EP3662041A1 - Schmiermittelzusammensetzung mit einem diester - Google Patents

Schmiermittelzusammensetzung mit einem diester

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Publication number
EP3662041A1
EP3662041A1 EP18745955.7A EP18745955A EP3662041A1 EP 3662041 A1 EP3662041 A1 EP 3662041A1 EP 18745955 A EP18745955 A EP 18745955A EP 3662041 A1 EP3662041 A1 EP 3662041A1
Authority
EP
European Patent Office
Prior art keywords
composition according
formula
linear
engine
methyl
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
Application number
EP18745955.7A
Other languages
English (en)
French (fr)
Other versions
EP3662041B1 (de
Inventor
Nicolas CHAMPAGNE
Gaël ROBINEAU
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TotalEnergies Onetech SAS
Original Assignee
Total Marketing Services SA
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Filing date
Publication date
Application filed by Total Marketing Services SA filed Critical Total Marketing Services SA
Publication of EP3662041A1 publication Critical patent/EP3662041A1/de
Application granted granted Critical
Publication of EP3662041B1 publication Critical patent/EP3662041B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • 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
    • C10M105/38—Esters of polyhydroxy compounds
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • 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
    • C10M129/74—Esters of polyhydroxy compounds
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
    • 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
    • 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
    • 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
    • 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
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/18—Anti-foaming property
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/54—Fuel economy
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to the field of engine lubricating compositions, in particular for a motor vehicle engine. It aims in particular to provide a lubricant composition with improved performance, particularly in terms of improved engine cleanliness and reduced fuel consumption.
  • Lubricating compositions also called “lubricants” are commonly used in engines for the main purpose of reducing the friction forces between the various moving metal parts in the engines. They are also effective to prevent premature wear or damage to these parts, especially their surface.
  • a lubricant composition is conventionally composed of a base oil to which are generally associated several additives dedicated to boosting the lubricating performance of the base oil, such as friction modifying additives, but also to provide additional performance.
  • additives dedicated to boosting the lubricating performance of the base oil, such as friction modifying additives, but also to provide additional performance.
  • detergent additives are very often considered in order to avoid the formation of deposits on the surface of the metal parts by dissolving the secondary products of oxidation and combustion.
  • the lubricant compositions represent an effective means for acting on the fuel consumption via their impact on the friction forces generated between the different parts of an engine.
  • the quality of the base oils, alone or in combination with viscosity index improving polymers and friction modifying additives is particularly decisive in order to obtain a saving in fuel consumption.
  • Patent application EP 2 913 386 also discloses a lubricating composition comprising from 50 to 97% by weight of a base oil and from 3 to 50% by weight of 2-ethylhexyl sebacate having fuel-oil properties. Eco.
  • the invention aims precisely to provide a lubricant composition, in particular dedicated to a vehicle engine, which combines both properties improved in terms of fuel economy and engine cleanliness.
  • the present invention thus relates, according to a first of its aspects, to a grade lubricating composition according to the classification SAEJ300 defined by the formula (X) W (Y), in which X represents 0 or 5; and Y represents an integer ranging from 4 to 20, said composition comprising at least one diester of formula (I):
  • R represent, independently of one another, a hydrogen atom or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, especially methyl;
  • s is 1, 2, 3, 4, 5 or 6;
  • n is 1, 2 or 3; it being understood that when s is different from 1, n may be identical or different; and - R a and R b , identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms;
  • R represents a linear or branched (C 1 -C 8) alkyl group
  • At least one of the beta-carbon groups R at the oxygen atoms of the ester functions represents a hydrogen atom.
  • s is 1, 2 or 3, in particular s is 1 or 2.
  • n is 2 or 3, in particular n is 2.
  • the diester of formula (I) is a diester of formula (F) below: hydrogen or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, especially a methyl group;
  • s is 1, 2 or 3, in particular s is 1 or 2;
  • n 2;
  • n 2;
  • R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms;
  • R or R ' represents a linear or branched (Ci-Cs) alkyl group.
