WO2002090471A3 - Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof - Google Patents

Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof Download PDF

Info

Publication number
WO2002090471A3
WO2002090471A3 PCT/US2002/013949 US0213949W WO02090471A3 WO 2002090471 A3 WO2002090471 A3 WO 2002090471A3 US 0213949 W US0213949 W US 0213949W WO 02090471 A3 WO02090471 A3 WO 02090471A3
Authority
WO
WIPO (PCT)
Prior art keywords
detergent composition
fuel
concentrate
ortho
phenol
Prior art date
Application number
PCT/US2002/013949
Other languages
French (fr)
Other versions
WO2002090471A2 (en
Inventor
Malcolm G J Macduff
Rodney J Mcatee
Mitchell M Jackson
David J Moreton
Original Assignee
Lubrizol Corp
Malcolm G J Macduff
Rodney J Mcatee
Mitchell M Jackson
David J Moreton
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, Malcolm G J Macduff, Rodney J Mcatee, Mitchell M Jackson, David J Moreton filed Critical Lubrizol Corp
Priority to US10/474,653 priority Critical patent/US20040168364A1/en
Priority to EP02734157A priority patent/EP1385924A2/en
Priority to AU2002305344A priority patent/AU2002305344A1/en
Publication of WO2002090471A2 publication Critical patent/WO2002090471A2/en
Publication of WO2002090471A3 publication Critical patent/WO2002090471A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Abstract

A detergent composition comprises a Mannich reaction product of a hydrocarbyl-substituted ortho-alkyl substituted phenol (1) or a mixture of the phenol (1) and a hydrocarbyl-substituted phenol (2), an aldehyde, and an amine where the phenol (1) is present in the mixture at about 50 mole % or higher. Concentrate and fuel compositions include the detergent composition. A method of controlling deposits in an internal combustion engine comprises operating the engine with the fuel composition which results in unexpectedly superior detergent performance.
PCT/US2002/013949 2001-05-04 2002-05-02 Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof WO2002090471A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US10/474,653 US20040168364A1 (en) 2001-05-04 2002-05-02 Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof
EP02734157A EP1385924A2 (en) 2001-05-04 2002-05-02 Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof
AU2002305344A AU2002305344A1 (en) 2001-05-04 2002-05-02 Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US28893001P 2001-05-04 2001-05-04
US28893101P 2001-05-04 2001-05-04
US60/288,931 2001-05-04
US60/288,930 2001-05-04

Publications (2)

Publication Number Publication Date
WO2002090471A2 WO2002090471A2 (en) 2002-11-14
WO2002090471A3 true WO2002090471A3 (en) 2003-11-27

Family

ID=26965339

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/013949 WO2002090471A2 (en) 2001-05-04 2002-05-02 Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof

Country Status (4)

