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WO2006131363A1 - Esters d'acides gras hydroxy-acide dithiophosphorique polymeriques, leur procede de production et leur utilisation comme additifs de lubrifiants - Google Patents

Esters d'acides gras hydroxy-acide dithiophosphorique polymeriques, leur procede de production et leur utilisation comme additifs de lubrifiants Download PDF

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Publication number
WO2006131363A1
WO2006131363A1 PCT/EP2006/005487 EP2006005487W WO2006131363A1 WO 2006131363 A1 WO2006131363 A1 WO 2006131363A1 EP 2006005487 W EP2006005487 W EP 2006005487W WO 2006131363 A1 WO2006131363 A1 WO 2006131363A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
fatty acid
acid ester
polymeric
dithiophosphoric
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
PCT/EP2006/005487
Other languages
German (de)
English (en)
Inventor
Volker SCHÄFER
Bernd Lindstaedt
Wolfgang Jarre
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.)
Lehmann and Voss and Co KG
Original Assignee
Lehmann and Voss and Co KG
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 Lehmann and Voss and Co KG filed Critical Lehmann and Voss and Co KG
Publication of WO2006131363A1 publication Critical patent/WO2006131363A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
    • C10M153/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants

Definitions

  • the polymeric Dithiophosphorklarehydroxyfettklaklaester invention are obtainable by two production routes, both of which take place in two steps.
  • epoxidized fatty acid esters are first reacted with substituted dithiophosphoric acids, not all of the epoxide groups of the fatty acid ester being attacked.
  • the polymerization is carried out with a multifunctional H-acidic compound via an intermolecular crosslinking and formation of hydroxyl groups.
  • epoxidized fatty acid esters are reacted with a multifunctional H-acidic compound such that the epoxidized fatty acid esters are intermolecularly crosslinked to form a polymeric intermediate having free epoxide groups.
  • the free epoxide groups are then reacted with the substituted dithiophosphoric acid to form hydroxyl groups.
  • inverse method Both production routes are described in detail below.
  • Polystyrene, MW 520, 250 mg / 50 ml THF p.a
  • the element contents of the product are:
  • the welding power of base oils ISO VG 46 according to DIN 51350/2 was determined, to which different amounts of the product from Example 1 or to zinc di-2-ethylhexyl dithiophosphate were added.
  • the obtained welding force values are summarized in the following table.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne de nouveaux esters d'acides gras hydroxy-acide dithiophosphorique polymériques. Ils sont préparés selon un procédé, selon lequel un ester d'acide gras époxydé est transformé avec un acide dithiophosphorique substitué de telle façon que les groupes époxy de l'ester d'acide gras ne soient pas tous attaqués. Puis une réticulation intermoléculaire a lieu avec formation de groupes hydroxyle. Selon un procédé alternatif, on procède à la réticulation de l'ester d'acide gras époxydé pour obtenir un produit intermédiaire polymérique exempt de groupes époxy transformés puis on fait réagir les groupes époxy libres avec l'acide dithiophosphorique substitué pour obtenir des groupes hydroxyle. Les esters d'acides gras hydroxy-acide dithiophosphorique polymériques conviennent de manière générale, comme additifs de lubrifiants, notamment pour améliorer l'action de protection contre l'usure et la stabilité au vieillissement de lubrifiants.
PCT/EP2006/005487 2005-06-08 2006-06-08 Esters d'acides gras hydroxy-acide dithiophosphorique polymeriques, leur procede de production et leur utilisation comme additifs de lubrifiants Ceased WO2006131363A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005026405A DE102005026405A1 (de) 2005-06-08 2005-06-08 Polymere Dithiophosphorsäurehydroxyfettsäureester, Verfahren zu deren Herstellung und deren Verwendung als Schmierstoffadditiv
DE102005026405.0 2005-06-08

Publications (1)

Publication Number Publication Date
WO2006131363A1 true WO2006131363A1 (fr) 2006-12-14

Family

ID=36992701

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/005487 Ceased WO2006131363A1 (fr) 2005-06-08 2006-06-08 Esters d'acides gras hydroxy-acide dithiophosphorique polymeriques, leur procede de production et leur utilisation comme additifs de lubrifiants

Country Status (2)

Country Link
DE (1) DE102005026405A1 (fr)
WO (1) WO2006131363A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5368776A (en) * 1992-02-27 1994-11-29 Rhein Chemie Rheinau Gmbh Corrosion protection additives based on epoxides
US5412140A (en) * 1992-12-16 1995-05-02 Rhein Chemie Rheinau Gmbh Metal-free dithiophosphoric acid derivatives
US5552070A (en) * 1992-09-17 1996-09-03 Rhein Chemie Rheinau Gmbh Phosphorylation of epoxides
US5573696A (en) * 1995-03-31 1996-11-12 Ethyl Corporation Oil-soluble phosphorus- and nitrogen-containing additives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2826592A (en) * 1954-01-27 1958-03-11 Shell Dev Epoxy esters of phosphorus-containing acids and their use in treating textiles
US3259579A (en) * 1954-11-29 1966-07-05 Exxon Research Engineering Co Esters of dithiophosphoric acids and lubricating oil compositions containing same
US4435338A (en) * 1980-09-29 1984-03-06 Ciba-Geigy Corporation Dithiophosphates
JPS6123622A (ja) * 1984-07-12 1986-02-01 Toyota Central Res & Dev Lab Inc エポキシ樹脂組成物
DE4221858A1 (de) * 1992-07-03 1994-01-05 Becker Carl Chemie Gmbh Addukte von 0,0-Dialkyldithiophosphorsäuren an ungesättigte Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schmiermitteladditive

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5368776A (en) * 1992-02-27 1994-11-29 Rhein Chemie Rheinau Gmbh Corrosion protection additives based on epoxides
US5552070A (en) * 1992-09-17 1996-09-03 Rhein Chemie Rheinau Gmbh Phosphorylation of epoxides
US5412140A (en) * 1992-12-16 1995-05-02 Rhein Chemie Rheinau Gmbh Metal-free dithiophosphoric acid derivatives
US5573696A (en) * 1995-03-31 1996-11-12 Ethyl Corporation Oil-soluble phosphorus- and nitrogen-containing additives

Also Published As

Publication number Publication date
DE102005026405A1 (de) 2006-12-14

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