EP0349093B1 - Phosphate ester lubricants - Google Patents

Phosphate ester lubricants Download PDF

Info

Publication number
EP0349093B1
EP0349093B1 EP89201758A EP89201758A EP0349093B1 EP 0349093 B1 EP0349093 B1 EP 0349093B1 EP 89201758 A EP89201758 A EP 89201758A EP 89201758 A EP89201758 A EP 89201758A EP 0349093 B1 EP0349093 B1 EP 0349093B1
Authority
EP
European Patent Office
Prior art keywords
traction
methylcyclohexyl
lubricants
phosphate
compounds
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.)
Expired - Lifetime
Application number
EP89201758A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0349093A1 (en
Inventor
Martin Philip Dare-Edwards
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to AT89201758T priority Critical patent/ATE73839T1/de
Publication of EP0349093A1 publication Critical patent/EP0349093A1/en
Application granted granted Critical
Publication of EP0349093B1 publication Critical patent/EP0349093B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/002—Traction fluids
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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 process relates to the use of certain phosphate ester compounds as lubricants, in particular their use in traction drives.
  • Traction is broadly defined as the adhesive friction of a body on a surface on which it moves.
  • a traction drive is a device in which torque is transmitted from an input element to an output element through nominal point or line contact typically with a rolling action by virtue of the traction between the contacting elements. While traction elements are commonly spoken of as being in contact, it is generally accepted that a fluid film is present therebetween. Almost all traction drives require fluids to remove heat, to prevent wear at the contact surfaces and to lubricate bearings and other moving parts associated with the drive. Thus, instead of metal to metal rolling contact there is a film of fluid introduced into the contact zone and interposed between the metal elements.
  • This fluid determines to a large extent the limits in performance and the capacity of the drive.
  • Most traction drives are designed to operate with a traction fluid which preferably has a coefficient of traction above about 0.06, a viscosity in the range of about 4-20,000 mPa.s over a temperature range of 40°C to -20°C and good thermal and oxidative stability.
  • the fluid should also be noncorrosive to common materials of construction and have good load-bearing and low wear-rate properties.
  • Mineral base oils are rather unsatisfactory lubricants for traction drives since in general their traction (friction) coefficient is low, which means that for any given load applied to the gears the maximal tangential force that may be transmitted by the friction wheels is low.
  • R1, R2 and R3 may be different or the same aryl, alkyl or cycloalkyl groups. If any of R1, R2 and R3 are aryl or cycloalkyl groups they may be substituted with from 1 to 5 side groups, each of which may be a further cyclic group or an alkyl group of 1 to 20 carbon atoms. If any of R1, R2 and R3 are alkyl groups, they may be primary, secondary or tertiary species containing from 1 to 20 carbon atoms.
  • the present invention provides the use as lubricants, and especially as traction fluids, or organophosphate esters of the general formula I wherein R1 and R2 are independently selected from 2-methylcyclohexyl and 3-methylcyclohexyl groups.
  • Organophosphate esters are known compounds, and therefore may be prepared by known procedures, such as the reaction of phosphoryl chloride with the appropriate alcohol in the presence of a base, such as pyridine or triethylamine, and suitably also a solvent.
  • a base such as pyridine or triethylamine
  • the viscosity characteristics of the above ester compounds are very suitable for use in e.g. friction wheel gears (traction drives) in which application they may be admixed with conventional grease thickeners.
  • Such thickeners can be of any number of materials commonly used to thicken mineral oils to lubricating viscosity, including both organic and inorganic compositions such as metallic soaps, synthetic polymers, organosiloxanes, clays, bentonite, and colloidal silica.
  • the viscosity properties of compounds to be used in traction drives are such that the compounds are operable between -30 and 150°C.
  • the compounds can be used as lubricants in various engineering applications. Since the above ester compounds show excellent lubricating performance in traction drives, the invention in particular provides the use of these ester compounds as traction fluids, and also the operation of a traction drive wherein such esters form the traction fluid.
  • the ester compounds of the present invention can be used per se as lubricants. They can be mixed with other lubricants such as mineral or synthetic oils, and various additives can be added to the ester compounds, such as VI-improvers, pour point depressants, dispersants, detergents, anti-oxidants and the like.
  • a mixture that can be of particular interest for traction fluid applications is a blend with a polyolefin, in particular a poly- alpha -olefin, especially polyisobutylene, since the presence of the polymer can usefully enhance the traction coefficient of the fluid blend.
  • the molecular weight of such polyolefin blend components is conveniently in the range 500-10,000, a specific example of a suitable polyisobutylene being "Hyvis", and the proportion of polyolefin may vary from zero to 70% by weight.
  • the crude oil was allowed to stand at room temperature overnight, was then filtered and unreacted methylcyclohexanol and other volatile impurities were removed by evaporation on a KDL-4 thin-film evaporator (at 85°C and 0.8mmHg (107 Pa)) to give the product as a clear viscous oil (1.75 kg) containing a mixture of different isomers.
  • the measuring device is a gear dynamometer with a pendulum which is swung out of its vertical balanced position when power is transmitted, the sine of the angle of inclination being a measure of the torque.
  • the torque measurement is pre-calibrated through the design and dimensions of the instrument.
  • the friction coefficient is defined by the torque measured divided by the product of the radial force times the radius of the lower disc.
  • Both discs used had a diameter of 50.0mm, the upper disc having a width of 3mm, the lower one having a width of 10mm.
  • the top shaft speed was 606rpm, and the mean tangential (or surface) velocity was 1.48 ms ⁇ 1.
  • the slip employed was 9.1%.
  • the kinematic viscosity properties of the compounds are also included in this 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Friction Gearing (AREA)
EP89201758A 1988-07-01 1989-06-30 Phosphate ester lubricants Expired - Lifetime EP0349093B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89201758T ATE73839T1 (de) 1988-07-01 1989-06-30 Phosphatesterschmiermittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888815754A GB8815754D0 (en) 1988-07-01 1988-07-01 Phosphate ester lubricants
GB8815754 1988-07-01

