DE1265330B - Lubricating oil - Google Patents
Lubricating oilInfo
- Publication number
- DE1265330B DE1265330B DER36811A DER0036811A DE1265330B DE 1265330 B DE1265330 B DE 1265330B DE R36811 A DER36811 A DE R36811A DE R0036811 A DER0036811 A DE R0036811A DE 1265330 B DE1265330 B DE 1265330B
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- phosphoric acid
- mol
- tertiary
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims description 22
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 18
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 125000002270 phosphoric acid ester group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 Ester compounds Chemical class 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000008028 secondary esters Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/2641—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen bonds only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/08—Halogenated waxes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Cl.:Int. Cl .:
ClOmClOm
Deutsche Kl.: 23 c-1/01 German class: 23 c -1/01
Nummer: 1 265 330Number: 1 265 330
Aktenzeichen: R 36811IV c/23 cFile number: R 36811IV c / 23 c
Anmeldetag: 17. Dezember 1963Filing date: December 17, 1963
Auslegetag: 4. April 1968Open date: April 4, 1968
Sekundäre bzw. tertiäre Phosphorsäureester sind als Schmierölzusätze bereits bekannt. Diese Verbindungen haben aber den Nachteil, daß sie nur bestimmte Wirkungen und nicht eine Kombination von einer Vielzahl vorteilhafter Wirkungen, wie Antirost-, Detergens- und Dispersionswirkung, und insbesondere keine Schlammdispergiereigenschaften aufweisen.Secondary or tertiary phosphoric acid esters are already known as lubricating oil additives. These connections but have the disadvantage that they only have certain effects and not a combination of a variety of beneficial effects such as anti-rust, detergent and dispersion effects, and in particular have no sludge dispersing properties.
Dieser Nachteil wird dadurch beseitigt, daß man Schmierölen eine Mischung aus tertiären und sekundären polyoxäthylierten Phosphorsäureestern der allgemeinen FormelnThis disadvantage is eliminated by using a mixture of tertiary and secondary lubricating oils polyoxyethylated phosphoric acid esters of the general formulas
>-(O-CH2-CH2),-O> - (O-CH 2 -CH 2 ), - O
Q >-(O-CH2-CH2),Q> - (O-CH 2 -CH 2 ),
P = OP = O
OH P=OOH P = O
in denen Ri einen Alkylrest mit 4 bis 18 Kohlenstoffatomen und y eine Zahl von 2 bis 12 bedeutet, wobei die Menge des tertiären Phosphorsäureesters mindestens 50% beträgt, zusetzt.in which Ri is an alkyl radical having 4 to 18 carbon atoms and y is a number from 2 to 12, the amount of the tertiary phosphoric acid ester being at least 50%.
Die erfindungsgemäßen Schmieröle besitzen eine ausgezeichnete Antirost-, Detergens- und Dispersionswirkung. The lubricating oils according to the invention have excellent anti-rust, detergent and dispersion properties.
In dem vorstehend aufgeführten Verbindungspaar bedeutet y eine Zahl, die die Äthylenoxydmenge in den Verbindungen angibt. Diese Zahl stellt Durchschnittswerte dar, da bei Verbindungen dieses Typs häufig Gemische mit verschiedenen Äthylenoxydmengen vorliegen. Es können auch 1 oder 2 Mol Propylenoxyd an Stelle der gleichen Menge Äthylenoxyd in jedem der vorstehend beschriebenen Additionsprodukte Verwendung finden. Im Rahmen der Erfindung sind Propylenoxyd und Äthylenoxyd in diesem Ausmaß äquivalent.In the pair of compounds listed above, y denotes a number which indicates the amount of ethylene oxide in the compounds. This number represents average values, since compounds of this type often contain mixtures with different amounts of ethylene oxide. It is also possible to use 1 or 2 moles of propylene oxide instead of the same amount of ethylene oxide in each of the addition products described above. In the context of the invention, propylene oxide and ethylene oxide are equivalent to this extent.
Ri kann sich in jeder beliebigen Stellung befinden, steht jedoch gewöhnlich und vorzugsweise in der para-Stellung zu der Äthylenoxydkette.Ri can be in any position, but is usually and preferably in the para position to the ethylene oxide chain.
