EP0444830A1 - Composition à base de succinimide - Google Patents

Composition à base de succinimide Download PDF

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Publication number
EP0444830A1
EP0444830A1 EP91301434A EP91301434A EP0444830A1 EP 0444830 A1 EP0444830 A1 EP 0444830A1 EP 91301434 A EP91301434 A EP 91301434A EP 91301434 A EP91301434 A EP 91301434A EP 0444830 A1 EP0444830 A1 EP 0444830A1
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EP
European Patent Office
Prior art keywords
polyamine
acylating agent
copper
oil
mole ratio
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.)
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Application number
EP91301434A
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German (de)
English (en)
Inventor
Roger Scattergood
David Kenvyn Walters
John F. Sieberth
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Afton Chemical Ltd
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Afton Chemical Ltd
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Publication date
Application filed by Afton Chemical Ltd filed Critical Afton Chemical Ltd
Publication of EP0444830A1 publication Critical patent/EP0444830A1/fr
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Definitions

  • the arylene group When R' is arylene, the arylene group will generally contain from 6 to 20 carbon atoms, e.g., phenylene, naphthylene, and the like.
  • the arylene groups may be alkyl substituted by from 1 to 14 carbon atoms. Exemplary of such alkarylene groups are -Ar(CH3)-, -Ar(C2H5)-, -Ar(CH3)2-, -Ar(CH3)3-, and the like, wherein "Ar” is a benzene ring.
  • R' is aralkylene
  • the alkylene groups as described above can be substituted by one or more (e.g., 1-3) aryl groups, e.g., phenyl, tolyl, etc.
  • Illustrative oil-soluble copper compounds which may be used in accordance with this invention include cuprous diphenyl dithiophosphate, cuprous di-sechexyl dithiophosphate, cuprous di-isooctyldithiophosphate, cupric naphthenate, cupric oleate, cupric dithiocarbamate, cupric diethyldithiocarbamate, cupric dibutyldithiocarbamate, cupric dioctyldithiocarbamate, lactone oxazoline complexed with copper thiocyanate, bis-oxazoline complexed with copper thiocyanate, bis-oxazoline complexed with copper acetate, copper acetylacetonate, copper octylacetoacetate, and the like.
  • the copper-containing antioxidant is employed in the lubricating oil compositions in amounts in the range of 40 to 500, and preferably in the range of 60 to 300, and most preferably, in the range of 100 to 200 parts by weight of copper, per million parts by weight of the lubricant.
  • the acyclic hydrocarbyl substituted succinic acylating agents include the hydrocarbylsubstituted succinic acids, the hydrocarbyl-substituted succinic anhydrides, the hydrocarbyl-substituted succinic acid halides (especially the acid fluorides and acid chlorides), and the esters of the hydrocarbyl-substituted succinic acids and lower alcohols (e.g., those containing up to 7 carbon atoms), etc., that is, hydrocarbyl-substituted compounds which can function as carboxylic acylating agents.
  • the preferred polyamines used in the practice of this invention are the alkylene polyamines represented by the formula H2N(CH2) n (NH(CH2) n ) m NH2 wherein n is 2 to 10 (preferably 2 to 4, more preferably 2 to 3, and most preferably 2) and m is 0 to 10, (preferably 1 to 6).
  • Illustrative are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, spermine, pentaethylene hexamine, propylene diamine (1,3-propanediamine), butylene diamine (1,4-butanediamine), hexamethylene diamine (1,6-hexanediamine), decamethylene diamine (1,10-decanediamine), and the like.
  • Preferred for use is tetraethylene pentamine or a mixture of ethylene polyamines which approximates tetraethylene pentamine such as "DOW E-100" (a commercial mixture available from Dow Chemical Company, Midland, Michigan).
  • the acylating agent utilized in step (ii) above is (1) one or a mixture of vicinal dicarboxylic acids containing from 4 to 30 (preferably 4 to 10) carbon atoms in the molecule and characterized in that the two carboxyl groups are separated from each other by two aliphatic carbon atoms, or (2) one or a mixture of anhydrides, acid halides, or esters of such dicarboxylic acids, or (3) any combination of (1) and (2).
