived from the reaction between a dicarboxylic acid and a polyhydric alcohol. The composition may further include an adhesion additive having an average molecular weight of at least about 1,000,000 and a high pressure agent, such as a trisulfide. A demulsibility agent may also be employed.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: July 31, 2001
    Assignee: General Oil Company
    Inventor: Anthony G. Junga
  • Patent number: 6258293
    Abstract: A refrigerating apparatus comprising a refrigeration cycle comprising at least a compressor, a condenser, a dryer, an expansion mechanism and an evaporator, a refrigerant composed mainly of a fluorocarbon type refrigerant containing no chlorine and having a critical temperature of 40° C. or higher, and a refrigerating machine oil comprising as base oil an ester oil of one or more fatty acids which contains at least two ester linkages in the molecule and has a viscosity at 40° C. of 2 to 70 cSt and a viscosity at 100° C. of 1 to 9 cSt.
    Type: Grant
    Filed: December 2, 1999
    Date of Patent: July 10, 2001
    Assignee: Hitachi, Ltd.
    Inventors: Tadashi Iizuka, Reishi Naka, Katsumi Fukuda, Makoto Tanaka, Yoshiharu Homma, Hiroaki Hata, Hirokatsu Kousokabe, Koji Nariyoshi, Hiroshi Iwata
  • Patent number: 6221272
    Abstract: A high quality lubricant for hermetically sealed domestic air conditioner and refrigerator compressors, especially those using chlorine free hydrofluorocarbon refrigerant working fluids, is provided by mixed esters of hindered polyols, most desirably pentaerythritol, with a mixture of carboxylic acids including at least some isopentanoic acid along with either or both of iso-nonanoic acid and dibasic acids such as adipic.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: April 24, 2001
    Assignee: Henkel Corporation
    Inventors: Nicholas E. Schnur, Eugene R. Zehler
  • Patent number: 6197731
    Abstract: Ester base stocks for two-cycle gasoline engine lubricant compositions are disclosed which produce lower amounts of observable smoke in the exhaust emitted as a result of combustion in a two-cycle gasoline engine, require no miscibility-enhancing solvents, have a viscosity of 3.0 cSt to 20.0 cSt at 100° C. and a smoke index of at least 75. Some of the esters are biodegradable.
    Type: Grant
    Filed: May 17, 1999
    Date of Patent: March 6, 2001
    Assignee: Henkel Corporation
    Inventors: Eugene R. Zehler, Bruce J. Beimesch
  • Patent number: 6153118
    Abstract: A refrigerator oil for use in compressors using therein a hydrogen-containing halogenocarbon as a refrigerant, consisting essentially of as a base oil at least two esters selected from the group consisting of a specific pentaerythritol ester such as an ester of pentaerythritol with a mono- or dicarboxylic acid, a specific polyol ester such as an ester of trimethylolethane with a mono- or dicarboxylic acid, a specific ester such as an ester of ethylene glycol and a dicarboxylic acid, and a specific polyol ester synthesized from a neopentyl type polyhydric alcohol, a monocarboxylic acid and a dicarboxylic acid; and further comprising at least one kind of an epoxy compound.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: November 28, 2000
    Assignee: Nippon Mitsubishi Oil Corp.
