EP0090629B1 - Borierter Zusatz für Schmieröl - Google Patents

Borierter Zusatz für Schmieröl Download PDF

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Publication number
EP0090629B1
EP0090629B1 EP83301723A EP83301723A EP0090629B1 EP 0090629 B1 EP0090629 B1 EP 0090629B1 EP 83301723 A EP83301723 A EP 83301723A EP 83301723 A EP83301723 A EP 83301723A EP 0090629 B1 EP0090629 B1 EP 0090629B1
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EP
European Patent Office
Prior art keywords
long chain
succinic acid
grams
borated
boron
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Expired
Application number
EP83301723A
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English (en)
French (fr)
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EP0090629A3 (en
EP0090629A2 (de
Inventor
Ronald Leslie Anderson
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BP Corp North America Inc
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BP Corp North America Inc
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Priority to AT83301723T priority Critical patent/ATE29732T1/de
Publication of EP0090629A2 publication Critical patent/EP0090629A2/de
Publication of EP0090629A3 publication Critical patent/EP0090629A3/en
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Publication of EP0090629B1 publication Critical patent/EP0090629B1/de
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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
    • 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
    • C10M133/56—Amides; Imides
    • 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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • 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
    • C10M2215/28—Amides; Imides
    • 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
    • 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
    • C10M2227/062—Cyclic esters
    • 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
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to a borated reaction product of a long chain aliphatic succinic acid compound and alkylene diamine having an average of at least 2.5 N-substituted hydroxyalkyl groups and lube oil additives containing said borated reaction products.
  • Lubrizol discloses in U.S. Patents 3,219,666 of Norman et al; 3,381,022 of Le Suer; 3,630,904 of Musser et al; 3,836,471 of Miller; 3,533,945 of Vogel; 3,282,955 of Le Suer; etc. that foreign particles in lubricating oils is a particular problem.
  • U.S. Patents 3,219,666 of Norman et al; 3,381,022 of Le Suer; 3,630,904 of Musser et al; 3,836,471 of Miller; 3,533,945 of Vogel; 3,282,955 of Le Suer; etc. that foreign particles in lubricating oils is a particular problem.
  • Patent 3,282,955 explains the problem at Column 1, lines 19 to 37 as follows: "One of the principal problems associated with present day automobile crankcase lubricants is that posed by the inevitable presence in the lubricant of foreign particles such as dirt, soot, water, and decomposition products resulting from breakdown of the lubricating oil. Even if there were none of this latter contaminant present the very nature of the design of the modern internal combustion engine is such that a significant amount of foreign matter will accumulate in the crankcase. Perhaps the most important of these contaminants is water because it seems to be responsible for the deposition of a mayonnaise-like sludge.
  • U.S. Patents 3,219,666 and 3,640,904 disclose that hydroxyalkyl substituted amines and polyamines can be reacted with long chain aliphatic succinic acid compounds and formulated into lubricating oil compositions.
  • U.S. Patent 3,282,955 discloses the formation of lubricating oil additives based upon borated reaction products of long chain succinic acid compounds and mono-amines, including N-substituted hydroxyalkylated amines.
  • Patent 3,533,945 discloses lube oil additives based upon borated reaction products of long chain aliphatic succinic acid compounds and polyols.
  • U.S. Patent 3,836,471 discloses lube oil compositions containing the reaction product of long chain aliphatic succinic acid compounds and at least one polyoxyalkylene alcohol demulsifier with the possibility of utilizing amines such as polyalkylene polyamines or hydroxyalkylated polyamines together with the polyoxyalkylene alcohol demulsifier.
  • U.S. Patent 3,630,904 discloses lube oil compositions containing additives formed by reacting adducts of a hydroxyalkylamine and an acylating agent with a long chain aliphatic succinic acid compound.
  • US Patent 4,097,389 of Andress discloses lube oil compositions containing borated oxazoline additives wherein the oxazoline component is a cyclized reaction product of a long chain succinic acid compound and a tris(hydroxymethyl) aminomethane.
  • US Patent 4,071,548 of Okamoto discloses lube oil compositions comprising borated reaction products of long chain aliphatic succinic acid esters and/or amides containing oxyalkylene chains of at least 5 oxyalkylene units.
  • US-A-3,254,025 discloses a lubricating oil additive prepared by reacting N-hydroxyalkyl substituted alkylene diamine with polyisobutylene-substituted succinic anhydride. The resulting products are borated. However, none of these references discloses borated reaction products of a long chain succinic acid compound and an alkylene diamine having an average of at least 2.5 N-hydroxyalkyl groups and lube oil groups containing these borated reaction products.
