DE1594584A1 - Lubricant mixture with improving additive mixture - Google Patents
Lubricant mixture with improving additive mixtureInfo
- Publication number
- DE1594584A1 DE1594584A1 DE1965S0097348 DES0097348A DE1594584A1 DE 1594584 A1 DE1594584 A1 DE 1594584A1 DE 1965S0097348 DE1965S0097348 DE 1965S0097348 DE S0097348 A DES0097348 A DE S0097348A DE 1594584 A1 DE1594584 A1 DE 1594584A1
- Authority
- DE
- Germany
- Prior art keywords
- amine
- acid
- salt
- derived
- lubricating oil
- 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.)
- Granted
Links
Classifications
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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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/284—Esters of aromatic monocarboxylic acids
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- C10M2207/285—Esters of aromatic polycarboxylic acids
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- C10M2207/286—Esters of polymerised unsaturated acids
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- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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Description
P 7431 \CH Milnohe?, dan 28» Mai 1965P 7431 \ CH Milnohe ?, dan 28 »May 1965
"Scbmiermittelgsiöisch mit verbesserndem Zusätze tofigöiaiöch""Lubricants with improving additives tofigöiaiöch"
Priorität,· 29. Jäai 1964 / Ü3A Anmelde~Nr· 371 184Priority, January 29, 1964 / Ü3A Registration number 371 184
Die Erfindung betrifft ein verbessertet* Schmierraittelgemisoh. Insbesondere bezieht sie sich auf ein Zusatzgemisch für ein Schmieröl und ein Scnmiermittelgemiech, das ein Schmieröl und Zueatsstoffe enthält.The invention relates to an improved lubricant mixture. In particular, it relates to an additive mixture for a Lubricating oil and a lubricant composition which is a lubricating oil and Contains additives.
GeaÄi elntr Aueführungβform der Erfindung handelt es eioh um ein Zueetegemieoh, das ein cyclieohee Amin sowie ein Sale eines aliphatieohen Amins mit wenigstens β Kohlenstoffatomen und einer Hnlogen-C^^-Alkylphosphonsäure enthalteGeaÄi an embodiment of the invention is eioh a Zueetegemieoh that has a cyclieohee amine as well as a sale of one aliphatic amine with at least β carbon atoms and containing a Hnlogen-C ^^ - alkylphosphonic acid
Eine Heitere Aueführungυform der Erfindung bezieht eioh auf ein Schaiermittelgemieoh, das dadurch gekennzeichnet ist, daü es ein Bohaierül und als Zusatzgemisch ein oyollaohea Aein «owle ein Salz eines aliphatischen Amine mit wenigstens β Kohlenstoffatoaen und einer tialogen-C^-Alkylphoaphoneäure enthält·Another embodiment of the invention relates to a Schaiermittelgemieoh, which is characterized by daü it is a bohaierül and as an additional mixture an oyollaohea aein «owle a salt of an aliphatic amine having at least β carbon atoms and a tialogen-C ^ -Alkylphoaphonic acid contains
Ο,Οί - 5 0·*·^' des oyoliBohtn Amine enthalten« Bei VtrwtndunfΟ, Οί - 5 0 · * · ^ 'des oyoliBohtn contain amines «At Vtrwtndunf
■ ύ 00M32/UU ^■ ύ 00M32 / UU ^
eines Gemieohes von cyclischen Aminen bezieht eich diese Menge auf die Gesamtmenge an cyclischen» Amin«A mixture of cyclic amines refers to this amount on the total amount of cyclic "amine"
Das cyclische Amin kann einen aromatischen Rest (ζ.B9 einen Benzoloder Naphtalinreet)' oder einen heterocyclischen Rest (ζ„Bo einen Pyridin-, Chinolin- oder Diazinrest) enthalten.The cyclic amine can contain an aromatic radical (ζ.B 9 a benzene or naphthalene residue) or a heterocyclic radical (ζ “Bo a pyridine, quinoline or diazine radical).
Beispiele für geeignete Aaine sind Phenyl-beta-naphtylamtJoi; Dielpha-naphtylaniin; Di-beta -naphtylamini Di-alpha, beta-naphtyt amin; Triphenylamin; Diphenylnaphtylamin; 2-Aminopyridin; 3-Aminopyridin; 2,6~Diaminopyridin; 4f4'~Dipyridylamini Phenyl-2-pyriäylamin; Naphtyl-2-pyridylamin^-Aminochinolin; und Phenyl 3-ohinclylamin. Bevorzugte Amine sind Phenyl-alpha-naphtylamin; !xäi.Irii 2,2<-Dipyridyl-amin und 4;-Aminopyridin.Examples of suitable Aaine are phenyl-beta-naphthylamino; Dielpha-naphthylanine; Di-beta -naphthylamine; di-alpha, beta-naphthylamine; Triphenylamine; Diphenylnaphthylamine; 2-aminopyridine; 3-aminopyridine; 2,6 ~ diaminopyridine; 4 f 4 '~ Dipyridylamini phenyl-2-pyriaylamine; Naphthyl-2-pyridylamine 1-4 aminoquinoline; and phenyl 3-ohinclylamine. Preferred amines are phenyl-alpha-naphthylamine; ! xäi.Irii 2,2 < -dipyridyl-amine and 4 ; -Aminopyridine.
Das Sohmiermittelgemisch kann 0,005 - 5 6ew.^t vorzugsweise 0,01 - 5 Gew.$ des Salzes enthalten. Bas Gewichtsverhältnis des Salzes zum cyclischen Amin kann 0,01/1 - 10/1, vorzugsweise 0,01/1 - 5/1 betragen. Diese Mengen beziehen sioh auf die Gesamtmengen des Salzes und dee oyolieohen Amins, falls dae Sohmiermittelgemieoh mehr ale ein SaIs und/oder Amin enthält.The Sohmiermittelgemisch may 0.005 -. 5 6EW ^ t preferably 0.01 - 5 wt. $ Of the salt contained. The weight ratio of the salt to the cyclic amine can be 0.01 / 1 to 10/1, preferably 0.01 / 1 to 5/1 . These amounts relate to the total amounts of the salt and the olefinic amine, if the cooking agent mixture contains more than one salt and / or amine.