    Inventors: Hiroshi Hasegawa, Noboru Ishida, Umekichi Sasaki, Tatsuyuki Ishikawa
  • Patent number: 6010989
    Abstract: The invention relates to an additive for improving the flow properties of paraffin-containing mineral oils and mineral oil distillates, comprising a mixture of at least one ethylene/vinyl ester copolymer or terpolymer and at least one paraffin dispersant, wherein said mixture contains ethers and/or esters as solubilizers, wherea) the ethers conform to the formula 1R--O--R' (1)in which R is a linear or branched alkyl or alkenyl group having 4 to 30 carbon atoms, and R' is a linear or branched alkyl or alkenyl group having 1 to 30 carbon atoms,b) the esters are derived from monobasic or polybasic carboxylic acids having 4 to 30 carbon atoms (acid radical) and from monohydric or polyhydric alcohols having 1 to 30 carbon atoms (alcohol radical), orc) the ethers and/or esters are cyclic, with a ring size of from 6 to 30 carbon atoms.The invention furthermore relates to a process for improving the flow properties of mineral oils and mineral oil distillates which comprises adding the novel additive thereto.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: January 4, 2000
    Assignee: Clariant GmbH
    Inventors: Matthias Krull, Werner Reimann
  • Patent number: 5942475
    Abstract: A crankcase engine lubricant which comprises the add mixture of the following components: (A) a lubricating oil which comprises the add mixture of the following components: a complex alcohol ester basestock and at least one additional basestock; and (B) an additive package; wherein the crankcase engine lubricant exhibits a percent fuel economy improvement in the range between about 0.3 to 5.0%, versus the lubricating oil without the complex alcohol ester basestock.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: August 24, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Richard H. Schlosberg, David Wayne Turner, Martin A. Krevalis, Fay H. Gordon, Ulrich Witten
  • Patent number: 5925602
    Abstract: Ester base stocks for two-cycle gasoline engine lubricant compositions are disclosed which produce lower amounts of observable smoke in the exhaust emitted as a result of combustion in a two-cycle gasoline engine, require no miscibility-enhancing solvents, have a viscosity of 3.0 cSt to 20.0 cSt at 100.degree. C. and a smoke index of at least 75. Some of the esters are biodegradable.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: July 20, 1999
    Assignee: Henkel Corporation
    Inventors: Eugene R. Zehler, Bruce J. Beimesch
  • Patent number: 5922658
    Abstract: A biodegradable two-cycle lubricant which is prepared from an add mixture of: (1) a biodegradable lubricating oil comprising an add mixture of the following components: a complex alcohol ester basestock which comprises the reaction product of an add mixture of the following: a polyhydroxyl compound represented by the general formula:R(OH).sub.nwherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that the hydrocarbyl group contains from about 2 to 20 carbon atoms; a polybasic acid or an anhydride of a polybasic acid, provided that the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1.6:1 to 2:1; and a monohydric alcohol, provided that the ratio of equivalents of the monohydric alcohol to equivalents of the polybasic acid is in the range between about 0.84:1 to 1.2:1; wherein the complex alcohol ester exhibits a viscosity in the range between about 100-700 cSt at 40.degree. C.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: July 13, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Carolyn Boggus Duncan, David Wayne Turner
  • Patent number: 5916854
    Abstract: A biodegradable lubricating base oil obtained by carrying out an addition reaction of an alkylene oxide and a transesterification in a mixture of fats and oils, a polyhydric alcohol or an aliphatic carboxylic acid, and an alkylene oxide, the mixture containing 5 to 150 mol of the alkylene oxide to 1 mol of the fats and oils; a biodegradable lubricating base oil obtained by carrying out esterification of all or part of the hydroxyl group in the above fats and oils derivative using an aliphatic carboxylic acid or ester derivative thereof. Further, a biodegradable lubricating oil composition containing the biodegradable lubricating base oil and the use thereof are also described.
    Type: Grant
    Filed: August 7, 1997
    Date of Patent: June 29, 1999
    Assignee: Kao Corporation
    Inventors: Shuichi Inaya, Hiroki Sawada, Yuichiro Kobayashi, Toshiya Hagihara
  • Patent number: 5912214
    Abstract: Ester base stocks for two-cycle gasoline engine lubricant compositions are disclosed which produce lower amounts of observable smoke in the exhaust emitted as a result of combustion in a two-cycle gasoline engine, require no miscibility-enhancing solvents, have a viscosity of 3.0 cSt to 20.0 cSt at 100.degree. C. and a smoke index of at least 75. Some of the esters are biodegradable.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: June 15, 1999
    Assignee: Henkel Corporation
    Inventors: Eugene R. Zehler, Bruce J. Beimesch
  • Patent number: 5854185
    Abstract: The present invention provides lubricant mixtures for use as base fluid in bearing grease comprising 25 to 90 percent w/w of a liquid ester having a viscosity at 40.degree. C. in the range 100 to 200 mm.sup.2 /s, and 75 to 10 percent w/w of a liquid poly-.alpha.-olefin having a viscosity at 100.degree. C. in the range 2 to 10 mm.sup.2 /s, and bearing grease compositions containing a major proportion of such lubricant mixtures, particularly such compositions containing a clay thickener.
