EP0218207B1 - Utilisation d'esters complexes dans des lubrifiants synthétiques et lubrifiants contenant ceux-ci - Google Patents

Utilisation d'esters complexes dans des lubrifiants synthétiques et lubrifiants contenant ceux-ci Download PDF

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Publication number
EP0218207B1
EP0218207B1 EP86113639A EP86113639A EP0218207B1 EP 0218207 B1 EP0218207 B1 EP 0218207B1 EP 86113639 A EP86113639 A EP 86113639A EP 86113639 A EP86113639 A EP 86113639A EP 0218207 B1 EP0218207 B1 EP 0218207B1
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EP
European Patent Office
Prior art keywords
lubricants
ester
synthetic
complex esters
acid
Prior art date
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EP86113639A
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German (de)
English (en)
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EP0218207A2 (fr
EP0218207A3 (en
Inventor
Richard Dr. Baur
Knut Dr. Oppenlaender
Roland Dr. Schwen
Hans-Henning Dr. Vogel
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
    • C10M129/82—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C10M105/46—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters

Definitions

  • the invention relates to the use of complex esters in synthetic lubricants. It also relates to a lubricant that contains at least one complex ester.
  • the HD oils (heavy duty) - to which additives were added for their additional tasks, such as aging and corrosion protection, high-pressure resistance, and as "dirt carriers" - were followed by the multigrade oils with flat viscosity curves and suitability for summer and winter operation, for longer oil change intervals and also already reduced fuel consumption, especially in winter and short-haul operations.
  • a flat viscosity curve means a reduced temperature dependence of the lubricating oil.
  • the viscosity index (VI) is a measure of the temperature dependence.
  • Complex esters are particularly suitable as synthesis components due to their low basic and low viscosity, their low volatility and high viscosity indices.
  • US-A-4 130 494 relates to the use of amine salts of phosphate esters as additives to synthetic lubricating oil compositions. These are intended to reduce unwanted deposits in the engines, especially in turbine engines.
  • US-A-4 155 861 relates to a lubricant which comprises a mixture of a monomeric ester of a branched dicarboxylic acid and an aliphatic primary monoalcohol and a complex ester of a dicarboxylic acid and hexanediol or trimethylhexanediol.
  • the lubricant should be characterized by universal applicability.
  • FR-A-1 508 458 describes the preparation of complex esters with a phosphate ester component.
  • adipic acid, neopentyl glycol and C 6 -C 10 -monocarboxylic acids are reacted with tributyl phosphate, and a complex ester is obtained which is claimed to have increased resistance to oxidation.
  • US Pat. No. 4,064,058 describes a basic lubricant composition which is essentially a mixture of a pentaerythrol ester and a neopentyl glycol ester, the neopentyl glycol ester being obtained by reacting neopentyl glycol with a C 4 -C 12 alkanedicarboxylic acid and a C 4 -C 12 alkanol was obtained.
  • the invention has for its object to provide complex esters for use in synthetic lubricants, and corresponding lubricants, which have good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss.
  • the dicarboxylic acid component is preferably adipic acid.
  • the invention also relates to a lubricant which contains at least one compound of the general formula 1 according to one of claims 1 or 2.
  • the lubricant is preferably in the form of a synthetic lubricating oil.
  • the complex esters of the general formula I can be used either individually or in a mixture.
  • the term mixture here means a mixture of complex esters of the general formula in which the index n and / or the index m can have all of the values mentioned.
  • the measured values n and m represent mean values.
  • the mean value of the index n can be e.g. represent any value between 1 and 3. The same applies to the index m.
  • the complex ester of the general formula 1 has the isooctyl, isodecanyl or isotridecanyl radical as the monoalcohol component.
  • the isodecanyl or isotridecanyl radical are particularly preferred.
  • the alcohols R-OH used in the esterification are commercially available isomer mixtures, such as those e.g. incurred during oxosynthesis.
  • R can, for example, have the following structures 2-ethyl-4-methylpentyl, 3,3-dimethylhexyl, 3,5-dimethylhexyl, 4,5-dimethylhexyl, 2-ethylhexyl, 3-methylheptyl, 5-methylheptyl -, 3,5,5-Trimethylheptyl-, 3,5-dimethyloctyl-, 4,7-dimethyloctyl-, 3,5,5,7-tetramethylnonyl- and their isomers.
  • lubricants for engines or motor vehicle engines, compressor oils, hydraulic fluids, insulating fluids for electrical devices, electrical contact oils, lubricating greases, chain lubricants, heat transfer fluids, vacuum pump oils, synthetic fiber lubricants, instrument oils, rust protection oils and rolling oils . All applications in lubricants that have a lubricating function are included.
  • the complex esters intended for use in accordance with the invention have a very good temperature-viscosity behavior, expressed by a high viscosity index and a low pour point, and a low evaporation loss according to Noack.
  • di-isooctyl, di-isodecyl or di-isotridecyl adipate can be transesterified with hydroxypivalic acid neopentyl glycol ester (HPN) or a direct esterification of the monoalcohol, the dicarboxylic acid and the diol can be carried out.
  • HPN hydroxypivalic acid neopentyl glycol ester
  • the dicarboxylic acid and the diol can be carried out.
  • the lubrication data are listed in the table below.
  • the lubrication data are listed in the table below.
  • the lubrication data are listed in the table below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Claims (4)