Daβ Salz kann sioh von einem oder mehreren aliphatischen Aminen ableiten. Solch ein Amin kann ein priaäree oder sekundäres Cg ,Q-, vorzugsweise C^ -j* Alkylmono- oder-polyamin sein. Das AsIn, kann eine tertiäre Alkylgruppe aufweisen» s.B. «in· Polyisobutylen- uRd/od&r Polyprop}lineruppt. Btiipiele fUr Amine alt siner tertiären Alkylgruppe sind I,lt3,3-T«trastthylbutylamlniThe salt can be derived from one or more aliphatic amines derive. Such an amine can be primary or secondary Cg, Q-, preferably C ^ -j * alkyl mono- or polyamine. The AsIn can have a tertiary alkyl group »see B. "in· Polyisobutylene and / or polyprop} lineruppt. Examples of amines old tertiary alkyl groups are I, lt3,3-T «trastthylbutylamine
methylpentylamin und 2i2,4,4f6f6-Hexamethylhexylamino methylpentylamine and 2 i 2,4,4f6 f 6-hexamethylhexylamine o
Andere Beispiele für ein soleheβ Amin sind in den US~Patentechriften Hr0 2 606 923 und 2 611 782 beschrieben. Dazu gehören tert. Tridecylamin, Ieoheptyldiäthyloarbinylamin und Iboootyläthyl-propyloarbinylamin. Solche Amine sind unter dem Handelenamen "Primene" erhältlich. Weitere Beispiele für geeignete Amine sind Diamylamin; DihejyLamin; £i(2-äthylhexyl)~amin; Diootylamin; Dideojl-amin; Didodecylamin; Ditetradecylamin; Dihexadeoylamin; Siootadeoyiamin; Dibromdioctadeoylamin; Ieopropylolfefylamin; Dirioinolylamin; Butylrioinolylamin; Butyl-2~ätfaylhexyl-Other examples of such an amine are described in US Pat. No. Hr 0 2,606,923 and 2,611,782. These include tert. Tridecylamine, Ieoheptyldiäthyloarbinylamin and Iboootyläthyl-propyloarbinylamine. Such amines are available under the trade name "Primene". Further examples of suitable amines are diamylamine; DihejyLamin; £ i (2-ethylhexyl) amine; Diootylamine; Dideojl-amine; Didodecylamine; Ditetradecylamine; Dihexadeoylamine; Siootadeoyiamine; Dibromodioctadeoylamine; Ieopropylolfefylamine; Dirioinolylamine; Butylrioinolylamine; Butyl-2-
amin; Silaurylaaini Methylolamin; Äthylootylamin; leoamylhexyl-•min* Didyclohexylamin; Sicyclopentylamin; Cyclohexyloctylamin;amine; Silaurylaaini methylolamine; Ethylootylamine; leoamylhexyl- • min * Didyclohexylamine; Sicyclopentylamine; Cyclohexyloctylamine;
butyl)i-5v5,3-r*ethyloyolohexylaiain; I)i-(l-ieobutyl-3-oethylbutyl)-amin; Ä-n-Dodeoyldiäthylentriamiii; H-n-Tetradecyldiäthylentriaain; Ootyläthylen-diamin; I-2-Xthylhexyl-H-hexadeoyltriäthylentetraiain; Heptyltrisethylen-diaJiin} H-Tetradeoyltripropylentetramin; H9N'- '. Diallyltrieethylendiaminj und 3-Htxyl-morpbolin. _ ..butyl) i-5v5,3-r * ethyloyolohexylaiain; I) i- (1-ieobutyl-3-oethylbutyl) amine; Ä-n-Dodeoyldiäthylenetriamiii; Hn-tetradecyldiethylenetriaaine; Ootylethylene diamine; I-2-Xthylhexyl-H-hexadeoyltriethylenetetraiaine; Heptyltrisethylene-diaJiin} H-tetradeoyltripropylenetetramine; H 9 N'- '. Diallyltrieethylenediamine and 3-Htxyl-morpboline. _ ..
Aain kann »uok ander· nioht-reaktive Gruppen in der Kohlen- , etoffkett· enthalten, s.B. Amid- oder Xtfaergruppen. ■' -v Aain can also contain other non-reactive groups in the carbon chain, such as amide or carbon groups. ■ '- v
Ale Halogen-C^-Alkylphoephoneäure wird vorittgffftei·· eine Halogtn-C^grAlkylphoephoneäure Yerwendet. Ei kann eine oder Dibalogen-C^-Alky!phosphorsäure sein. Pie Säur· kann duroh folgende allgemeine Formel dargestellt «ardentAll halo-C ^ -alkylphoephone acid is primarily one Halogtn-C ^ grAlkylphoephone acid Y used. I can do one or dibalogen-C ^ -alky! phosphoric acid. Pie acid · can The following general formula is represented by «ardent
IlIl
R-P-(OH)2 RP- (OH) 2
in der R eine Mono= bis Perhalogen-C^.-Alky!gruppe bedeutet. Vorzugsweise enthält die Säure wenigstens ein Haolgenatom, das an das alpha-Kohlenotoffatom gebunden ist. Das Jtialogenatom kann Brom oder Fluor sein, vorzugsweise ist es ein Chloratom.in which R is a mono = to perhalo-C ^ .- alky! group. Preferably the acid contains at least one halogen atom bonded to the alpha carbon atom. The dialogen atom can be bromine or fluorine, preferably it is a chlorine atom.