    Type: Grant
    Filed: November 25, 1997
    Date of Patent: December 29, 1998
    Assignee: Shell Oil Company
    Inventors: Robert John Gordon Roth, Georgina Ann Winterburn
  • Patent number: 5853609
    Abstract: A high quality lubricant for hermetically sealed domestic air conditioner and refrigerator compressors, especially those using chlorine free hydrofluorocarbon refrigerant working fluids, is provided by mixed esters of hindered polyols, most desirably pentaerythritol, with a mixture of carboxylic acids including at least some iso-pentanoic acid along with either or both of iso-nonanoic acid and dibasic acids such as adipic.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 29, 1998
    Assignee: Henkel Corporation
    Inventors: Nicholas E. Schnur, Eugene R. Zehler
  • Patent number: 5851968
    Abstract: The electrical resistivity of hindered polyol ester lubricants can be raised to very high levels by treating the lubricants with activated alumina, preferably after the acid values of the lubricants treated have already been reduced to low levels by conventional refining with alkali or other acid scavengers.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: December 22, 1998
    Assignee: Henkel Corporation
    Inventor: Nicholas E. Schnur
  • Patent number: 5840662
    Abstract: The frictional durability of lubricating oils, including power transmitting fluids and in particular automatic transmission fluids, are improved by incorporating a combination of low potency friction modifiers, ashless and/or metal-containing antioxidants, and oil-soluble phosphorus-containing compounds.
    Type: Grant
    Filed: August 28, 1997
    Date of Patent: November 24, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Roger Keith Nibert, Raymond Frederick Watts, Ricardo Alfredo Bloch
  • Patent number: 5780399
    Abstract: An oil-soluble polyester having a weight average molecular weight of 10,000 to 1 000,000, which is a polycondensate prepared by polycondensing the following ingredients (A), (B) and (C):(A) a divalent higher carboxylic acid ingredient,(B) a divalent alcohol ingredient comprising a glycol represented by the following formula:HO--CH.sub.2 --CR.sup.1 R.sup.2 --CH.sub.2 --OHwherein R.sup.1 and R.sup.2 represent a alkyl group, and the sum of carbon numbers in R.sup.1 and R.sup.2 is at least three, and(C) 0.1 to 15% by mole, based on the total of ingredients (A) and (B), of at least one multi-valent ingredient selected from a carboxylic acid with a valency of at least three and an alcohol with a valency of at least three. This oil-soluble polyester is useful as an additive for a lubricating oil.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: July 14, 1998
    Assignees: Nippon Zeon Co., Ltd., Harima Chemicals, Inc., Nippon Oil Company, Ltd.
    Inventors: Yoshihide Ishikawa, Shinsuke Hasegawa, Michio Miyamoto, Shizuo Kitahara, Yutaka Shikatani, Jinichi Igarashi
  • Patent number: 5750750
    Abstract: A complex alcohol ester which comprises the reaction product of an add mixture of the following: a polyhydroxyl compound represented by the general formula:R(OH).sub.nwherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that the hydrocarbyl group contains from about 2 to 20 carbon atoms; a polybasic acid or an anhydride of a polybasic acid, provided that the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1.6:1 to 2:1; and a monohydric alcohol, provided that the ratio of equivalents of the monohydric alcohol to equivalents of the polybasic acid is in the range between about 0.84:1 to 1.2:1; wherein the complex alcohol ester exhibits a pour point of less than or equal to -20.degree. C., a viscosity in the range between about 100-700 cSt at 40.degree. C. and having a polybasic acid ester concentration of less than or equal to 70 wt. %, based on the complex alcohol ester.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: May 12, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Carolyn Boggus Duncan, Paul R. Geissler, David Wayne Turner, William Joseph Munley, Jr., Martin A. Krevalis
  • Patent number: 5744434
    Abstract: A synthetic ester composition which exhibits thermal and oxidative stability, lower friction coefficient and lower wear, wherein the ester composition comprises the reaction product of: a branched or linear alcohol having the general formula R(OH).sub.n, wherein R is an aliphatic or cyclo-aliphatic group having from about 2 to 20 carbon atoms and n is at least 2; and at least one branched mono-carboxylic acid which has a carbon number in the range between about C.sub.5 to C.sub.13 ; wherein the synthetic ester composition has between about 5-35% unconverted hydroxyl groups, based on the total amount of hydroxyl groups in the branched or linear alcohol.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: April 28, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Richard Henry Schlosberg, Haven S. Aldrich, Lavonde Denise Sherwood-Williams, John S. Szobota, Martin Anthony Krevalis, Daniel P. Leta, David Gary Lawton Holt, Fay H. Gordon
  • Patent number: 5744432
    Abstract: Water-based stamping lubricants are comprised of: (1) water; (2) a polyester that is water-soluble or readily emulsifiable made by reacting one or more dicarboxylic acids and a polyalkylene glycol; (3) one or more ethoxylated alkylalcohols; (4) the salt of a phosphate ester of an ethoxylated alkyl alcohol; (5) an alkanolamine.