  • At least one of the groups R or R 'in the diester of formula (F) represents a (C 1 -C 5) alkyl group, in particular (C 1 -C 4) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
  • R a and R b in formulas (I) and (F) above have a linear sequence of 7 to 14 carbon atoms, in particular 8 to 12 carbon atoms. carbon, more particularly from 8 to 11 carbon atoms and in particular from 8 to 10 carbon atoms.
  • R a and R b both represent n-octyl or n-dodecanoyl groups, preferably n-octyl groups.
  • lubricating compositions incorporating such a diester of formula (I), in particular of formula (F) above, prove to be particularly effective for their use as lubricant of an engine, in particular of a vehicle engine.
  • the present invention thus relates, in another of its aspects, to the use of a composition as described above as a lubricant for an engine, in particular a vehicle engine.
  • GB 716 086 dated 1951 proposes to use a diester in lubricating compositions.
  • this use is considered in a context very different from that of the invention.
  • the lubricant compositions considered in GB 716 086 are not in conformity with those considered according to the invention and in particular intended to be used in aircraft engines which are exposed to very large temperature variations.
  • Synthetic esters are described as being more valuable than mineral oils in that they have higher viscosity indexes and flash points, and lower pour points than mineral oils of comparable viscosity.
  • the lubricating compositions in question are of grade according to the SAEJ300 classification defined by the formula (X) W (Y), in which X represents 0 or 5; and Y represents an integer ranging from 4 to 20.
  • This grade qualifies a selection of lubricating compositions specifically intended for a motor vehicle engine application and which satisfy, in particular, quantified specificities with respect to different parameters such as cold start viscosity, cold pumpability, low shear kinematic viscosity and dynamic high shear viscosity.
  • a diester of formula (I) as defined above, and in particular of formula (F) above, as an additive in a lubricant composition of grade considered according to the invention reduces the fuel consumption of an engine.
  • the lubricant compositions of the invention meet the qualification of "Fuel-Eco", in that they provide access to reduced fuel consumption.
  • the invention also relates to the use of a diester of formula (I) as defined above, and in particular of formula (F) above, as an additive in a lubricating composition of grade according to the classification SAEJ300 defined by the formula (X) W (Y), in which X represents 0 or 5, and Y represents an integer ranging from 4 to 20, and dedicated to an engine, in particular to a vehicle engine, for reduce the fuel consumption of the engine.
  • the use of such a diester, having good detergency properties, in a lubricant composition according to the invention advantageously makes it possible to improve engine cleanliness.
  • the invention relates to the use of a diester of formula (I) as defined above, and in particular of formula (F) above, as an additive in a grade lubricant composition.
  • a diester of formula (I) as defined above, and in particular of formula (F) above, as an additive in a grade lubricant composition.
  • SAEJ300 defined by the formula (X) W (Y), in which X represents 0 or 5, and Y represents an integer ranging from 4 to 20, and dedicated to an engine, in particular to a vehicle engine, to improve engine cleanliness.
  • a lubricant composition according to the invention has the specificity of containing at least one diester of general formula (I)
  • R represent, independently of one another, a hydrogen atom or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, especially methyl;
  • s is 1, 2, 3, 4, 5 or 6; in particular s is 1, 2 or 3 and more particularly s is 1 or 2;
  • n is 1, 2 or 3; in particular n is 2 or 3 and more particularly n is 2, it being understood that when s is different from 1, n may be identical or different; and
  • R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms;
  • R represents a linear or branched (C 1 -C 8) alkyl group
  • At least one of the beta-carbon groups R at the oxygen atoms of the ester functions represents a hydrogen atom.
  • a diester of formula (I) according to the invention will be more simply referred to as a diester of the invention.
  • Ct-z where t and z are integers, a carbon chain may have from t to z carbon atoms; for example C 1-4 a carbon chain which may have from 1 to 4 carbon atoms;
  • Alkyl a saturated, linear or branched aliphatic group; for example a C 1-4 -alkyl represents a carbon chain of 1 to 4 carbon atoms, linear or branched, more particularly methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl.
