EP0000514A1 - 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
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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EP
European Patent Office
Prior art keywords
alkyl
formula
optionally substituted
stabilizer
phenol
Prior art date
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EP78100387A
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German (de)
English (en)
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EP0000514B1 (fr
Inventor
Siegfried Rosenberger
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Novartis AG
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Ciba Geigy AG
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    • 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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
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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
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    • C10M2223/04—Phosphate esters
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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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
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/045—Metal containing thio derivatives
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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)
EP78100387A 1977-07-21 1978-07-13 Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant Expired EP0000514B1 (fr)

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 (fr) 1979-02-07
EP0000514B1 EP0000514B1 (fr) 1982-01-13

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EP78100387A Expired EP0000514B1 (fr) 1977-07-21 1978-07-13 Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant

Country Status (6)

Country Link
US (1) US4225450A (fr)
EP (1) EP0000514B1 (fr)
JP (1) JPS5422414A (fr)
CA (1) CA1102782A (fr)
DE (1) DE2861529D1 (fr)
IT (1) IT1097362B (fr)

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EP0349131A2 (fr) * 1988-06-06 1990-01-03 Ethyl Petroleum Additives, Inc. Composition lubrifiante
EP0376889A1 (fr) * 1988-12-28 1990-07-04 Ciba-Geigy Ag Composition lubrifiante
EP0546830A1 (fr) * 1991-12-12 1993-06-16 Exxon Research And Engineering Company Huile lubrifiante contenant un additif anti-usure, anti-oxydant et anti-friction

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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
ES2776135T3 (es) 2010-09-24 2020-07-29 Ecolab Usa Inc Método para lubricar un transportador
WO2012122202A1 (fr) * 2011-03-10 2012-09-13 The Lubrizol Corporation Composition lubrifiante contenant un thiocarbamate
EP2969864B1 (fr) 2013-03-11 2024-04-24 Ecolab USA Inc. Lubrification de plaques de transfert utilisant une huile ou des émulsions d'huile dans l'eau
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

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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

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GB1125900A (en) 1966-08-30 1968-09-05 Ici Ltd Stabilisation of resin
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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)

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Publication number Priority date Publication date Assignee Title
EP0349131A2 (fr) * 1988-06-06 1990-01-03 Ethyl Petroleum Additives, Inc. Composition lubrifiante
EP0349131A3 (en) * 1988-06-06 1990-01-31 Ethyl Petroleum Additives, Inc. Lubricant composition
EP0376889A1 (fr) * 1988-12-28 1990-07-04 Ciba-Geigy Ag Composition lubrifiante
EP0546830A1 (fr) * 1991-12-12 1993-06-16 Exxon Research And Engineering Company Huile lubrifiante contenant un additif anti-usure, anti-oxydant et anti-friction

Also Published As

Publication number Publication date
CA1102782A (fr) 1981-06-09
EP0000514B1 (fr) 1982-01-13
JPS6250520B2 (fr) 1987-10-26
IT7825943A0 (it) 1978-07-20
DE2861529D1 (en) 1982-02-25
US4225450A (en) 1980-09-30
IT1097362B (it) 1985-08-31
JPS5422414A (en) 1979-02-20

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