    Type: Grant
    Filed: October 28, 1996
    Date of Patent: April 28, 1998
    Assignee: Henkel Corporation
    Inventors: Jeff A. Barnhorst, Roger H. Garst, Ronald H. Gordon, Eugene R. Zehler
  • Patent number: 5736492
    Abstract: The invention provides alkenyl-substituted dicarboxylic derivatives, having (a) an alkenyl group derived from an atactic propylene oligomer substantially of the formula ##STR1## where n is in the range 15 to 120, having number average molecular weight (M.sub.n) in the range 700 to 5000, and molar ratio dicarboxylic moieties to atactic propylene oligomer in the range 1:1 to 1.5:1; and having (b) an ester group derived from a polyol, which are useful as dispersant additives; a process for making the ester derivatives, additive concentrates containing such ester derivatives, and lubricating oil compositions.
    Type: Grant
    Filed: August 2, 1996
    Date of Patent: April 7, 1998
    Assignee: Shell Oil Company
    Inventors: Michael Thomas Clark, Hendrik Tijmen Verkouw
  • Patent number: 5716916
    Abstract: A polyol ester-based lubricant comprising a polyol ester (A) and a polyol ester (B);the polyol ester (A) comprising an ester of a neopentyl polyol and an acid residue of carbon number of 6-17, in which alpha-carbon in the acid residue of the polyol ester is tertiarily branched, and when alkyl groups having 4 or more carbon atoms are bonded to the alpha-carbon, the alkyl groups are branched, andthe polyol ester (B) comprising an ester of a neopentyl polyol and an acid residue of carbon number of 6-17, in which alpha-carbon in the acid residue of the polyol ester is secondarily or tertiarily branched and alkyl groups bonded to the alpha-carbon are straight is provided. This polyol ester-based lubricant has high performance, as demonstrated by high compatibility with substitute fluorocarbons in a kinematic viscosity range of 28 to 40 cst at 40.degree. C., excellent hydrolysis resistance, and a low pour point.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: February 10, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yoshihiro Shiokawa, Yoshifumi Sato, Kinji Kato
  • Patent number: 5681800
    Abstract: A biodegradable synthetic ester base stock which comprises a blend of the following base stocks: (A) the reaction product of: (1) a branched or linear alcohol having the general formula R(OH).sub.n, wherein R is an aliphatic or cyclo-aliphatic group having from about 2 to 20 carbon atoms and n is at least 2; and (2) mixed acids comprising about 30 to 80 molar % of a linear acid having a carbon number in the range between about C.sub.5 to C.sub.12, and about 20 to 70 molar % of at least one branched acid having a carbon number in the range between about C.sub.5 to C.sub.10 and wherein no more than 10% of the branched acids used to form the biodegradable synthetic ester base stock contains a quaternary carbon; wherein the ester base stock exhibits the following properties: at least 60% biodegradation in 28 days as measured by the Modified Sturm test, a pour point of less than -25.degree. C.; and a viscosity of less than 7500 cps at -25.degree. C.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: October 28, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Carolyn Boggus Duncan, Leah Katherine Meade