Die verschiedenen Ri-Alkylgruppen können normale Struktur, Iso-Struktur, tertiäre oder jede andere Struktur haben, solange die Größe der Gruppe beachtet wird.The various Ri-alkyl groups can be normal Structure, isostructure, tertiary or any other structure as long as the size of the group is taken into account will.
Die in den erfindungsgemäßen Schmierölen enthaltenen sekundären und tertiären Phosphorsäure-Schmieröl The secondary and tertiary phosphoric acid lubricating oils contained in the lubricating oils of the present invention
Anmelder:Applicant:
Rohm & Haas Company,Rohm & Haas Company,
Philadelphia, Pa. (V. St. A.)Philadelphia, Pa. (V. St. A.)
Vertreter:Representative:
Dr. W. Beil, A. Hoeppener und Dr. H. J. Wolff,Dr. W. Beil, A. Hoeppener and Dr. H. J. Wolff,
Rechtsanwälte,Lawyers,
6230 Frankfurt-Höchst, Adelonstr. 586230 Frankfurt-Höchst, Adelonstr. 58
Als Erfinder benannt:
Harry Joseph White, Riverside, N. J.;
Richard Corey Mansfield,
Cherry Hill, N. J. (V. St. A.)Named as inventor:
Harry Joseph White, Riverside, NJ;
Richard Corey Mansfield,
Cherry Hill, NJ (V. St. A.)
Beanspruchte Priorität:Claimed priority:
V. St. ν. Amerika vom 18. Dezember 1962V. St. ν. America December 18, 1962
(245 379),(245 379),
vom 5. Dezember 1963dated December 5, 1963
(326 658)(326 658)
esterverbindungen werden durch Umsetzung von Phosphoroxychlorid mit einem Alkohol der folgenden allgemeinen Formel:Ester compounds are obtained by reacting phosphorus oxychloride with an alcohol of the following general formula:
(OCH2CH2),OH(OCH 2 CH 2 ), OH
in der Ri und y vorstehende Bedeutung haben, hergestellt. in which Ri and y have the preceding meaning.
Die in den erfindungsgemäßen Schmierölen enthaltenen Phosphorsäureester liegen in unterschiedlichen Mengenverhältnissen vor, wobei jedoch immer mindestens 50% des tertiären Phosphorsäureesters, vorzugsweise mindestens 60%, bezogen auf die phosphorhaltigen Produkte, vorliegen müssen. Der Rest der phosphorhaltigen Verbindungen ist der sekundäre Ester, wie vorstehend angegeben. Solange mindestens 50% oder vorzugsweise 60% tertiärer Phosphorsäureester in dem erfindungsgemäßen phosphorhaltigen Produkt vorliegen, lassen sich stets die erfindungsgemäßen wertvollen Ergebnisse feststellen.The phosphoric acid esters contained in the lubricating oils according to the invention are different Quantitative proportions, but always at least 50% of the tertiary phosphoric acid ester, preferably at least 60%, based on the phosphorus-containing products, must be present. Of the The remainder of the phosphorus-containing compounds is the secondary ester, as indicated above. So long at least 50% or preferably 60% of tertiary phosphoric acid esters in the phosphorus-containing according to the invention Product are present, the valuable results according to the invention can always be determined.