  • n in formula (I) above is 2 or 3, and more particularly n is 2.
  • At least one of the R groups represents a (C 1 -C 6) alkyl group, in particular (C 1 -C 4) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
  • the diester of formula (I) according to the invention may be more particularly a diester of formula (F) below:
  • R and R ' represent, independently of one another, a hydrogen atom or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, in particular a methyl group;
  • s is 1, 2 or 3, in particular s is 1 or 2;
  • n 2;
  • n 2;
  • R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms;
  • R or R ' represents a linear or branched (Ci-Cs) alkyl group.
  • a diester according to the invention is of formula (F) in which at least one of R or R 'represents a (C 1 -C 5) alkyl group, in particular (C 1 -C 4) alkyl, linear or branched, more preferably methyl, ethyl or propyl; advantageously methyl.
  • the diester according to the invention may have the following formula (Fa):
  • R and R ' represent, independently of each other, a hydrogen atom or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl;
  • n 2;
  • n 2;
  • R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms;
  • At least one of the groups R or R ' represents a linear or branched (Ci-Cs) alkyl group, in particular methyl, ethyl or propyl, advantageously methyl.
  • At least one of the R groups represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; and at least one of R 'represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
  • the diester of the invention may be of formula (Fa) in which one of the R groups represents a linear or branched (Ci-Cs) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; and one of the groups R 'represents a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl; the other groups R and R 'representing hydrogen atoms.
  • the diester of the invention may have the following formula (F 'a):
  • one of the groups R 1 and R 2 represents a linear or branched (C 1 -C 5) alkyl group, the other representing a hydrogen atom;
  • one of the groups R 3 and R 4 represents a linear or branched (C 1 -C 5) alkyl group, the other representing a hydrogen atom;
  • R a and R b identical or different, are as defined above.
  • diester of the invention may be of formula (I "a) in which:
  • one of the groups R 1 and R 2 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom;
  • one of the groups R 3 and R 4 represents a methyl, ethyl or propyl group, advantageously methyl, the other representing a hydrogen atom.
  • the diester according to the invention can have the following formula (Fb):
  • R represent, independently of each other, a hydrogen atom or a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl;
  • n 2;
  • R a and R b identical or different, represent independently of each other, hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms.
  • At least one of R represents a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl.
  • the diester of the invention may be of formula (Fb) in which one of the R groups represents a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others represent hydrogen atoms.
  • the diester of the invention may be of formula (I) in which s is 3.
  • n which are identical, are equal to 2.
  • one of the Rs represents a group ( Ci-C5) alkyl, linear or branched, in particular methyl, ethyl or propyl, advantageously methyl, the others representing hydrogen atoms.
  • R a and R b in formula (I), ( ⁇ ), (a), (I "a) and (b), identical or different, represent hydrocarbon groups, saturated or unsaturated, linear or branched, having a linear sequence of 6 to 18 carbon atoms.
  • hydrocarbon group is meant any group having a carbon atom directly attached to the remainder of the molecule and having mainly an aliphatic hydrocarbon character.
  • R a and R b have a linear sequence of 7 to 17 carbon atoms, in particular of 7 to 14 carbon atoms, in particular of 8 to 12 carbon atoms and more particularly of 8 to 11 carbon atoms, in particular from 8 to 10 carbon atoms.
  • linear sequence from t to z carbon atoms is meant a saturated or unsaturated carbon chain, preferably saturated, comprising from t to z carbon atoms one after the other, the carbon atoms possibly present at the branches of the carbon chain are not taken into account in the number of carbon atoms (tz) constituting the linear sequence.
  • R a and R b are derived from plant, animal or petroleum origin.
  • R a and R b which are identical or different, represent groups saturated.
  • R a and R b which are identical or different, represent linear groups.
  • R a and R b represent saturated linear C 6 to C 18 , in particular C 7 to C 17 , especially C 7 to C 14 , preferably C 8 to C 12 , and more preferably C 8 to C n, hydrocarbon groups. especially in Cs to C 10 .
