EP0923629A1 - Verwendung von hochmolekularen tensiden zur verbesserung der filtrierbarkeit in hydraulischen schmierölen - Google Patents

Verwendung von hochmolekularen tensiden zur verbesserung der filtrierbarkeit in hydraulischen schmierölen

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Publication number
EP0923629A1
EP0923629A1 EP98917295A EP98917295A EP0923629A1 EP 0923629 A1 EP0923629 A1 EP 0923629A1 EP 98917295 A EP98917295 A EP 98917295A EP 98917295 A EP98917295 A EP 98917295A EP 0923629 A1 EP0923629 A1 EP 0923629A1
Authority
EP
European Patent Office
Prior art keywords
filterability
reaction product
lubricating fluid
succinic anhydride
oil
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.)
Ceased
Application number
EP98917295A
Other languages
English (en)
French (fr)
Inventor
Olivier Clement
Christophe Le Sausse
Dominique Batelier
Jacques Cazin
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.)
Chevron Oronite SAS
Original Assignee
Chevron Chemical SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chevron Chemical SA filed Critical Chevron Chemical SA
Publication of EP0923629A1 publication Critical patent/EP0923629A1/de
Ceased legal-status Critical Current

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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10M2227/061—Esters derived from boron
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to lubricating fluids having improved filterability characteristics, and effective additives to improve the filterability characteristics of lubricating fluids such as hydraulic oils.
  • the present invention relates more particularly to lubricating fluids and additives comprising an effective amount of a filterability improving agent which comprises at least one polar group consisting of a succinic acid derivative and at least one polyolefinic chain and having a molecular weight (Mn ) from around 500 to around 2500.
  • lubricating oils such as hydraulic fluids and the like, contain additives which are designed to provide optimum performance in terms of inhibiting wear, protecting against rust, the ability to demulsification, thermal stability, hydrolysis stability and oxidation stability, air release capacity and limitation of foaming.
  • hydraulic oils must have extremely good filterability properties which are measured and evaluated using a number of detailed filterability tests such as AFNOR NFE 48690, 48691 and 48693, CETOP RP 124H, DENISON and PALL.
  • the most common means known to date include the use of metal carboxylates as described in GB 2,293,389, reducing the ZDDP concentrations from about 8 mM / kg of oil to an equal or lesser value at about 4 mM / kg of oil, or else the formulation of the additives with particular agents improving the viscosity index which are less harmful for the filterability.
  • filterability improving agents comprising at least one polar group and at least one polyolefin chain having a particular length. More advantageously, when using the compounds described below, the filterability performance is improved but this improvement obtained is generally not detrimental for the main performance criteria and can even have positive effects in certain cases.
  • the present invention relates generally to a lubricating fluid, in particular a hydraulic oil, comprising: 1) a dominant quantity of an oil of viscosity suitable for lubrication; and
  • Z represents i) a succinic acid ester comprising the reaction product of a succinic anhydride and an aliphatic polyhydric alcohol; or ii) a succinimide comprising the reaction product of a succinic anhydride and a polyamine, said reaction product being treated with a post-treatment agent;
  • R represents a polyolefin having a molecular weight (Mn) of 500 to 2,500 and an Mw / Mn ratio of 1 to 5.
  • post-treatment agents are cyclic carbonates, boric acid and boric acid derivatives.
  • the present invention also relates to an additive for a lubricating fluid composition.
  • the additive comprises an effective amount of a filterability improving agent corresponding to the above description.
  • the present invention also relates to the use of such compounds for increasing the filterability of oil compositions, in particular hydraulic oils.
  • additives and compounds of the present invention are particularly useful for increasing the filterability of hydraulic oils, they can also be used to improve the filterability of other types of oils.
  • the present invention is now described in more detail below.
  • alkenyl or alkyl substituted succinic anhydrides comprising the reaction of a polyolefin and a maleic anhydride has been described in practice.
  • the alkenyl or alkyl group R has an Mn value of approximately 500 to approximately 2500 and an Mw / Mn ratio of approximately 1 to approximately 5.
