EP4108745A1 - Ether-based lubricant compositions, methods and uses - Google Patents

Ether-based lubricant compositions, methods and uses Download PDF

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Publication number
EP4108745A1
EP4108745A1 EP22169847.5A EP22169847A EP4108745A1 EP 4108745 A1 EP4108745 A1 EP 4108745A1 EP 22169847 A EP22169847 A EP 22169847A EP 4108745 A1 EP4108745 A1 EP 4108745A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
lubricant composition
oxidant
cycloalkyl
aminic
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Withdrawn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
EP22169847.5A
Other languages
German (de)
English (en)
French (fr)
Inventor
Ieuan Stephen Adams
Angela BREAKSPEAR
Gordon David Lamb
John Michael REDSHAW
Kevin Richard West
Rebecca YATES
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.)
Castrol Ltd
Original Assignee
Castrol Ltd
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 Castrol Ltd filed Critical Castrol Ltd
Publication of EP4108745A1 publication Critical patent/EP4108745A1/en
Withdrawn legal-status Critical Current

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    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • 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
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028—Overbased salts 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbased sulfonic acid 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • 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
    • C10N2030/52—Base number [TBN]
    • 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
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2040/25—Internal-combustion engines

Definitions

  • the ether base stock of the lubricant composition is selected from a subset of the compounds of formula (A), namely a compound of formula (1): where:
  • aliphatic hydrocarbyl refers to a group comprising hydrogen and carbon atoms, where one or more carbon atoms may optionally be replaced with -O-, which group may be saturated or unsaturated, preferably saturated, and contains from 1 to 40 carbon atoms.
  • hydrocarbyl groups include hydrocarbyl groups containing from 2 to 28 carbon atoms, such as from 3 to 26 carbon atoms or from 4 to 24 carbon atoms.
  • p is 0, 1 or 2, such as 0 or 1.
  • the compounds may have a Noack volatility of less than about 26%, such as less than about 20%, less than about 16 %, or less than about 12 % by weight. Noack volatility may be measured according to CEC-L-40-A-93.
  • n is 0, 1 or 2, such as 0 or 1.
  • R 6 is C 1-20 alkyl, such as C 1-16 alkyl.
  • R 6 is C 1-20 alkyl, such as C 1-16 alkyl.
  • X is C 1-20 alkylene, such as C 3-15 alkylene.
  • the phenolic anti-oxidant is selected from alkylated monophenols, alkylated hydroquinones, hydroxylated thiodiphenyl ethers, alkylidenebisphenols, acylaminophenols, and sulphurised alkyl phenols and alkali and alkaline earth metal salts thereof.
  • the lubricant composition may also comprise other antioxidants which are not aminic or phenolic in nature.
  • the lubricant compositions of the invention may additionally comprise antioxidants selected from hydroxylated thiodiphenyl ethers, thiopropionates, metallic dithiocarbamates, 1,3,4-dimercaptothiadiazole and derivatives, oil soluble copper compounds (for example, copper dihydrocarbyl thio- or thio-phosphate, copper salts of a synthetic or natural carboxylic acids, for example a C 8 to C 18 fatty acid, an unsaturated acid or a branched carboxylic acid, for example basic, neutral or acidic Cu(I) and/or Cu(II) salts derived from alkenyl succinic acids or anhydrides), alkaline earth metal salts of alkylphenolthioesters, suitably containing C 5 to C 12 alkyl side chains, barium t-octylphenyl sulphide, phosphos
  • Fig. 1 is a graph of percentage increase in Kinematic Viscosity at 100 °C against time corresponding to results of CEC-L-109 testing of blended compositions containing Guerbet-derived base stock (GE3) and/or a Group III base stock (Yubase 4) together with varying amounts of aminic oxidant and/or phenolic oxidant as well as other lubricant additives.
  • GE3 Guerbet-derived base stock
  • Yubase 4 Group III base stock

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP22169847.5A 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses Withdrawn EP4108745A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN2016110345 2016-12-16
PCT/EP2017/082924 WO2018109123A1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses
EP17816808.4A EP3555248B1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP17816808.4A Division EP3555248B1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses

Publications (1)

Publication Number Publication Date
EP4108745A1 true EP4108745A1 (en) 2022-12-28

Family

ID=60702780

Family Applications (2)

Application Number Title Priority Date Filing Date
EP22169847.5A Withdrawn EP4108745A1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses
EP17816808.4A Active EP3555248B1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP17816808.4A Active EP3555248B1 (en) 2016-12-16 2017-12-14 Ether-based lubricant compositions, methods and uses

Country Status (6)

Country Link
US (1) US20200115651A1 (https=)
EP (2) EP4108745A1 (https=)
JP (3) JP7107938B2 (https=)
CN (2) CN115895763B (https=)
PL (1) PL3555248T3 (https=)
WO (1) WO2018109123A1 (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11773343B2 (en) 2021-11-17 2023-10-03 Afton Chemical Corporation Engine oil formulation with improved Sequence VIII performance