  • R a and R b represent linear C 6 alkyl groups. to IC8, in particular C 7 -C 17, especially C 7 -C 14, preferably Cs to C 12 and more preferably Cs to C, particularly Cs to C 10.
  • R a and R b are identical.
  • R a and R b are both n-octyl or n-undecyl, preferably n-octyl.
  • the diesters of formula (I) according to the invention may be available commercially or prepared according to synthetic methods described in the literature and known to those skilled in the art. These synthetic methods more particularly implement an esterification reaction between a diol compound of formula HO - ([C (R) 2 ] n -O) s -OH and compounds of formula R a -COOH and R b - COOH, with R a and R b , identical or different, being as defined above.
  • (F) above can be obtained by esterification reaction between a mono- or polypropylene glycol, in particular monopropylene glycol (MPG) or dipropylene glycol (DPG), and one or more carboxylic acids R a -COOH and R b -COOH adequate.
  • MPG monopropylene glycol
  • DPG dipropylene glycol
  • R representing a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms;
  • one of the groups R 'representing a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms, can be obtained via an esterification reaction between dipropylene glycol (DPG) and one or more suitable carboxylic acids R a -COOH and R b -COOH.
  • DPG dipropylene glycol
  • one of the groups R representing a linear or branched (C 1 -C 5) alkyl group, in particular a methyl, ethyl or propyl group, advantageously methyl, the others representing hydrogen atoms,
  • MPG monopropylene glycol
  • R a -COOH and R b -COOH suitable.
  • the diesters of formula (I) may be mixed with one or more base oils, in particular as defined below, to form a ready-to-use lubricant composition. Alternatively, they may be added alone, or in admixture with one or more other additives, as defined below, as additives to be added to a base oil mixture to improve the properties of the lubricant composition.
  • a diester of formula (I) according to the invention may be used in a lubricating composition alone or in combination with one or more other diesters of formula (I).
  • a lubricating composition according to the invention may thus comprise a mixture of diesters of formula (I) formed at least 50% by weight of one or more diesters of formula (I) for which R a and R b represent groups C 6 -C 10 saturated linear hydrocarbon radicals, in particular C 8 -C 10 alkyl groups.
  • a lubricating composition according to the invention comprises, at least as a diester of formula (I) according to the invention, a diester or mixture of diesters resulting from the esterification reaction between the monopropylene glycol ( MPG) or dipropylene glycol (DPG) and a C 7 -C 19 carboxylic acid, in particular between MPG or DPG and nonanoic or undecanoic acid.
  • a lubricating composition according to the invention comprises, at least as a diester of formula (I) according to the invention, a diester or mixture of diesters resulting from the esterification reaction between the MPG or the DPG and the nonanoic acid. It is up to those skilled in the art to adapt the diester content (s) of formula (I) according to the invention to be used in a lubricating composition.
  • a lubricating composition according to the invention may comprise from 1 to 30% by weight of diester (s) of formula (I), relative to the total weight of the composition.
  • it may comprise from 5 to 30% by weight of diester (s) of formula (I), in particular from 5 to 25% by weight, more particularly from 10 to 25% by weight, still more particularly from 10 to 25% by weight. 20% by weight.
  • a lubricating composition according to the invention may comprise, in addition to one or more diesters of formula (I) as defined above, one or more base oils, as well as additives, in particular as defined in the remainder of the text.
  • a lubricating composition according to the invention may further comprise one or more base oils.
  • base oils may be chosen from the base oils conventionally used in the field of lubricating oils, such as mineral, synthetic or natural oils, animal or vegetable oils or mixtures thereof.
  • the base oils used in the lubricant compositions according to the invention may in particular be oils of mineral or synthetic origins belonging to groups I to V according to the classes defined in the API classification (Table A), or their equivalents according to the classification. ATIEL, or mixtures thereof. Viscosity index
  • Mineral base oils include all types of bases obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalphating, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing.
  • the synthetic base oils may be esters of carboxylic acids and alcohols or polyalphaolefins.