  • suitable acylating agents for use in step (ii) are:
  • Such acylating agent thus encompasses such compounds as maleic anhydride, maleic acid, fumaric acid, malic acid, thiomalic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, chloromaleic acid, ethylmaleic anhydride, dimethylmaleic anhydride, ethylmaleic acid, dimethylmaleic acid, hexylmaleic acid, succinic acid, succinic anhydride, butylsuccinic anhydride, octenylsuccinic anhydride, hexenylsuccinic anhydride, octadecenylsuccinic anhydride, eicosenylsuccinic anhydride, docosenylsuccinic anhydride, etc., and the corresponding acid halides, or esters which are preferably esters of lower alcohols.
  • the succinimide dispersants utilized pursuant to this invention are prepared by a process which comprises (i) reacting at least one polyamine with at least one oil soluble acyclic hydrocarbyl substituted succinic acylating agent in which such acyclic hydrocarbyl substituent contains an average of at least 40 carbon atoms, such reaction being conducted using proportions such that the acylating agent is reacted with the polyamine in a mole ratio of from 1.05 to 2.85 moles per mole of polyamine, and (ii) reacting the product so formed with (a) at least one vicinal dicarboxylic acid acylating agent containing 4 to 30 carbon atoms in the molecule and in which the two carboxyl groups are separated from each other by two aliphatic carbon atoms, or (b) an anhydride, acid halide, or ester of at least one such dicarboxylic acid acylating agent, or (c) a combination of (a) and (b), using in the reaction of
  • the additive concentrates of this invention will generally contain a suitable diluent or solvent such as a natural or synthetic lubricating oil of appropriate viscosity, together with the above-described oil-soluble copper-containing antioxidant and the above-described succinimide dispersant.
  • a suitable diluent or solvent such as a natural or synthetic lubricating oil of appropriate viscosity
  • the concentrate will contain the copper-containing antioxidant or mixture of copper-containing antioxidants and the succinimide or mixture of succinimide dispersants in relative amounts such that there is 0.0001 to 0.5, preferably from 0.0004 to 0.1, and most preferably from 0.001 to 0.01 part by weight of copper per part by weight of the succinimide dispersant(s).
  • departures from these ranges are permissible and are within the scope of this invention whenever such departures are deemed necessary or appropriate under any given set of circumstances.
  • Natural oils including vegetable oils such as rapeseed oil can also be used either alone or in combination with other lubricant types.
  • the term lubricating oil for this disclosure includes all the foregoing.
  • the succinimide dispersant may be conveniently dispersed as a concentrate of 10 to 80 weight percent of mineral oil, e.g., Solvent 100 Neutral oil with or without other additives being present, and such concentrates are a further embodiment of this invention.
  • Finished lubricating oil compositions and additive concentrates of this invention are prepared containing the oil-soluble copper-containing antioxidant and a succinimide dispersant produced as described above, together with conventional amounts of one or more other additives to provide their normal attendant functions.
  • conventional additives as viscosity index improvers, dispersant viscosity index improvers, rust inhibitors, metal detergent additives, antiwear additives, extreme pressure additives, and the like.
  • additional antioxidants such as phenolic antioxidants, amine antioxidants, etc., can be utilized in the compositions of this invention.
  • additional additives that can be used in forming finished lubricants or finished additive concentrates of this invention are such substances as the zinc dialkyl (C3-C8) dithiophosphate wear inhibitors, generally present in amounts of about 0.5 to 5 weight percent.
  • Useful detergents include the oil-soluble normal basic or over-based metal, e.g., calcium, magnesium, barium, etc., salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, oil-soluble fatty acids, alkyl salicylic acids, sulfurized or unsulfurized alkyl phenates, and hydrolyzed or unhydrolyzed phosphosulfurized polyolefins.
  • Viscosity index improvers include hydrocarbon polymers grafted with, for example, nitrogen-containing monomers, olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates or alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrrolidone or dimethylamino-alkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer such as maleic anhydride which may be further reacted with an alcohol or an alkylene polyamine, styrene/maleic anhydride polymers post-treated with alcohols and amines, etc.