Monochlormethylphosphonsäure; l-Monoohloräthyl-phoephonsäure; 1,l-Dichlorpropylphöephoneäure; Ferohloräthylphosphonsäure; Diohlormethylphosphonsäure; Perehlor-methylphosphonsäure; Monobrommethylphophonsäure; 1,l-Chlorbrompropylphosphonsäurej Dibrommethylphosphonsäurej Monofluormethylphosphoneäure} und 1,1-Difluoräthyl-phosphonsäure.Monochloromethylphosphonic acid; l-monoohloräthyl-phoephonic acid; 1,1-dichloropropylphöephone acid; Ferrous ethylphosphonic acid; Diohlomethylphosphonic acid; Perehloromethylphosphonic acid; Monobromomethylphophonic acid; 1, l-chlorobromopropylphosphonic acid j Dibromomethylphosphonic acid, monofluoromethylphosphonic acid, and 1,1-difluoroethyl-phosphonic acid.
Das Salz kann durch direkte Neutralisation der dalogen-C^ ,-Alkylphoephoneäure oder-eäuren mit einer stöohiometrieohen lienge des aliphatischen Amins oder der Amine hergestellt werden.The salt can be obtained by direct neutralization of the dalogen-C ^, -alkylphoephone acid or acids with a stoichiometry Lienge of the aliphatic amine or amines can be produced.
Die Neutralisation verläuft bei normalen oder mäßig erhöhten Temperaturen und kann in Gegenwart eines inerten Verdünnungen alttele oder Lb'aungimittele (z.B. eines Kohlenwaeaeretoffee, Xthere oder Ketone) durchgeführt werden. Die Herstellung dee Salzes ist in der US-Patentschrift 2 858 332 beschrieben. Das Salz kann durch ein Alkalimetall modifiziert werden, wie es in der US~Patentsohrift 3 U2 267 beschrieben ist. So kann da· vollständige Aminosalz einer Phoephoneäure hergestellt werden, das dann in einem niedrigsiedenden Lösungsmittel mit eine» Al-The neutralization proceeds at normal or moderately elevated levels Temperatures and can in the presence of an inert dilution alttele or Lb'aungi means (e.g. a coal waea toffee, Xthers or ketones). Making dee Salt is described in U.S. Patent 2,858,332. That Salt can be modified by an alkali metal as described in US Pat. No. 3 U2,267. So there can complete amino salt of a phoephone acid are produced, which then in a low-boiling solvent with an »Al-
009132/1SU009132 / 1SU
BAD ORIGINALBATH ORIGINAL
kalimetallhydroxydi - carbonat oder -alkoholet behandelt wird, so daß in dem Salz eine Aminogruppe durch ein Alkalimetallatom ersetzt wird» Bevorzugte Alkalimetalle sind Natrium, Kalium und Lithium.Potash metal hydroxydicarbonate or alcohol is treated, so that in the salt an amino group through an alkali metal atom is replaced »Preferred alkali metals are sodium, potassium and lithium.
Als Schmieröl kann ein Mineral Schmieröl oder vorzugsweise ein synthetisches Schmieröl vorwendet werden. Beispiele für synthetische Schmieröle sind aliphatischs Ester, Silicone, Polyalkylene oxyde, Polyphenyläther, fluorierte Kohlenwasserstoffe, Polyolefine und Phosphorsäureester. Beispiele für Silicone sind Methy!silicon, Methylphenylsilicon und Methylohlorphenylsilicon. Beispiele für Polyalkylenoxyde sind Polyisopropylenoxyd, Polyisopropylenoxyd-diäther und Polyisopropyienoxyd-diester. Zu den fluorierten Kohlenwasserstoffen gehören fluorierte UIe und perfluorierte Kohlenwasserstoffe.As the lubricating oil, a mineral or, preferably, lubricating oil can be used synthetic lubricating oil can be used. Examples of synthetic Lubricating oils are aliphatic esters, silicones, polyalkylene oxides, polyphenyl ethers, fluorinated hydrocarbons, polyolefins and phosphoric acid esters. Examples of silicones are methyl silicon, Methylphenyl silicone and methylohlophenyl silicone. Examples for polyalkylene oxides are polyisopropylene oxide and polyisopropylene oxide dieters and polyisopropylene oxide diesters. To the fluorinated Hydrocarbons include fluorinated UIe and perfluorinated Hydrocarbons.
Das synthetische Sohmieröl kann ein einfacher Ester (Reaktionsprodukt eines Monohydroxyalkohols und einer Monooarboneäure), ein Polyester (Reaktionsprodukt eines Alkohole und einer Säure, wobei eins von beiden mehr als eine funktioneile Gruppe aufweist) oder ein zusammengesetzter Ester (Reaktionsprodukt einer mehrwertigen Carbonsäure mit mehr als einem Alkohol oder eines mehrwertigen Alkohols mit mehr als einer Säure) sein. Dae synthetische Sohmieröl kann als ein Gemisch solcher Eeter vorliegen, es kann z.B. einen größeren Anteil eines zusammengesetzten Esters und einen kleineren Anteil eines Dieetere enthalten.The synthetic cooking oil can be a simple ester (reaction product of a monohydroxy alcohol and a monooarboxylic acid), a polyester (reaction product of an alcohol and an acid, one of which has more than one functional group) or a composite ester (reaction product of a polybasic carboxylic acid with more than one alcohol or a polybasic Alcohol with more than one acid). The synthetic cooking oil can exist as a mixture of such substances e.g. contain a major proportion of a composite ester and a minor proportion of a diester.
8AD ORIGINAL8AD ORIGINAL
008832/15U008832 / 15U
ist das synthetische Schmieröl ein Ester eines ^„ρο*"" vorzugsweise C, .^-Alkohole und einer Gx^O"9 vor2US"SWo:S-8e ^a in-Carbonsäure (vorzugsweise einer aliphatischen Carbonsäure).the synthetic lubricating oil is an ester of a ^ "ρο *""preferably C,. ^ - alcohols and a Gx ^ O" 9 vor2U S " SWo: S - 8e ^ a in -carboxylic acid (preferably an aliphatic carboxylic acid).