  • the polyalphaoleils used as base oils are, for example, obtained from monomers comprising from 4 to 32 carbon atoms, for example from decene, octene or dodecene, and whose viscosity at 100 ° C. is between 1.5 and 15 mm 2 .s _1 according to ASTM D445.
  • Their average molecular weight is generally between 250 and 3000 according to ASTM D5296.
  • Mixtures of synthetic and mineral oils can also be used.
  • lubricating bases there is generally no limitation on the use of different lubricating bases to make the lubricating compositions according to the invention, except that they must have properties, in particular viscosity, viscosity index, sulfur content. , oxidation resistance, adapted for use for vehicle engines. Well Of course, they must also not affect the properties provided by the oil or the diesters of general formula (I) with which they are combined.
  • a lubricating composition according to the invention comprises a base oil chosen from oils of group II, III and IV of the API classification.
  • a lubricating composition according to the invention may comprise at least one Group III base oil.
  • a lubricating composition according to the invention may comprise at least 50% by weight of base oil (s) relative to its total weight, in particular at least 60% by weight of base oil (s), and more particularly between 60 and 99% by weight of base oil (s).
  • the group III oil or oils are at least 50% by weight, in particular at least 60% by weight of the total weight of the base oils of the composition.
  • a lubricating composition according to the invention may furthermore comprise all types of additives suitable for use in a lubricant for a vehicle engine, in particular a motor vehicle.
  • additives may be introduced individually and / or in the form of a mixture similar to those already available for sale for commercial motor vehicle lubricant formulations with a performance level as defined by ACEA ( Association of European Automobile Manufacturers) and / or ⁇ (American Petroleum Institute), well known to those skilled in the art.
  • ACEA Association of European Automobile Manufacturers
  • ⁇ American Petroleum Institute
  • a lubricating composition according to the invention may thus comprise one or more additives chosen from friction-modifying additives, anti-wear additives, extreme pressure additives, detergent additives, antioxidant additives, viscosity index (VI) improvers. , pour point depressants (PPD), dispersants, antifoams, thickeners, and mixtures thereof.
  • friction modifying additives they may be chosen from compounds providing metal elements and compounds free of ash.
  • transition metal complexes such as Mo, Sb. Sn, Fe, Cu, Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
  • the ashless friction modifier additives are generally of organic origin and may be selected from monoesters of fatty acids and polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides, amines oily fatty acid esters or glycerol esters.
  • the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • a lubricant composition according to the invention comprises at least one friction-modifying additive, in particular based on molybdenum.
  • the molybdenum-based compounds may be chosen from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and mixtures thereof.
  • a lubricant composition according to the invention comprises at least one Mo-DTC compound and at least one Mo-DTP compound.
  • a lubricating composition may in particular comprise a molybdenum content of between 1000 and 2500 ppm.
  • such a composition allows for additional fuel savings.
  • a lubricant composition according to the invention may comprise from 0.01 to 5% by weight, preferably from 0.01 to 5% by weight, more particularly from 0.1 to 2% by weight, or even more particularly from 0.1 to 1.5% by weight, based on the total weight of the lubricant composition, of friction modifying additives, advantageously including at least one molybdenum-based friction modifying additive.
  • friction modifying additives advantageously including at least one molybdenum-based friction modifying additive.
  • the anti-wear additives and the extreme pressure additives they are more particularly dedicated to protecting the friction surfaces by forming a protective film adsorbed on these surfaces. There is a wide variety of anti-wear additives.
  • the anti-wear additives chosen from polysulfide additives, sulfur-containing olefin additives or phospho-sulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically dialkyldithiophosphates, are particularly suitable for lubricating compositions according to the invention. zinc or ZnDTP.
  • the preferred compounds have the formula Zn ((SP (S) (OR) (OR ')) 2 , in which R and R', which may be identical or different, independently represent an alkyl group, preferably containing from 1 to 18 carbon atoms.
  • a lubricant composition according to the invention may comprise from 0.01 to 6% by weight, preferably from 0.05 to 4% by weight, more preferably from 0.1 to 2% by weight, relative to the weight total composition, anti-wear additives and extreme pressure additives.