  • Antiwear activity can be provided by about 0.01 to 2 weight percent of the aforementioned metal dihydrocarbyl dithiophosphates and the corresponding precursor esters, phosphosulfurized pinenes, sulfurized olefins and hydrocarbons, sulfurized fatty esters and alkyl polysulfides.
  • Preferred are the zinc dihydrocarbyl dithiophosphates which are salts of dihydrocarbyl esters of dithiophosphoric acids.
  • additives include effective amounts of friction modifiers or fuel economy additives such as the alkyl phosphonates as disclosed in U.S. 4,356,097, aliphatic hydrocarbyl substituted succinimides as disclosed in EPO 0020037, dimer acid esters, as disclosed in U.S. 4,105,571, oleamide, etc., which are present in the oil in amounts of 0.1 to 5 weight percent.
  • fuel economy additives such as the alkyl phosphonates as disclosed in U.S. 4,356,097, aliphatic hydrocarbyl substituted succinimides as disclosed in EPO 0020037, dimer acid esters, as disclosed in U.S. 4,105,571, oleamide, etc.
  • Glycerol oleates are another example of fuel economy additives and these are usually present in very small amounts, such as 0.05 to 0.2 weight percent based on the weight of the formulated oil.
  • maleic anhydride (MA) is added to the first stage reaction product in amount equivalent to 1.25 moles per mole of TEPA used in the first stage and the resultant mixture is heated at 165-170°C for 1.5 hours.
  • the succinimide is thus formed using a total mole ratio of anhydrides to TEPA of 3.05:1.
  • the mole ratio of PIBSA:MA in this synthesis is 1.44:1.
  • the reaction product is suitably diluted with 100 solvent neutral mineral oil such that the nitrogen content of the blend is about 1.8%.
  • Example 2 The same general procedure as in Example 1 is employed except that the PIBSA:TEPA mole ratio in the first stage is 2.3:1 and that in the second stage the MA is used in amount equivalent to a mole ratio of 1:1 relative to the TEPA used in the first stage.
  • the total mole ratio of anhydrides to polyamine is thus 3.3:1, and the mole ratio of PIBSA:MA is 2.3:1.
  • Example 1 The procedure of Example 1 is repeated except that in the first stage the PIBSA and TEPA are reacted in a mole ratio of 2.05:1 and in the second stage the MA is used in amount equivalent to a mole ratio of 2:1 relative to the TEPA used in the first stage.
  • the total mole ratio of anhydrides to polyamine is 4.05:1
  • the PIBSA:MA mole ratio is 1.03:1.
  • maleic acid is added to the first stage reaction product in amount equivalent to one mole per mole of TEPA used in the first stage and the resultant mixture is heated at 165-170°C for 1.5 hours.
  • the succinimide is thus formed using a total mole ratio of acylating agents to TEPA of 3.05:1, and the mole ratio of PIBSA to maleic acid is 2.05:1.
  • the reaction product is suitably diluted with mineral oil base stock to provide a handleable concentrate.
  • Example 6 The procedure of Example 6 is repeated except that fumaric acid is used in the second stage in amount equivalent to a mole ratio of 1:1 relative to the TEPA used in the first stage.
  • the total mole ratio of acylating agents to polyamine is 3.05:1
  • the mole ratio of PIBSA to fumaric acid is 2.05:1.
  • Example 7 The procedure of Example 7 is repeated using an equivalent amount of malic acid in lieu of fumaric acid in the second stage.
  • the total mole ratio of acylating agents to polyamine is 3.05:1
  • the mole ratio of PIBSA to malic acid is 2.05:1.
  • Example 8 The procedure of Example 8 is repeated using in the second stage an equivalent amount of succinic acid in lieu of malic acid.
  • the total mole ratio of of acylating agents to polyamine is 3.05:1, and the mole ratio of PIBSA to succinic acid is 2.05:1.
  • PIBSA is reacted with TEPA in the first stage in a mole ratio of 2.3:1.