  • additives prepared from the reaction product of long chain aliphatic succinic acid compounds and alkylene polyamines are excellent lube oil additives, they are inferior to additives where the alkylene polyamine is hydroxyalkylated. In general, the more hydroxyalkyl moieties the greater the dispersancy.
  • the products based on hydroxyalkylated polyamines have the drawback that they tend to attack engine seals particularly those of the fluorocarbon polymer type thereby limiting the use of lubricating oils containing these dispersants. Accordingly, there is a need for high dispersancy lube oil additives that do not attack engine seals based on fluorocarbon polymers.
  • the general object of this invention is to provide a lube oil additive having high dispersancy which is compatible with fluorocarbon engine seals. Other objects appear hereinafter.
  • a method of producing a lube oil additive which comprises the steps of (1) reacting an unsubstituted alkylene diamine with at least 2.5 mols of propylene oxide per mol of alkylene diamine at 50 to 300°C, (2) reacting from 0.5 to 2.0 mols of the resulting N-hydroxyalkyl alkylene diamine with each mol of an alpha long chain aliphatic succinic acid or anhydride at from 0 to 250°C and (3) borating the reaction product of step 2 at 50 to 250°C with sufficient concentration of boron compound to yield a long chain succinic acid product containing at least 0.15% by weight boron.
  • the additives produced by the method of this invention are particularly well balanced products. While we have found that it is generally desirable to use long chain succinic acid amides and esters based on polyalkylene polyamines having a relatively high concentration of N-hydroxyalkyl moieties because the more N-hydroxyalkyl substituents the cleaner the engine, we have also found that the more amino groups in the polyamine the greater the degradation of fluorocarbon polymer seals. This means that while it is desirable to have a high level of hydroxyalkyl moieties in the additive to enhance engine cleanliness and reduce sludge formation, alkylene amines containing more than 2 amino groups cannot be utilized in this invention. Hydroxyalkylated monoamines do not provide adequate dispersancy.
  • the diamine have at least 2.5 N-hydroxyalkyl groups, preferably 2.5 to 4 N-hydroxyalkyl groups, in order to provide acceptable levels of engine cleanliness. Boration is necessary in order to stabilize the additive and reduce engine seal attack. Other things being equal, omission of boration leads to unacceptably high levels of fluorocarbon engine seal attack. However, boration of additives prepared from N-unsubstituted diamines does not reduce fluorocarbon engine seal attack. Accordingly, the lube oil additives of this invention are particularly well balanced.
  • the lube oil additives of this invention can be prepared by borating reaction products of an alpha long chain succinic acid compound and an alkylene diamine having on an average at least 2.5 N-hydroxyalkyl groups.
  • the alkylene diamines useful as starting materials in the method of this invention may have the structure NH 2 -R-NH 2 wherein R is an alkylene group of from 2 to 24 carbon atoms, such as ethylene, 1,2-propylene, trimethylene, hexamethylene, dodecamethylene, tetracosene, etc.
  • R is an alkylene group of from 2 to 24 carbon atoms, such as ethylene, 1,2-propylene, trimethylene, hexamethylene, dodecamethylene, tetracosene, etc.
  • alkylene diamines containing from about 6 to 12 methylene units are preferred, in order to provide a dispersant having the most advantageous properties, particularly compatibility with the lubricating oil.
  • Hexamethylenediamine is preferred because of its relatively low cost and compatibility of additives prepared from it with lube oils.
  • the hydroxyalkylating reactant is propylene oxide.
  • Ethylene oxide is disadvantageous since hydroxyethylated alkylene diamines tend to yield borated dispersants which are slightly incompatible with lubricating oils in the sense that they yield hazy borated products. Ethylene oxide also has the disadvantage that it has a tendency to hydroxyethylate N-hydroxyethylated groups on the diamine thereby reducing the efficiency of the reaction. In contrast propylene oxide yields borated additives which are fully compatible with the lubricating oils and has a reduced tendency to react with N-hydroxypropylated amines. Butylene oxide tends to be less reactive than either ethylene oxide or propylene oxide and is substantially more expensive.
  • the hydroxyalkylating agent can be used in a concentration of about 2 to 6 mols per mol of alkylene diamine. In general approximately 2.5 to 4.5 mols of propylene oxide per mol of diamine is preferred since the final products have about 2.5 to 4 N-hydroxyalkyl groups which provides the best properties at the lowest cost.
  • the alkylene diamine can be hydroxyalkylated under conventional conditions, i.e. by reaction at 50 to 300°C from 1 to 10 hours.
  • the long chain aliphatic succinic acid compounds useful in this invention can be prepared by any of the techniques described in the aforesaid patents, which have been incorporated by reference.
  • an acid compound particularly an ethylenically unsaturated dicarboxylic acid compound (acid or anhydride), such as maleic acid, maleic anhydride, fumaric acid, etc.
  • a suitable olefin or halogenated olefin at a temperature of about 100 to 300°C yielding an alkenyl or alkyl substituted succinic anhydride.
  • the unsaturated groups in the alkenyl group can be removed by standard hydrogenation procedures.
