EP0968260A1 - Esters d'acide phosphorique s'utilisant comme additifs haute pression - Google Patents

Esters d'acide phosphorique s'utilisant comme additifs haute pression

Info

Publication number
EP0968260A1
EP0968260A1 EP98913630A EP98913630A EP0968260A1 EP 0968260 A1 EP0968260 A1 EP 0968260A1 EP 98913630 A EP98913630 A EP 98913630A EP 98913630 A EP98913630 A EP 98913630A EP 0968260 A1 EP0968260 A1 EP 0968260A1
Authority
EP
European Patent Office
Prior art keywords
group
alkyl
phosphoric acid
formula
aryl
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.)
Withdrawn
Application number
EP98913630A
Other languages
German (de)
English (en)
Inventor
Peter Pyka
Barbara Vollnhals
Bernd Pomrehn
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
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 Clariant GmbH filed Critical Clariant GmbH
Publication of EP0968260A1 publication Critical patent/EP0968260A1/fr
Withdrawn legal-status Critical Current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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/08—Ammonium or amine salts
    • 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
    • C10M2223/043—Ammonium or amine salts thereof
    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • Coolants that are not miscible with water are mineral oils or synthetic oils with or without additives. Cooling lubricants containing active ingredients are also referred to as "alloyed cooling lubricants”.
  • Non-water-miscible cooling lubricants serve, for example, to improve the lubricity, wear behavior, corrosion protection, aging resistance and foam behavior.
  • the type and amount of additives used depend on the severity of the respective area of application.
  • Non-water-miscible cooling lubricants are characterized above all by their good ability to be scratched and good pressure absorption capacity.
  • solid-state contact between workpiece and tool occurs in the area of mixed friction in practically all cases. The roughness peaks determine the friction behavior and wear of the friction partners located in the mixed friction area. Direct metal contact in these zones can result in very high temperatures, which can lead to welding and tearing of particles from the metal structure.
  • the points of contact and thus heated due to the friction of the surface of the friction partners change and form so-called chemical reaction layers that have more favorable mechanical properties.
  • the group of EP additives includes chemical compounds that contain chlorine, phosphorus or sulfur as an effective element. Due to high friction temperatures, metal soaps, metal chloride films, metal phosphite or metal phosphate films and metal sulfide films form on the metal surfaces, which form readily adhering, easily shearable reaction layers at the contact points. The reaction layers formed are effective until they are melted by an increase in temperature as a result of frictional heat. The reactivity of these additives is therefore temperature-dependent, so that very specific temperature action ranges can be assigned to the different additives. Fats cover the lower temperature range.
  • Chlorine-containing additives work in a temperature range from approx. 180 ° C to 620 ° C, phosphorus-containing additives are assigned a temperature action range from 240 ° C to 900 ° C. Sulfur additives cover the upper temperature range from approx. 530 ° C to over 1000 ° C.
  • Phosphoric acid esters as EP components are also described in the following patents: US 2,391,631, US 4,693,839, US 2,285,853, US 4,769,178,
  • EP-A-146140B1 describes the use of acidic
  • Phosphoric acid monoestem as a lubricating component.
  • Phosphoric acid esters as EP additives.
  • the group of chlorine-containing additives mainly the highly effective chlorinated paraffins, are a widely used additive group. Due to ecological and toxicological concerns, the Oslo and Paris Commission issued a ban on the use of short-chain chlorinated paraffins from 1999 onwards.
  • the invention thus relates to the use of mixtures of one or more phosphoric acid esters of the formula (I) with one or more amines of the formula (II)
  • R 1 is a hydrogen atom or a C 1 -C 20 alkyl
  • C 2 is preferably - C 13 alkyl group, a C 2 -C 2 o-alkenyl, C 2 -C 13 alkenyl group, preferably, an optionally by C r C 5 -Alkyl or C 1 -C 5 -alkanol-substituted C 6 -C 10 aryl group or an alkyl / aryl polyethylene glycol ether group with up to 18 C atoms, preferably with 12 to 18 C atoms
  • R 2 is a C ⁇ C ⁇ alkyl group , preferably C 2 -C 13 alkyl group, a C 2 -C 20 alkenyi group, preferably C 2 - C 13 alkenyl group, a C 6 -C 10 aryl group optionally substituted by C r C 5 alkyl or C r C 5 alkanol, or an alkyl / aryl poly
  • the mixtures used are either a combination of amine and a compound of formula (I) with different radicals R 1 and R 2 , or a combination of amine and several compounds of formula (I), where, if in one compound of the formula (I) R 1 and R 2 are the same, then in another compound of the formula (I) the radicals R 1 and R 2 must be different. In any case, there must be a total of two different residues in the phosphorus compounds.
  • Hydroxyalkyl groups are, for example, monoethanolamine, diethanolamine or triethanolamine, the term amines also includes diamines.
  • the amine used for neutralization depends on the phosphoric acid esters used.
  • R 1 is hydrogen, a butyl or ethylene glycol group and R 2 is a butyl or ethylene glycol group are also very suitable, and where R 1 is not equal to R 2 in at least one phosphoric acid ester of the formula (I).
  • the EP additive according to the invention can be incorporated into the respective base liquid as a solubilizer with the aid of fatty substances (eg tall oil fatty acid, oleic acid, etc.).
  • the base liquids used are naphthenic or paraffinic base oils, synthetic oils (e.g. polyglycols, mixed polyglycols), polyolefins, carboxylic acid esters, etc.
  • Chlorparaffin ® Hordaflex SP chain length C14-C17 chlorine content: approx. 56% (m / m)
  • Esterification component 1 5 T.
  • Recipes 2 to 6 according to the invention: Recipe 2: 9 T. phosphoric acid mono- / diester with butanol / glycol as
  • Esterification component 11 T. Di- (2-ethylhexyl) amine 20 T. fat 60 T. naphthenic mineral oil Recipe 3: 5 T. basic recipe 20 T. fat 75 T. naphthenic mineral oil
  • the lubricant is checked in a four-ball system.
  • three balls standing balls
  • the fourth ball running ball
  • the ball cup filled with lubricant is operated with a certain force by means of a lever pressed against the fourth sphere, the four spheres are arranged in a pyramid shape so that the three Contact points of the ball-with the fixed balls at increasing load, the Hertz 'sche surface pressure and thus the demands on the lubricant increases.
  • Rolling bearing steel 100 Cr 6 with a hardness of approx. 63 HRC is used as the ball material.