Publications (2)

Publication Number Publication Date
EP0349093A1 EP0349093A1 (en) 1990-01-03
EP0349093B1 true EP0349093B1 (en) 1992-03-18

Family

ID=10639747

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89201758A Expired - Lifetime EP0349093B1 (en) 1988-07-01 1989-06-30 Phosphate ester lubricants

Country Status (17)

Country Link
EP (1) EP0349093B1 (enrdf_load_stackoverflow)
JP (1) JP2749878B2 (enrdf_load_stackoverflow)
KR (1) KR0134774B1 (enrdf_load_stackoverflow)
CN (1) CN1019021B (enrdf_load_stackoverflow)
AT (1) ATE73839T1 (enrdf_load_stackoverflow)
AU (1) AU613207B2 (enrdf_load_stackoverflow)
BR (1) BR8903177A (enrdf_load_stackoverflow)
CA (1) CA1336185C (enrdf_load_stackoverflow)
DE (1) DE68901010D1 (enrdf_load_stackoverflow)
ES (1) ES2030262T3 (enrdf_load_stackoverflow)
FI (1) FI95594C (enrdf_load_stackoverflow)
GB (1) GB8815754D0 (enrdf_load_stackoverflow)
GR (1) GR3004107T3 (enrdf_load_stackoverflow)
MY (1) MY106974A (enrdf_load_stackoverflow)
PT (1) PT91001B (enrdf_load_stackoverflow)
SG (1) SG45393G (enrdf_load_stackoverflow)
ZA (1) ZA894897B (enrdf_load_stackoverflow)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5817606A (en) * 1996-08-08 1998-10-06 Rohm And Haas Company Viscosity index improving additives for phosphate ester-containing hydraulic fluids
JP5188309B2 (ja) * 2008-07-30 2013-04-24 コスモ石油ルブリカンツ株式会社 難燃性ギヤ油組成物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2285854A (en) * 1934-02-23 1942-06-09 Du Pont Lubrication

