US3867296A - Process for preparing clear bright oleaginous aluminum dispersions - Google Patents

Process for preparing clear bright oleaginous aluminum dispersions Download PDF

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Publication number
US3867296A
US3867296A US373564A US37356473A US3867296A US 3867296 A US3867296 A US 3867296A US 373564 A US373564 A US 373564A US 37356473 A US37356473 A US 37356473A US 3867296 A US3867296 A US 3867296A
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United States
Prior art keywords
aluminum
alumina
oil
acids
weight percent
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Expired - Lifetime
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US373564A
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English (en)
Inventor
Mack W Hunt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vista Chemical Co
ConocoPhillips Co
Original Assignee
Continental Oil Co
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Publication date
Priority to CA155,062A priority Critical patent/CA980330A/en
Priority to DE2257342A priority patent/DE2257342C3/de
Priority to FR7303458A priority patent/FR2173980B3/fr
Priority to GB779973A priority patent/GB1426092A/en
Application filed by Continental Oil Co filed Critical Continental Oil Co
Priority to US373564A priority patent/US3867296A/en
Application granted granted Critical
Publication of US3867296A publication Critical patent/US3867296A/en
Priority to BE162234A priority patent/BE836019Q/xx
Assigned to VISTA CHEMICAL COMPANY reassignment VISTA CHEMICAL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CONOCO INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/0004—Preparation of sols
    • B01J13/0047—Preparation of sols containing a metal oxide
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
    • C01F7/34—Preparation of aluminium hydroxide by precipitation from solutions containing aluminium salts
    • C01F7/36—Preparation of aluminium hydroxide by precipitation from solutions containing aluminium salts from organic aluminium salts
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    • C10L1/10—Liquid carbonaceous fuels containing additives
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    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/922—Colloid systems having specified particle size, range, or distribution, e.g. bimodal particle distribution
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/924—Significant dispersive or manipulative operation or step in making or stabilizing colloid system
    • Y10S516/928—Mixing combined with non-mixing operation or step, successively or simultaneously, e.g. heating, cooling, ph change, ageing, milling