  • antioxidant additives they are essentially dedicated to delaying the degradation of the lubricating composition in service. This degradation can notably result in the formation of deposits, the presence of sludge or an increase in the viscosity of the lubricant composition. They act in particular as radical inhibitors or destroyers of hydroperoxides.
  • antioxidant additives commonly used mention may be made of phenolic-type antioxidants, antioxidant-type amine additives and phosphosulfur antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can be ash generators. Phenolic antioxidant additives may be ash-free or may be in the form of neutral or basic metal salts.
  • the antioxidant additives may especially be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted by at least one C 1 -C 2 alkyl group, ⁇ , ⁇ '-dialkyl-aryl diamines and mixtures thereof.
  • the sterically hindered phenols are chosen from compounds comprising a phenol group including at least one carbon of carbon carrying the alcohol function is substituted with at least one C 1 -C 10 alkyl group, preferably a C 1 -C 6 alkyl group, preferably a C 4 alkyl group, preferably with the ter-butyl group.
  • Amino compounds are another class of antioxidant additives that can be used, optionally in combination with phenolic antioxidant additives.
  • amine compounds are aromatic amines, for example aromatic amines of formula NR 5 R 6 R 7 in which R 5 represents an optionally substituted aliphatic or aromatic group, R 6 represents an aromatic group, optionally substituted, R 7 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 8 S (O) z R 9 in which R 8 represents an alkylene group or an alkenylene group, R 9 represents an alkyl group, a alkenyl group or an aryl group and z represents 0, 1 or 2.
  • Sulfurized alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.
  • the lubricant composition according to the invention may contain all types of antioxidant additives known to those skilled in the art.
  • the lubricating composition comprises at least one ash-free antioxidant additive.
  • a lubricating composition according to the invention may comprise from 0.1 to 2% by weight, relative to the total weight of the composition, of at least one antioxidant additive.
  • detergent additives they generally make it possible to reduce the formation of deposits on the surface of the metal parts by dissolving the secondary products of oxidation and combustion.
  • the detergent additives that can be used in a lubricant composition according to the invention are generally known to those skilled in the art.
  • the detergent additives may be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
  • the associated cation may be a metal cation of an alkali metal or alkaline earth metal.
  • the detergent additives are preferably chosen from alkali metal or alkaline-earth metal salts of carboxylic acids, sulphonates, salicylates, naphthenates, as well as the salts of phenates.
  • the alkaline and alkaline-earth metals are preferably calcium, magnesium, sodium or barium. These metal salts generally comprise the metal in stoichiometric amount or in excess, therefore in an amount greater than the stoichiometric amount.
  • the excess metal bringing the overbased character to the detergent additive is then generally in the form of a metal salt insoluble in the base oil, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
  • a lubricating composition according to the invention may comprise from 0.5 to 8%, preferably from 0.5 to 4% by weight, relative to the total weight of the lubricant composition, of detergent additive.
  • a lubricating composition according to the invention may comprise less than 4% by weight of detergent additive (s), in particular less than 2% by weight, in particular less than 1% by weight, or even be free of detergent additive.
  • pour point depressant additives also called “PPD” agents for “Pour Point Depressant” in English
  • PPD Point Depressant
  • pour point reducing agents there may be mentioned alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
  • the dispersing agents ensure the suspension and evacuation of the insoluble solid contaminants constituted by the secondary oxidation products that form when the lubricant composition is in use.
  • They can be chosen from Mannich bases, succinimides and their derivatives.
  • a lubricant composition according to the invention may comprise from 0.2 to 10% by weight of dispersing agent (s), relative to the total weight of the composition.
  • Viscosity Index (VI) improvers particularly viscosity index improvers, provide good cold strength and minimum viscosity at high temperatures.
  • viscosity index improver polymers include polymeric esters, homopolymers or copolymers, hydrogenated or non-hydrogenated styrene, butadiene and isoprene, homopolymers or copolymers of olefin, such as ethylene or propylene, polyacrylates and polymethacrylates (PMA).