Beispiele für Ester 'ale synthetische Schmieröle £»ind ÄthyV-palmitatj Xthyllaurat; Butylstearat; üi-(2~äthyihexyl)-Bebacat; Di-(2~äthylhexyl)-aüelat; Äthylglycoldilaurat; Ia-(2-äthylhexyl)-phthalat; Di-(l,3-=-methylbutyl)-adipat; Di-(l-äthylpropyl)=-a2elat; Diisopropyloxylat; Dicyclohexyl-sebaoat; Glyceriii-tri-n-heptoat; Di-(undecyl)-azelat; und 1lietraäthylenglycol-di-(2-äthylencaproat) und Gemische davon. Ein bevorzugtes Gemisch von Estern besteht aus 5>ö - 80 Gew.% Bi8<-(2,2,4-trimethylpentyl)-azelat und 20 - 50 Gew,# 1,1,1-TrimethylpropantriheptanoatpExamples of esters ale synthetic lubricating oils and ethyl palmitate, ethyl laurate; Butyl stearate; üi- (2 ~ ethyihexyl) -bacate; Di- (2-ethylhexyl) -elate; Ethyl glycol dilaurate; Ia- (2-ethylhexyl) phthalate; Di (1,3 - = - methylbutyl) adipate; Di- (1-ethylpropyl) = - a2elat; Diisopropyloxylate; Dicyclohexyl sebaoate; Glyceryl tri-n-heptoate; Di (undecyl) azelate; and 1 l i etraäthylenglycol-di- (2-äthylencaproat) and mixtures thereof. A preferred mixture of esters consists of 5-80% by weight of Bi8 <- (2,2,4-trimethylpentyl) azelate and 20-50% by weight of 1,1,1-trimethylpropane triheptanoate
Bevorzugt als synthetische Schmieröle sind die Ester von Monooar bonsäure mit 4-12 Kohlenstoffatomen und Polyalkoholen, z.B. Pentaerythrit, Dipentaerythrit und Trimethylolpropan.Preferred synthetic lubricating oils are the esters of Monooar bonic acid with 4-12 carbon atoms and polyalcohols, e.g. Pentaerythritol, dipentaerythritol and trimethylolpropane.
Beispiele für diese Ester sind Pentaerythritbutyrat; Pentaerytbrittetrabutyrat; Pentaerythrittetraväleratj Pentaerythrittetraoaproat; Pentaerythritdibutyratdioaproat; Pentaerythrjtbutyratcaproatdivateratj Pentaerythritbutyrattrivalerat; Pentaerythritbutyrattrioaproat; Pentaerythrittributyratcaproat; gemisohte gesättigte U, ^Q~?ettsäureester von Pentaerythrit; Bipentaerythrithexavalerat; Dipentaerythrithexeoaproat; Dipentaerythrithexaheptoatj Dipen- taeryihrithexaoaprylat\ Dipentaerythrittributeratoaproat; Dipentaerythrittrivfflerattrinonylat, gemiaohte Diperi^isrythritbexaeeter von C^^iQ-IfiiiteUuren und Trimethylolpropanheptylat. Pentaerythrit-Examples of these esters are pentaerythritol butyrate; Pentaerytebrittetrabutyrate; Pentaerythritol tetraväleratj pentaerythritol tetraoaproate; Pentaerythritol dibutyrate dioaproate; Pentaerythritol butyrate caproate derivative; pentaerythritol butyrate trivalate; Pentaerythritol butyrate trioaproate; Pentaerythritol tributyrate caproate; mixed saturated fatty acid esters of pentaerythritol; Bipentaerythritol hexavalerate; Dipentaerythritol hexeoaproate; Dipentaerythritol hexaheptoatj Dipentaerythritol hexaoaprylate \ Dipentaerythritol tributeratoaproate; Dipentaerythrittrivfflerattrinonylat, mixed Diperi ^ isrythritbexaeeter von C ^^ iQ-IfiiiteUuren and Trimethylolpropaneheptylat. Pentaerythritol
009832/1614009832/1614
Λ)Λ)
ester von aliphatischen C,^2~Monocarl>onsäuren e*nd ausgezeichnete synthetische Scfcftieröleo Sie sind im Handel erhältlich von der Heroules CüheAioal Company,esters of aliphatic C, ^ 2 ~ monocarboxylic acids and excellent synthetic animal oils. They are commercially available from the Heroules CuheAioal Company,
Die öle synthetische Schmieröle verwendeten Ester können durch eine einfache Umsetzung dsr Alkohols und Säuren in den für die Herstellung des gewünschten Produktes geeigneten Verhältnissen hergestellt «erden. Bis Umsetzung findet vorzugsweise in einem Lbeungemittel (fc„B. einem aromatischen Kohlenwasserstoff) und in Gegenwert eines Katalysators (a<,B. HOl, HF, HBr, H2SO^, Η*ΡΟΛ, 0001a oder Bf*) statt. Die Herstellung einiger Ester ist in den ÜS-Satentschriften 3 038 859 und 3 121 109 beschriebenThe esters used in synthetic lubricating oils can be produced by a simple reaction of the alcohol and acids in the proportions suitable for the production of the desired product. Until conversion takes place preferably in a solvent (fc "B. An aromatic hydrocarbon) and the equivalent of a catalyst (a <, B. HOl, HF, HBr, H 2 SO ^, Η * ΡΟ Λ , 0001a or Bf *) instead. The preparation of some esters is described in the US Patents 3,038,859 and 3,121,109
Beispiele für einwertige Alkohole, die zur Herstellung der ale synthetische Sohmierüle verwendeten Sstar geeignet sind, sind Methyl-, Butyl-, Ieoootyl>t Dodeoyl* und Ootadeoyltlkohol. Et können tuch *'Oxo "»alkohole, die durch Umaetaung von Olefinen mit Kohl«noonöxyd und Waeeöretaff hergestellt werden, verwendet werden. K#o-alkohole (dse sind Alkohole, die ktint «atfterstoff atome am beta-Kohlengtoffatom tragen) werden beroraugt. Beispiele für solche Alkohole und 2,2,4-Trimethylpentanol-l und 2,2-Dimtthyl propanoleExamples of monohydric alcohols sstar used to prepare the synthetic ale Sohmierüle are suitable are methyl, butyl, Ieoootyl> t * and Dodeoyl Ootadeoyltlkohol. Also oxo alcohols, which are produced by converting olefins with carbon dioxide and water, can be used Examples of such alcohols and 2,2,4-trimethylpentanol-1 and 2,2-dimethyl propanols
eytithetiBohe ßohniieröle verwendeten Beter geeignet Sind, lind liialkohole, ζ,Β. 2-A'thyl-l,3-hexandiol, 2-tropyl-3f3-h«pt»ndiol, . 2«Butyl-l,3-butandiol, S^-Dimeöityl-l/i-butandiol, und Polypropylenglykole alt einem Molekulargewicht von 100 - 300. Auch Alkohole mit 3, 4t 5 oder mehr Hvdroxylgrurmen pro Molekül können verwendeteytithetiBohe ßohniieröle used Beter are suitable, lind liialkohole, ζ, Β. 2-ethyl-1,3-hexanediol, 2-tropyl-3 f 3-h «pt» ndiol,. 2 «Butyl-l, 3-butanediol, S ^ -Dimeöityl-l / i-butane diol, and polypropylene glycols old a molecular weight of 100 - 300 can also alcohols having 3, 4 t 5 or more per molecule used Hvdroxylgrurmen
BAD ORIGINALBATH ORIGINAL
werden, sie werden bevorzugt, Beispiele für diese Alkohole sind Pentaerythrit!, Dipentaerythrit und 1,1,1-Trimetbylolpropan. Ee können auch Gemische von Alkoholen verwendet werden.are, they are preferred, are examples of these alcohols Pentaerythritol !, dipentaerythritol and 1,1,1-trimetbylolpropane. Ee Mixtures of alcohols can also be used.
