EP0000514A1 - Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel - Google Patents
Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel Download PDFInfo
- Publication number
- EP0000514A1 EP0000514A1 EP78100387A EP78100387A EP0000514A1 EP 0000514 A1 EP0000514 A1 EP 0000514A1 EP 78100387 A EP78100387 A EP 78100387A EP 78100387 A EP78100387 A EP 78100387A EP 0000514 A1 EP0000514 A1 EP 0000514A1
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- European Patent Office
- Prior art keywords
- alkyl
- formula
- optionally substituted
- stabilizer
- phenol
- 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.)
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- 0 *C(CC1)CC(*)[C@]1O Chemical compound *C(CC1)CC(*)[C@]1O 0.000 description 5
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- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- 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
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- 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
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- 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
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- C10M2223/042—Metal salts thereof
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- 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
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
Definitions
- the present invention relates to lubricants stabilized with pheroldithiocarbamides, or to the use of phenol-dithiocarbamides for stabilizing lubricants.
- additives are generally added to mineral and synthetic lubricants to improve their performance properties.
- additives which are intended to protect the devices to be lubricated from frictional wear.
- wear inhibitors are required to increase the load-bearing capacity of the lubricant and not to have a corrosive effect on the metal parts to be protected.
- Alkyl-substituted phenols and dithiocarbamides such as the commercial products 2,6-di-tert-butyl-4-methylphenol or S-benzyl-N, N-diethyldithiocarbamide, which are already widely used, are already general also.
- US Pat. No. 3,412,026 describes a lubricant composition containing a small proportion of a mixture of antimony-N, N-dialkyldithiocarbamate and dialkylhydroxybenzyl-N, N-diphenyl-dithiocarbamate with good stability.
- GB-PS 1 024 651 describes metal salts of carbamides containing 2,6-dialkylphenol, which can be used as antioxidants and antiwear additives in lubricants. However, it was found that the effects of these metal salt additives are impaired by the formation of residues.
- R, R 1 and R 2 ' are as C 1 -C 12 alkyl branched or unbranched alkyl, such as methyl, ethyl, n-propyl, Isopropyl, n-butyl, tert-butyl, n-pentyl, ⁇ -methylpentyl, hexyl, 2,4-dimethylpentyl, octyl, 6-methylheptyl, 2-ethylhexyl, decyl, dodecyl.
- Alkyl groups with 1-8, but especially those with 1-4 C atoms are preferred.
- R is C 5 -C 6 cycloalkyl, cyclopentyl, cycloheptyl and especially cyclohexyl.
- R 3 and R 4 are linear or branched, in particular C 1 -C 18 alkyl, which is optionally substituted one or more times, but preferably only once, by -OH or -CN.
- Examples are methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, n-pentyl, ⁇ -methylpertyl, hexyl, 2,4-dimethylpentyl, octyl, 6-methylheptyl, 2-ethylhexyl, decyl, dodecyl, octadecyl , Octadecylethyl, eicosyl, doccsyl, pentacosyl, triacontyl, all optionally preferably once substituted with -OH or -CN.
- R 3 and R 4 are as -0- uninterrupted C 2 - C 30 alkyl, for example methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-n-butoxyethyl, 3-n-butoxyethyl, 2-n-octoxyethyl, 2nd -n-octadecyloxyethyl, 4-n-3utoxy-octyl, 8-n-octoxybutyl, 12-n-dodecyloxyoctadecyl.
- R 3 and R 4 are C 2 -C 30 alkenyl branched or unbranched alkenyl with one or more double bonds.
- Linear C 2 -C 20 alkenyl with a double bond such as vinyl, allyl, butenyl, hexenyl, octenyl, decenyl, dodecenyl, hexadecenyl, octadecenyl, oleyl is preferred.
- R, R 3 and R 4 are C 6 -C 10 aryl which is optionally substituted by C 1 -C 6 alkyl, but may be substituted several times, in particular once, in particular by linear or branched C 1 -C 6 alkyl, phenyl or naphthyl, such as methylphenyl or methylnaphthyl. These are in particular p-substituted phenyl or 1-naphthyl substituted in the 4-position, but preferably unsubstituted phenyl or 1-naphthyl.
- R, R 3 and R 4 are as C 7 -C 22 aralkyl phenalkyl or naphthalkyl, the alkyl part in each case consisting of branched or unbranched C 1 -C 12 but especially C 1 -C 4 alkyl.
- Preferred aralkyl radicals are ⁇ -phenethyl and in particular benzyl.
