WO2014185966A4 - Fuel additive composition - Google Patents

Fuel additive composition Download PDF

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Publication number
WO2014185966A4
WO2014185966A4 PCT/US2014/000101 US2014000101W WO2014185966A4 WO 2014185966 A4 WO2014185966 A4 WO 2014185966A4 US 2014000101 W US2014000101 W US 2014000101W WO 2014185966 A4 WO2014185966 A4 WO 2014185966A4
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WO
WIPO (PCT)
Prior art keywords
additive composition
fuel additive
set forth
fuel
amine
Prior art date
Application number
PCT/US2014/000101
Other languages
French (fr)
Other versions
WO2014185966A1 (en
Inventor
Alfred K. Jung
Marc Walter
Ludwig Voelkel
Peter Schreyer
Stephen M. ZELD
Alex ATTLESEY
Thomas E. Hayden
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to KR1020157034961A priority Critical patent/KR20160006754A/en
Priority to SG11201509341VA priority patent/SG11201509341VA/en
Priority to JP2016513942A priority patent/JP2016518503A/en
Priority to EP14729746.9A priority patent/EP2997115A1/en
Priority to CN201480039904.3A priority patent/CN105378040A/en
Priority to BR112015028627A priority patent/BR112015028627A2/en
Priority to AU2014265971A priority patent/AU2014265971A1/en
Priority to CA2912513A priority patent/CA2912513A1/en
Publication of WO2014185966A1 publication Critical patent/WO2014185966A1/en
Publication of WO2014185966A4 publication Critical patent/WO2014185966A4/en

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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
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • 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
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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)
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
    • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
    • 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
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
    • 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
    • C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
    • C10L2250/08—Emulsion details
    • 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
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines
    • 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
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/24—Mixing, stirring of fuel components

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

A fuel additive composition includes a polyalkenylsuccinimide, a mono or polyfunctional polyisobutene amine, and a carrier oil selected from the group of mineral oils, polyethers, polyetheramines, esters, and combinations thereof. The polyalkenylsuccinimide includes the reaction product of a hydrocarbyl dicarboxylic acid producing reaction intermediate and a nucleophilic reactant. The hydrocarbyl dicarboxylic acid producing reaction intermediate includes the reaction product of a polyolefin comprising C2 to Ci8 olefin units and having a number average molecular weight (Mn) of about 500 to 5,000 g/mol and a C4 to Cio monounsaturated acid reactant. The hydrocarbyl dicarboxylic acid producing reaction intermediate includes from 0.5 to 10 dicarboxylic acid producing moieties per molecule of the polyolefin. The nucleophilic reactant is selected from the group of amines, alcohols, amino alcohols, and combinations thereof.