Beiepiele für Carbonsäuren, die zur Herstellung der als synthetische Schmieröle verwendeten Ester geeignet sind, sind ein- und zweibasische aliphatisohe Carbonsäuren, z.B. Buttersäure, Valerianaäure, Sebacinsäure, Azelainsäure, Suber-insäure, Bernsteinsäure, Caproneäure, Adipinsäure, Äthylsuberinsäure, Diäthy!adipinsäure, Oxalsäure, Malonsäure, Glutarsäure, Pentadecandicarboneäure, Eiglykoleäüre, Thiodiglykolsäure, Essigsäure, Propionsäure, Caprinsäure, Laurinsäure, Palmitinsäure und Pimelinsäure und Gemieohe daron sowie Gemische von aliphatischen C^_12»Monooarbon-Bäuren. Examples of carboxylic acids which are suitable for producing the esters used as synthetic lubricating oils are monobasic and dibasic aliphatic carboxylic acids, for example butyric acid, valeric acid, sebacic acid, azelaic acid, suberic acid, succinic acid, caproic acid, adipic acid, ethyl suberic acid, diethy / adipic acid, oxalic acid , Malonic acid, glutaric acid, pentadecanedicarboxylic acid, egglycolic acid, thiodiglycolic acid, acetic acid, propionic acid, capric acid, lauric acid, palmitic acid and pimelic acid and mixtures of aliphatic C ^ _ 12 »mono-carboxylic acids.
Erfindung wird nun durch die folgenden Beispiele erläutert, die einige Zusammensetzungen für erfindungBgeinäße Schmiermittel angeben.The invention will now be illustrated by the following examples which show some compositions for lubricants according to the invention indicate.
60Gew^ Bie~(2,2v4-trime1ihylpentyl)~azelat) Basisöl 40Gewji 1,1,1-Trimethylpropantriheptanoat) "A* + lGew# Phenyl-alpha-naphtylamin60wt Bie ^ ~ (2.2 v 4-trime1ihylpentyl) ~ azelate) base oil 40Gewji 1,1,1-Trimethylpropantriheptanoat) "A * + # lGew phenyl-alpha-naphthylamine
+ OD2Gew5C des Salzes von gemiechten primären C1R pl-tert.Alkylemi+ O D 2Gew5C of the salt of liked primary C 1R pl -tert.Alkylemi
104 nen und Monoohlormethyl-phoephonsäure 104 nen and monohydric methylphosphonic acid
009832.'15U009832.'15U
60Gew$ C. 7 aliphatisoher C. ,,-Monocarbonsäureestar) von Pentaerythrit )60Gew $ C. 7 aliphatisoher C. ,, - monocarboxylic acid star) of pentaerythritol)
4QGew# C^ .,^Säureester von Dipentaerythrit )
+ IGewji Diphenylamin
+ 0v2Gew# eines Salzes von gemischten primären C-, □ n 4QGew # C ^., ^ Acid esters of dipentaerythritol) + IGewji diphenylamine
+ 0 v 2Wew # of a salt of mixed primary C-, □ n
Alkylaminen ♦ und MonochlormethylphosphoneäurtAlkylamines and monochloromethylphosphonic acid
Basisöl "B" von Beispiel II'+ lGew# 2,2·-Base Oil "B" of Example II '+ Weight # 2.2 · -
Dlpyridylamin + 0o2Gew^ eines Salzes von gemischten · primären C18a&2.*tert.Alkylaminen und Monoohloratthylphosphoneäure Dlpyridylamin + 0 o 2Wew ^ of a salt of mixed · primary C 18a & 2. * Tert -alkylamines and mono-chlorathylphosphonic acid
Basißöl "A" von Beispiel I + IGew^ 4-Aminopyridin + 0>2Ge»3£ eines Salzes von gemischten primären G^q^a. A3 kylaminen ur.d 1 f 1 -DiohloräthylphosphoneäureBase Oil "A" of Example I + IGew ^ 4-aminopyridine + 0> 2Ge »3L of a salt of mixed primary G ^ q ^ a. A3 kylaminen ur.d 1 f 1 -Diohloräthylphosphonicäure
Basisöl "B" von Beispiel II + lGew# Diphenylamin + _„„ SrS^-Dipy.ridylaßiinfeines üalzes von gemischtenBase oil "B" from Example II + 1 weight # Diphenylamine + _ "" SrS ^ -Dipy.ridylaßiinfeines üaltes of mixed
f Aliiylaminen und Monoohlorm.e.tby.lphoephon-0»0075Gowji Kupierdibutyldithiocarbamat + ' 0*001 Gtwjt tinte Silioonöltf Aliiylaminen and Monoohlorm.e.tby.lphoephon-0 »0075Gowji Kupierdibutyldithiocarbamat + '0 * 001 Gtwjt ink silicone oil
Beigpiel VI Example VI
Baoisöl "B" von Beieplel Ii + iGew?i Phenyl-elpba-naphthylamlnBaois Oil "B" from Beieplel Ii + iGew? I Phenyl-elpba-naphthylamine
eines Sei «es von gtiuiochttn primärtn . text. AlkylaiQinen und Monoohlormethy.lphoephon- und O.O575'Jew^ Benatoijriazol + 0oÜ01Gew# einesone thing be it from gtiuiochttn primary. text. AlkylaiQinen and Monoohlormethy.lphoephon- and O.O575'Jew ^ Benatoijriazol + 0 o Ü01Gew # one
BAD ORIGINALBATH ORIGINAL
009832/16U009832 / 16U
Die Vorteile, die sich durch die Verwendung einer Kombination des Salzes eines aliphatischen Amins und einer üalogenalkylphosphonsäure zusammen mit einem cyclischen Amin ergeben, werden im folgenden beschrieben. The benefits of using a combination of the salt of an aliphatic amine and a halogenalkylphosphonic acid together with a cyclic amine are described below.