809 537/521809 537/521
Um höchste Ausbeuten an angestrebten sekundären und tertiären Phosphorsäureestern sicherzustellen, ist es erforderlich, 3 Mol des Alkohols auf 1 Mol des Phosphoroxychlorids zu verwenden. Um zu erreichen, daß ein Produkt der angestrebten Zusammensetzung erhalten wird, verwendet man vorteilhafterweise einen leichten Überschuß an Alkohol über das 3 : 1-Verhaltnis hinaus. Verhältnisse von bis zu 3,5 Mol Alkohol zu 1 Mol Phosphoroxychlorid sind besonders geeignet. Der überschüssige Alkohol braucht vom sekundären und tertiären Phosphatesterprodukt nicht abgetrennt zu werden, da für die Zwecke der Erfindung erwünschte Ergebnisse erhalten werden, wenn das Phosphorsäureesterprodukt eine kleinere Menge an vorstehend beschriebenem überschüssigem Alkohol enthält. Es können auch kleine Mengen des Chlorids der Reaktionsteilnehmer gebildet werden. Auch diese kleinen Chloridmengen brauchen von dem phosphorhaltigen Produkt nicht abgetrennt zu werden, da sie die wertvollen Ergebnisse der Erfindung nicht beeinträchtigen.In order to ensure the highest yields of desired secondary and tertiary phosphoric acid esters, it is necessary to use 3 moles of the alcohol to 1 mole of the phosphorus oxychloride. To achieve, that a product of the desired composition is obtained is advantageously used a slight excess of alcohol over the 3: 1 ratio. Ratios of up to 3.5 moles of alcohol to 1 mole of phosphorus oxychloride are particularly suitable. The excess alcohol does not need to be separated from the secondary and tertiary phosphate ester product, since for the For purposes of the invention, desirable results can be obtained when using the phosphoric ester product contains a minor amount of the excess alcohol described above. It can too small amounts of the chloride of the reactants are formed. Even those small amounts of chloride do not need to be separated from the phosphorus-containing product, as they provide the valuable results do not affect the invention.
Es sollte ein Reaktionssystem verwendet werden, daß soweit wie möglich frei von Feuchtigkeit ist, da sich jede merkliche Menge Feuchtigkeit mit dem Phosphoroxychlorid umsetzt und dadurch die Mengen der angestrebten Produkte verringert. Gegebenenfalls kann eine kleine Menge Amin im Reaktionsprodukt verwendet werden, das dort jeden noch vorhandenen Chlorwasserstoff beseitigt und dadurch den Säuregehalt des Produkts verringert.A reaction system should be used as free from moisture as possible every noticeable amount of moisture reacts with the phosphorus oxychloride and thereby the amounts of the targeted products. Optionally, a small amount of amine can be used in the reaction product, any remaining amine there Eliminates hydrogen chloride, thereby reducing the acidity of the product.
Die polyoxyäthylenierten grad- und verzweigtkettigen Alkylphenylalkohole werden nach bekannten Verfahren hergestellt.The polyoxyethylene straight and branched chain alkylphenyl alcohols are known according to Process made.
Die Mischung aus sekundären ' und tertiären Phosphorsäureestern ist in dem Schmieröl löslich.The mixture of secondary and tertiary phosphoric acid esters is soluble in the lubricating oil.
Die erfindungsgemäßen Schmieröle werden durch Zusatz der beanspruchten Mischung in einer Menge von 0,001 bis 10,0 Gewichtsprozent, vorzugsweise 0,2 und 2,0 Gewichtsprozent hergestellt. Die erfindungsgemäßen Schmieröle besitzen folgende erwünschte Eigenschaften: Löslichkeit in den vorgesehenen ölen, im wesentlichen Nichtlöslichkeit in Wasser und eine hochgradige Wirkung als Antirost-, Detergens- und Dispersionsmittel.The lubricating oils according to the invention are made by adding the claimed mixture in an amount from 0.001 to 10.0 percent by weight, preferably 0.2 and 2.0 percent by weight. The invention Lubricating oils have the following desirable properties: Solubility in the intended oils, Substantial insolubility in water and a high level of anti-rust, detergent and anti-rust properties Dispersant.
Als Schmieröle werden Mineralöle oder synthetische Schmieröle verwendet.
Versuche:Mineral oils or synthetic lubricating oils are used as lubricating oils.
Try:
Der Panel Coker Test ist in den Annalen des Fifth World Petroleum Congress (1959) von R. M. J ο 1 i e in dem Artikel »Laboratory Screening Test für Lubricating Oil Detergents and Dispersants«, beschrieben. Eine Probe der zu testenden Verbindung wird in einem öl gelöst, das 1,0% eines wärmeunbeständigen Zinkdialkyldithiophosphats enthält. Die Lösung wird in eine erhitzte Pumpe gegeben und 2 Stunden gegen eine auf 300 "C erwärmte Platte gespritzt. Die Gewichtszunahme der Platte wird bestimmt und mit dem Gewicht einer Platte verglichen, die mit einem öl bespritzt ist, das die Testverbindung nicht enthält.The Panel Coker Test is featured in the Annals of the Fifth World Petroleum Congress (1959) by R. M. J ο 1 i e in the article »Laboratory Screening Test for Lubricating Oil Detergents and Dispersants«, described. A sample of the compound to be tested is dissolved in an oil containing 1.0% of a heat labile Contains zinc dialkyldithiophosphate. The solution is placed in a heated pump and Sprayed for 2 hours against a plate heated to 300 ° C. The increase in weight of the plate is determined and compared to the weight of a plate splashed with an oil containing the test compound does not contain.