- R 3 and R 4 together form tetramethylene, hexamethylene or in particular pentamethylene, which are optionally substituted by C 1 -C 6 alkyl or are interrupted by -O- or -N-, they form a piperidine, in particular with the nitrogen atom which binds them Morpholine or a piperazine ring.
- the dithiocarbamide group is bonded to the phenol ring in O or in particular in m or p, but preferably in the p position to the hydroxyl group.
- the dithiocarbamide groups are bonded to the phenol in the 2,4-position or preferably in the 3,5-position.
- m-hydroxybenzyldithiocarbamides to be used according to the invention can be obtained by generally known methods, for example by using mono- or di-chloromethylphenols of the formulas with the equivalent amounts of corresponding Na dithiocarbamates of the formula in an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
- ortho- and in particular the para-hydroxybenzyldithiocarbamides are obtainable analogously in the manner cited above for the meta derivatives, but they are preferably prepared by known methods by reacting molar amounts of a corresponding substituted phenol of the formula with formaldehyde, carbon disulfide and an amine of the formula
- the compounds of formula 1 are substances known per se which have already been used as stabilizers for rubber (GB-PS 1 049 535) and copolymer resins (GB-PS 1 125 900).
- the compounds of the formula I act as stabilizers against the effects of oxidation and corrosion, and as "extreme pressure” and “antiwear” additives in lubricants.
- Mineral and synthetic lubricating oils and their mixtures which contain 0.001 to 5% by weight, based on the lubricant, and preferably 0.02-3% of a compound of the formula I, have excellent lubricating properties, which are due to greatly reduced wear and tear lubricating friction partner become clear.
- lubricants in question are familiar to the person skilled in the art and e.g. in the "Lubricant Pocket Book” (Hüthig Verlag, Heidelberg, 1974). Mineral oils are particularly suitable.
- the lubricating oil formulation can additionally contain other additives that are added to improve certain performance properties, such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
- additives such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
- antioxidants are:
- metal passivators examples are:
- rust inhibitors are:
- Viscosity index improvers are:
- Polymethacrylates vinyl pyrrolidone / methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
- pour point depressants examples are:
- Polybutenyl succinic acid imides Polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
- Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides.
- the mixture is then poured into about 1 liter of ice water, the toluene phase is separated off after the addition of a further 100 ml of toluene, shaken out with water, dried over calcium chloride and evaporated in vacuo.
- the S- (3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyl-dithiocarbamide remains as a brownish viscous oil and is already sufficiently pure and suitable for use as a stabilizer elementary analytical and chromatographic largely uniform.
- p- and o-hydroxybenzyldithiocarbamides to be used according to the invention are listed in the following table. They are obtained by known methods, preferably by reacting appropriate phenols (column 2 of the table) with formaldehyde, carbon disulfide and the corresponding secondary amine (column 3 of the table) (for example according to US Pat. No. 2,757,174).
- Example 7 If the sodium N, N-di-ethyl-dithiocarbamate in Example 7 is replaced by the corresponding N, N-di-n-octyl compound, the 3,5-di- (N, N -di-n-octyl-thiocarbamoylmercapto-methyl) -2,4,6-trimethylphenol with an mp of about 60 ° C.
- the glass vessel is in a stainless steel bomb with a pressure gauge.
- the bomb rotates axially at 100 rpm. at an angle of 30 ° to the horizontal, in an oil bath at 150 ° C.
- the oxygen pressure initially, is approx. 6 atm (90 psi) before heating up, rises at 150 ° C to just under 14 atm (200 psi) and remains until the *
- the Shell Vitrea 41 brand was used as the base oil. setting oxidation constant. The test is complete when the pressure drops by 1.7 Atm (25 psi). The time is recorded in minutes.
- Test oil Shell Rotary Vacuum Oil (viscosity 11cSt./100°C).
- Test oil Shell Rotary Vacuum Oil (viscosity 11 cSt./100 ° C).
- ⁇ NZ increase in the neutralization number in mg KOH / g test oil.
- Catenex 41 (Shell's trade name) was used as the base oil.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- Die vorliegende Erfindung betrifft mit pheroldithiocarbamiden stabilisierte Schmiermittel, bzw. cie Verwendung von Phenol-dithiocarbamiden zum Stabilisieren von Schmiermitteln.
- Mineralischen und synthetischen Schmierstoffen werden im·allgemeinen verschiedene Zusatzstoffe zur Ver- besserung ihrer Gebrauchseigenschaften beigegeben. Insbesondere besteht ein Bedarf an Additiven, welche die zu schmierenden Vorrichtungen vor Reibungsabnutzung schützen sollen. An solche Verschleissinhibitoren wird die Anforderung gestellt, dass sie das Lasttragevermögen des Schmierstoffes erhöhen und nicht korrodierend auf cie zu schützenden Metallteile wirken.