Ee ist festgestellt worden, daß durch das Zusammenwirken des Salzes mit dem cyclischen Amin eine erhöhte Widerstandsfähigkeit gegen Oxydation erreicht wird. Diese Wirkung wird duroh die nachstehende Tabelle I erläutert, die die Ergebnisse eines Luftoxydationstestes bei 2040C wiedergibt.It has been found that the interaction of the salt with the cyclic amine increases the resistance to oxidation. This effect is explained duroh the following Table I, which shows the results of a Luftoxydationstestes at 204 0 C.
Bei diesem Test wird Luft mit einer Geschwindigkeit von 70 ml/Min duroh eine Probe von 20 g durchgeleitet, die als Katalysator 0,002£ Kupfer und 0,002* Eisen (als löslicht Octoate) enthält. Dae Basissohmieröl (Öl"E") besteht aus 60Gew£ von aliphatischen C^ »-Monooarbonsäursestern des Pentaerythritβ und 40 Gew.J( γοη aliphatischen Monocarbonsäureester» des taerythrite·In this test, air is passed through a sample of 20 g at a rate of 70 ml / min, which acts as a catalyst £ 0.002 copper and 0.002 * iron (as soluble octoate) contains. The base resisting oil (Oil "E") is made up of 60% by weight of aliphatic C ^ »-Monooarboxylic acid esters of pentaerythritol and 40 Gew.J (γοη aliphatic monocarboxylic acid ester »des taerythrite
naphthylamin
öl E + O.2Gsw?6 Sale 11A11O
Öl E + lGtw# Phenyl-alpha-
naphtylamin + 0.2Gew^
SaU "A"oil E + weight # Phenyl-alpha
naphthylamine
oil E + O.2Gsw? 6 Sale 11 A 11 O
Oil E + lGtw # Phenyl-alpha-
naphthylamine + 0.2 wt ^
SaU "A"
1
51 .25th
1
51.
4624
46
x) Sal» "A" int «in gemischte» SaIs von Monqchloraethylphoephon sMurt und eintm Gemisch von prioUiren x) Sal "" A "int" in mixed "SaIs of Monqchloraethylphoephon sMurt and a mixture of priorities
00II32/1IU00II32 / 1IU
BAD ORiGINALBAD ORiGINAL
Die Induktionszeit dee durch ein oyclisches Amiη stabilisierten Baßisöls verdoppelt sich faet durch die Zugabe dee Salzes, daβ eich ohne das Amin als unwirksames Oxydationsverhütungsmittel erweist.The induction time dee stabilized by a cyclic Amiη Bass oil doubles by adding salt eich proves to be an ineffective antioxidant without the amine.
Einen weiteren Beweis für die günstigen Wirkungen liefern die in der folgenden Tabelle II aufgeführten Ergebnisse des Oxydatlons-Korrosions-Testes. Das Öl n F", /bestehend aus 95 Gew# von aliphatischen C. «-Monocarbonsäureestern des Pentaerythrits und 5 Gew# von aliphatischen Ce ^Q-Monocarbonsäureestern des Dipentaerythrite) wird allein, mit dem Salz und alt dem cyclischen Amin jeweils für sich sowie mit der Kombination von Sale und Amin einem ähnlichen lest unterworfen, wie er in federal Test Method Standard Nr. 791 als Verfahren 5308,4 beschrieben ist.Further evidence of the beneficial effects is provided by the results of the oxidation corrosion test shown in Table II below. The oil n F ", / consisting of 95 wt # of aliphatic C.« monocarboxylic acid esters of pentaerythritol and 5 wt # of aliphatic Ce ^ Q monocarboxylic acid esters of dipentaerythrite) is used alone, with the salt and the cyclic amine in each case as well with the combination of Sale and Amin subjected to a read similar to that described in Federal Test Method Standard No. 791 as Method 5308.4.
6,45 cm eines jeden in der Tabelle aufgeführten Metallee (72 Stunden) auf 320C erhitzt. Luft wird mit einer Geschwindigkeit von 5 l/Sΐα, blaeenwelee durch die Probe geleitet. Die Korrosion wird als Gewichtsverlust pro Flächeneinheit dtr Oberfläche gemessen.6.45 Metallee of each listed in Table cm (72 hours), heated to 32 0 C. Air is passed through the sample at a rate of 5 l / Sΐα, blaeenwelee. The corrosion is measured as the weight loss per unit area dtr of surface.