Bei diesem Test führten handelsübliche Zusätze in Mengen von 1 Gewichtsprozent zu Schlammablagerungen von 25 bis 50 mg. Die erfindungsgemäß verwendbaren Zusätze führten zu Ergebnissen, die im Bereich der im Handel verwendeten Mittel lagen, und viele von ihnen waren so wirksame Detergentien und Dispersionsmittel, daß Ablagerungen von weniger als 25 mg erfolgten. Besonders hervorragend zeigte sich folgende Mischung:In this test, commercial additives in amounts of 1 percent by weight resulted in sludge deposits from 25 to 50 mg. The additives which can be used according to the invention led to results which were within the range of the agents used commercially, and many of them were such effective detergents and dispersants that deposits of less than 25 mg occurred. Showed particularly outstanding the following mixture:
[C9H19C6H4(OCH2CH2)5O]3P = O[C 9 H 19 C 6 H 4 (OCH 2 CH 2 ) 5 O] 3 P = O
OHOH
[C9H)9C6H4(OCH2CH2)5O]2P = O Beispiel 1[C 9 H ) 9 C 6 H 4 (OCH 2 CH 2 ) 5 O] 2 P = O Example 1
Zu 604 Teilen (1,38 Mol) eines Anlagerungsproduktes aus 5 Mol Äthylenoxyd und Nonylphenol mit einer Hydroxylzahl von 128 werden unter Rühren bei 5 bis 15 C 3/4 Stunden lang 61,5 Teile (0,40 Mol) Phosphoroxychlorid zugegeben. Das Gemisch wird Va Stunde lang bei 5 bis 100C gerührt und dann eine weitere Va Stunde auf 25 0C erwärmt. Das System wird dann bis zu 20 mm Hg evakuiert und 1 Stunde lana; auf 100 C erhitzt. Das Rühren wird 41/·» Stunden bei "lOO bis HOC und 10 bis 20 mm Hg unter Entfernung von Chlorwasserstoff fortgesetzt. Das Gemisch wird gekühlt und analysiert. Es enthält 2,12°/p Phosphor, insgesamt 0,7 Gewichtsprozent Chlor, hat eine Säurezahl von 3,7 und eine hydrolysierbare Säurezahl von 13,4.To 604 parts (1.38 mole) of an adduct of 5 moles ethylene oxide and nonyl phenol having a hydroxyl number of 128 are (0.40 mol) of phosphorus oxychloride was added with stirring at 5 to 15 C 3/4 hours 61.5 parts. The mixture is stirred for about an hour at 5 to 10 ° C. and then heated to about 25 ° C. for a further half hour. The system is then evacuated to 20 mm Hg and lana for 1 hour; heated to 100 C. Stirring is continued for 4 1 / · »hours at" loo to HOC and 10 to 20 mm Hg while removing hydrogen chloride. The mixture is cooled and analyzed. It contains 2.12 ° / p phosphorus, a total of 0.7 weight percent chlorine, has an acid number of 3.7 and a hydrolyzable acid number of 13.4.