Claims

AMENDED CLAIMS
received by the International Bureau on 14 November 2014(14.11.2014)
What is claimed is:
1. A fuel additive composition comprising:
(D) a po!yalkenylsuccinirnide comprising the reaction product of;
(2) a hydrocarby! dicarboxylic acid producing reaction intermediate comprising the reaction product of;
(c) a poiyolefm comprising C? to C-, s olefin units and having a cumber average molecular weight (M„) of about 500 to 5,000 g moL and
(d) a C4 to Cio monounsaturated acid reaetant, wherein said hydrocarbyl dicarboxylic acid producing reaction intermediate includes from 0.5 to 10 dicarboxylic acid producing moieties per molecule of said poiyolefm; and
(2) a nucleophilic reaciant selected from the group of amines, alcohols, amino aicohols, and combinations thereof:
(E) a mono or polyfunetionai polyisobutene. amine comprising:
a reaction product formed via hydroformylation of a second reactive polyisobutene having a content of terminal double bonds of greater than 50 mo! % to form an oxo intermediate and subsequent reductive animation of said oxo intermediate; and/or
a reaction product of the second reactive polyisobutene having a content of terminal double bonds of greater than 50 rnoi % and a second amine having the following formula:
HNR2R3
wherein R2 and J are each independently H, a Ci- g- aikyi, C2-Cis-aik nyi, Gt-Cjs-cyeioa!kyl, Ci~C;«-alkylaryl, h droxy-Cf-Ciralkyl, poly(oxyalkyl), polyalkylene polyamine or a polyalkylene amine radical; or, together with the nitrogen atom to which they are bonded, form a heterocyclic ring; and
(F) a carrier oil selected from the group of mineral oils, polyethers, polyetheramines, esters, and combinations thereof.
2, A fuel additive composition as set forth in claim 1 further comprising (D) a demulsifier package.
47
3. A fuel additive composition as set forth in claim 2 wherein said demulsifief package (D) comprises a dernulsifler selected from a salt of a fatty acid, an alky! amino eatboxyiic acid, an organo sulfur compound, a polyetheroi, and combinations thereof,
4. A fuel additive composition as set forth in claim 3 wherein said polyetheroi is selected from alkoxylated alky] phenol resins, alkoxylated alky] phenol formaldehyde resins, alkoxylated epox resins, alkoxylated po!yethyienefmines, amine alkoxy!ates, ctlioxlyated polyetherois, propoxylaled polyetherois, ethoxylated-propoxylated polyetherois, and combinations thereof.
5. A fuel additive composition as set forth in claim 4 wherein said polyetheroi is a block copolymer.
6. A fuel additive composition as set forth in claim 4 wherein said polyetheroi is a random copolymer.
7. A fuel additive composition as set forth in any one of claims 2 through 6 wherein said demuislfier package (D) is substantially free of sulfur.
8. A fuel additive composition as set forth in any one of claims 3 through 6 wherein said organo sulfur compound comprises a sulfonic acid.
9. A fuel additive composition as set forth in any preceding claim wherein said poiyolefln (a) is a first reactive polyisobutene having a content of terminal double bonds of greater than SO moi %.
10. A fuel additive composition as set forth in any preceding claim wherein said C4 to CI O monounsaturated acid reactant (b) is selected from the group of maleic acid, maleic anhydride, functional derivatives thereof, and combinations thereof.
1 1. A fuel additive composition as set forth in any preceding claim wherein said hydrocarbyl dicarboxyiic acid producing reaction intermediate (1) is a polyalkenyisuecinic anhydride,
12. A fuel additive composition as set forth in any preceding claim wherein said hydrocarbyl dicarboxyiic acid producing reaction intermediate (1) is a poiyisobutenyisuceinie anhydride.
13. A fuel additive composition as set forth in any preceding claim wherein said nucleophiiie reactant (2) comprises tetraethyienepentamtne.
14. A fuel additive composition as set forth in any preceding claim wherein said nucleophiiie reactant (2) is a 2 to C o polyalky!ene polyamine which includes from 2 to 9 nitrogen atoms per molecule and wherein 0, 1 to 3.0 mol of dicarboxyiic acid moieties are reacted per equivalent of nucleophiiie reactant to form said polyaikenylsuccmimide (A).
48
15. A fuel additive composition as set forth in any preceding claim wherein said poiyalkenylsuccinimide (A) is the reaction product of said reaction intermediate (1) which is further defined as a polyisobutylene of having a number average molecular weight (M„) of about 500 to 5,000 molecular weight substituted with succinic anhydride moieties, and said nuc!eophilic reactant (2) which is further defined as a Qt to C 0 poiyaiky!ene poiyamine which includes from 3 to 9 nitrogen atoms per molecule.
16. A fuel additive composition as set forth in any preceding claim wherein said po3ya3kenylsuceimmide (A) comprises the reaction product of:
(3) a polyisobutenylsuocinic anhydride; and
(4) a first amine;
wherein said poiyisobutenyisuccime anhydride is first reacted with an alcohol, then reacted with said first amine to form said polyisobutenyisuccinimide, and wherein said alcohol, which is either unreacted or cleaved, is optionally removed,
17. A fuel additive composition as set forth in claim 16 wherein said alcohol is selected from the group consisting of moriohydric alcohols of the formula JR OH, where R! is straight-chain or branched, cyclic or branched cyclic alky! of 1 to 16 carbon atoms, and combinations thereof.
18. A fuel additive composition as set forth in claim 16 or 17 wherein said first amine has the following formula:
HaNiCHz^-NH-fiCHj Hja-iCHa NHa
where x and y are each independently an integer from 1 to 5 and z is an integer from 0 to 8, or mixtures thereof,
19. A fuel additive composition as set forth in any preceding claim wherein said polyalkenylsueciiiimkJe (A) has the following general structure:
(B) a polyisobutenyisuccinimide having the following structure;
Figure imgf000004_0001
wherein m is an integer of from 2-80.
20. A fuel additive composition as set forth in claim 1 wherein said second reactive polyisobutene has a d!spersity of less than 6. 21 , A fuel additive composition as set forth in claim 20 wherein said second reactive polyisobutene has a number average molecular weight (Mr,) of from 500 to 5,000
22, A fuel additive composition as set forth in any preceding claim wherein said carrier oil (C) comprises a propoxylate carrier oil having the following formula:
4-[0-CH2-CH(CIT3)]„-OH
wherein n is an integer of from 8 to 35, and RA is straight-chain or branched Cg-Cir aikyi or Cs-Cig-alkenyi,
23, A fuel additive composition as set forth in any preceding claim wherein said carrier oil (C) comprises propoxyfaied isotridecanol.
24, A fuel additive composition as set forth in any one of claims 2 through 23 comprising 1 to 75 parts by weight of said polyalfcenyisuceinimide (A), 5 to 70 parts by weight of said polyisobutene amine (B), 2 to 94 parts by weight of sa id carrier oil (C), and less than 5 parts by weight of said demulsifier package (D), based on ] 00 parts by weight of said fuel additive composition.
25, An additivated fuel comprising 1 0 to 10,000 mg of said fuel additive composition set forth in any preceding claim per 1 kg of fuel.
26, An additivated fuel as set forth in claim 25 in which less than 1.5 mg of sulfur per kg of additivated fuel is contributed by the fuel additive composition to the additivated fuel
27, A method of reducing fuel consumption of an internal combustion engine comprising the step of adding the fuel additive composition of any preceding claim to fuel.