  • the olefins or halo substituted olefins contain from about 8 to 500 carbon atoms or more and can include homopolymers and copolymers of mono olefins such as ethylene, propylene, 1-butene, isobutene, etc.
  • mono olefins such as ethylene, propylene, 1-butene, isobutene, etc.
  • any of the techniques utilized in this art can be employed to produce the long chain succinic acid compound.
  • the long chain aliphatic succinic acid compounds are then reacted with the N-substituted hydroxyalkyl diamine under conditions normally employed in this art at a temperature of from 0 to 250°C.
  • a solvent such as benzene, toluene, naphtha, lube oil, xylene and n-hexane or the like can be used to facilitate the control of the reaction.
  • From about .5 to 2 mols of long chain aliphatic succinic acid compounds can be reacted per mol of N-substituted hydroxyalkyl alkylene diamine. It will be noted that the long chain aliphatic succinic acid compound for purposes of this reaction is difunctional while the N-substituted hydroxy alkylene diamine is tetrafunctional irrespective of the degree of substitution of the alkylene diamine.
  • the boron compounds useful in this invention include boron oxide, boron dihalides (boron trifluoride, boron tribromide, boron trichloride) boron acids, such as tetraboric acid, metaboric acid and simple esters of the boron acids (trialkyl borates containing 1 to 8 carbon alkyl groups such as methyl, ethyl, n-octyl, 2-ethylhexyl, etc.).
  • the boron compounds can be reacted with the long chain succinic acid-hydroxy alkylene diamine product at a temperature of from about 50 to 250°C preferably from about 100 to 170°C with a sufficient concentration of boron compound to yield a long chain succinic acid product containing at least .15 percent by weight boron (excluding lube oil).
  • the boron compound can be reacted in a ratio of from 0.1 to 10 moles of boron compound per equivalent of starting long chain succinic acid compound in step 1. This step can be -carried out in the presence of diluent or solvent. In general, the more boron incorporated, the lower the seal attack.
  • percent boron content is always based on lube oil and additive concentration.
  • the pale yellow N-hydroxypropylated hexamethylenediamine having on an average about 3 hydroxypropyl groups per hexamethylenediamine moiety remained a liquid at room temperature for several days but slowly crystallized to a low melting solid.
  • the reaction mass was cooled to 130°C and treated with 250 ml xylene and 35.3 grams of boric acid (0.571 moles). The mixture was then refluxed at 140°C with azeotropic removal of water and finally heated to 180°C with a nitrogen purge to remove the xylene.
  • the product (including base oil) was filtered with celite and contained 0.23% boron (0.25% B theoretical) and 0.63 nitrogen (0.66% nitrogen theoretical).
  • This Example illustrates the production of a borated reaction product of a long chain aliphatic succinic acid compound and an unsubstituted alkylene diamine.
  • Twelve hundred grams of a 40.5 percent active solution (in oil) of polybutenyl-succinic anhydride (0.217 moles) having a molecular weight of 2240 and 50.4 grams hexamethylenediamine (0.43 moles) was heated at 100°C for two hours in a 3 liter, 3-necked, round bottom flask. The temperature was then raised to 150°C and nitrogen was blown through the solution to remove excess hexamethylenediamine.
  • the resultant product was treated with ninety-seven grams of boric acid suspended in a Mannich condensation product of polybutylphenol, tetraethylenepentamine and formaldehyde (2.72% boron) overnight at 95°C to yield a product containing 0.20% by weight boron and 0.47% nitrogen.
  • This Example illustrates the production of a borated reaction product of a long chain aliphatic succinic acid compound and alkylene diamine having an average of about 2 N-substituted hydroxypropyl groups.
  • This Example illustrates the production of an unborated reaction product of polybutenyl-succinic anhydride and hydroxypropylated hexamethylenediamine having approximately three hydroxypropyl groups per hexamethylenediamine moiety.
  • This Example illustrates the preparation of a borated reaction product of polybutenyl-succinic anhydride and hydroxypropylated hexamethylenediamine having approximately three hydroxypropyl groups per hexamethylenediamine moiety and a relatively high boron content.
  • One hundred nineteen grams of the hexamethylenediamine propylene oxide reaction product of Example I, one thousand forty-five grams of a 55% active oil solution of polybutenyl-succinic anhydride having a molecular weight of fourteen hundred (.41 moles) and five hundred seventy-one grams SX-5 base oil were heated at 190°C for two hours with a nitrogen purge in a 5 liter, 3-necked flask.
  • This Example illustrates a comparison of sequence VD engine test of dispersants made according to Examples I, II, IV and V.
  • Dispersants prepared in accordance with the preceding Examples were tested by suspending a fluorocarbon seal in oil solution at 149°C (300°F) for seven days and the change in physical properties (tensile strength percent elongation) was then measured.
  • This Example illustrates the production of a borated reaction product of polybutenyl-succinic anhydride and hydroxyethylated hexamethylenediamine having approximately four hydroxyethyl groups per hexamethylenediamine moiety.
  • Three hundred seventy grams hexamethylenediamine (3.19 moles) were heated to 180°C in a one liter, 3-necked round bottom flask fitted with an overhead stirrer fritted glass gas dispersion tube, thermometer and heating mantle.