  • maleic anhydride is reacted using 0.75 mole per mole of TEPA used in the first stage.
  • the product thus is formed with a total mole ratio of acylating agents to TEPA of 3.05:1.
  • the mole ratio of PIBSA to MA is 3.07:1.
  • Example 15 To individual portions of the respective additive concentrates of Example 15 are added the following components such that the finished concentrates contain 5.5, 17.6, and 27.5% of overbased sulfonates; 1.7, 10.2, and 21.25% of zinc dialkyl dithiophosphate; and/or 0.002, 0.006, and 0.02% of antifoam agent.
  • Example 15 The additive concentrates of Example 15 are blended with mineral lubricating oil base stocks and synthetic lubricating oil base stocks such as diester oils and hydrogenated poly- ⁇ -olefin lubricants in amounts such that the copper content of the finished lubricant is in one instance 40 ppm, in another instance 80 ppm, in still another instance 100 ppm, in yet another instance 140 ppm, in a further instance 160 ppm, in yet a further instance 200 ppm, and in a still further instance 300 ppm.
  • Viscosity index improver is included in the base oils in amounts between 0.5 and 5% to achieve desired viscosity specifications.
  • Example 17 The procedure of Example 17 is repeated using the finished additive concentrates of Example 16.

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  • Organic Chemistry (AREA)
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EP91301434A 1990-02-26 1991-02-22 Composition à base de succinimide Withdrawn EP0444830A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0532264A2 (fr) * 1991-09-09 1993-03-17 Betz Europe, Inc. Traitement thermique d'une matière liquide hydrocarbonée
GB2288815A (en) * 1994-04-08 1995-11-01 Exxon Chemical Patents Inc Lubricating oil anti-wear additives
US5466387A (en) * 1993-06-16 1995-11-14 Agip Petroli S.P.A. Oil-soluble adducts of disuccinimides and anhydrides of unsaturated bicarboxylic aliphatic acids
WO1995031522A1 (fr) * 1994-05-16 1995-11-23 Exxon Chemical Patents Inc. Compositions lubrifiantes
EP0709447A1 (fr) * 1994-10-25 1996-05-01 Exxon Research And Engineering Company Composés aromatiques polycyliques pour le contrÔle amélioré des dépÔts
WO1996012779A1 (fr) * 1994-10-25 1996-05-02 Exxon Research And Engineering Company Nouveaux additifs a base de cobalt regulant les depots
EP1195427A2 (fr) * 2000-09-28 2002-04-10 Nippon Mitsubishi Oil Corporation Compositions lubrifiantes convenant comme huiles moteur
JP2008260946A (ja) * 1996-10-29 2008-10-30 Idemitsu Kosan Co Ltd 新規なコハク酸イミド化合物とその製造方法及び該化合物を含有した潤滑油添加剤、並びに該化合物を配合したディーゼルエンジン用潤滑油組成物
WO2015021135A1 (fr) * 2013-08-09 2015-02-12 The Lubrizol Corporation Dépôts réduits dans un moteur provenant d'agent dispersant traité au cuivre

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GB2056482A (en) * 1979-08-13 1981-03-18 Exxon Research Engineering Co Lubricating oil compositions
EP0072645A2 (fr) * 1981-08-17 1983-02-23 Exxon Research And Engineering Company Succinimide dispersant amélioré pour huile lubrifiante
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
EP0277729A1 (fr) * 1987-01-21 1988-08-10 Ethyl Corporation Compositions lubrifiantes anti-usures ayant des teneurs faibles en phosphore
EP0280580A2 (fr) * 1987-02-27 1988-08-31 Exxon Chemical Patents Inc. Lubrifiants à basse teneur en phosphore
EP0294045A2 (fr) * 1987-05-11 1988-12-07 Exxon Chemical Patents Inc. Agent modifiant le mélange à base d'amine dans des compositions d'huile lubrifiante