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 l'utilisation de mélanges d'un ou de plusieurs esters d'acide phosphorique de la formule (I) avec une ou plusieurs amines de la formule (II) comme additifs haute pression dans des réfrigérants lubrifiants non miscibles dans l'eau. Dans ces formules, les substituants ont la signification définie dans la description.
EP98913630A 1997-03-12 1998-03-04 Esters d'acide phosphorique s'utilisant comme additifs haute pression Withdrawn EP0968260A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19710160 1997-03-12
DE19710160A DE19710160A1 (de) 1997-03-12 1997-03-12 Phosphorsäureester als Hochdruckadditive
PCT/EP1998/001196 WO1998040451A1 (fr) 1997-03-12 1998-03-04 Esters d'acide phosphorique s'utilisant comme additifs haute pression

Publications (1)

Publication Number Publication Date
EP0968260A1 true EP0968260A1 (fr) 2000-01-05

Family

ID=7823090

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98913630A Withdrawn EP0968260A1 (fr) 1997-03-12 1998-03-04 Esters d'acide phosphorique s'utilisant comme additifs haute pression

Country Status (7)

Country Link
US (1) US6103675A (fr)
EP (1) EP0968260A1 (fr)
JP (1) JP2001514689A (fr)
DE (1) DE19710160A1 (fr)
HU (1) HUP0001588A3 (fr)
PL (1) PL187948B1 (fr)
WO (1) WO1998040451A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69902181T2 (de) * 1998-08-20 2003-03-06 Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage Schmierölzusammensetzungen als hydraulische flüssigkeiten
SE514315C2 (sv) * 1998-09-07 2001-02-12 Rolf Skoeld Ett förfarande för mekanisk bearbetning av en metall, som innehåller koppar eller aluminium
RU2501847C1 (ru) * 2012-04-16 2013-12-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Алтайский государственный технический университет им. И.И. Ползунова" (АлтГТУ) Смазочно-охлаждающая жидкость для шлифования плазменных покрытий на никелевой основе
EP2930229B1 (fr) * 2014-04-09 2020-12-23 Italmatch SC, LLC Inhibiteurs de corrosion exempts de bore pour fluides de transformation des métaux
US9828566B2 (en) * 2015-07-06 2017-11-28 Afton Checmical Corporation Boron free corrosion inhibitors for metalworking fluids