Definitions

  • ABSTRACT Forelgn Apphcatlon Prmmy Data A process for preparing clear bright oleaginous alumi- Oct. 26,1972 Canada ..l55062 num dispersions Comprising admixing an Oi] Soluble dispersing agent, an oleaginous carrier and a volatile [52] US. Cl 25 /3 2 8' solvent with a dispersible alumina, heating and recov- 252/ 52/33. 252/3 2, 2 2/308, 252/309 ering a clear bright oleaginous aluminum dispersion. [51] Int. Cl Cl0m l/40 [58] Field of Search 252/19, 26, 33, 33.4, 37,
  • This invention relates to the dispersion of metals in oleaginous materials. This invention further relates to a process for dispersing aluminum in oleaginous materials. This invention further relates to a process for dispersing aluminum in oleaginous materials by the use of sulfonic acids and carboxylic acids as dispersing agents.
  • U.S. Pat. No. 3,018,172 to Tillman shows a process for preparing dispersions of aluminum in mineral oils and the like by a process wherein aluminum alkoxide is dispersed in an alkanol, mixed with a mineral oil containing an oil soluble detergent material such as sulfonate materials and thereafter hydrolyzed to produce a dispersion of alumina.
  • the process requires a hydrolysis step in an oil media which necessitates mixing an aqueous portion with an oily portion and, of course, subsequent separation of the aqueous and oily portions.
  • Australian Patent 200,149 discloses a process for dispersing alumina in oleaginous materials containing sulfonic acids by a mechanical milling technique; however, the dispersions obtained are not shown to be clear high quality dispersions but rather are primarily intended for use as fuel oil additives and the like.
  • an oil soluble dispersing agent selected from the group consisting of oil soluble sulfonic acids in which the hydrocarbon portion has a molecular weight from about 300 to about 1000 and carboxylic acids containing at least about 8 carbon atoms, an oleaginous carrier and a volatile solvent with alumina prepared by the water hydrolysis of aluminum alkoxides and having the following properties:
  • Aluminum dispersions in oleaginous materials such as those produced by the process of the present invention are useful as fuel oil additives, jet fuel additives, motor fuel additives, lubricant additives and the like.
  • the dispersions of the present invention are particularly useful since such dispersions contain substantial amounts of aluminum in a clear bright dispersion suitable for use in high quality motor oils and the like.
  • aluminum containing dispersions are prepared by admixing an oil soluble dispersing agent, an oleaginous carrier, and a volatile solvent with a dispersible alumina and heating the mixture to remove said volatile solvent and recover the aluminum containing dispersion.
  • Suitable oil-soluble dispersing agents include the oilsoluble sulfonic acids and carboxylic acids.
  • oil-soluble sulfonic acids refers to those materials wherein the hydrocarbon portion of the molecule has a molecular weight in the range of about 300 to about 1,000. Preferably, this molecular weight is in the range of about 370 to about 700.
  • These oilsoluble sulfonic acids can be either synthetic sulfonic acids or the so-called mahogany or natural sulfonic acids. The term mahogany sulfonic acid is believed to be well understood, since it is amply described in the literature.
  • the term synthetic sulfonic acids refers to those materials which are prepared by sulfonation of hydrocarbon feedstocks which are prepared synthetically.
  • the synthetic sulfonic acids can be derived from either alkyl or alkaryl hydrocarbons. In addition, they can be derived from the hydrocarbons having cycloalkyl (i.e. naphthenic) groups in the side chains attached to the benzene ring.
  • the alkyl groups in the alkaryl hydrocarbons can be straight or branched chain.
  • the alkaryl radical can be derived from benzene, toluene, ethyl benzene, xylene isomers, or naphthalene.
  • Postdodecylbenzene is a bottoms product of the manufacture of dodecylbenzene.
  • the alkyl groups of postdodecylbenzene are branched chain.
  • Postdodecylbenzene consists of monoalkylbenzenes and dialkylbenzenes in the approximate mole ratio of 2:3 and has typical properties as follows:
  • centistokes l0C. centistokes 2,800 C,, centistokes 280 40C., centistokes 78 80C., centistokes l8 Aniline point, C. 69 Pour Point, F.
  • dimer alkylate has a long, branched-chain alkyl group. Briefly described, dimer alkylate is prepared by the following steps:
  • dimerization of a suitable feedstock such as cat poly gasoline
  • the dimerization step uses a Friedel-Crafts alkylation sludge as the catalyst.
  • This process and the resulting product are described in U.S. Pat. No. 3,410,925, issued Nov. 12, 1968 to Eby et al. In order to make my disclosure even more complete, U.S. Pat. No. 3,410,925 is made a part of this disclosure.
  • oil-soluble sulfonic acids are preferred for use in my process.
  • examples of. other suitable sulfonic acids include the following: monoand poly-wax-substituted naphthalene sulfonic acid, dinonyl naphthalene sulfonic acid, diphenyl ether sulfonic acid, naphthalene disulfide sulfonic acid, dicetyl thianthrene sulfonic acid, dilauryl beta-naphthol sulfonic acid, dicapry] nitronaphthalene sulfonic acid, unsaturated paraffin wax sulfonic acid, hydroxy substituted paraffin wax sulfonic acid, tetraamylene sulfonic acid, monoand poly-chloro-substituted paraffin wax sulfonic acid, nitrosoparaffin wax sulfonic acid; cycloaliphatic sulf