  • a lubricant composition according to the invention may comprise from 1 to 15% by weight of additive (s) improving the viscosity index, relative to the total weight of the lubricating composition.
  • the anti-foam additives may be chosen from polar polymers such as polymethylsiloxanes or polyacrylates.
  • a lubricant composition according to the invention may comprise from 0.01 to 3% by weight of anti-foam additive (s), relative to the total weight of the lubricant composition.
  • the lubricant compositions according to the invention find a particularly advantageous application as lubricants for an engine, in particular for a vehicle engine and more particularly for a light vehicle.
  • a lubricating composition according to the invention has a particularly advantageous viscosity grade.
  • the viscosity grade of a lubricating composition according to the invention can be chosen in particular from:
  • Y represents an integer ranging from 4 to 20, in particular ranging from 4 to 16 or from 4 to 12;
  • the grade according to the SAEJ300 classification of a lubricant composition according to the invention is chosen from 0W4, 0W8, 0W12, 0W16, 0W20, 5W4, 5W8, 5W12, 5W16 and 5W20.
  • a lubricant composition according to the invention may have a grade according to the SAEJ300 classification of 0W20 or 0W16.
  • the kinematic viscosity measured at 100 ° C. according to the ASTM D445 standard of a lubricating composition according to the invention is between 3 and 15 mm 2 .
  • s "1 in particular between 3 and 13 mm 2.
  • s " 1 is measured at 100 ° C. according to the ASTM D445 standard of a lubricating composition according to the invention.
  • the viscosity measured at high temperature and high shear, HTHS (for "high temperature high-shear viscosity measurement” in English), measured at 150 ° C., is equal to or greater than 1.7 mPa.s, preferably between 1.7 and 3.7 mPa.s, advantageously between 2.3 and 3.7 mPa.s.
  • the HTHS measurement is performed at high shear (10 6 s -1 ) and at 150 ° C according to standard methods CEC-L-36-A-90, ASTM D4683 and ASTMD4741.
  • a lubricant composition according to the invention has a Noak volatility, determined according to the ASTM D5800 standard, less than or equal to 15%, in particular less than or equal to 14%.
  • a lubricant composition according to the invention in particular by the use of a diester of formula (I) according to the invention, advantageously makes it possible to combine at the same time good properties in terms of reduction of consumption. fuel and engine cleanliness.
  • the invention thus relates to the use of a diester of formula (I) according to the invention in a grade lubricating composition according to the SAEJ300 classification defined by the formula (X) W (Y), in which X represents 0 or 5 , and Y represents an integer ranging from 4 to 20, in particular dedicated to an engine, in particular a vehicle engine.
  • the engine cleanliness is measured by rating engine piston fouling after an engine test implementing a lubricant composition to be tested, particularly with respect to a Group III base oil.
  • lubricating compositions according to the invention and comparative compositions, for example comprising monoesters or diesters other than those of the invention, replacing a diester according to the invention, have been formulated with the following components shown in Table 1:
  • esters according to the invention and to the invention have been obtained by esterification reaction between a compound having at least two alcohol functions and at least two fatty acids, said acids possibly being identical or different.
  • esters outside the invention have also been obtained by esterification reaction between a fatty acid having at least two carboxylic acid functions and at least two compounds having at least one alcohol function, said alcohols being identical or different.
  • Tables 2 and 3 below show the details of the lubricant compositions according to the invention and comparative compositions and their physicochemical characteristics.
  • the lubricating compositions are obtained by simply mixing at room temperature, the following components:
  • a conventional additive package comprising a dispersant, detergents, an antiwear,
  • a viscosity index improver 1 which is a conventional polymer of hydrogenated styrene polyisoprene commercially available from the company Infineum under the trade name "SV®",
  • a viscosity index improver 2 which is a conventional polymer of hydrogenated styrene polyisoprene commercially available from Infineum under the trade name "SV®",
  • a viscosity index improver 3 which is a conventional polymer of polymethacrylate commercially available from the company Evonik under the trade name "Viscoplex®",
  • a friction modifier which is a conventional organomolybdenum compound commercially available from the company Adeka under the trade name "Sakuralube®”
  • a pour point depressant additive which is a conventional polymer of polymethacrylate commercially available from the company Evonik under the trade name "Viscoplex®”
  • the test is performed using an EB 1.2 L Turbo engine, whose power is 81 kW at 5500 rpm, driven by an electric generator to impose a rotation speed of between 900 and 4500 revolutions / min while a torque sensor can measure the friction torque generated by the movement of the parts in the engine.