  • Polyolefin polymers suitable for reaction with maleic anhydride include polymers comprising a predominant amount of C 2 to C 5 mono-olefins, for example ethylene, propylene, butylene, isobutylene and pentene.
  • a highly valued polyolefin polymer is polyisobutene.
  • the preferred succinic anhydride as the reactant is
  • PIBSA i.e. poiy-isobutenyl succinic anhydride.
  • the filterability improving agent comprises a succinimide comprising the reaction product of a succinic anhydride with a polyamine
  • the alkenyl or alkyl substituent of the succinic anhydride serving as reactant consists of polymerized isobutene having a value of Mn d approximately 1200 to approximately 2500.
  • the alkenyl or alkyl substituent of the succinic anhydride serving as reactant consists of a polymerized isobutene having an Mn value of approximately 2100 to approximately 2400. Polyisobutenes having a value of Mn of about 2200 are highly appreciated.
  • the filterability improving agent comprises a succinic acid ester comprising the reaction product of a succinic anhydride and an aliphatic polyhydric alcohol
  • the alkenyl or alkyl substituent of succinic anhydride serving as reactant advantageously consists of a polymerized isobutene having an Mn value of 500 to 1,500. preferably a polymerized isobutene having an Mn value of 850 to 1200 is used.
  • Reactant consisting of polyhydric alcohol A particular class of filterability enhancing agents includes the reaction product of an alkenyl or alkyl substituted succinic anhydride and an aliphatic polyhydric alcohol.
  • aliphatic polyhydric alcohols examples include glycerol, pentaerythritol and sorbitol.
  • the aliphatic polyhydric alcohol is pentaerythritol.
  • the resulting ester consisting of a succinate is a filterability improving agent, designated by the code FE1.
  • Reactor consisting of a polyamine
  • the polyamine to be reacted with alkenyl or alkyl succinic anhydride to produce the polyamine alkenyl or alkyl succinimide is generally a polyalkylene polyamine having an average ratio of the number of nitrogen atoms per molecule ranging from 2 up to a maximum of about 12.
  • Suitable polyamines which can be used include the following: ethylenediamine (EDA), diethylenetriamine (DETA), triethylene tetramine (TETA), tetraethylene pentamine (TEPA), a heavy polyamine (HPA) containing approximately 5 to 7 nitrogen atoms per molecule. Mixtures of the above polyamines can also be used.
  • EDA ethylenediamine
  • DETA diethylenetriamine
  • TETA triethylene tetramine
  • TEPA tetraethylene pentamine
  • HPA heavy polyamine
  • Preferred polyamines are those having an average ratio of the number of nitrogen atoms per molecule from 2 to about 7. Highly preferred polyamines are those having an average ratio of the number of nitrogen atoms per molecule from about 5 to about 7.
  • the average ratio of the number of nitrogen atoms per molecule is calculated as follows:
  • % of N percentage of nitrogen in the polyamine or the mixture of polyamines
  • Mpa numerical average of the molecular weight of the polyamine or of the mixture of polyamines.
  • a suitable molar charge of the polyamine to alkyl- or alkenyl-succinic anhydride for the production of polyamino-alkyl- or alkenyl-succinimides is in the range of about 0.35: 1 to about 1: 1, but preferably from about 0.4: 1 to about 0.5: 1.
  • polyamino-alkenyl- or alkyl-succinimides obtained in the manner described above are also reacted with an after-treatment agent chosen between a cyclic carbonate and boric acid or a derivative of boric acid.
  • an after-treatment agent chosen between a cyclic carbonate and boric acid or a derivative of boric acid.
  • the preparation of such post-treatment polyamino-alkenyl- or alkyl-succinimides has been described in practice.
  • Preferred post-treatment agents are cyclic carbonates.
  • a particularly preferred cyclic carbonate is 1, 3-dioxalane-2-one (ethylene carbonate).
  • Ethylene carbonate is commercially available or can be prepared by methods well known in the art.
  • reaction of polyamino-alkenyl- or alkyl-succinimides with cyclic carbonates is described in United States Patent No. 4,612,132 which is cited by reference herein.
  • the reaction product of a polyisobutenyl succinic anhydride having a polyisobutenyl tail having an Mn value of about 2200 (PIBSA 2200) and an HPA, using a molar charge of HPA or PIBSA 2200 in the range of about 0.4: 1 to about 0.5: 1 was further post-treated with ethylene carbonate.
  • the resulting polyamino-alkenyl succinimide having undergone a post-treatment constituted an agent improving the filterability designated by the code FE2.
  • concentration of the filterability agents described above should be adjusted so that the desired effect (improvement of the oil filterability characteristics) is obtained without adverse effect on other performances resulting from the action of other additives which may be present in the oil composition. More particularly, it is considered that excessive concentrations of the compounds used in the context of The present invention may in certain cases have harmful effects, in particular the effects of oxidation, deterioration of thermal stability and hydrolysis of the finished oil.