STATEMENT t IIER Α¾ ΐ€¾ J ;gjt

Independent claim 1 has been amended to further define the mono or poiyfunctional poiyisobutene amine (B). Support for this amendment can be found in at least paragraphs [0020] and [0021] of the original specification. Accordingly, no new matter is added.

Notably, claims 20 and 2 i , which are now included in amended claim I, were already deemed novel by the Examiner in the Written Opinion,

Further, with respect to amended claim 1, the Applicant respectfully asserts that references Dl, D2, and D3 fail to disclose, teach, or even suggest ihe mono or poly-functional poiyisobutene amine (B) now claimed in amended claim Ϊ , Said differently, the cited references aione or in combination do not disclose each and every element of amended claim 1 , For these reasons, the Applicants submit that independent claim 1 and claims dependent thereon are novel and involve an inventive step.

PCT/US2014/000101 2013-05-14 2014-05-14 Fuel additive composition WO2014185966A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
KR1020157034961A KR20160006754A (en) 2013-05-14 2014-05-14 Fuel additive composition
SG11201509341VA SG11201509341VA (en) 2013-05-14 2014-05-14 Fuel additive composition
JP2016513942A JP2016518503A (en) 2013-05-14 2014-05-14 Fuel additive composition
EP14729746.9A EP2997115A1 (en) 2013-05-14 2014-05-14 Fuel additive composition
CN201480039904.3A CN105378040A (en) 2013-05-14 2014-05-14 Fuel additive composition
BR112015028627A BR112015028627A2 (en) 2013-05-14 2014-05-14 fuel additive composition, additive fuel, and method for reducing fuel consumption of an internal combustion engine
AU2014265971A AU2014265971A1 (en) 2013-05-14 2014-05-14 Fuel additive composition
CA2912513A CA2912513A1 (en) 2013-05-14 2014-05-14 Fuel additive composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361823083P 2013-05-14 2013-05-14
US61/823,083 2013-05-14

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WO2014185966A1 WO2014185966A1 (en) 2014-11-20
WO2014185966A4 true WO2014185966A4 (en) 2015-01-08

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JP (1) JP2016518503A (en)
KR (1) KR20160006754A (en)
CN (1) CN105378040A (en)
AU (1) AU2014265971A1 (en)
BR (1) BR112015028627A2 (en)
CA (1) CA2912513A1 (en)
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WO (1) WO2014185966A1 (en)

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CN106118794B (en) * 2016-07-04 2019-07-09 赣南师范大学 A kind of solid alcohol and its safe preparation method
WO2018069460A1 (en) * 2016-10-12 2018-04-19 Chevron Oronite Technology B.V. Marine diesel lubricant oil compositions
CN108559557A (en) * 2018-05-16 2018-09-21 上海纽孚尔能源技术有限公司 Microemulsified kitchen waste grease preparing bio-fuel
CN110551240B (en) 2018-05-31 2022-05-03 中国石油化工股份有限公司 Amino polymer, preparation method and application thereof
CN110862529B (en) * 2019-11-01 2022-09-06 武汉帕浦安科技有限公司 Polyether polyol for fuel additive and preparation method and application thereof
WO2022056212A1 (en) 2020-09-14 2022-03-17 Ecolab Usa Inc. Cold flow additives for plastic-derived synthetic feedstock
EP4416248A1 (en) 2021-10-14 2024-08-21 Ecolab Usa Inc. Antifouling agents for plastic-derived synthetic feedstocks
US11820955B2 (en) 2022-02-28 2023-11-21 International Petroleum Products & Additives Company, Inc. Dispersants derived from aromatic polyamines, lubricants, and methods

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US5089028A (en) * 1990-08-09 1992-02-18 Mobil Oil Corporation Deposit control additives and fuel compositions containing the same
US5405419A (en) * 1994-05-02 1995-04-11 Chevron Chemical Company Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool
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US5752989A (en) * 1996-11-21 1998-05-19 Ethyl Corporation Diesel fuel and dispersant compositions and methods for making and using same
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EP2997115A1 (en) 2016-03-23
SG11201509341VA (en) 2015-12-30
CA2912513A1 (en) 2014-11-20
AU2014265971A1 (en) 2015-12-03
JP2016518503A (en) 2016-06-23
KR20160006754A (en) 2016-01-19
BR112015028627A2 (en) 2017-07-25
US20140338253A1 (en) 2014-11-20
CN105378040A (en) 2016-03-02
WO2014185966A1 (en) 2014-11-20

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