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2285853A (en) * 1934-02-23 1942-06-09 Du Pont Lubrication
US2285854A (en) * 1934-02-23 1942-06-09 Du Pont Lubrication
US2391631A (en) * 1943-03-05 1945-12-25 Du Pont Compositions and processes
US2602049A (en) * 1948-12-24 1952-07-01 Gulf Oil Corp Antioxidants for mineral oil lubricants and compositions containing the same
FR1093271A (fr) * 1953-04-24 1955-05-03
US3203895A (en) * 1962-03-22 1965-08-31 Universal Oil Prod Co Lubricating oils containing amine salts of phosphates
US3310489A (en) * 1964-03-20 1967-03-21 Mobil Oil Corp Lubricant composition
US3657123A (en) * 1970-03-23 1972-04-18 Atlantic Richfield Co Lubricant compositions
GB1365943A (en) * 1970-09-16 1974-09-04 Gaf Corp Metalworking additive and composition and process for making the same
FR2130981A5 (fr) * 1971-03-29 1972-11-10 Rhone Poulenc Sa
US3979308A (en) * 1974-03-27 1976-09-07 Texaco Inc. Lubricant compositions with improved viscosity index
JPS58104999A (ja) * 1981-12-18 1983-06-22 Kao Corp 水分散型金属圧延油組成物
JPS59227986A (ja) * 1983-06-10 1984-12-21 Kao Corp 金属加工油組成物
JPS60130693A (ja) * 1983-12-19 1985-07-12 Hitachi Ltd 金属加工用潤滑油及びその使用方法
DE3406427A1 (de) * 1984-02-22 1985-08-29 Hütögépgyár, Jászberény Schmiermittel, insbesondere zum schmieren von werkzeugen zum spanlosen verformen
EP0157731B1 (fr) * 1984-02-24 1988-10-12 Ciba-Geigy Ag Additifs pour lubrifiants
JPS61213296A (ja) * 1985-03-19 1986-09-22 Kao Corp 金属材料の冷間圧延用潤滑油
JP2656522B2 (ja) * 1986-06-13 1997-09-24 ザ ルブリゾル コーポレーション リン含有の潤滑剤および機能流体組成物
WO1988003144A1 (fr) * 1986-10-21 1988-05-05 The Lubrizol Corporation Sels metalliques solubles dans l'huile d'esters d'acide phosphorique
US4752416A (en) * 1986-12-11 1988-06-21 The Lubrizol Corporation Phosphite ester compositions, and lubricants and functional fluids containing same
GB8907474D0 (en) * 1989-04-03 1989-05-17 Ethyl Petroleum Additives Ltd Lubricant compositions
US5552068A (en) * 1993-08-27 1996-09-03 Exxon Research And Engineering Company Lubricant composition containing amine phosphate
US5789358A (en) * 1995-12-22 1998-08-04 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiosemicarbazide derivatives
US5801130A (en) * 1995-12-22 1998-09-01 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9840451A1 *

Also Published As

Publication number Publication date
PL335615A1 (en) 2000-05-08
PL187948B1 (pl) 2004-11-30
HUP0001588A3 (en) 2005-06-28
HUP0001588A2 (hu) 2000-09-28
WO1998040451A1 (fr) 1998-09-17
DE19710160A1 (de) 1998-09-17
US6103675A (en) 2000-08-15
JP2001514689A (ja) 2001-09-11

Similar Documents

Publication Publication Date Title
DE69634442T2 (de) Biologisch abbaubare schmierflüssigkeiten auf pflanzlicher basis
DE845226C (de) Schmiermittel
DE69820429T2 (de) Gegen Hydrolyse beständiges Borat enthaltendes Handschaltgetriebe-Schmieröladditiv zum Erhöhen der Dauerhaftigkeit von Synchrongetrieben
DE102005013572B4 (de) Schmierölzusammensetzung und deren Verwendung
DE10084148B4 (de) Schmierfettzusammensetzung für Gleichlaufgelenke
DE2413145C2 (de) Kupferkorrosionsinhibitor auf der Basis von Benzotriazol
DE69232889T2 (de) Schmieröle und Schmierfette
DE2145296A1 (de) Additiv für eine Metallverarbeitungs-Komposition, sowie dessen Verwendung
DE1188751B (de) Korrosionsschutzgemische
DE2307600B2 (de) Hochdruckschmiermittelzusatz
DE962466C (de) Schmieroelmischung
DE69907643T2 (de) Schmiermittelzusammensetzung
DE69327453T3 (de) Verwendung von anorganischen phosphorverbindungen als friktionsverbesserer in schmiermittelzusammensetzungen für flüssigkeitskupplungen oder flüssigkeitsbremsen
EP3820978A1 (fr) Graisse lubrifiante écologique destinée à des câbles en acier
DE3876432T2 (de) Hydraulische fluessigkeiten.
DE2819967B2 (de) Schmierölzusammensetzung
EP0968260A1 (fr) Esters d'acide phosphorique s'utilisant comme additifs haute pression
US4767554A (en) Polycarboxylic acid ester drawing and ironing lubricant emulsions and concentrates
DE112011103822T5 (de) Schmiermittel für Schlagwerkausrüstung
DE1162964B (de) Hydraulische Fluessigkeit und Schmiermittel
DE68916200T2 (de) Rost- und korrosionsverhindernde Zusammensetzungen.
DE1115395B (de) Schmiermittel auf Mineralschmieroelbasis
DE3688654T2 (de) Extreme Hochdruckadditive zur Verwendung in Metallschmierung.
DE1085995B (de) Emulgierbares Rostschutzmittel
DE2027403C2 (de) Dauerschmierfett

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19991012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): CH DE DK ES FR GB IT LI NL

17Q First examination report despatched

Effective date: 20021015

RBV Designated contracting states (corrected)

Designated state(s): DE ES FR GB IT

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20051013