  • Suitable carboxylic acids which can be used in preparing the aluminum dispersions include napthenic acids, such as the substituted cyclopentane monocarboxylic acids, the substituted cyclohexane monocarboxylic acids and the substituted cyclohexane monocarboxylic acids and the substituted aliphatic polycyclic monocarboxylic acids containing at least 15 carbon atoms.
  • napthenic acids such as the substituted cyclopentane monocarboxylic acids, the substituted cyclohexane monocarboxylic acids and the substituted cyclohexane monocarboxylic acids and the substituted aliphatic polycyclic monocarboxylic acids containing at least 15 carbon atoms.
  • Specific examples include cetyl cyclohexane carboxylic acids, dioctyl cyelopentane carboxylic acids, dilauryl decahydronaphthalene and stearyloctahydro indene carboxylic acids
  • Suitable oil-soluble fatty acids are those containing at'least about 8 carbon atoms.
  • Naturally occurring mixtures of predominantly unsaturated fatty acids, such as tall oil fatty acids are particularly suitable. Examples of commercially available tall oil fatty acids include the Crofatols", available from Crosby Chemical Company and the Acintols". available from Arizona Chemical Company.
  • oleaginous carriers are suitable in the process of my invention.
  • the principal requisites in the oleaginous carrier are that it acts as a solvent for the dispersing agent used, has a viscosity from about 60 to about 500 SUS at F and has a boiling point of at least C. at normal atmospheric pressure.
  • Suitable oleaginous carriers include materials boiling in the lubricating oil range and lower boiling refinery hydrocarbon streams, such as Stoddard solvent and diesel fuels.
  • nonvolatile diluents boiling in the lubricating oil range which can be used include mineral lubricating oils obtained by any of the conventional refining procedures; synthetic lubrication oils, such as polymers of propylene, polyoxyalkylenes, polyoxypropylene, dicarboxylic acid esters, and esters of phosphorus; synthetic hydrocarbon lubricating oils. such as dialkylbenzenes, diphenylalkanes, alkylated tetrahydronaphthalenes, and mixtures of these materials; vegetable oils, such as corn oil, cotton seed oil, and castor oil; and animal oils, such as lard oil and sperm oil.
  • the mineral lubricating oils and the synthetic lubricating oils are considered more suitable, with the mineral lubricating oils being preferred.
  • Volatile solvent refers to hydrocarbon solvents having a boiling point at normal atmospheric pressure of less than about 300F.
  • Some specific examples of such solvents are: petroleum naptha, hexane, heptane, octane, benzene, toluene, glycol ethers, monohydric alcohols containing from about 1 to about 6 carbon atoms and the like.
  • Very desirable solvents are hexane, heptane, benzene, butanol and the monomethyl ether of ethylene glycol.
  • the process of the present invention can be carried out using only the alumina and oil soluble dispersing agent, however, it is expected that great difficulty will be obtained in admixing the components and the like.
  • the volatile solvent may be omitted, however, it has been found that the addition of such solvents is beneficial in achieving intimate mixing of the components, reduction of viscosity during processing and the like. While such modifications are possible, it is pointed out that the preferred practice of the present invention is accomplished by the admixture of the oil soluble dispersing agent, the oleaginous carrier and volatile solvent prior to the addition of the alumina. Following the addition of the alumina further mixing of the components is desirable prior to heating the mixture to remove the solvent by distillation.
  • an inert stripping gas may be used in the latter stages of the heating operation to improve the effectiveness of the distillation in removing the last traces of the organic solvent.
  • the product When proper amounts of alumina are added, the product may be recovered directly from the distillation vessel after removal of the volatile solvent. In many applications it may be desirable to add an excess of alumina to achieve a maximum dispersion of aluminum in the end product. in such instances, it would be desirable to use a filtration step to obtain the clear bright product.
  • the aluminum dispersions so produced contain up to about weight percent aluminum. While we do notwish to be bound by any particular theory, it is believed that portions of the aluminum are present as the aluminum sulfonate and the remaining portions are present as dispersions of alumina.
  • the aluminum dispersions so produced contain up to about 20 weight percent aluminum. Those dispersions containing more than about 6 weight percent aluminum are preferred since less of the dispersion is required to incorporate a given amount of aluminum into blends to which the dispersion is added. In many applications those dispersions containing more than 10 weight percent aluminum are preferred. A preferred range is from 8 to about 20 weight percent aluminum.