Country Link
US (1) US20040168364A1 (en)
EP (1) EP1385924A2 (en)
AU (1) AU2002305344A1 (en)
WO (1) WO2002090471A2 (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10256161A1 (en) * 2002-12-02 2004-06-09 Basf Ag Use of amines and / or Mannich adducts in fuel and lubricant compositions for direct injection gasoline engines
US20070151144A1 (en) * 2003-05-06 2007-07-05 Samsung Electronics Co., Ltd. Detergent comprising the reaction product an amino alcohol, a high molecular weight hydroxy aromatic compound, and an aldehydye
DE102004005108A1 (en) 2004-02-02 2005-10-27 Basf Ag Process for the preparation of polyisobutenylphenols
US7597726B2 (en) * 2006-01-20 2009-10-06 Afton Chemical Corporation Mannich detergents for hydrocarbon fuels
US20070245621A1 (en) * 2006-04-20 2007-10-25 Malfer Dennis J Additives for minimizing injector fouling and valve deposits and their uses
US20080040968A1 (en) * 2006-08-17 2008-02-21 Malfer Dennis J Fuel additive compounds and method of making the compounds
US8430936B2 (en) * 2007-11-30 2013-04-30 Baker Hughes Incorporated Stabilization of fatty oils and esters with alkyl phenol amine aldehyde condensates
WO2013159571A1 (en) * 2012-04-26 2013-10-31 中国石油化工股份有限公司 Lubricating oil composition and preparation method therefor
WO2014110551A1 (en) * 2013-01-14 2014-07-17 The Trustees Of Columbia University In The City Of New York Antioxidant flavonoid derivatives
US20150052804A1 (en) * 2013-08-23 2015-02-26 Chevron U.S.A. Inc. Diesel fuel composition
CN104560240B (en) * 2013-10-23 2016-06-22 中国石油化工股份有限公司 Wear-resistant cleaning agent composition, Dresel fuel compositions and the method improving the wear-resistant cleansing performance of diesel oil
CN104946352B (en) * 2014-03-25 2017-11-03 中国石油化工股份有限公司 Lubricant oil composite
US10221267B2 (en) 2016-12-13 2019-03-05 Afton Chemical Corporation Microstructure-controlled copolymers of ethylene and C3-C10 alpha-olefins
US10584297B2 (en) 2016-12-13 2020-03-10 Afton Chemical Corporation Polyolefin-derived dispersants
US20190177632A1 (en) * 2017-12-12 2019-06-13 Afton Chemical Corporation Fuel compositions containing detergents derived from ethylene-alpha olefin copolymers
CN108359032B (en) * 2018-01-25 2021-03-12 东营市浩瀚生化科技有限公司 Chemically modified Mannich base and preparation method and application thereof
CN111499526A (en) * 2020-05-27 2020-08-07 新乡市瑞丰新材料股份有限公司 Preparation method of ashless lubricating oil detergent

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3649229A (en) * 1969-12-17 1972-03-14 Mobil Oil Corp Liquid hydrocarbon fuels containing high molecular weight mannich bases
US3736357A (en) * 1965-10-22 1973-05-29 Standard Oil Co High molecular weight mannich condensation products from two different alkyl-substituted hydroxy-aromatic compounds
US3994698A (en) * 1972-02-29 1976-11-30 Ethyl Corporation Gasoline additive concentrate composition
EP0182940A1 (en) * 1984-11-13 1986-06-04 Mobil Oil Corporation Mannich base oil additives
WO1996028495A1 (en) * 1995-03-10 1996-09-19 Exxon Chemical Patents Inc. Mannich base polymers
EP0870819A2 (en) * 1997-04-10 1998-10-14 Ethyl Corporation Additives for minimizing intake valve deposits, and their use
WO2001025293A1 (en) * 1999-10-06 2001-04-12 Basf Aktiengesellschaft Method for producing mannich adducts that contain polyisobutylene phenol
WO2001025294A1 (en) * 1999-10-06 2001-04-12 Basf Aktiengesellschaft Method for producing mannich adducts that contain polyisobutylene phenol
WO2001042399A1 (en) * 1999-12-13 2001-06-14 Ethyl Corporation Fuels compositions for direct injection gasoline engines containing mannich detergents

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984550A (en) * 1956-09-06 1961-05-16 Nalco Chemical Co Color stabilization of petroleum oils and compositions therefor
US4117011A (en) * 1974-05-06 1978-09-26 Ethyl Corporation Additives
US5697988A (en) * 1991-11-18 1997-12-16 Ethyl Corporation Fuel compositions
US5634951A (en) * 1996-06-07 1997-06-03 Ethyl Corporation Additives for minimizing intake valve deposits, and their use
GB9618546D0 (en) * 1996-09-05 1996-10-16 Bp Chemicals Additives Dispersants/detergents for hydrocarbons fuels
US6048373A (en) * 1998-11-30 2000-04-11 Ethyl Corporation Fuels compositions containing polybutenes of narrow molecular weight distribution
US6179885B1 (en) * 1999-06-22 2001-01-30 The Lubrizol Corporation Aromatic Mannich compound-containing composition and process for making same
US6800103B2 (en) * 2001-02-02 2004-10-05 Ethyl Corporation Secondary amine mannich detergents
US20030014910A1 (en) * 2002-06-06 2003-01-23 Aradi Allen A. Fuel compositions for direct injection gasoline engine containing mannich detergents