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

Claims (4)

1. Verfahren zur Herstellung eines Schmieröladditivs, dadurch gekennzeichnet, daß man (1) ein unsubstituiertes Alkylendiamin mit wenigstens 2,5 Mol Propylenoxid pro Mol Alkylendiamin bei 50 bis 300°C umsetzt, (2) 0,5 bis 2,0 Mol des erhaltenen N-Hydroxyalkylalkylendiamins mit jeweils 1 Mol einer a-langkettigen aliphatischen Bernsteinsäure oder eines Bernsteinsäureanhydrids bei 0°C bis 250°C umsetzt und (3) das Reaktionsprodukt der Stufe (2) bei 50 bis 250°C mit einer solchen Menge an Borverbindung zur Reaktion bringt, daß sich als Produkt eine langkettige Bernsteinsäure ergibt, die wenigstens 0,15 Gewichtsprozent Bor enthält.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das Propylenoxid in einer Konzentration von etwa 2,5 bis 4,5 Mol pro Mol Diamin vorhanden ist.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß das Alkylendiamin Hexamethylendiamin ist.
4. Verfahren nach <«.gendeinem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß die Borverbindung in einem Verhältnis von 0,1 bis 10 Mol Borverbindung pro Äquivalent an bei der Stufe (1) als Ausgangsmaterial verwendeter langkettiger Bernsteinsäure oder Bernsteinsäureanhydrid umgesetzt wird.
EP83301723A 1982-03-29 1983-03-28 Borierter Zusatz für Schmieröl Expired EP0090629B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83301723T ATE29732T1 (de) 1982-03-29 1983-03-28 Borierter zusatz fuer schmieroel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36295582A 1982-03-29 1982-03-29
US362955 1982-03-29