  • the sulfonic acid was derived from a mixture of synthetic alkylbenzenes consisting of 35 weight percent monoalkylbenzene derived from a straight chain mono olefin and having an average molecular weight of about 420, 15 weight percent mono-alkylbenzene derived from a branched chain mono olefin and having an average molecular weight of about 379 and 50 weight percent dialkylbenzene derived from straight chain mono olefins and having an average molecular weight of about 370.
  • An additional 250 gallons of hexane was added.
  • the mixer was then turned on and 46 gallons of water was added followed by the addition of 3900 lbs of DISPAL alumina with continued mixing for about 30 minutes. The mixture was then heated to reflux and maintained at reflux for about 2.75 hours. 404 gallons ofa 300 SUS napthenic oil was then added and the solvents, i.e. hexane and water were removed as overhead by heating to 300F. Carbon dioxide stripping gas was introduced at cubic feet per minute during the latter stages of the heating step. The product remaining in the vessel weighed 9250 lbs and was a bright, clear, liquid dispersion containing 29 wt aluminum sulfonate, 38 weight percent naphthenic oil and 33 weight per- Cent A1203.
  • EXAMPLE 11 A one liter vessel was charged with 116.7 grams of sulfonic acid dissolved in 400 grams of hexane. The acid was derived in the same manner as that used in Example I. 37.9 grams of 80 SUS neutral oil commonly described as 80 pale oil was added to the mixture and thereafter 12.5 grams of DISPAL alumina was added. The mixture was stirred well for about 30 minutes at room temperature and then heated to about 150C for about 20 minutes. Nitrogen gas was admitted as a strip ping gas in the latter part of the heating step.
  • the product remaining in the bottom of the vessel weighed 94.8 grams and had the following properties: 30 weight percent aluminum sulfonate, 4.8 weight percent aluminum, 0.32 percent BS&W and electron micrograph tests disclosed that the average particle size was less than 0.1 micron with the majority of particles being 0.01 micron or less.
  • Sample 2 was an alumina marketed by Kaiser Chemical Co., P. O. Box 1031, Baton Rouge, La., under the trademark KCSA and has the properties shown.
  • Sample No. 3 was alumina marketed by E. l. Du Pont de Nemours & Co. Inc., Wilmington 98. Del. under the trademark BAYMAL" and has the properties shown.
  • Sample 4 was alumina prepared by the water hydrolysis of alumina alkoxides and thereafter contacted with methyl alcohol and dried. The product alumina had the properties shown above. Sample was prepared by the water hydrolysis of alumina alkoxides followed by purification and aging with heat prior to drying. The properties were as shown in Column 5.
  • Sample 6 was a mixture of 75% DISPAL alumina and 25% BAYMAL alumina. A slurry of the mixture was spray dried to produce an alumina product having the properties shown above.
  • a process for preparing clear, bright aluminumcontaining dispersions containing at least 6 weight percent aluminum comprising:
  • an oil soluble dispersing agent selected from the group consisting of oil soluble sulfonic acids in which the hydrocarbon portion has a molecular weight between about 350 and 1000 and hydrocarbyl carboxylic acids containing at least 8 carbon atoms
  • an oleaginous carrier selected from the group consisting of mineral lubricating oils, synthetic lubricating oils, vegetable oils and animal oils and a volatile hydrocarbon solvent having a boiling point at atmospheric pressure below about 300F.
  • alumina prepared by the water hydrolysis of aluminum alkoxides and having the following properties:
  • carboxylic acid is selected from the group consisting of naphthenic acids, hydrocarbyl substituted cyclohexane monocarboxylic acids, hydrocarbyl substituted polycyclic hydrocarbyl monocarboxylic acids containing at least 15 carbon atoms and naturally occurring mixtures of predominantly unsaturated fatty acids.
  • said volatile solvent is selected from the group consisting of petroleum naptha, hexane, heptane, octane, benzene, toluene, glycol ethers and monohydric alcohols containing from about 1 to about 6 carbon atoms.
  • said volatile solvent is selected from the group consisting of hexane, heptane, benzene, butanol and the monomethyl ethers of ethylene glycol.
  • said oleaginous carrier is selected from mineral lubricating oils, and synthetic lubricating oils.
  • said oil soluble dispersing agent is an oil soluble sulfonic acid having an average molecular weight of about 420
  • said volatile solvent is hexane
  • said oleaginous carrier is pale oil
  • said heating is conducted at C for about 20 minutes and nitrogen is introduced as a stripping gas during the heating step.
  • oils vegetable oils and animal oils, prepared by the process of claim 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Geology (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
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US373564A 1972-02-28 1973-06-25 Process for preparing clear bright oleaginous aluminum dispersions Expired - Lifetime US3867296A (en)