- Alkylsubstituierte Phenole und Dithiocarbamide, wie beispielsweise die bereits vielseitig verwendeten Handelsprodukte 2,6-Di-tert.-butyl-4-methylphenol bzw. S-Benzyl-N,N-diäthyl-dithiocarbamid, sind bereits allgemein auch. im Schmiermittelsektor als Antioxydantien bekannt. In der US-PS 3,412,026 wird eine Schmiermittelzusammensetzung enthaltend einen kleinen Anteil einer Mischung von Antimon-N,N-dialkyldithiocarbamat und Dialkylhydroxybenzyl-N,N-diphenyl-dithiocarbamat mit guter Stabilität beschrieben. Die GB-PS 1 024 651 beschreibt Metallsalze von 2,6-Dialkylphenol enthaltenden Carbamiden, die als Antioxydantien und Antiwear-Additive in Schmiermitteln einzusetzen sind. Es zeigte sich jedoch, dass diese Metallsalz-Zusätze durch Bildung von Rückständen in ihrer Wirkung beeinträchtigt werden.
- Es wurde nun gefunden, dass in Schmiermitteln überraschenderweise durch Zugabe eines kleinen Anteils an Phenol-dithiocarbaminsäureestern eine sehr gute Antioxydations- und Antikorrosionswirkung erzielt werden kann. Diese Verbindungen, die gegenüber den oben erwähnten Schmiermittelzusätzen keinen Metallsalzcharakter haben, ergeben ebenfalls ausgezeichnete Resultate als "Extreme-Pressure"- und "Antiwear"-Additive.
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- R C1-C12 Alkyl, C5-C7 Cycloalkyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl,
- R1 und R2 jeweils unabhängig voneinander H oder R bedeuten und
- n die Zahlen 1 oder 2 sein kann, wobei im Falle von n = 1
- R3 gegebenenfalls durch -OH oder -CN substitutiertes C1-C30 Alkyl oder durchl -O- unterbrochenes C2-C30 Alkyl, sowie ferner C2-C30 Alkehyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl, eine Gruppe der Formel -NR1'R2', worin R1' und R2' unabhängig voneinander Wasserstoff oder C1-C12 Alkyl bedeuten, eine Gruppe der Formel II
- R,R1 und R2 obige Bedeutung haben und R5 Wasserstoff oder eine Gruppe der. Formel III
- R,R1 und R2 die oben definierte Bedeutung haben, und R4 gegebenenfalls durch -OH oder -CN substituiertes C1-C30 Alkyl oder durch -0- unterbrochenes C2-C30 Alkyl, sowie ferner C2-C30 Alkenyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl oder R5 bedeutet, oder R3 und R4 zusammen Tetramethylen, Pentamethylen oder Hexamethylen bilden, die gegebenenfalls durch CI-C6 Alkyl substituiert oder durch -0-,
- R3 gegebenenfalls durch -OH oder -CN substituiertes C1-C30 Alkyl oder durch -0- unterbrochenes C2-C34 Alkyl, sowie ferner C2-C30 Alkenyl, gegebenenfalls mit C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl,
- R 4 H oder R3 ist oder R3 und R4 zusammen Tetramethylen, Pentamethylen oder Hexamethylen bilden, die gegebenenfalls durch C1-C6 Alkyl substituiert oder durch -0- oder
- R, R1 und R2' sind als C1-C12 Alkyl verzweigtes oder unverzweigtes Alkyl, wie Methyl, Aethyl, n-Propyl, Isopropyl, n-Butyl, tert.-Butyl, n-Pentyl, α-Methylpentyl, Hexyl, 2,4-Dimethylpentyl, Octyl, 6-Methylheptyl, 2-Aethyl-hexyl, Decyl, Dodecyl. Bevorzugt sind Alkylgruppen mit 1-8, insbesondere aber solche mit 1-4 C-Atomen.
- R ist als C5-C6 Cycloalkyl, Cyclopentyl, Cycloheptyl und insbesondere Cyclohexyl.
- R3 und R4 sind als C1-C30 Alkyl lineares oder verzweigtes, insbesondere C1-C18 Alkyl, das gegebenenfalls ein- oder mehrmals, jedoch bevorzugt nur einmal durch -OH oder -CN substituiert ist. Beispiele sind Methyl, Aethyl, Propyl, Isopropyl, Butyl, tert.-Butyl, n-Pentyl, α-Methylpertyl, Hexyl, 2,4-Dimethylpentyl, Octyl, 6-Methylheptyl, 2-Aethyl-hexyl, Decyl, Dodecyl, Octadecyl, Octadecyläthyl, Eicosyl, Doccsyl, Pentacosyl, Triacontyl, alle gegebenenfalls bevorzugt einmal mit -OH oder -CN substituiert. Bevorzugt int lineares unsubstituiertes und ununterbrochenes C1-C18 Alkyl.