Also Published As

Publication number Publication date
AU613207B2 (en) 1991-07-25
ES2030262T3 (es) 1992-10-16
MY106974A (en) 1995-08-30
PT91001A (pt) 1990-02-08
ATE73839T1 (de) 1992-04-15
SG45393G (en) 1993-06-25
GB8815754D0 (en) 1988-08-10
AU3713289A (en) 1990-01-04
EP0349093A1 (en) 1990-01-03
FI95594C (fi) 1996-02-26
CA1336185C (en) 1995-07-04
CN1019021B (zh) 1992-11-11
KR0134774B1 (ko) 1998-04-18
FI95594B (fi) 1995-11-15
BR8903177A (pt) 1990-02-13
PT91001B (pt) 1995-01-31
DE68901010D1 (de) 1992-04-23
JP2749878B2 (ja) 1998-05-13
KR900001826A (ko) 1990-02-27
GR3004107T3 (enrdf_load_stackoverflow) 1993-03-31
FI893169L (fi) 1990-01-02
CN1039053A (zh) 1990-01-24
FI893169A0 (fi) 1989-06-28
JPH0253893A (ja) 1990-02-22
ZA894897B (en) 1990-06-27

Similar Documents

Publication Publication Date Title
EP0266848B1 (en) Ester compound lubricants
US4374032A (en) Lubricant composition containing borated oxazoline friction reducer
US3440894A (en) Tractants and method of use
US4370248A (en) Borated hydroxyl-containing acid esters and lubricants containing same
EP2157159B1 (en) Hydraulic fluid
US4594171A (en) Friction reducing additives and compositions thereof
CA1276649C (en) Polycarboxylic acid esters and lubricants containing these esters
EP0349093B1 (en) Phosphate ester lubricants
US5043497A (en) Lubricating oil for traction drives
Murphy et al. Structural guides for synthetic lubricant development
EP0350125B1 (en) Traction fluid lubricants
US4392973A (en) Method for transmitting power by traction utilizing borate esters as traction fluids and a device for using the method
RO116413B1 (ro) Metoda de lubrifiere a sistemelor de contactare metal-metal, in operatiile de prelucrare a metalelor
US5866522A (en) Sulfur containing aromatic lubricant and method of using same
US4335004A (en) Lubricating compositions containing diesters of dimercapto ethers
US4076639A (en) Lubricant compositions
KR940009417B1 (ko) 스피로디포스페이트-함유 작동 조성물
US4613343A (en) N-alkoxyalkylenediamine [organic acid reaction products] diamides and lubricants containing same
US4253978A (en) Phosphorus-containing compounds and lubricants containing same
US4104181A (en) Additives comprising (N, N-diorganothiocarbamyl) phosphorothioites and lubricant compositions containing the same
US4786426A (en) Lubricant composition
US3275636A (en) Amine hexafluotitanates
WO2006059687A1 (ja) 軸受用潤滑油
US3418240A (en) Lubricants containing a triorganosilyl phosphonate as an extreme pressure agent
CA1287617C (en) Traction fluid

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

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

17P Request for examination filed

Effective date: 19900523

17Q First examination report despatched

Effective date: 19901026

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

REF Corresponds to:

Ref document number: 73839

Country of ref document: AT

Date of ref document: 19920415

Kind code of ref document: T

ITF It: translation for a ep patent filed
REF Corresponds to:

Ref document number: 68901010

Country of ref document: DE

Date of ref document: 19920423

ET Fr: translation filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2030262

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3004107

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

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

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
EPTA Lu: last paid annual fee
EAL Se: european patent in force in sweden

Ref document number: 89201758.3

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19970521

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 19970530

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19970603

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 19970613

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 19970617

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19970901

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

Ref country code: GR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 19980701

BERE Be: lapsed

Owner name: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

Effective date: 19980630

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20000301

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20020429

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20020524

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20020528

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20020612

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20020621

Year of fee payment: 14

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030701

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040101

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040101

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20030630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040227

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20040101

EUG Se: european patent has lapsed
REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050630