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CA155,062A CA980330A (en) 1972-02-28 1972-10-26 Process for preparing clear bright oleaginous aluminum dispersions
DE2257342A DE2257342C3 (de) 1972-02-28 1972-11-22 Verfahren zur Herstellung aluminiumhaltiger Dispersionen
FR7303458A FR2173980B3 (de) 1972-02-28 1973-01-31
GB779973A GB1426092A (en) 1972-02-28 1973-02-16 Aluminium dispersions
US373564A US3867296A (en) 1972-02-28 1973-06-25 Process for preparing clear bright oleaginous aluminum dispersions
BE162234A BE836019Q (fr) 1972-02-28 1975-11-27 Procede de preparation de dispersions d'aluminium

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076638A (en) * 1975-09-22 1978-02-28 Petrolite Corporation Oil-soluble aluminum compositions
US4123231A (en) * 1977-02-04 1978-10-31 Petrolite Corporation Clear, bright oil-soluble aluminum-containing compositions
US4259193A (en) * 1977-08-04 1981-03-31 Exxon Research & Engineering Co. Overbased sulphonates
US4664841A (en) * 1981-02-27 1987-05-12 Ricoh Co., Ltd. Fine particle substance-containing non-aqueous dispersions
US4718955A (en) * 1985-12-04 1988-01-12 Morton Thiokol, Inc. Method of recovering powered aluminum from aluminum-polymer mixtures
US4877647A (en) * 1986-04-17 1989-10-31 Kansas State University Research Foundation Method of coating substrates with solvated clusters of metal particles
US5516744A (en) * 1994-08-15 1996-05-14 Carnegie Mellon University Alumina catalysts support manufacture
US5516743A (en) * 1994-08-15 1996-05-14 Carnegie Mellon University Alumina catalyst support preparation
US6004911A (en) * 1995-12-27 1999-12-21 Denso Corporation Processing oil suitable for aluminum materials and removable via heating
WO2001003824A1 (de) * 1999-07-07 2001-01-18 Sasol Germany Gmbh Verfahren zur herstellung von in organischen lösungsmitteln dispergierbaren metalloxiden
US6224846B1 (en) 1999-08-21 2001-05-01 Condea Vista Company Method for making modified boehmite alumina
US20050239945A1 (en) * 2004-04-26 2005-10-27 Martin Thomas J Method of producting modified metal oxides that are dispersible in an organic matrix
EP1900794A2 (de) * 2006-09-14 2008-03-19 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe
EP1947162A3 (de) * 2007-01-16 2010-01-06 Afton Chemical Corporation Sichere Verbrennungsadditive und Formulierungsverfahren

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2593166A1 (fr) * 1986-01-20 1987-07-24 Solvay Procede de fabrication d'une poudre d'oxyde metallique pour materiaux ceramiques et poudre de zircone obtenue par ce procede.
FR2964654B1 (fr) * 2010-09-14 2012-10-12 Pylote Procede de preparation de nanoparticules d'oxyde de metal modifiees dispersibles en milieu organique

Citations (3)