Publications (3)

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EP0090629A2 EP0090629A2 (de) 1983-10-05
EP0090629A3 EP0090629A3 (en) 1984-09-05
EP0090629B1 true EP0090629B1 (de) 1987-09-16

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EP83301723A Expired EP0090629B1 (de) 1982-03-29 1983-03-28 Borierter Zusatz für Schmieröl

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EP (1) EP0090629B1 (de)
JP (1) JPH0672232B2 (de)
AT (1) ATE29732T1 (de)
AU (1) AU560164B2 (de)
CA (1) CA1199318A (de)
DE (1) DE3373672D1 (de)
ES (1) ES521059A0 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637886A (en) * 1982-12-27 1987-01-20 Exxon Research & Engineering Co. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
CA1235977A (en) * 1983-07-25 1988-05-03 Robert J. Basalay Boration of polyamine dispersants with polyborate esters
US4747850A (en) * 1984-07-20 1988-05-31 Chevron Research Company Modified succinimides in fuel composition
US4746446A (en) * 1984-07-20 1988-05-24 Chevron Research Company Modified succinimides
US4747965A (en) * 1985-04-12 1988-05-31 Chevron Research Company Modified succinimides
US4840744A (en) * 1984-07-20 1989-06-20 Chevron Research Company Modified succinimides and lubricating oil compositions containing the same
US4802893A (en) * 1984-07-20 1989-02-07 Chevron Research Company Modified Succinimides
US4612132A (en) * 1984-07-20 1986-09-16 Chevron Research Company Modified succinimides
US4702851A (en) * 1984-08-22 1987-10-27 Chevron Research Company Dispersant additives for lubricating oils and fuels
US4584117A (en) * 1984-08-22 1986-04-22 Chevron Research Company Dispersant additives for lubricating oils and fuels
ZA89991B (en) * 1988-02-23 1989-10-25 Ici Australia Operations Explosive composition
US5205947A (en) * 1988-11-07 1993-04-27 Exxon Chemical Patents Inc. Dispersant additives comprising amine adducts of dicarboxylic acid monoepoxy thiol reaction products
US4954572A (en) * 1988-11-07 1990-09-04 Exxon Chemical Patents Inc. Dispersant additives prepared from monoepoxy alcohols
US5057617A (en) * 1988-11-07 1991-10-15 Exxon Chemical Patents Inc. Dispersant additives prepared from monoepoxy thiols
CA2008258C (en) * 1989-01-30 2001-09-11 Jacob Emert Oil soluble dispersant additives modified with monoepoxy monounsaturated compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3087936A (en) * 1961-08-18 1963-04-30 Lubrizol Corp Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound
CA1168649A (en) * 1981-03-23 1984-06-05 Robert E. Malec Lubricating compositions

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CA1199318A (en) 1986-01-14
ATE29732T1 (de) 1987-10-15
ES8405061A1 (es) 1984-05-16
EP0090629A3 (en) 1984-09-05
AU560164B2 (en) 1987-04-02
JPH0672232B2 (ja) 1994-09-14
AU1260183A (en) 1983-10-06
EP0090629A2 (de) 1983-10-05
ES521059A0 (es) 1984-05-16
JPS58176296A (ja) 1983-10-15
DE3373672D1 (en) 1987-10-22

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