US3762890A - Stabilized polyvalent metal soap composition - Google Patents

Stabilized polyvalent metal soap composition Download PDF

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Publication number
US3762890A
US3762890A US00230141A US3762890DA US3762890A US 3762890 A US3762890 A US 3762890A US 00230141 A US00230141 A US 00230141A US 3762890D A US3762890D A US 3762890DA US 3762890 A US3762890 A US 3762890A
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manganese
soap
percent
composition
propionic acid
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A Collins
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Mooney Chemical Inc
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Mooney Chemical Inc
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/50Use of additives, e.g. for stabilisation
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10CWORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
    • C10C1/00Working-up tar
    • C10C1/04Working-up tar by distillation
    • C10C1/14Winning of tar oils from tar
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof
    • C10L1/1881Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/16Hydrocarbons
    • C10L1/1616Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/16Naphthenic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/14Group 7
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/16Groups 8, 9, or 10
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • ABSTRACT A hydrocarbon solution of a hydrolizable manganese soap, by inclusion of propionic acid, in amounts of about 5 percent 10 percent in the total solution for usual manganese content, is markedly stabilized against hydrolysis of the soap and from consequent precipitation of the metal content from solution, especially by stabilization against formation of an emulsion with water, and thereby is effectively preserved from hydrolysis; thus, for example, in the case of fuel oils preventing difficulties in pumping, or ultimately at the burner due to sputtering, which can result from emulsification and- /or precipitation; with manganese neodecanoate solutions of varied manganese content, a propionic acid/- manganese weight ratio of at least about 1.0.
  • compositions containing these soaps are subject to contact with water, either in storage or field handling of a composition itself, or perhaps after incorporation in some other substance such as fuel oil.
  • Contact with water if extensive either in duration or in interfacial area, may lead to a hydrolysis of the soap and a corresponding precipitation of the metal in an insoluble simpler compound, such as an oxide or hydroxide, thus rendering the metal at least unavailable for its intended purpose, if not engendering other problems, as a solid in a liquid storage or handling system.
  • manganese soap compositions such as manganese neodecanoate, or mixed manganese neodecanoate and other manganese branched chain carboxylates, in solution in light mineral oil or mineral spirits, are useful additive compositions in fuel oils.
  • these compositions emulsify with water and in consequence of the extensive area exposed to water, the total of the interface area of the unnumerable micelles, hydrolysis, of the contained manganese soap substance occurs rather rapidly, resulting in a precipitation of manganese dioxide, thus diminishing the effective, that is dissolved, manganese compound content of the composition.
  • manganese dioxide may result in undesirable sludging in storage tanks, and in extreme conditions, to possible plugging of nozzles, valves and like operating or maintenance situations. Even the emulsion itself can plug nozzles or valves; and can, upon reaching a burner, cause spattering and extinction of the flame.
  • neodecanoic acid hereinafter named in the composition examples is a standardized isomeric mixtureo f ten carbon neo acids marketed by Enjay Corporation in commercial quantities, and accordingly the term neodecanoate refers to a product derived from such acid.
  • the resultant manganese neodecanoate solution product 1,000 parts, containing about 6.0 percent manganese and having an acid number of about 10, when testedby vigorous shaking of a sample with an equal volume of water, emulsified readily, and exhibited heavy .precipitation of manganese dioxide after a few hours standing.
  • EXAMPLE 3 A composition prepared similarly to Example 2 with 630 parts of neo decanoic acid, 81 parts manganese, in
  • Example 2 73 parts of the oil, with 7 parts water, 3 parts acetic acid, 53 parts polypropylene glycol, but with 133 parts propionic acid, gave stability results identical to those of Example 2, the product composition containing 8 percent manganese, about 13 percent propionic acid, and having an acid number of 96. Again the propionic acid-manganese ratio is 1.67.
  • EXAMPLE 4 PROPlONlC ACID EFFECT In a manner similar to Examples 2 and 3, there were made up and then tested manganese neodecanoate product solutions adjusted to 6 percent manganese content, with the amount of diluent oil varied to accommodate the changes in propionic acid percentage content for ratios of propionic acid to manganese, as follows:
  • a homogeneous liquid composition comprising:
  • propionic acid in an amount effective to stabilize the composition against emulsification with water and hydrolysis-caused precipitation of manganese dioxide.
  • composition as described in claim 1, wherein said soap is manganese neodecanoate.
  • composition as described in claim 1, wherein said hydrocarbon liquid is mineral spirits or light mineral oil.
  • said hydrocarbon liquid is mineral spirits or light mineral oil.
  • a composition as described in claim 4 containing from about 6 to 10 percent by weight manganese as the neodecanoate, and a minimum of from about 10 to l3 percent by weight of propionic acid.
  • a composition as described in claim 5 including at least about 4 percent by weight of polypropylene glycol.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Materials Engineering (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00230141A 1973-09-26 1972-02-28 Stabilized polyvalent metal soap composition Expired - Lifetime US3762890A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4516473A GB1403142A (en) 1973-09-26 1973-09-26 Stabilized polyvalent metal soap composition