1. Utilisation d'esters complexes de formule générale (I)
Figure imgb0012
dans laquelle R est mis pour un reste iso-octyle, isodécanyle ou isotridécanyle, m est mis pour 4 ou 6, n est mis pour 1, 2 ou 3 et X représente le radical hydroxypivalate de néopentylglycol de formule Il
Figure imgb0013
individuellement ou en mélange dans des lubrifiants synthétiques.
2. Utilisation selon la revendication 1, caractérisée en ce que m dans la formule générale 1 est mis pour 4.
3. Lubrifiant contenant au moins un composé de formule générale I selon la revendication 1 ou 2.
4. Lubrifiant selon la revendication 3 sous forme d'une huile lubrifiante synthétique.
EP86113639A 1985-10-10 1986-10-02 Utilisation d'esters complexes dans des lubrifiants synthétiques et lubrifiants contenant ceux-ci Expired - Lifetime EP0218207B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3536197 1985-10-10
DE19853536197 DE3536197A1 (de) 1985-10-10 1985-10-10 Verwendung von komplexestern in synthetischen schmiermitteln und diese enthaltende schmiermittel

Publications (3)

Publication Number Publication Date
EP0218207A2 EP0218207A2 (fr) 1987-04-15
EP0218207A3 EP0218207A3 (en) 1988-01-27
EP0218207B1 true EP0218207B1 (fr) 1990-01-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP86113639A Expired - Lifetime EP0218207B1 (fr) 1985-10-10 1986-10-02 Utilisation d'esters complexes dans des lubrifiants synthétiques et lubrifiants contenant ceux-ci

Country Status (2)

Country Link
EP (1) EP0218207B1 (fr)
DE (2) DE3536197A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03217494A (ja) * 1990-01-22 1991-09-25 Kao Corp 冷凍機油
DE4006828A1 (de) * 1990-03-05 1991-09-12 Hoechst Ag Verwendung von komplexen esteroelen als schmiermittel fuer kaeltemittelverdichter
SG59958A1 (en) * 1993-06-30 1999-02-22 Nof Corp Synthetic lubricating oil and working fluid composition for refrigeration machine
US5391312A (en) * 1993-08-02 1995-02-21 Albemarle Corportion Lubricant additives
DE19546117A1 (de) * 1995-12-11 1997-06-12 Henkel Kgaa Nichttoxische Wärmeträgeröle
US5942475A (en) * 1996-09-06 1999-08-24 Exxon Chemical Patents Inc. Engine oil lubricants formed from complex alcohol esters
KR100690351B1 (ko) 2005-07-15 2007-03-12 주식회사 엘지화학 하이드록시 피발일 하이드록시 피발레이트 에스테르 가소제조성물 및 이의 제조방법

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB768119A (en) * 1954-03-17 1957-02-13 Exxon Research Engineering Co Improvements in or relating to complex ester synthetic lubricants
NL247300A (fr) * 1959-01-14
US4064058A (en) * 1972-03-01 1977-12-20 Hercules Incorporated Mixed synthetic ester grease base stock

Also Published As

Publication number Publication date
DE3536197A1 (de) 1987-04-16
EP0218207A2 (fr) 1987-04-15
EP0218207A3 (en) 1988-01-27
DE3668184D1 (de) 1990-02-15

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