EP0309105A1 (fr) * 1987-09-16 1989-03-29 Exxon Chemical Patents Inc. Additifs améliorant les propriétés antirouilles de compositions oléagineuses
EP0331397A2 (fr) * 1988-02-29 1989-09-06 Exxon Chemical Patents Inc. Additifs dispersants solubles dans des huiles et utiles dans des compositions huileuses

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GB2056482A (en) * 1979-08-13 1981-03-18 Exxon Research Engineering Co Lubricating oil compositions
US4505718A (en) * 1981-01-22 1985-03-19 The Lubrizol Corporation Organo transition metal salt/ashless detergent-dispersant combinations
EP0072645A2 (fr) * 1981-08-17 1983-02-23 Exxon Research And Engineering Company Succinimide dispersant amélioré pour huile lubrifiante
EP0277729A1 (fr) * 1987-01-21 1988-08-10 Ethyl Corporation Compositions lubrifiantes anti-usures ayant des teneurs faibles en phosphore
EP0280580A2 (fr) * 1987-02-27 1988-08-31 Exxon Chemical Patents Inc. Lubrifiants à basse teneur en phosphore
EP0294045A2 (fr) * 1987-05-11 1988-12-07 Exxon Chemical Patents Inc. Agent modifiant le mélange à base d'amine dans des compositions d'huile lubrifiante
EP0309105A1 (fr) * 1987-09-16 1989-03-29 Exxon Chemical Patents Inc. Additifs améliorant les propriétés antirouilles de compositions oléagineuses
EP0331397A2 (fr) * 1988-02-29 1989-09-06 Exxon Chemical Patents Inc. Additifs dispersants solubles dans des huiles et utiles dans des compositions huileuses

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0532264A2 (fr) * 1991-09-09 1993-03-17 Betz Europe, Inc. Traitement thermique d'une matière liquide hydrocarbonée
EP0532264A3 (en) * 1991-09-09 1993-07-21 Betz Europe, Inc. Heat processing of liquid hydrocarbonaceous medium
US5466387A (en) * 1993-06-16 1995-11-14 Agip Petroli S.P.A. Oil-soluble adducts of disuccinimides and anhydrides of unsaturated bicarboxylic aliphatic acids
GB2288815A (en) * 1994-04-08 1995-11-01 Exxon Chemical Patents Inc Lubricating oil anti-wear additives
WO1995031522A1 (fr) * 1994-05-16 1995-11-23 Exxon Chemical Patents Inc. Compositions lubrifiantes
US5731273A (en) * 1994-05-16 1998-03-24 Exxon Chemical Patents Inc. Lubricating compositions
WO1996012779A1 (fr) * 1994-10-25 1996-05-02 Exxon Research And Engineering Company Nouveaux additifs a base de cobalt regulant les depots
EP0709447A1 (fr) * 1994-10-25 1996-05-01 Exxon Research And Engineering Company Composés aromatiques polycyliques pour le contrÔle amélioré des dépÔts
JP2008260946A (ja) * 1996-10-29 2008-10-30 Idemitsu Kosan Co Ltd 新規なコハク酸イミド化合物とその製造方法及び該化合物を含有した潤滑油添加剤、並びに該化合物を配合したディーゼルエンジン用潤滑油組成物
EP0839840B2 (fr) † 1996-10-29 2016-01-20 Idemitsu Kosan Company Limited Additif pour huile lubrifiante contenant un composé de succinimide et son utilisation dans les moteurs diesel
EP1195427A2 (fr) * 2000-09-28 2002-04-10 Nippon Mitsubishi Oil Corporation Compositions lubrifiantes convenant comme huiles moteur
EP1195427A3 (fr) * 2000-09-28 2003-04-09 Nippon Mitsubishi Oil Corporation Compositions lubrifiantes convenant comme huiles moteur
WO2015021135A1 (fr) * 2013-08-09 2015-02-12 The Lubrizol Corporation Dépôts réduits dans un moteur provenant d'agent dispersant traité au cuivre
CN105637073A (zh) * 2013-08-09 2016-06-01 路博润公司 由用铜处理的分散剂而减少的发动机沉积物
US20160298052A1 (en) * 2013-08-09 2016-10-13 The Lubrizol Corporation Reduced engine deposits from dispersant treated with copper

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