Ein Gemisch aus diesem Stoff und 10 Gewichtsprozent Wasser wird gerührt und 1 Stunde am Rückflußkühler erhitzt, dann 2 Stunden auf 105 C unter Rückfluß erhitzt und unter 2stündigem Erhitzen auf 100 bis 110 C und 20 bis 25 mm Hg von Wasser befreit. Das Produkt ist dann eine Säurezahl von 13,2 und eine hydrolysierbare Säurezahl von 13,4 und hat die folgenden in Gewichtsprozent angegebenen Bestandteile :A mixture of this substance and 10 percent by weight of water is stirred and refluxed for 1 hour heated, then heated under reflux at 105 ° C. for 2 hours and heated up with heating for 2 hours 100 to 110 C and 20 to 25 mm Hg freed from water. The product then has an acid number of 13.2 and a hydrolyzable acid number of 13.4 and has the following components in percent by weight :
[CjH19CH4(OCH2CH2I5O]3P = O[CjH 19 CH 4 (OCH 2 CH 2 I 5 O] 3 P = O
OHOH
(55)(55)
[CH19C0H4(OCH2CH2I5O]2P = O (22)[CH 19 C 0 H 4 (OCH 2 CH 2 I 5 O] 2 P = O (22)
C9H19C6H4(OCH2CH2I5OH (14)C 9 H 19 C 6 H 4 (OCH 2 CH 2 I 5 OH (14)
C9H19C0H4(OCH2CH2J5CI (9)C 9 H 19 C 0 H 4 (OCH 2 CH 2 J 5 CI (9)
Ein Gemisch aus 400 Teilen Toluol und 138 Teilen (0,345 Mol) des Anlagerungsproduktes aus 4 Mol Äthylenoxyd und Nonylphenol wird 1 Stunde am Rückflußkühler erhitzt, während das vorhandene Wasser mittels eines angeschlossenen Wasserabscheiders entfernt wird. Das Gemisch wird dann unter Feuchtigkeitsausschluß auf IOC gekühlt, und es werden 15,3 Teile (0,10 Mol) Phosphoroxychlorid Vi Stunde lang bei 5 bis 10 C zugegeben. Das Gemisch wird dann innerhalb von IV2 Stunden auf 450C erwärmt. Das System wird an ein Vakuum angeschlossen und der Druck auf 50 mm Hg reduziert. Die Temperatur wird dann im Verlauf einer weiteren Stunde auf 100 C gebracht und das Gemisch bei 100 bis 110 C und 5 bis 10 mm Hg 2 Stunden lang gerührt. 47,5 Teile einer Probe A werden entnommen. Der aus 92,5 Teilen bestehende Rest wird mit 2,3'Teilen eines tertiären Alkyl-primären-Amins mit 11 bis 15 C-Atomen verdünnt, und der pH-Wert auf 7 bis 8 eingestellt. Das Produkt B wird zusammen mit dei' Probe A als Schrnierölzüsatz getestet. Beide Produkte sind ausgezeichnete Schmierölzusätze. Die sekirrf-A mixture of 400 parts of toluene and 138 parts (0.345 mol) of the adduct of 4 mol of ethylene oxide and nonylphenol is heated under a reflux condenser for 1 hour while the water present is removed by means of a connected water separator. The mixture is then cooled to IOC with exclusion of moisture, and 15.3 parts (0.10 mol) of phosphorus oxychloride are added over a period of 5 to 10 ° C. over a period of four hours. The mixture is then heated within IV2 hours at 45 0 C. The system is connected to a vacuum and the pressure is reduced to 50 mm Hg. The temperature is then brought to 100 ° C. in the course of a further hour and the mixture is stirred at 100 to 110 ° C. and 5 to 10 mm Hg for 2 hours. 47.5 parts of a sample A are taken. The remainder, consisting of 92.5 parts, is diluted with 2.3 parts of a tertiary alkyl primary amine containing 11 to 15 carbon atoms, and the pH is adjusted to 7 to 8. Product B is tested together with sample A as a lubricating oil additive. Both products are excellent lubricating oil additives. The sekirrf
dären und tertiären Phosphorsäureesterprodukte haben die folgenden Formeln:Dary and tertiary phosphoric acid ester products have the following formulas:
[C9H19C6H4(OCH2CH2J4O]3P = O
und[C 9 H 19 C 6 H 4 (OCH 2 CH 2 J 4 O] 3 P = O
and
OHOH
[C9H19QH4(OCH2CH2)4OJ2P = O[C 9 H 19 QH 4 (OCH 2 CH 2 ) 4 OJ 2 P = O
IOIO