  • the filterability enhancers of the present invention are particularly useful for improving the filterability characteristics of lubricating oils and, preferably, hydraulic oils. They are effective regardless of the presence or absence of an agent improving the viscosity index in the oil.
  • the improvement in filterability can be obtained for markedly different viscosity intervals.
  • an improvement in filterability can be obtained for qualities ranging from ISO VG 15 to 150, preferably for qualities ranging from ISO VG 32 to 68.
  • the AFNOR NFE 48691 filterability test comprises the following stages: formulation of the oil - incorporation of 0.2% by weight of water and mixture to form a storage emulsion at 70 ° C. for 72 hours , then storage at room temperature (24 hours). filtration of 300 ml of the oil on a Millipore filter of 0.8 ⁇ m at a pressure which depends on the filtration speed. measurement of the time required to filter 50, 100, 200 and 300 ml of oil and calculation of the corresponding IFE values.
  • the filterability indices calculated for test oils containing agents improving the filterability were greatly improved compared to reference formulations not comprising the agents improving the filterability and, in fact, are close to the "ideal" filterability index which is equal to 1.
  • the incorporation of low concentrations of the filterability agents used in the present invention in additives does not generally appear to be harmful for other properties such as wear inhibition performance, resistance to oxidation or thermal stability or resistance to hydrolysis of hydraulic oils. This was measured using tests such as the FZG seizure test, the Denison and Vickers Vane tests and piston pump tests and the Cincinnati Milacron thermal stability tests as well as the ASTM D943 and ASTM D4310 and oxidation tests.
  • the basic lubricant can be chosen from hydraulic / transmission fluids, hydraulic fluids for brakes, fluids for power steering and fluids for tractors, the precise composition of which may vary slightly.
  • the lubricating oils of the present invention contain a dominant quantity of an oil of viscosity suitable for lubrication.
  • This oil can be any hydrocarbon-based lubricating oil or a basic synthetic lubricating oil. It can be derived from synthetic or natural sources and it can consist of a paraffinic, naphtenic or asphalt base oil or a mixture thereof.
  • the oil of lubricating viscosity is prepared from a crude mineral oil by physical separation methods, such as distillation, deasphalting and dewaxing, or it can be prepared by chemical conversion, such as catalytic or non-catalytic hydrotreatment of mineral oil fractions, or by a combination of physical separation processes and chemical conversion; or it may consist of a basic synthetic hydrocarbon oil.
  • the oil of viscosity suitable for lubrication has a kinematic viscosity of 5 to 220 cSt at 40 ° C.
  • additives which are well known in the art, may be present in the improved filterability hydraulic fluid of the present invention.
  • additives may include, for example, antioxidants, viscosity index improvers, detergents, rust inhibitors, demulsifiers, foam inhibitors, corrosion inhibitors, pour point lowering agents and other antiwear agents.
  • Anti-oxidants include sterically hindered alkylphenols such as 2,6-di-tertio-butylphenol, 2,6-di-tertio-butyl-p-cresol and 2,6-di-tertio-butyl-4- (2-octyl-3-propanoic) phenol; N, N-di (alkylphenyl) amines; and alkylated phenylenediamines.
  • Viscosity index improvers include polymeric aikylmethacrylates and olefinic copolymers, such as an ethylene-propylene copolymer or styrene-butadiene copolymer.
  • Detergents include calcium alkylsalicylates, calcium alkylphenates and calcium alkarylsulfonates.
  • Anti-rust additives include alkenyl succinic acids (short chains), their partial esters and their nitrogen derivatives; and synthetic alkarylsulfonates, such as metallic dinonylnaphthalenesulfonates.
  • Demulsifiers include alkoxylated phenols and phenol-formaldehyde resins as well as synthetic alkylarylsulfonates, such as metallic dinonylnaphthalenesulfonates.
  • Foaming inhibitors include polymers of alkyl methacrylate and polymers of dimethylsilicone.
  • Corrosion inhibitors include 2,5-dimercapto-1, 3,4-thiadiazoles and their derivatives, mercapto-benzothiazoles, alkyltriazoles and benzotriazoles.
  • Pour Point Lowering Agents include polymethacrylates.
  • Anti-wear agents zinc alkyldithiophosphates (preferred), aryl phosphates and phosphites, sulphide esters, phosphosulphide compounds, and metallic or ashless dithiocarbamates.