  • the friction torque induced by the test lubricant is compared for each speed and each temperature to the torque induced by the reference lubricant composition (SAE 0W30).
  • the speed ranges, the variation of the speed as well as the temperature were chosen to cover, in the most representative way possible, the points of the NEDC certified cycle.
  • the instructions implemented are:
  • compositions according to the invention make it possible to increase the Fuel Eco in contrast to compositions comprising no ester or esters different from the esters of the invention.
  • the test is carried out using a Nissan HR12DDR engine, whose power is 180 kW at 6500 rpm, driven by an electric generator to impose a rotation speed of between 1000 and 4400 revolutions / min while a torque sensor makes it possible to measure the friction torque generated by the movement of the parts in the engine.
  • the friction torque induced by the test lubricant is compared for each regime and each average torque temperature induced by the reference lubricating composition (SAE 0W16) that was evaluated before and after the test lubricant.
  • the speed ranges, the variation of the speed as well as the temperature were chosen to cover, in the most representative way possible, the points of the NEDC certified cycle.
  • the instructions implemented are:
  • the friction gain is evaluated for each lubricant composition (C2, C3, CC4 to CC6) as a function of the temperature and the speed of the engine and in comparison with the friction of the reference lubricant composition.
  • compositions according to the invention make it possible to increase the Fuel Eco in contrast to the compositions comprising no ester or esters different from the esters of the invention, such as 2-ethylhexyl sebacate.
  • the test is carried out using a Hyundai L13-B engine, whose power is 81 kW at 5500 rpm, driven by an electric generator to impose a speed of rotation between 650 and 5000 revolutions / min while a torque sensor can measure the friction torque generated by the movement of the parts in the engine.
  • the friction torque induced by the test lubricant is compared for each speed and each temperature to the torque induced by the reference lubricating composition (SAE 0W16).
  • the speed ranges, the variation of the speed as well as the temperature were chosen to cover, in the most representative way possible, the points of the NEDC certified cycle.
  • the instructions implemented are:
  • the friction gain is evaluated for each lubricant composition (C4 and CC7) as a function of the temperature and the speed of the engine and in comparison with the friction of the reference lubricant composition.
  • compositions according to the invention make it possible to increase the Fuel Eco in contrast to the compositions comprising no ester or esters different from the esters of the invention, such as 2-ethylhexyl sebacate.
  • CC8 are evaluated according to the following method.
  • Each lubricating composition (10 kg) is evaluated during a cleanliness test of a diesel engine with a common rail for cars.
  • the engine has a displacement of 1.4 L for 4 cylinders. Its power is 80 kW.
  • the cycle time of the test is 96 hours alternating idle speed and 4 000 rpm.
  • the temperature of the lubricating composition is 145 ° C. and the temperature of the water of the cooling system is 100 ° C. No emptying or extra makeup composition is performed during the test. EN 590 fuel is used.
  • the test is carried out in two phases for a total duration of 106 hours and according to a first rinsing and lapping step for 10 hours and then in a second step with the evaluated composition (4 kg), finally according to an endurance stage of a duration of 96 hours with the evaluated composition (4 kg).

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
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FR1757485A FR3069864B1 (fr) 2017-08-03 2017-08-03 Composition lubrifiante comprenant un diester
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FR3069864A1 (fr) 2019-02-08
KR20200055707A (ko) 2020-05-21
US20210122992A1 (en) 2021-04-29
CN111094523A (zh) 2020-05-01
EP3662041B1 (de) 2022-05-11
FR3069864B1 (fr) 2019-08-16
WO2019025446A1 (fr) 2019-02-07

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