GB1530198A - Amino phenols useful as additives for fuels and lubricant - Google Patents

Amino phenols useful as additives for fuels and lubricant

Info

Publication number
GB1530198A
GB1530198A GB42575/76A GB4257576A GB1530198A GB 1530198 A GB1530198 A GB 1530198A GB 42575/76 A GB42575/76 A GB 42575/76A GB 4257576 A GB4257576 A GB 4257576A GB 1530198 A GB1530198 A GB 1530198A
Authority
GB
United Kingdom
Prior art keywords
substituent
hydroxyl
nitro
aromatic
proviso
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
Application number
GB42575/76A
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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 Lubrizol Corp filed Critical Lubrizol Corp
Publication of GB1530198A publication Critical patent/GB1530198A/en
Expired 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
    • 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
    • C10M133/54—Amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F8/00—Chemical modification by after-treatment
    • C08F8/04—Reduction, e.g. hydrogenation
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    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/042—Siloxanes with specific structure containing aromatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
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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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/048—Siloxanes with specific structure containing carboxyl groups
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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    • 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
    • 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
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • C—CHEMISTRY; METALLURGY
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

1530198 Aminophenols LUBRIZOL CORP 13 Oct 1976 [14 Oct 1975 12 April 1976] 42575/76 Heading C2C [Also in Divisions C5 and C3] The invention relates to an aminophenol of formula wherein R is substantially saturated hydrocarbon substituent of at least 10 aliphatic carbon atoms; a, b, and c are each independently an integer of 1 up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b, and c does not exceed the unsatisfied valences of Ar; and Ar is an aromatic moiety, e.g. benzene or naphthalene having 0 to 3 optional substituents selected from C 1-6 alkyl, C 1-6 alkoxyl, nitro, halo, or combinations of two or more of said optional substituents; with the proviso that when Ar is a benzene nucleus having only one hydroxyl and one R substituent, the R substituent is ortho or para to said hydroxyl substituent. This compound is obtained by nitrating with at least one nitrating agent at least one compound of formula wherein R is substantially saturated hydrocarbon group of at least 10 aliphatic carbon atoms; a and c are each an integer of 1 up to three times the number of aromatic rings present in Ar<SP>1</SP> with the proviso that the sum of a, b and c does not exceed the unsatisfied valences of Ar<SP>1</SP>; and Ar<SP>1</SP> is an aromatic nucleus having 0 to 3 optional substituents selected from C 1-6 alkyl, C 1-6 alkoxyl, nitro, halo, and combinations of two or more such substituents, with the provisos that (a) Ar<SP>1</SP> has at least one hydrogen atom directly bonded to a carbon atom which is part of an aromatic ring, and (b) when Ar<SP>1</SP> is a benzene having only one hydroxyl and one R substituent, the R substituent is ortho or para to said hydroxyl substituent, to form a first reaction mixture containing a nitro intermediate, and (ii) reducing at least 50% of the nitro groups in the first reaction mixture to amino groups.
GB42575/76A 1975-10-14 1976-10-13 Amino phenols useful as additives for fuels and lubricant Expired GB1530198A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62235875A 1975-10-14 1975-10-14
US67617276A 1976-04-12 1976-04-12

Publications (1)

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GB1530198A true GB1530198A (en) 1978-10-25

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ID=27089190

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GB42575/76A Expired GB1530198A (en) 1975-10-14 1976-10-13 Amino phenols useful as additives for fuels and lubricant

Country Status (13)