  • the hydraulic fluidity with improved filterability of the present invention can be produced by mixing the oil of viscosity proper to the lubrication and the agent improving the filterability together with the other additives described above possibly present in the oil of viscosity suitable for lubrication.
  • the constituents of this mixture can interact during the mixing operation by modifying the filterability improving agent and / or the other additives.
  • the various preferential conditions indicated above apply both to lubricating fluids and to the process for the production of a hydraulic fluid as well as to the uses according to the present invention.
  • BASIC ADDITIVE FORMULATION a basic additive formulation comprising functional amounts of zinc dithiophosphate, ashless dithiocarbamate, calcium-containing detergent, phenolic antioxidant, anti-rust additives , demulsifiers, a foaming inhibitor based on a silicone polymer was produced by mixing so that the formulation of basic additives (XOIE 303J) represents 0.80% by weight of the formulation of finished oil.
  • the finished oil formulation had a kinematic viscosity at 40 ° C equal to about 46 cSt.
  • COMPARATIVE EXAMPLE A The formulation of base additives was mixed in a refined base oil with a solvent "A”, with the addition of an APE additive (PMA type) at a dose of 0.2% by weight.
  • EXAMPLE 1 An amount of 0.05% by weight of FE1 was added to the finished oil in Comparative Example A.
  • EXAMPLE 2 An amount of 0.05% by weight of FE2 was added to the finished oil of Comparative Example A.
  • COMPARATIVE EXAMPLE B The formulation of base additives was mixed in a refined base oil with a solvent "B” with the addition of an APE additive (PMA type) at a dose of 0.2% by weight.
  • EXAMPLE 3 An amount of 0.05% by weight of FE1 was added to the finished oil of Comparative Example A.
  • COMPARATIVE EXAMPLE C The formulation of base additives was mixed in a refined base oil with a solvent "C” with the addition of an APE additive (PMA type) at a dose of 0.2% by weight of addition an AlV (PMA type) at a dose of 4.65% by weight.
  • PMA type APE additive
  • AlV AlV
  • EXAMPLE 4 An amount of 0.05% by weight of FE1 was added to the finished oil of Comparative Example C.
  • COMPARATIVE EXAMPLE D The formulation of base additives was mixed in a "specialty of base formulation" "D" containing a certain amount of AlV (PMA type).
  • EXAMPLE 5 An amount of 0.05% by weight of FE1 was added to the finished oil of Comparative Example D.
  • COMPARATIVE EXAMPLES E and F In this example, tests were carried out in order to evaluate the optimal concentration of FE1 in filterability tests using two different base oils.
  • COMPARATIVE EXAMPLE E the base additive formulation was mixed in a refined base oil with a solvent "B” with the addition of an APE additive (PMA type) at a dose of 0.2% by weight.
  • EXAMPLE 8 An amount of 0.05% by weight of FE1 was added to the finished oil of Comparative Example E.
  • EXAMPLE 9 An amount of 0.01% by weight of FE1 was added to the finished oil of Comparative Example F.
  • EXAMPLE 10 An amount of 0.03% by weight of FE1 was added to the finished oil of Comparative Example F.
  • EXAMPLE 11 An amount of 0.05% by weight of FE1 was added to the finished oil of Comparative Example F.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP98917295A 1997-04-11 1998-04-02 Verwendung von hochmolekularen tensiden zur verbesserung der filtrierbarkeit in hydraulischen schmierölen Ceased EP0923629A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9704505 1997-04-11
FR9704505A FR2762006B1 (fr) 1997-04-11 1997-04-11 Utilisation de surfactants de haut poids moleculaire comme agents ameliorant la filtrabilite dans des lubrifiants hydrauliques
PCT/FR1998/000669 WO1998046707A1 (fr) 1997-04-11 1998-04-02 Utilisation de surfactants de haut poids moleculaires comme agents ameliorant la filtrabilite dans des lubrifiants hydrauliques

Publications (1)

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EP0923629A1 true EP0923629A1 (de) 1999-06-23

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US (1) US6624123B2 (de)
EP (1) EP0923629A1 (de)
JP (1) JP4089836B2 (de)
CA (1) CA2257800C (de)
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WO (1) WO1998046707A1 (de)

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EP1844129A1 (de) * 2005-01-13 2007-10-17 The Lubrizol Corporation Emulsionszusammensetzung
US20090301936A1 (en) * 2008-05-15 2009-12-10 Desmond Smith Composition and use thereof
KR101565794B1 (ko) * 2008-12-16 2015-11-05 삼성전자주식회사 게더링 효과를 향상시킬 수 있는 실리콘 기판 및 실리콘 웨이퍼, 상기 실리콘 웨이퍼의 열처리 방법

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JP4089836B2 (ja) 2008-05-28
CA2257800C (en) 2007-09-04
US6624123B2 (en) 2003-09-23
WO1998046707A1 (fr) 1998-10-22
US20020032127A1 (en) 2002-03-14
FR2762006A1 (fr) 1998-10-16
JP2000513041A (ja) 2000-10-03
FR2762006B1 (fr) 2003-09-12

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