Ein Gemisch aus 100 Teilen Toluol, 118,6 Teilen (0,30 Mol) des Anlagerungsprodukts von 4 Mol Äthylenoxyd an Nonylphenol und 30,6 Teilen (0,30 Mol) Triäthylamin wird tropfenweise 2 Stunden lang zu einem gerührten Gemisch von 15,3 Teilen (0,10 Mol) Phosphoroxychlorid und 100 Teilen Toluol bei 0 bis 5 C zugegeben. Das Gemisch wird weitere 2 Stunden bei 0 bis 5C C gerührt, auf Raumtemperatur gebracht, das ausgefällte Triäthylaminhydrochlorid abfiltriert und das Gemisch langsam unter Rühren und Kühlen in eine überschüssige verdünnte Natriumhydroxydlösung gegossen. Die obere· Schicht wird abgetrennt, und die untere wäßrige Schicht wird mit Toluol gewaschen. Der Toluolextrakt wird mit der oberen Schicht vereinigt, die dann vom Lösungsmittel befreit, in Heptan aufgenommen und über Nacht stehengelassen wird. Die oben schwimmende Flüssigkeit wird von einem kleinen Salzrückstand dekantiert, filtriert und von dem Lösungsmittel befreit, so daß 78 Teile eines klaren bernsteinfarbenen Öls erhalten werden. Das Phosphoresterprodukt ist ein Gemisch aus sekundären und tertiären Phosphorsäureestern. A mixture of 100 parts of toluene, 118.6 parts (0.30 mol) of the adduct of 4 mol of ethylene oxide with nonylphenol and 30.6 parts (0.30 mol) of triethylamine is added dropwise over 2 hours to a stirred mixture of 15.3 Parts (0.10 mol) of phosphorus oxychloride and 100 parts of toluene are added at 0 to 5 ° C. The mixture is stirred for a further 2 hours at 0 to 5 ° C., brought to room temperature, the precipitated triethylamine hydrochloride is filtered off and the mixture is slowly poured into an excess of dilute sodium hydroxide solution with stirring and cooling. The upper layer is separated and the lower aqueous layer is washed with toluene. The toluene extract is combined with the upper layer, which is then freed from the solvent, taken up in heptane and left to stand overnight. The liquid floating above is decanted from a small residue of salt, filtered and freed from the solvent, so that 78 parts of a clear amber-colored oil are obtained. The phosphoric ester product is a mixture of secondary and tertiary phosphoric acid esters.
B e i s ρ i e 1 5B e i s ρ i e 1 5
Zu einem gerührten Gemisch von 150 Teilen (0,345 Mol) des Anlagerungsprodukts aus 3,8 Mol Äthylenoxyd an Dodecylphenol und 33 Teilen (0,34 Mol) Triäthylamin werden 1 Stunde lang bei 50 bis 55°C 15,3 Teile (0,10 Mol) Phosphoroxychlorid zugegeben. Das Gemisch wird weitere 2 Stunden bei 50 bis 55: C gerührt, filtriert, mit 1,5 Teilen eines tertiären Alkylprimären-Amins mit 11 bis 15 C-Atomen verdünnt, '/2 Stunde bei 30 bis 60C gerührt und dann eine weitere 1^ Stunde bei 30 bis 6O0C und 10 bis 50 mm Hg gerührt.To a stirred mixture of 150 parts (0.345 mol) of the adduct of 3.8 mol of ethylene oxide with dodecylphenol and 33 parts (0.34 mol) of triethylamine are added 15.3 parts (0.10 mol ) Phosphorus oxychloride added. The mixture is further 2 hours at 50 to 55: C stirred, filtered, diluted with 1.5 parts of a tertiary Alkylprimären-amine with 11 to 15 carbon atoms, '/ stirred for 2 hour at 30 to 60C, and then another 1 ^ Stirred hour at 30 to 6O 0 C and 10 to 50 mm Hg.
Bei den vorstehenden Herstellungsbeispielen 2 bis 5 besteht die Endstufe der Umsetzung jeweils in der Hydrolyse des Reaktionsgemisches nach dem Verfahren des Beispiels 1 unter Verwendung von 10 Gewichtsprozent Wasser, bezogen auf das Reaktionsgemisch. In the above Preparation Examples 2 to 5, the final stage of the reaction is in each case Hydrolysis of the reaction mixture according to the procedure of Example 1 using 10 percent by weight Water, based on the reaction mixture.