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US3762890A true US3762890A (en) 1973-10-02

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US (1) US3762890A (en])
JP (1) JPS5061406A (en])
CA (1) CA1009457A (en])
DE (1) DE2349446A1 (en])
FR (1) FR2245756B1 (en])
GB (1) GB1403142A (en])
NL (1) NL7313377A (en])

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5461172A (en) * 1993-08-09 1995-10-24 Mooney Chemicals, Inc. Light-colored manganese carboxylates
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes
EP1344813A1 (en) * 2002-03-13 2003-09-17 Infineum International Limited Fuel additive compositions for diesel engine equipped with a particulate trap
US20030182848A1 (en) * 2002-03-13 2003-10-02 Collier Philip E. Diesel fuel additive compositions for improvement of particulate traps
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3205732A1 (de) * 1982-02-18 1983-08-25 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur verbesserung der verbrennung von kraftstoffen fuer dieselmotoren

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes
US5534039A (en) * 1991-05-13 1996-07-09 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5562742A (en) * 1991-05-13 1996-10-08 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5461172A (en) * 1993-08-09 1995-10-24 Mooney Chemicals, Inc. Light-colored manganese carboxylates
EP1344810A1 (en) * 2002-03-13 2003-09-17 Infineum International Limited Fuel additive compositions for diesel engine equipped with a particulate trap
EP1344813A1 (en) * 2002-03-13 2003-09-17 Infineum International Limited Fuel additive compositions for diesel engine equipped with a particulate trap
US20030182848A1 (en) * 2002-03-13 2003-10-02 Collier Philip E. Diesel fuel additive compositions for improvement of particulate traps
US20030221362A1 (en) * 2002-03-13 2003-12-04 Collier Philip E. Fuel additive compositions for diesel engine equipped with a particulate trap
US20060230672A1 (en) * 2002-03-13 2006-10-19 Collier Philip E Diesel fuel additive compositions for improvement of particulate traps
US7585336B2 (en) 2002-03-13 2009-09-08 Infineum International Limited Fuel additive compositions for diesel engine equipped with a particulate trap
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US20070111907A1 (en) * 2005-11-16 2007-05-17 Esche Carl K Jr Additives and lubricant formulations for providing friction modification
US7709423B2 (en) 2005-11-16 2010-05-04 Afton Chemical Corporation Additives and lubricant formulations for providing friction modification
US20070149418A1 (en) * 2005-12-22 2007-06-28 Esche Carl K Jr Additives and lubricant formulations having improved antiwear properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
US7767632B2 (en) 2005-12-22 2010-08-03 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties

Also Published As

Publication number Publication date
FR2245756A1 (en]) 1975-04-25
JPS5061406A (en]) 1975-05-27
NL7313377A (nl) 1975-04-02
DE2349446A1 (de) 1975-04-03
FR2245756B1 (en]) 1977-08-12
GB1403142A (en) 1975-08-13
AU479405A (en]) 1975-04-10
CA1009457A (en) 1977-05-03

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