- R3 und R4 sind als durch -0- unrerbrochenes C2- C30 Alkyl beispielsweise Methoxymethyl, Aethoxymethyl, 2-Methoxyäthyl, 2-Aethoxyäthyl, 2-n-Butoxyäthyl, 3-n-Butoxyäthyl, 2-n-Octoxyäthyl, 2-n-Octadecyloxyäthyl, 4-n-3utoxy- octyl, 8-n-Octoxybutyl, 12-n-Dodecyloxyoctadecyl.
- R 3 und R4 sind als C2-C30 Alkenyl verzweigtes oder unverzweigtes Alkenyl mit einer oder mehreren Doppelbindungen. Bevorzugt ist lineares C2-C20 Alkenyl mit einer Doppelbindung wie beispielsweise Vinyl, Allyl, Butenyl, Hexenyl, Octenyl, Decenyl, Dodecenyl, Hexadecenyl, Octadecenyl, Oleyl.
- R, R3 und R4 sind als gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl gegebenenfalls mehrmals jedoch insbesondere einmal durch lineares oder verzweigtes C1-C6 Alkyl substituiertes Phenyl oder Naphthyl, wie beispielsweise Methylphenyl oder Methylnaphthyl. Dabei handelt es sich insbesondere um p-substituiertes Phenyl oder in 4-Stellung substituiertes 1-Naphthyl, vorzugsweise jedoch um unsubstituiertes Phenyl oder 1-Naphthyl.
- R, R3 und R4 sind als C7-C22 Aralkyl Phenalkyl oder Naphthalkyl, wobei der Alkylteil jeweils aus verzweigtem oder unverzweigtem C1-C12 insbesondere jedoch C1-C4 A lkyl besteht. Bevorzugte Aralkylreste sind α-Phen- äthyl und insbesondere Benzyl.
- Bilden R3 und R4 zusammen Tetramethylen, Hexamethylen oder insbesondere Pentamethylen, die gegebenenfalls durch C1-C6 Alkyl substituiert oder durch -O- oder -N- unterbrochen sind, so bilden sie mit dem sie bindenden Stickstoffatom insbesondere ein Piperidin-, ein Morpholin-oder ein Piperazin-Ring.
- Die Dithiocarbamidgruppe ist bei n = 1 in O-oder insbesondere in m- oder p-, jedoch bevorzugt in p-Stellung zur Hydroxylgruppe an den Phenolring gebunden.
- Bei n = 2 sind die Dithiocarbamidgruppen in 2,4-oder vorzugsweise in 3,5-Stellung an das Phenol gebunden.
- Hervorzuheben sind Schmiermittel, die als Stabilisator eine Verbindung der Formel I enthalten, worin
- R und R1 C1-C8 Alkyl, Phenyl oder Benzyl und
- R2 Wasserstoff oder C1-C8 Alkyl sind,
- R3 und R4 gleich sind und C1-C18 Alkyl oder C2-C20 Alkenyl bedeuten und
- n die Zahlen 1 oder 2 sein kann, wobei im Falle von n = 1 die Dithiocarbamidgruppe in m- oder p-snilung zur Hydroxylgruppe des Phenols steht und
- bei n = 2 die beiden Dithiocarbamidgruppen in 3,5-Stellung am Phenol gebunden sind.
-
- R und R1 C1-C4 Alkyl
- R2 Wasserstoff oder Methyl sind und
- R3 und R4 gleich sind und lineares C1-C18 Alkyl bedeuten.
-
- R und R1 C1-C4 Alkyl,
- R3 und R4 gleich sind und lineares C1-C12 Alkyl bedeuten.
-
- R und R1 C1-C4 Alkyl,
- R3 und R4 gleich sind und lineares C2-C12 Alkyl bedeuten.
- Die erfindungsgemäss zu verwendenden m-Hydroxybenzyl-dithiocarbamide können nach allgemein bekannten Methoden erhalten werden, indem man beispielsweise Mono-oder Di-Chlormethylphenole der Formeln
- Die ortho- und insbesondere die para-Hydroxybenzyl-dithiocarbamide sind in der vorstehend für die meta-Derivate zitierten Weise analog erhältlich,bevorzugt werden sie aber nach bekannten Methoden hergestellt durch Reaktion molarer Mengen eines entsprechenden substituierten Phenols der Formel
- Die Verbindungen der Formel 1 sind an sich bekannte Stoffe,die bereits als Stabilisatoren von Kautschuk (GB-PS 1 049 535) und von Copolymer-Harzen (GB-PS 1 125 900) Verwendung gefunden haben.