Country Link
JP (1) JPS5248638A (en)
AU (1) AU512423B2 (en)
BE (2) BE847218A (en)
CA (1) CA1096886A (en)
DE (1) DE2646241A1 (en)
DK (2) DK153141C (en)
FI (2) FI63054C (en)
FR (1) FR2327982A1 (en)
GB (1) GB1530198A (en)
IT (1) IT1121681B (en)
MX (1) MX147153A (en)
NL (1) NL7611251A (en)
SE (2) SE423402B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2116583A (en) * 1982-03-12 1983-09-28 Lubrizol Corp Lubricant and fuel additives containing aminophenols
GB2124255A (en) * 1982-07-26 1984-02-15 Ass Octel Treatment of vanadium- containing fuel oils
EP0905150A1 (en) * 1997-09-30 1999-03-31 Chevron Chemical Company LLC Substituted biphenyl polyalkyl ethers and fuel compositions containing the same
EP0905120A2 (en) * 1997-09-30 1999-03-31 Chevron Chemical Company LLC Substituted biphenyl polyalkyl esters and fuel compositions containing the same
CN115975701A (en) * 2021-10-14 2023-04-18 中国石油化工股份有限公司 Lubricating oil composition for marine medium-speed trunk piston engine and preparation method thereof
CN115975693A (en) * 2021-10-14 2023-04-18 中国石油化工股份有限公司 Industrial lubricating oil composition and preparation method thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN145085B (en) * 1976-01-28 1978-08-19 Lubrizol Corp
FR2471365B1 (en) * 1979-12-10 1986-09-26 Lubrizol Corp AMINOPHENOL / HETEROCYCLE CONDENSATION PRODUCTS AND FUELS, LUBRICANTS AND CONCENTRATES OF ADDITIVES CONTAINING THEM
US5637119A (en) * 1995-12-29 1997-06-10 Chevron Chemical Company Substituted aromatic polyalkyl ethers and fuel compositions containing the same
JP2007153981A (en) * 2005-12-02 2007-06-21 Mitsui Chemicals Inc Olefinic polymer having aromatic ring at one end and application thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2367377A (en) * 1940-02-03 1945-01-16 Socony Vacuum Oil Co Inc Mineral oil compoisition and improving agents therefor
US2502708A (en) * 1945-03-31 1950-04-04 Harvel Corp Nitro-hydrogenated cardanols and process for preparing same
GB662509A (en) * 1948-08-21 1951-12-05 British Resin Prod Ltd The manufacture of 4-amino cardanol and compositions thereof
US2868844A (en) * 1957-01-22 1959-01-13 Ethyl Corp Selective nitration process
US3149933A (en) * 1960-08-25 1964-09-22 Bayer Ag Process for stabilizing liquid fuels
DE1271877B (en) * 1963-04-23 1968-07-04 Lubrizol Corp Lubricating oil
US3576743A (en) * 1969-04-11 1971-04-27 Lubrizol Corp Lubricant and fuel additives and process for making the additives

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2116583A (en) * 1982-03-12 1983-09-28 Lubrizol Corp Lubricant and fuel additives containing aminophenols
GB2151257A (en) * 1982-03-12 1985-07-17 Lubrizol Corp Lubricant and fuel additives containing aminophenol
GB2124255A (en) * 1982-07-26 1984-02-15 Ass Octel Treatment of vanadium- containing fuel oils
EP0905150A1 (en) * 1997-09-30 1999-03-31 Chevron Chemical Company LLC Substituted biphenyl polyalkyl ethers and fuel compositions containing the same
EP0905120A2 (en) * 1997-09-30 1999-03-31 Chevron Chemical Company LLC Substituted biphenyl polyalkyl esters and fuel compositions containing the same
EP0905120A3 (en) * 1997-09-30 2001-09-05 Chevron Chemical Company LLC Substituted biphenyl polyalkyl esters and fuel compositions containing the same
CN115975701A (en) * 2021-10-14 2023-04-18 中国石油化工股份有限公司 Lubricating oil composition for marine medium-speed trunk piston engine and preparation method thereof
CN115975693A (en) * 2021-10-14 2023-04-18 中国石油化工股份有限公司 Industrial lubricating oil composition and preparation method thereof

Also Published As

Publication number Publication date
DK461576A (en) 1977-04-15
AU1859676A (en) 1978-04-20
FI762917A (en) 1977-04-15
JPS627184B2 (en) 1987-02-16
AU512423B2 (en) 1980-10-09
FI62555C (en) 1983-01-10
DK461676A (en) 1977-04-15
IT1121681B (en) 1986-04-10
DE2646241A1 (en) 1977-04-28
DK153141B (en) 1988-06-20
DK160208B (en) 1991-02-11
DE2646241C2 (en) 1989-02-23
FI762916A (en) 1977-04-15
SE423402B (en) 1982-05-03
BE847219A (en) 1977-04-13
DK160208C (en) 1991-07-15
FR2327982B1 (en) 1980-10-03
FI62555B (en) 1982-09-30
NL7611251A (en) 1977-04-18
FI63054C (en) 1983-04-11
CA1096886A (en) 1981-03-03
SE7611381L (en) 1977-04-15
FR2327982A1 (en) 1977-05-13
JPS5248638A (en) 1977-04-18
BE847218A (en) 1977-04-13
DK153141C (en) 1988-12-05
SE423384B (en) 1982-05-03
SE7611382L (en) 1977-04-15
MX147153A (en) 1982-10-19
FI63054B (en) 1982-12-31

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Effective date: 19951013