BAD OFlJGJNALBAD OFlJGJNAL
009832/1614009832/1614
ο οο ο
Dipyridylamin ■-·'■Oil P + weight # 2.2'-
Dipyridylamine ■ - · '■
Dipyrjfylamin +
OolGen^ SaIa "A*Oil P + .lweight # 2,2'- : ~~
Dipyrylamine +
OolGen ^ SaIa "A *
'it0.1
'it
B.!B.!
O ί O ί
r-r-
'Sals "A" ist ein gemischtes Salz von Monochlormethylphoephonsäure und einem Gemisch ▼00 primären'Sals "A" is a mixed salt of monochloromethylphosphonic acid and a mixture ▼ 00 primary
cn cocn co
CJl OOCJl OO
Aus diesen Ergebnissen können mehrere Folgerungen gezogen werden. Sine ziemlich starke Korrosion von Kupfer, Eisen und/oder Magnesium wird bei dem synthetischen Basisöl allein ohne Zusätzetoffe, oder wenn es entweder nur das cyclische Amiη oder nur das Salz ala Zusatzstoff enthält, festgestellt. Enthält es jedoch sowohl das Salz als auch das oyolische Amin, so wird die Korrosion bei allen Metallen beträchtlich herabgesetzt.Several inferences can be drawn from these results. The rather strong corrosion of copper, iron and / or magnesium is caused by the synthetic base oil alone without additives, or if it is either only the cyclic amine or only the salt ala contains additive. However, it includes both the salt as well as the oyolic amine, so will the corrosion all metals considerably reduced.
Die Ergebnisse in Tabelle II erläutern nicht nur.die ausgezeichneten korroeioneverhindernden Eigenschaften des Zusatzgemisches Ton SaIs und cyclisohem Amin, sondern auch die erhöhte Widerstandsfähigkeit gegen Oxydation. Die Zunahme der Säurezahl und der Viskosität (ale qualitatirt Maße für die Stabilität) sind ' beträchtlich niedriger für das öl, das das Sale und das oyolieoh· lain enthält, als für das öl ohne Zusatzstoff oder nur mit tinea Bestandteil de· Suaatsfsmieobee.The results in Table II not only illustrate the excellent ones Corrosion-preventing properties of the additive mixture Clay SaIs and cyclisohem amine, but also the increased resistance against oxidation. The increase in acid number and the viscosity (all qualitative measures for the stability) 'considerably lower for the oil that the Sale and the oyolieoh contains lain than for the oil with no additive or only with tinea Part of the Suaatsfsmieobee.
Die «a* StJts und Aas oyoüeohe AsIn enthaltenden öle eind auoh dadurefc besoaders vorteilhaft, daß sie eine äußerst geringe Bleikorrosion tiigt»* Trüber wirkten synthetische Sohaitraittel, die «ytllsebe Aal&t «la Antioxydationsmittel entbleiten, In Abweeenfctit »leikorrttionsYerhinderndtr Mittel, wie 2,6-Di-tert.butyl-4-4iej*t hy laeino-p-o resol, im allgemeinen korrodierend auf Blei. SÜLti VlH viel leiobttr angegriffen als andere MeUlIe, wie Stahl, , Magnesium, Kupfer und Silber, ferner kann die Bleiniob! aus den Korroeloneergebniseen anderer Metalle werden. Pen Unterschied ewisohen den Werten für ÄeUt0rro#lon und für die normale Xorrpslon seift el« ?er-The oils containing "a * StJts and Aas oyoüeohe AsIn and auoh dadurefc besoaders advantageous that they have an extremely low lead corrosion tiigt »* Synthetic Sohaitrile, the «Ytllsebe eel & t« la antioxidant deflead, In Abweeenfctit »Anti-corrosion agents, such as 2,6-di-tert.butyl-4-4iej * t hy laeino-p-o resol, generally corrosive to lead. SÜLti VlH much leiobttr attacked than other mullies, such as steel, , Magnesium, copper and silver, and lead niob! from the corrosive results of other metals will. Pen difference across the values for ÄeUt0rro # lon and for normal Xorrpslon soaps el «? Er
009132/1814009132/1814
gleich der Ergebnisse für die Zusammensetzung 3 in der nachstehenden Tabelle III mit jenen der Zusammensetzung 2 in der Tabelle II. Der Vergleich zeigt, daß in einem Pentaerythritester-Öl 2,2'»Dipyridylamin für die meisten Metalle als korrosionaverhinderndes Mittel wirkt, daß es aber die Bleikorrosion fördert.same as the results for Composition 3 in the following Table III with those of Composition 2 in Table II. The comparison shows that in a pentaerythritol ester oil 2.2 '»Dipyridylamine for most metals as a corrosion preventive Agent works, but it promotes lead corrosion.
Die duroh die cyclischen Amine hervorgerufene Bleikorrosion wird im wesentlichen durch die Zugabe dee Salzes ausgeschaltet. Das zeigt die nachstehende Tabelle III, die die Ergebnisse der Bleikorrosionsteste für das öl "F" (die in Tabelle II beschriebene Pentaerythritesterbasis) allein, für das öl 11F" mit einem eye-* liechen Amin als Antioxydationsmittel und für das öl "F" mit dem Salz und dem cyclischen Amin, angibt.The lead corrosion caused by the cyclic amines is essentially eliminated by the addition of the salt. This is shown in Table III below, which shows the results of the lead corrosion tests for the oil "F" (the pentaerythritol ester base described in Table II) alone, for the oil 11 F "with an eye- * liechen amine as an antioxidant, and for the oil" F " with the salt and the cyclic amine.