- Die Verbindungen der Formel I wirken schon in- sehr geringen Mengen als Stabilisatoren gegen Oxidations- und Korrosionswirkung, sowie als "Extrem Pressure"-, und "Antiwear"-Additive in Schmiermitteln. So zeigen mineralische und synthetische Schmieröle, sowie deren Gemische, welche 0,001 bis 5 Gew.-% bezogen auf das Schmiermittel, und vorzugsweise 0,02-3% einer Verbindung der Formel I -enthalten, ausgezeichnete Schmiereigenschaften, welche durch stark reduzierte Abnutzungserscheinungen der zu schmierenden Reibpartner deutlich werden.
- Die in Frage kommenden Schmiermittel sind dem Fachmann geläufig und z.B. im "Schmiermittel-Taschenbuch" (Hüthig Verlag, Heidelberg, 1974) beschrieben. Besonders geeignet sind Mineralöle.
- Die Schmierölformulierung kann zusätzlich noch andere Additive enthalten, die zugegeben werden, um gewisse Gebrauchs-Eigenschaften zu verbessern, wie Antioxidantien, Metallpassivatoren, Rostinhibitoren, Viskositätsindex-Verbesserer, Stockpunkterniedriger, Dispergiermittel/Tenside und andere Verschleissschutz-Additive.
-
- a) Alkylierte und nicht-alkylierte aromatische Amine und Mischungen davon, z.B.:
- Dioctyldiphenylamin, (2,,2,3,3-Tetramethyl-butyl)-phenyl-α-und -β-naphthylamine, Phenothiazin, Dioctylphenothiazin, Phenyl-α-naphthylamin, N,N'-Di-sec.-butyl-p-phenylendiamin. ,
- b) Sterisch gehinderte Phenole, z.B.:
- 2,6-Di-tert.-butyl-p-cresol, 4,4'-Bis-(2,6-diisopropyl- phenol), 2,4,6-Triisopropylphenol, 2,2'-Thio-bis-(4-methyl-6-tert.-butyl-phenol), 4,4'-Methylen-bis-(2,6-di-tert.-butylphenol).
- c) Alkyl-, Aryl- oder Alkaryl-phosphite, z.b.:
- Trinonylphosphit, Triphenylphosphit, Diphenyldecylphosphit.
- d) Ester von Thiodipropionsäure oder Thiodiessigsäure, z.B.:
- Dilaurylthiodipropionat oder Dioctylthiodiacetat.
- e) Salze von Carbamin- und Dithiophosphor-säuren, z.B.:
- Antimon-diamyldithiocarbamat, Zink-diamyldithiophosphat.
- f) Kombination von zwei oder mehr Antioxidantien der obigen, z.B.:
- ein alkyliertes Amin und ein sterisch gehindertes Phenol.
-
- a) für Kupfer, z,B.:
- Benzotriazol, Tetrahydrobenzotriazol, 2-Mercaptobenzotriazol, 2,5-Dimercaptothiadiazol, Salicyliden-propylendiamin, Salze von Salicylaminoguanidin.
- b) für Blei, z.B.:
- Sebacinsäurederivate, Chinizarin, Propylgallat,
- c) Kombination von zwei oder mehr der obigen Additive.
-
- a) Organische Säuren, Ihre Ester, Metallsalze und Anhydride, z.B.:
- N-Oleoyl-sarcosin, Sorbitan-mono-oleat, Blei-naphthenat, Dodecenylbernsteinsäure-anhydrid.
- b) Stickstoffhaltige Verbindungen, z.B.:
- I. Primäre, sekundäre oder tertiäre aliphatische oder cycloaliphatische Amine und Amin-Salze von organischen und anorganischen Säuren, z.B. öllösliche Alkylammoniumcarboxylate.
- II. Heterocyclische Verbindungen z.B.: Substituierte Imidazoline und Oxazoline.
- c) Phosphorhaltige Verbindungen, z.B.:
- Aminsalze von Phosphorsäurepartialestern,
- d) Schwefelhaltige Verbindungen, z.B.:
- Barium-dinonylnaphthalin-suifonate; Calciumpetroleum- sulfonate,
- e) Kombinationen von zwei oder mehr der obigen Additive.
