EP0000514B1 - Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant - Google Patents

Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant Download PDF

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Publication number
EP0000514B1
EP0000514B1 EP78100387A EP78100387A EP0000514B1 EP 0000514 B1 EP0000514 B1 EP 0000514B1 EP 78100387 A EP78100387 A EP 78100387A EP 78100387 A EP78100387 A EP 78100387A EP 0000514 B1 EP0000514 B1 EP 0000514B1
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EP
European Patent Office
Prior art keywords
alkyl
formula
compound
stabiliser
lubricants
Prior art date
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Expired
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EP78100387A
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German (de)
English (en)
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EP0000514A1 (fr
Inventor
Siegfried Rosenberger
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Novartis AG
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Ciba Geigy AG
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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Definitions

  • the present invention relates to lubricants stabilized with phenol-N, N-dioctyl-dithio-carbamates, or to the use of phenol-N, N-dioctyl-dithiocarbamates 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 dithiocarbams such as the already widely used commercial products 2,6-di-tert-butyl-4-methylphenol or S-benzyl-N, N-diethyldithiocarbamate, are already generally known in the lubricant sector as antioxidants.
  • 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-A-1 024 651 describes metal salts of carbamides containing 2,6-dialkylphenol which are to 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. W.M. Denton, "Screening of Compounds for Anti-Oxidant Activity in Motor Oil," Inst. Of Pet Review, 2/66, 46-54, describes S- (3,5-di-tert-butyl-4-hydroxy- benzyl) -N, N-di-n-butyl-dithiocarbamate as a lubricant additive.
  • the dithiocarbamate group is bonded to the phenol ring in the o- or in particular in the m- or p-, but preferably in the p-position to the hydroxyl group.
  • Lubricants which are a stabilizer are a compound of the formula contain, wherein R and R 1 are C 1 -C 4 alkyl.
  • lubricants that act as a stabilizer, a compound of the formula included, wherein R and R 1 are C 1 -C 4 alkyl.
  • the invention also relates to compounds of the formula wherein RC 1 -C 1Z alkyl, C 5 -C 7 cycloalkyl, C 6 -C 10 aryl optionally substituted by C 1 -C 6 alkyl, C 7 -C 22 aralkyl and R 1 and R 2 each independently represent H or R. .
  • hydroxybenzyl-N, N-dioctyl-dithiocarbamates 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.
  • an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
  • the ortho- and in particular the para-hydroxybenzyl-dithiocarbamates can be obtained 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 the formula act as stabilizers against the oxidation and corrosion effects in lubricants.
  • Mineral and synthetic lubricating oils and mixtures thereof 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 on the lubricants Friction partners 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:
  • Polymethacrylates vinyl pyrrolidone methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
  • pour point depressants examples are:
  • dispersants / surfactants are polybutenyl succinic acid imides.
  • Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides.
  • Example 1 S- (3-Hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyldithiocarbamate.
  • 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-dithiocarbamate remains as a brownish viscous oil and is already sufficiently pure and suitable for use as a stabilizer elementary analytical and chromatographic largely uniform.
  • di-n-octyl (Example 2) to be used according to the invention and the di-n-butyl (Example 3) derivatives to be compared 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 5 Oil Oxidation Test, Standard Version According to ASTM D 2272 (Rotary Bomb Oxidation Test)
  • 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 is initially around 6 atm (90 psi) before heating, rises to 150 ° C to just under 14 atm (200 psi) and remains constant until oxidation begins.
  • the test is complete when the pressure drops by 1.7 Atm (25 psi). The time is recorded in minutes.

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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)

Claims (12)

1. Lubrifiants contenant, comme stabilisant, un composé répondant à la formule I
Figure imgb0024
dans laquelle
R représente un alkyle en C1-C12, un cycloalkyle en C5-C7, un aryle en C6-C10 éventuellement porteur d'un alkyle en C1-C6, ou un aralkyle en C7-C22,
R1 et R2 représentent chacun, indépendamment l'un de l'autre, H ou R et
R3 représente un octyle.
2. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule 1 dans lequel:
R et R1 représentent chacun un alkyle en C1-C8, un phényle ou un benzyle,
R2 représente l'hydrogène ou un alkyle en C1-C8 et
R3 représente un octyle,
et dans lequel le groupe dithiocarbamate est en position méta ou en position para relativement au groupe hydroxy du phénol.
3. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé répondant à la formule IV
Figure imgb0025
dans laquelle
R et RI représentent chacun un radical alkyle en C1-C4 et
R2 représente l'hydrogène ou le radical méthyle.
4. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule
Figure imgb0026
dans laquelle R et RI représentent chacun un radical alkyle contenant de 1 à 4 atomes de carbone.
5. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule
Figure imgb0027
dans laquelle R et R1 représentent chacun un alkyle en C1-C4.
6. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, le N,N-di-n-octyl-dithiocarbamate de S-(hydroxy-3-tert-butyl-4 diméthyl-2,6 benzyle).
7. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, le N,N-di-n-octyl-dithiocarbamate de S-(di-tert-butyl-3,5 hydroxy-4 benzyle).
8. Application de composés de formule I comme stabilisants de lubrifiants selon la revendication 1.
9. Application de composés de formule 1 comme stabilisants d'huiles minérales selon la revendication 1.
10. Composés répondant à la formule
Figure imgb0028
dans laquelle
R représente un alkyle en C1-C12, un cycloalkyle en C5-C7, un aryle en C6-C10 éventuellement . porteur d'un alkyle en C1-C6, ou un aralkyle en C7-C22, et
R, et R2 représentent chacun, indépendamment l'un de l'autre, H ou R.
EP78100387A 1977-07-21 1978-07-13 Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant Expired EP0000514B1 (fr)

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CH906177 1977-07-21

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EP0000514B1 true EP0000514B1 (fr) 1982-01-13

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GB966224A (en) * 1960-10-06 1964-08-06 Canadian Ind Hydroxybenzyl dithiocarbamates and stabilization of olefine polymers
NL286923A (fr) 1962-01-03
NL298236A (fr) 1962-09-24
FR1482630A (fr) * 1965-06-09 1967-05-26 Us Rubber Co Composés chimiques à action fongicide ou bactéricide pour l'agriculture ou l'industrie
GB1125900A (en) 1966-08-30 1968-09-05 Ici Ltd Stabilisation of resin
US3412026A (en) * 1966-12-12 1968-11-19 Shell Oil Co Lubricant compositions containing dithiocarbamates
US3462368A (en) * 1967-02-27 1969-08-19 Ethyl Corp Hydrocarbyl-hydroxyphenyl dithiocarbamates and their use as antioxidants

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IT7825943A0 (it) 1978-07-20
CA1102782A (fr) 1981-06-09
US4225450A (en) 1980-09-30
DE2861529D1 (en) 1982-02-25
IT1097362B (it) 1985-08-31
JPS5422414A (en) 1979-02-20
EP0000514A1 (fr) 1979-02-07
JPS6250520B2 (fr) 1987-10-26

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