Die öle werden dem MacCoull Ryder-Test und dem SOD Blelkörroeions« test unterworfen. Der EacCoull-Byder-Test läuft 5 Stunden bei 1630C. Dieeer Test ist ist einzelnen in SAS Journal £0, 8, S. 336 (Aug. 1942) beschrieben. In dem SOD Bleikorroeioneteat werden rasch rotierend· Tafeln von Blei und Kupfer in einer ölprobe 1 Stunde auf 1630O erhitit, während blaaenweiaa Luft duroh die Probe geleitet wird. Dieter Teat ist im einseinen in federal Teat Method Standard Vr. 791a, Verfahren 5321,1 beeohritbtn. Die geteeteten Genieehe und die erhaltenen Ergebniaee Bind in der naohatehenden Tabelle IXI angegeben.The oils are subjected to the MacCoull Ryder test and the SOD bleaching test. The EacCoull-Byder test runs for 5 hours at 163 0 C. Dieeer test is described in the individual SAS Journal £ 0, 8, p 336 (Aug. 1942). In the SOD Bleikorroeioneteat rapidly rotating · panels of lead and copper are erhitit in an oil sample for 1 hour at 163 0 O, while air is blaaenweiaa duroh passed the test. Dieter Teat is in the federal Teat Method Standard Vr. 791a, procedure 5321.1 carried out. The marriages tested and the results obtained are given in Table IXI above.
009I32/1SU009I32 / 1SU
Tatelle IIITatelle III
Bleikorrosion
Gewichtsverlust in g
(1630C 5 St0)MacCoull Hyder
Lead corrosion
Weight loss in g
(163 0 C 5 St 0 )
korroaion,
me/6p45om2
Gew,-Verlust
(1630C 1 St.)SOD lead
corroaion,
me / 6p45om2
Weight loss
(163 0 C 1 pc.)
2
j5
4
51
2
j5
4th
5
öl F + lGew£ Phenyl-alpha-
naphtylamin
öl F ♦ lQfe*$ 2,2»-
SipyrjLdyiamin
öl F + lGewjt Phenyl-alpha-
naphthy-lamin + 0.26ew^
SalE,MAM
öl F + lGewji 2,2·-
Dipyridylamin + 0.1Ge*^
Salz "A*oil ρ x >'· !
oil F + l weight £ phenyl-alpha
naphtylamine
oil F ♦ lQfe * $ 2.2 »-
SipyrjLdyiamine
oil F + l Weight phenyl-alpha
naphthy-lamin + 0.26ew ^
SalE, M A M
oil F + lGewji 2.2 -
Dipyridylamine + 0.1Ge * ^
Salt "A *
•
-2„3174
-Io8285
-Ο»0025
-O*0024-O »0296
•
-2 "3174
-Io8285
-Ο »0025
-O * 0024
-5 »94
•
-Oo06-o5.70
-5 »94
•
-Oo06
Pentaerythrit und SötiijG allphatieohe Cc^0*-Mono>
oarboneäureeeter tod Dipentaerythrit.'95Geiij £ alifchatisolie C,. ^ Monocarboxylic acid ester clay
Pentaerythritol and SötiijG allphatieohe Cc ^ 0 * -Mono>
oarboneäureeeter tod dipentaerythritol.
I
■ · -J
■- :v M.
I.
■ · -J
■ -: v
8AD ORIGINAL 8AD ORIGINAL
^09832/15U^ 09832 / 15U
Claims (1)
ableitete .33 «lubricant mixture according to claim 31» characterized in that the salt of!, L-dichloroethylphosphonic acid
derived.
Amins mit wenigstens 8 Kohlenstoffatomen und eiti-c Halogen-C^j-Alkylphoephonsäiare enthält«34 * Additional mixture for ei: i lubricating oil, characterized gekennzeiohnr ^ "dal n it a oycliBchee On ^ and a salt of aliphat- ß o KISSING
Amine with at least 8 carbon atoms and eiti-c halogen-C ^ j-Alkylphoephonsäiare contains "
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US371184A US3309314A (en) | 1964-05-29 | 1964-05-29 | Lubricant compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1594584A1 true DE1594584A1 (en) | 1970-08-06 |
DE1594584B2 DE1594584B2 (en) | 1976-09-16 |
Family
ID=23462850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1965S0097348 Granted DE1594584B2 (en) | 1964-05-29 | 1965-05-28 | OXYDATION AND LEAD CORROSION RESISTANT ESTER LUBRICATION OIL |
Country Status (6)
Country | Link |
---|---|
US (1) | US3309314A (en) |
AT (1) | AT257792B (en) |
BE (1) | BE664644A (en) |
DE (1) | DE1594584B2 (en) |
GB (1) | GB1086886A (en) |
NL (1) | NL140008B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1102010A (en) * | 1965-11-15 | 1968-02-07 | Shell Int Research | A lubricant |
US3793199A (en) * | 1970-06-08 | 1974-02-19 | Texaco Inc | Friction reducing agent for lubricants |
US3773665A (en) * | 1971-11-17 | 1973-11-20 | Mobil Oil Corp | Lubricants containing amine antioxidants |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2559754A (en) * | 1950-06-29 | 1951-07-10 | Du Pont | Fluoroalkanephosphonic compounds |
US2683691A (en) * | 1951-08-18 | 1954-07-13 | Shell Dev | Extreme pressure lubricants |
US2777819A (en) * | 1954-04-27 | 1957-01-15 | Shell Dev | Lubricating compositions |
US3121691A (en) * | 1960-05-24 | 1964-02-18 | Sinclair Research Inc | Lubricant composition |
US3126344A (en) * | 1961-01-03 | 1964-03-24 | Synthetic ester lubricating oil |
-
1964
- 1964-05-29 US US371184A patent/US3309314A/en not_active Expired - Lifetime
-
1965
- 1965-05-28 AT AT488465A patent/AT257792B/en active
- 1965-05-28 DE DE1965S0097348 patent/DE1594584B2/en active Granted
- 1965-05-28 GB GB22787/65A patent/GB1086886A/en not_active Expired
- 1965-05-28 BE BE664644D patent/BE664644A/xx unknown
- 1965-05-28 NL NL656506779A patent/NL140008B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NL6506779A (en) | 1965-11-30 |
GB1086886A (en) | 1967-10-11 |
AT257792B (en) | 1967-10-25 |
BE664644A (en) | 1965-11-29 |
DE1594584B2 (en) | 1976-09-16 |
US3309314A (en) | 1967-03-14 |
NL140008B (en) | 1973-10-15 |
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Legal Events
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C3 | Grant after two publication steps (3rd publication) | ||
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