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US2469041A (en) * 1946-09-02 1949-05-03 Standard Vacuum Oil Company Methods for preparing aluminum soaps and certain classes of useful compositions containing aluminum soaps
US3018172A (en) * 1957-05-13 1962-01-23 Continental Oil Co Aluminum-containing additive for fuel oil compositions and method of preparing the same
US3250710A (en) * 1963-06-03 1966-05-10 Continental Oil Co Preparation of over-based sulfonate composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2469041A (en) * 1946-09-02 1949-05-03 Standard Vacuum Oil Company Methods for preparing aluminum soaps and certain classes of useful compositions containing aluminum soaps
US3018172A (en) * 1957-05-13 1962-01-23 Continental Oil Co Aluminum-containing additive for fuel oil compositions and method of preparing the same
US3250710A (en) * 1963-06-03 1966-05-10 Continental Oil Co Preparation of over-based sulfonate composition

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076638A (en) * 1975-09-22 1978-02-28 Petrolite Corporation Oil-soluble aluminum compositions
US4123231A (en) * 1977-02-04 1978-10-31 Petrolite Corporation Clear, bright oil-soluble aluminum-containing compositions
US4259193A (en) * 1977-08-04 1981-03-31 Exxon Research & Engineering Co. Overbased sulphonates
US4664841A (en) * 1981-02-27 1987-05-12 Ricoh Co., Ltd. Fine particle substance-containing non-aqueous dispersions
US4718955A (en) * 1985-12-04 1988-01-12 Morton Thiokol, Inc. Method of recovering powered aluminum from aluminum-polymer mixtures
US4877647A (en) * 1986-04-17 1989-10-31 Kansas State University Research Foundation Method of coating substrates with solvated clusters of metal particles
US5516744A (en) * 1994-08-15 1996-05-14 Carnegie Mellon University Alumina catalysts support manufacture
US5516743A (en) * 1994-08-15 1996-05-14 Carnegie Mellon University Alumina catalyst support preparation
US6004911A (en) * 1995-12-27 1999-12-21 Denso Corporation Processing oil suitable for aluminum materials and removable via heating
US6846435B1 (en) 1999-07-07 2005-01-25 Sasol Germany Gmbh Method for producting metal oxides dispersibles in organic solvents
WO2001003824A1 (de) * 1999-07-07 2001-01-18 Sasol Germany Gmbh Verfahren zur herstellung von in organischen lösungsmitteln dispergierbaren metalloxiden
US6224846B1 (en) 1999-08-21 2001-05-01 Condea Vista Company Method for making modified boehmite alumina
US20050239945A1 (en) * 2004-04-26 2005-10-27 Martin Thomas J Method of producting modified metal oxides that are dispersible in an organic matrix
WO2005104699A2 (en) * 2004-04-26 2005-11-10 Sasol North America Inc. Method of producing modified metal oxides that are dispersible in an organic matrix
WO2005104699A3 (en) * 2004-04-26 2005-12-01 Sasol North America Inc Method of producing modified metal oxides that are dispersible in an organic matrix
US20080146681A1 (en) * 2004-04-26 2008-06-19 Martin Thomas J Method Of Producing Modified Metal Oxides That Are Dispersible In An Organic Matrix
EP1900794A2 (de) * 2006-09-14 2008-03-19 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe
EP1900794A3 (de) * 2006-09-14 2009-02-11 Afton Chemical Corporation Biologisch abbaubare leistungssteigernde Additive für Brennstoffe
US8778034B2 (en) 2006-09-14 2014-07-15 Afton Chemical Corporation Biodegradable fuel performance additives
US9562498B2 (en) 2006-09-14 2017-02-07 Afton Chemical Corporation Biodegradable fuel performance additives
EP1947162A3 (de) * 2007-01-16 2010-01-06 Afton Chemical Corporation Sichere Verbrennungsadditive und Formulierungsverfahren
US20100304962A1 (en) * 2007-01-16 2010-12-02 Aradi Allen A Safe combustion additive and methods of formulation

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DE2257342B2 (de) 1977-07-21
FR2173980A1 (de) 1973-10-12
GB1426092A (en) 1976-02-25
DE2257342A1 (de) 1973-09-20
DE2257342C3 (de) 1978-03-02
BE836019Q (fr) 1976-03-16
CA980330A (en) 1975-12-23
FR2173980B3 (de) 1976-01-30

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