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3736357A (en) * 1965-10-22 1973-05-29 Standard Oil Co High molecular weight mannich condensation products from two different alkyl-substituted hydroxy-aromatic compounds
US3649229A (en) * 1969-12-17 1972-03-14 Mobil Oil Corp Liquid hydrocarbon fuels containing high molecular weight mannich bases
US3994698A (en) * 1972-02-29 1976-11-30 Ethyl Corporation Gasoline additive concentrate composition
EP0182940A1 (en) * 1984-11-13 1986-06-04 Mobil Oil Corporation Mannich base oil additives
WO1996028495A1 (en) * 1995-03-10 1996-09-19 Exxon Chemical Patents Inc. Mannich base polymers
EP0870819A2 (en) * 1997-04-10 1998-10-14 Ethyl Corporation Additives for minimizing intake valve deposits, and their use
WO2001025293A1 (en) * 1999-10-06 2001-04-12 Basf Aktiengesellschaft Method for producing mannich adducts that contain polyisobutylene phenol
WO2001025294A1 (en) * 1999-10-06 2001-04-12 Basf Aktiengesellschaft Method for producing mannich adducts that contain polyisobutylene phenol
WO2001042399A1 (en) * 1999-12-13 2001-06-14 Ethyl Corporation Fuels compositions for direct injection gasoline engines containing mannich detergents

Also Published As

Publication number Publication date
AU2002305344A1 (en) 2002-11-18
US20040168364A1 (en) 2004-09-02
EP1385924A2 (en) 2004-02-04
WO2002090471A2 (en) 2002-11-14

Similar Documents

Publication Publication Date Title
WO2002090471A3 (en) Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof
EP1518918A3 (en) Fuels compositions and methods for using same
EP0870819A3 (en) Additives for minimizing intake valve deposits, and their use
IL210454A (en) Antibody against a cytokine zcytor17 ligand
WO2001066673A3 (en) Fuel additive compositions and fuel compositions containing detergents and fluidizers
WO2004050806A3 (en) Use of amines and/or mannich adducts in fuel and lubricant compositions for direct injection spark ignition engines
CA2387243A1 (en) Organic colloidal dispersion of a rare earth compound monocrystalline particles
WO2001086126A3 (en) Multiple operating mode engine and method of operation
WO2003014267A3 (en) Fuel composition containing detergent combination and methods thereof
EP1070838A3 (en) Method of reducing nitrogen oxide (NOx) emissions of piston engine
BR9507273A (en) Aqueous fuel for an internal combustion engine and method for its preparation
BR0209209A (en) Fuel additive composition, fuel composition, method of solubilizing a nitrogen compound in a fuel composition, uses a nitrogen compound, oleic alkanolamide and alkoxylated oleic acid, method of operating an internal combustion engine , and, fuel additive
EP1247971A3 (en) Control system and method for an internal combustion engine
WO2003083020A3 (en) Method of operating internal combustion engine by introducing detergent into combustion chamber
WO2003070861A3 (en) Method for operating internal combustion engine with a fuel composition
CA2406762A1 (en) Fuel additive packets for gasoline fuels having improved viscosity properties and good ivd performance
CA2220282A1 (en) Internal combustion engine
WO2001097952A3 (en) A process for reducing pollutants from the exhaust of a diesel engine
WO2003038015A3 (en) Method
ATE328986T1 (en) FUEL ADDITIVE FOR VALVE SEAT BACKBACK PREVENTION
CA2358227A1 (en) Process for producing an amide compound
AU2001249973A1 (en) Fuel additives
EP1531176A3 (en) Hydrocarbyl substituted dispersants and compositions containing the dispersants
CA2441187A1 (en) Acetyllysine-recognizing monoclonal antibody and process for producing the same
EP1043737A3 (en) Ignition coil for internal combustion engines

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PH PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 10474653

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2002734157

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2002734157

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP

WWW Wipo information: withdrawn in national office

Ref document number: 2002734157

Country of ref document: EP