Citations (11)

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GB817054A (en) * 1954-08-07 1959-07-22 Hoechst Ag Manufacture of esters
WO1999021902A1 (en) 1997-10-28 1999-05-06 Castrol Limited Processes for preparing grafted copolymers
WO2003099890A2 (en) 2002-05-24 2003-12-04 Castrol Limited Preparation of monomers for grafting to polyolefins, and lubricating oil compositions containing grafted copolymer
EP1533362A1 (en) 2003-11-18 2005-05-25 Infineum International Limited Lubricating oil composition
US20050198894A1 (en) 2004-03-11 2005-09-15 Crompton Corporation Lubricant and fuel compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
US20060090393A1 (en) 2004-10-29 2006-05-04 Rowland Robert G Epoxidized ester additives for reducing lead corrosion in lubricants and fuels
WO2006099250A1 (en) 2005-03-11 2006-09-21 Castrol Limited Multiple function graft polymer
CN101006164A (zh) * 2004-08-30 2007-07-25 出光兴产株式会社 流体轴承用润滑油组合物
US7622431B2 (en) 2006-01-04 2009-11-24 Chemtura Corporation Lubricating oil compositions
WO2016129148A1 (ja) * 2015-02-09 2016-08-18 株式会社Moresco 潤滑剤組成物及びその利用、並びに脂肪族エーテル化合物
WO2016203310A1 (en) * 2015-06-18 2016-12-22 Castrol Limited Ether compounds and related compositions

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EP1577371A4 (en) 2002-12-24 2008-11-05 Idemitsu Kosan Co LUBRICANT BASE OIL AND LUBE OIL COMPOSITION
JP4563082B2 (ja) * 2004-06-03 2010-10-13 出光興産株式会社 潤滑油基油及び潤滑油組成物
JP2007056276A (ja) 2006-12-04 2007-03-08 Idemitsu Kosan Co Ltd 潤滑油基油
US9243201B2 (en) 2011-10-26 2016-01-26 Exxonmobil Research And Engineering Company Low viscosity lubricating oil base stocks and processes for preparing same
MX2014004207A (es) * 2011-10-28 2014-05-28 Idemitsu Kosan Co Composicion de aceite de lubricacion.
US20140207235A1 (en) * 2013-01-23 2014-07-24 Warsaw Orthopedic, Inc. Expandable allograft cage
US10125335B2 (en) * 2013-06-28 2018-11-13 Castrol Limited Lubricating compositions containing isoprene based components
EP3122846B1 (en) * 2014-03-27 2018-12-12 Dow Global Technologies LLC Dispersant suitable for lubricant formulations
JP6259728B2 (ja) 2014-06-30 2018-01-10 出光興産株式会社 潤滑油組成物

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB817054A (en) * 1954-08-07 1959-07-22 Hoechst Ag Manufacture of esters
WO1999021902A1 (en) 1997-10-28 1999-05-06 Castrol Limited Processes for preparing grafted copolymers
WO2003099890A2 (en) 2002-05-24 2003-12-04 Castrol Limited Preparation of monomers for grafting to polyolefins, and lubricating oil compositions containing grafted copolymer
EP1533362A1 (en) 2003-11-18 2005-05-25 Infineum International Limited Lubricating oil composition
US20050198894A1 (en) 2004-03-11 2005-09-15 Crompton Corporation Lubricant and fuel compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
US20070281873A1 (en) * 2004-08-30 2007-12-06 Idemitsu Kosan Co., Ltd Lubricant Composition for Fluid Dynamic Bearing
CN101006164A (zh) * 2004-08-30 2007-07-25 出光兴产株式会社 流体轴承用润滑油组合物
US20060090393A1 (en) 2004-10-29 2006-05-04 Rowland Robert G Epoxidized ester additives for reducing lead corrosion in lubricants and fuels
WO2006099250A1 (en) 2005-03-11 2006-09-21 Castrol Limited Multiple function graft polymer
US7622431B2 (en) 2006-01-04 2009-11-24 Chemtura Corporation Lubricating oil compositions
WO2016129148A1 (ja) * 2015-02-09 2016-08-18 株式会社Moresco 潤滑剤組成物及びその利用、並びに脂肪族エーテル化合物
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Also Published As

Publication number Publication date
EP3555248B1 (en) 2022-04-27
CN110462010B (zh) 2023-01-10
CN115895763B (zh) 2024-09-13
JP2022160461A (ja) 2022-10-19
US20200115651A1 (en) 2020-04-16
JP7107938B2 (ja) 2022-07-27
JP2020502338A (ja) 2020-01-23
JP2024081643A (ja) 2024-06-18
WO2018109123A1 (en) 2018-06-21
EP3555248A1 (en) 2019-10-23
CN115895763A (zh) 2023-04-04
CN110462010A (zh) 2019-11-15
PL3555248T3 (pl) 2022-08-29

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