- Polymethacrylate, Vinylpyrrolidon/Methacrylat-Copolymere, Polybutene, Olefin-Copolymere, Styrol/AcrylatCopolymere.
- Polymethacrylate, alkylierte Naphthalinderivate.
- Polybutenylbernsteinsäure-imide. Polybutenylphosphonsäurederivate, basische Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.
- Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte vegetabilische Oele, Zinkdialkyldithiophosphate, Tritolyl-phosphat, chlorierte Paraffine, Alkyl- und Aryldisulfide.
- Die Herstellung der in den erfindungsgemässen Schmiermitteln als Stabilisatoren zu verwendenden Verbindungen, sowie die Verwendung und Wirkung der erfindungsgemässen Schmiermittelzusammensetzungen, wird in den folgenden Beispielen näher beschrieben.
- 34 g N,N-Di-n-octyldithiocarbaminsäure-Natriumsalz werden in 300 ml Acetonitril gelöst und unter Rühren bei 10°C innert 30 Minuten mit einer Lösung von 22,7 g 3-Hydroxy-4-tert.-butyl-2,6-dimethyl-benzylchlorid (Darstellung siehe Makromolekulare Chemie, Band 9 (1952), Seiten 21/22) in 50 ml Toluol versetzt. Das Reaktionsgemisch wird dann ca. 15 Stunden bei 20-25°C gerührt,wobei eine Natriumchlorid-Abscheidung zu beobachten ist.
- Anschliessend wird das Gemisch in ca. 1 Liter Eiswasser eingegossen, die Toluolphase nach Zugabe von weiteren 100 ml Toluol abgetrennt,mit Wasser ausgeschüttelt, über Calciumchlorid getrocknet und im Vakuum eingedampft. Das S-(3-Hydroxy-4-tert.-butyl-2,6-dimethylbenzyl)-N,N-di-n-octyl-dithiocarbamid bleibt als bräunliches viskoses Oel zurück und ist für den Einsatz als Stabilisator bereits genügend rein und elementar-analytisch sowie chromatographisch weitgehend einheitlich.
-
- Weitere erfindungsgemäss zu verwendende p- und o-Hydroxybenzyldithiocarbamide sind in der folgenden Tabelle aufgeführt. Sie werden nach bekannten Methoden, vorzugsweise durch Umsetzen entsprechender Phenole (Kolonne 2 der Tabelle) mit Formaldehyd, Schwefelkohlenstoff und dem entsprechenden sekundären Amin (Kolonne 3 der Tabelle) erhalten (z.B. nach US-PS 2,757,174).
- In den folgenden Beispielen sind weitere erfindungsgemäss zu verwendende bifunktionelle Dithiocarbamide erläutert.
-
- 17,1 g Natrium-N,N-diäthyl-dithiocarbamat werden in 160 ml Acetonitril suspendiert und bei 10°C'unter Rühren innert 30 Minuten mit einer Lösung von 11,7 g 3,5-Dichlormethyl-2,4,6-trimethylphenol (Darstellung siehe Makromolekulare Chemie, Band 9 (1952), Seite 13) in 100 ml Chloroform versetzt.
- Der Ansatz wird dann 10 Stunden bei Raumtemperatur gerührt und das ausgeschiedene Natriumchlorid durch 'Zusatz von 50 ml Wasser gelöst. Die organische Phase wird abgetrennt, mit Wasser gewaschen und über Calciumchlorid getrocknet. Der feste Abdampfrückstand wird aus Acetonitril umkristallisiert. Das so erhaltene 3,5-Di-(N,N-diäthyi- thiocarbamoylmercaptomethyi)-2,4,6-trimethylphenol schmilzt bei 146°C.
- Ersetzt man in Beispiel 7 das Natrium-N,N-di- äthyl-dithiocarbamat durch die entsprechende N,N-Di-n-octyl-verbindung, so erhält man bei sonst gleicher Arbeitsweise das 3,5-Di-(N,N-di-n-octyl-thiocarbamoylmercapto- methyl)-2,4,6-trimethylphenol mit einem Smp. von ca. 60°C.
- Eine Oelprobe von 50 ml "Rotary-Vacuum-Oil" der Fa. SHELL (Viskosität 11 cSt./100°C)* wird unter Zusatz von 0,25 g Stabilisator in einem Glasgefäss zusammen mit 5 ml dest. Wasser und einer blankpolierten, mit Petrol- äther gewaschenen katalytisch wirkenden Cu-Spirale in einer Sauerstoff-Atmosphäre oxydiert.