Claims (1)
P = OOH
P = O
USA.-Patentschrift Nr. 3 060 008.Considered publications:
U.S. Patent No. 3,060,008.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24537962A | 1962-12-18 | 1962-12-18 | |
US326658A US3340191A (en) | 1962-12-18 | 1963-12-05 | Fuel and lubricant compositions |
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Publication Number | Publication Date |
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DE1265330B true DE1265330B (en) | 1968-04-04 |
Family
ID=26937191
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT1251584D Pending DE1251584B (en) | 1962-12-18 | ||
DER36811A Pending DE1265330B (en) | 1962-12-18 | 1963-12-17 | Lubricating oil |
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Application Number | Title | Priority Date | Filing Date |
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DENDAT1251584D Pending DE1251584B (en) | 1962-12-18 |
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GB (1) | GB1069079A (en) |
NL (1) | NL302079A (en) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3974080A (en) * | 1975-10-29 | 1976-08-10 | Union Carbide Corporation | Silicone hydraulic fluids |
US4346148A (en) * | 1979-05-04 | 1982-08-24 | The Lubrizol Corporation | Phosphorus-containing compositions, lubricants containing them and metal workpieces coated with same |
US4579672A (en) * | 1983-05-10 | 1986-04-01 | Exxon Research & Engineering Co. | Functional fluids and lubricants having improved water tolerance |
DE3511760A1 (en) * | 1985-03-30 | 1986-10-02 | Akzo Gmbh, 5600 Wuppertal | AGENT AGAINST FELLING AND DEPOSITING ASPHALTED AND THE LIKE |
CA2143856A1 (en) * | 1992-09-04 | 1994-03-17 | Rudolph Klima | Lubricants for paper coatings |
DE69432153T2 (en) * | 1993-12-20 | 2003-11-27 | Infineum Usa L.P., Linden | INCREASING THE FRICTION RESISTANCE OF POWER TRANSFER LIQUIDS BY USING OIL-SOLUBLE COMPETITIVE ADDITIVES |
FR2762005B1 (en) * | 1997-04-11 | 2000-03-31 | Chevron Res & Tech | USE OF LOW MOLECULAR WEIGHT SURFACTANTS AS FILTER-IMPROVING AGENTS IN HYDRAULIC LUBRICANTS |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3060008A (en) * | 1960-10-19 | 1962-10-23 | Fmc Corp | Novel phosphorus compounds |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2536685A (en) * | 1947-06-02 | 1951-01-02 | Shell Dev | Synthetic lubricant |
GB663557A (en) * | 1948-11-08 | 1951-12-27 | Standard Oil Dev Co | Lubricating oil composition |
US2723237A (en) * | 1950-09-30 | 1955-11-08 | Texas Co | Phosphoric acid esters of diethylene glycol ethers and lubricants containing the same |
US2999740A (en) * | 1956-11-27 | 1961-09-12 | Tidewater Oil Company | Surface ignition suppression |
US2959473A (en) * | 1956-12-10 | 1960-11-08 | Socony Mobil Oil Co Inc | Anti-stall gasoline composition |
NL112686C (en) * | 1957-04-05 | |||
US2930680A (en) * | 1957-11-08 | 1960-03-29 | Exxon Research Engineering Co | Fuels containing wear-reducing and rust preventing additives |
US3000824A (en) * | 1957-11-13 | 1961-09-19 | Exxon Research Engineering Co | Lubricating oil composition |
US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
BE596967A (en) * | 1959-11-12 |
-
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- DE DENDAT1251584D patent/DE1251584B/de active Pending
- NL NL302079D patent/NL302079A/xx unknown
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- 1963-12-05 US US326658A patent/US3340191A/en not_active Expired - Lifetime
- 1963-12-14 ES ES294501A patent/ES294501A1/en not_active Expired
- 1963-12-17 DE DER36811A patent/DE1265330B/en active Pending
- 1963-12-18 BE BE641455A patent/BE641455A/xx unknown
-
1965
- 1965-12-03 GB GB49779/63A patent/GB1069079A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3060008A (en) * | 1960-10-19 | 1962-10-23 | Fmc Corp | Novel phosphorus compounds |
Also Published As
Publication number | Publication date |
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DE1251584B (en) | 1967-10-05 |
US3340191A (en) | 1967-09-05 |
BE641455A (en) | 1964-06-16 |
ES294501A1 (en) | 1964-05-01 |
GB1069079A (en) | 1967-05-17 |
NL302079A (en) |
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