- Das Glasgefäss befindet sich in einer Bombe aus rostfreiem Stahl mit Manometer. Die Bombe dreht sich axial mit 100 U/Min. in einem Winkel von 30° zur Horizontalen, in einem Oelbad bei 150°C. Der Sauerstoffdruck ,beträgt anfangs, vor dem Aufheizen ca. 6 Atm (90 psi), steigt bei 150°C auf knapp 14 Atm (200 psi) und bleibt bis zur ein-
*In einer zweiten Testreihe wurde als Grundöl die Marke Shell Vitrea 41 benützt.
setzenden Oxidation konstant. Die Prüfung ist beendet bei einem Druckabfall um 1,7 Atm (25 psi). Aufgezeichnet wird die Zeit in Minuten. -
- Modifizierte Version mit löslichem Cu- und Fe-Katalysator.
- Bedingungen: 4 Stunden Sauerstoff einleiten bei 150°C (4 Liter O2/h).
- Bestimmung der Säurezahl nach Testende; Tabellen- wert: mg KOH-Verbrauch pro g Testöl.
- Stabilisatorkonzentration: 0,5%
-
- Bedingungen: Lufteinleiten 3 Tage bei 174°C
- Stabilisatorkonzentration: 0,5%
- Testöl: Shell Rotary Vacuum Oil (Viskosität 11 cSt./100°C).
- Tabellenwerte: ΔV: Viskositätsanstieg bei 37,5°C (100°F) in %
-
- Mit dem Shell-Vierkugel-Apparat wurden folgende Werte bestimmt: (Tentative method IP 239/69, Extreme pressure and wear lubricant test for oils and greases, four-ball machine).
- 1) I.S.L. : Initial Seizure Load: Das ist die Last, bei der der Oelfilm innerhalb einer Belastungsdauer von 10 Sekunden zusammenbricht.
- 2) W.L. = Weld Load (Schweisslast): Das ist die Last, bei der die 4 Kugeln innerhalb von 10 Sekunden zusammenschweissen.
- 3) W.S.D. = Wear Scar Diameter in mm: Das ist der mittlere Verschleissdurchmesser bei einer Belastung von 70 kg bzw. 40 kg während 1 Stunde.
- Als Basisöl wurde Catenex 41 (Handelsbezeichnung der Firma Shell) verwendet.
-
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH906177 | 1977-07-21 | ||
CH9061/77 | 1977-07-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000514A1 true EP0000514A1 (de) | 1979-02-07 |
EP0000514B1 EP0000514B1 (de) | 1982-01-13 |
Family
ID=4347895
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100387A Expired EP0000514B1 (de) | 1977-07-21 | 1978-07-13 | Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel |
Country Status (6)
Country | Link |
---|---|
US (1) | US4225450A (de) |
EP (1) | EP0000514B1 (de) |
JP (1) | JPS5422414A (de) |
CA (1) | CA1102782A (de) |
DE (1) | DE2861529D1 (de) |
IT (1) | IT1097362B (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0349131A2 (de) * | 1988-06-06 | 1990-01-03 | Ethyl Petroleum Additives, Inc. | Schmiermittelgemisch |
EP0376889A1 (de) * | 1988-12-28 | 1990-07-04 | Ciba-Geigy Ag | Schmierstoffzusammensetzung |
EP0546830A1 (de) * | 1991-12-12 | 1993-06-16 | Exxon Research And Engineering Company | Verschleissschutz-, Antioxidations- und reibungsverminderndes Additiv enthaltendes Schmieröl |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4734210A (en) * | 1985-07-30 | 1988-03-29 | Ciba-Geigy Corporation | Additives for lubricant compositions |
US5370806A (en) * | 1989-12-21 | 1994-12-06 | Mobil Oil Corporation | Borated dihydrocarbyl dithiocarbamate lubricant additives and composition thereof |
US5560853A (en) * | 1990-08-30 | 1996-10-01 | Pennzoil Products Company | Dithiocarbamoyl diols and borate esters thereof for use in lubricant compositions |
US6046144A (en) * | 1997-06-02 | 2000-04-04 | R.T. Vanderbilt Co., Inc. | Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions |
US7112558B2 (en) | 2002-02-08 | 2006-09-26 | Afton Chemical Intangibles Llc | Lubricant composition containing phosphorous, molybdenum, and hydroxy-substituted dithiocarbamates |
US7741257B2 (en) * | 2005-03-15 | 2010-06-22 | Ecolab Inc. | Dry lubricant for conveying containers |
US7745381B2 (en) | 2005-03-15 | 2010-06-29 | Ecolab Inc. | Lubricant for conveying containers |
US7915206B2 (en) * | 2005-09-22 | 2011-03-29 | Ecolab | Silicone lubricant with good wetting on PET surfaces |
US7727941B2 (en) * | 2005-09-22 | 2010-06-01 | Ecolab Inc. | Silicone conveyor lubricant with stoichiometric amount of an acid |
US7741255B2 (en) | 2006-06-23 | 2010-06-22 | Ecolab Inc. | Aqueous compositions useful in filling and conveying of beverage bottles wherein the compositions comprise hardness ions and have improved compatibility with pet |
CN103119143A (zh) | 2010-09-24 | 2013-05-22 | 艺康美国股份有限公司 | 包括乳液的输送机润滑剂和使用它们的方法 |
CN103502404A (zh) | 2011-03-10 | 2014-01-08 | 路博润公司 | 含有硫代氨基甲酸酯化合物的润滑组合物 |
EP2969864B1 (de) | 2013-03-11 | 2024-04-24 | Ecolab USA Inc. | Schmierung von transferplatten unter verwendung einer öl- oder öl-in-wasser-emulsion |
CN105601551B (zh) * | 2014-11-24 | 2017-08-22 | 中国石油化工股份有限公司 | 一种含硫受阻酚类化合物及其制备方法和应用 |
CN104611094B (zh) * | 2015-01-30 | 2017-02-22 | 西安热工研究院有限公司 | 一种汽轮机油复合抗氧剂及其制备方法与添加方法 |
CN111040823B (zh) * | 2020-01-02 | 2022-06-28 | 济南佳进新材料有限公司 | 抗磨剂、其应用、其制备方法、无灰液压油组合物及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3117947A (en) * | 1960-10-06 | 1964-01-14 | Canadian Ind | Polyolefine antioxidants |
FR1482630A (fr) * | 1965-06-09 | 1967-05-26 | Us Rubber Co | Composés chimiques à action fongicide ou bactéricide pour l'agriculture ou l'industrie |
US3412026A (en) * | 1966-12-12 | 1968-11-19 | Shell Oil Co | Lubricant compositions containing dithiocarbamates |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL286923A (de) | 1962-01-03 | |||
NL298236A (de) | 1962-09-24 | |||
GB1125900A (en) | 1966-08-30 | 1968-09-05 | Ici Ltd | Stabilisation of resin |
US3462368A (en) * | 1967-02-27 | 1969-08-19 | Ethyl Corp | Hydrocarbyl-hydroxyphenyl dithiocarbamates and their use as antioxidants |
-
1978
- 1978-07-13 EP EP78100387A patent/EP0000514B1/de not_active Expired
- 1978-07-13 DE DE7878100387T patent/DE2861529D1/de not_active Expired
- 1978-07-13 US US05/924,416 patent/US4225450A/en not_active Expired - Lifetime
- 1978-07-19 CA CA307,663A patent/CA1102782A/en not_active Expired
- 1978-07-20 IT IT25943/78A patent/IT1097362B/it active
- 1978-07-21 JP JP8927578A patent/JPS5422414A/ja active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3117947A (en) * | 1960-10-06 | 1964-01-14 | Canadian Ind | Polyolefine antioxidants |
FR1482630A (fr) * | 1965-06-09 | 1967-05-26 | Us Rubber Co | Composés chimiques à action fongicide ou bactéricide pour l'agriculture ou l'industrie |
US3412026A (en) * | 1966-12-12 | 1968-11-19 | Shell Oil Co | Lubricant compositions containing dithiocarbamates |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0349131A2 (de) * | 1988-06-06 | 1990-01-03 | Ethyl Petroleum Additives, Inc. | Schmiermittelgemisch |
EP0349131A3 (en) * | 1988-06-06 | 1990-01-31 | Ethyl Petroleum Additives, Inc. | Lubricant composition |
EP0376889A1 (de) * | 1988-12-28 | 1990-07-04 | Ciba-Geigy Ag | Schmierstoffzusammensetzung |
EP0546830A1 (de) * | 1991-12-12 | 1993-06-16 | Exxon Research And Engineering Company | Verschleissschutz-, Antioxidations- und reibungsverminderndes Additiv enthaltendes Schmieröl |
Also Published As
Publication number | Publication date |
---|---|
IT7825943A0 (it) | 1978-07-20 |
JPS5422414A (en) | 1979-02-20 |
JPS6250520B2 (de) | 1987-10-26 |
EP0000514B1 (de) | 1982-01-13 |
US4225450A (en) | 1980-09-30 |
IT1097362B (it) | 1985-08-31 |
CA1102782A (en) | 1981-06-09 |
DE2861529D1 (en) | 1982-02-25 |
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