DK169584B1 - Polybutyl- eller polyisobutylaminer, fremgangsmådetil fremstilling deraf og brændstof- og smøremiddelblandinger, der indeholder disse - Google Patents
Polybutyl- eller polyisobutylaminer, fremgangsmådetil fremstilling deraf og brændstof- og smøremiddelblandinger, der indeholder disse Download PDFInfo
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- DK169584B1 DK169584B1 DK170087A DK170087A DK169584B1 DK 169584 B1 DK169584 B1 DK 169584B1 DK 170087 A DK170087 A DK 170087A DK 170087 A DK170087 A DK 170087A DK 169584 B1 DK169584 B1 DK 169584B1
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- Prior art keywords
- polybutyl
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- general formula
- same
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- 239000000203 mixture Substances 0.000 title claims description 23
- 239000000446 fuel Substances 0.000 title claims description 20
- 239000000314 lubricant Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title description 7
- 229920001083 polybutene Polymers 0.000 claims description 26
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 17
- 229920002367 Polyisobutene Polymers 0.000 claims description 11
- 238000005576 amination reaction Methods 0.000 claims description 10
- 238000007037 hydroformylation reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000006294 amino alkylene group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- -1 polybutylene Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002816 fuel additive Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 229920001748 polybutylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000892 gravimetry Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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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
- C10M133/58—Heterocyclic compounds
-
- 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
- C10L1/22—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
- C10L1/22—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
- 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
- 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
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives 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
- 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
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Description
DK 169584 B1
Opfindelsen angår polybutyl- eller polyisobutylaminer, fremgangsmåde til fremstilling heraf og brændstof- og smøremiddelblandinger indeholdende polybutyl- eller poly-isobutylaminer.
5
Polybutenylaminer og anvendelsen deraf som brændstof- og smøremiddelblandinger har været kendt i lang tid og er f.eks. beskrevet i US patent nr. 3 275 554 og i DE-A-2 125 039.
10
De kendte polybutenylaminer fremstilles ved halogenering af polybutener og omsætning af halogeniderne med aminer.
Ved fremstillingen af disse produkter opstår der ionogent halogen, der i så vidtgående omfang som muligt skal fjer-15 nes.
I den kendte teknik foreligger der derfor talrige forsøg på at forbedre de kendte produkter, især da fjernelsen af det ionogene halogen ikke blot kræver omstændelige 20 forholdsregler, men da der også i omsætningsprodukterne stadig forbliver betydelige halogenmængder, jf.
DE-A-2 245 918.
I DE-A-2 702 604 er der beskrevet såkaldte reaktive poly-25 isobutener, der kan omsættes med maleinsyreanhydrid (MSA) og oligo- eller polyaminer til mineraloliehjælpemidler.
De således fremstillelige mineraloliehjælpemidler udviser den store fordel, at de næsten er halogenfri. En ulempe er den vanskelige tillej ring af MSA (en reaktion i for-30 bindelse med en tjæredannelse, dvs. uønskede biprodukter.
Det er opfindelsens formål at tilvejebringe brændstofeller smøremiddelblandinger med tilsætningsmidler, som forhindrer aflejringer i indføringssystemet i forbræn-35 dingsmotorer, henholdsvis udviser en særlig god disperge-ringsmiddelvirkning. Dette formål opnås med polybutyl-eller polyisobutylaminerne ifølge opfindelsen.
DK 169584 B1 2
Polybutyl- eller polyisobutylaminerne Ifølge opfindelsen, der er af den i indledningen til krav 1 angivne art, er ejendommelige ved det i den kendetegnende del af krav 1 angivne.
5
Opfindelsen angår endvidere en fremgangsmåde til fremstilling af forbindelser med den almene formel 1 via trinnet omfattende forbindelserne med den almene formel V, at man hydroformylerer et tilsvarende polybuten eller 10 polyisobuten med en rhodium- eller cobaltkatalysator i nærværelse af CO og ^ ved temperaturer mellem 80 og 200 °C og CO/H^-tryk på indtil 600 bar, og at man derpå gennemfører en hydrerende aminering af oxoproduktet. Amineringsreaktionen gennemføres ved temperaturer mellem 80 og 15 200 "C og tryk indtil 600 bar, fortrinsvis 80-300 bar.
De således opnåede produkter udmærker sig i forhold til de i henhold til DE-0S-1 545 487 ved halogenering og aminering opnåede produkter, hvad angår fravær af chlorfor-20 bindeiser og forbedret ydeevne.
Ved fremstillingsmetoden anvender man hensigtsmæssigt et velegnet, inert opløsningsmiddel for at reducere reaktionsblandingens viskositet. Som opløsningsmidler er 25 fremfor alt svovlfattigt alifatiske, cycloalifatiske og aromatiske carbonhydrider velegnede. Man foretrækker især alifatiske opløsningsmidler, der er frie for svovlforbindelser, og som indeholder under 1% aromater. De har den fordel, at der ved høje amineringstemperaturer ikke bli-30 ver frigjort nogen hydreringsvarme, og at der ikke bliver forbrugt noget hydrogen. Ved aminerings- og hydroformyle-ringsreaktionen ligger opløsningsmiddelindholdet i afhængighed af den polymeres og opløsningsmidlets viskositet mellem 0 og 70 vægt-%. Højere fortyndinger er lige så 35 uøkonomiske som en opløsningsmiddeludveksling mellem oxidering og aminering.
3 DK 169584 B1
Ved fremgangsmåden ifølge opfindelsen kan man uden videre opnå polybutenomsætninger mellem 80 og 90%. Polybutener-ne, der overvejende er opbygget af isobutenenheder (isobutenindholdet ligger for det meste over 80 vægt-%), 5 har f.eks. en molekylvægt på 300-5000, fortrinsvis 500-2500. Man kan ifølge opfindelsen anvende reaktive polybutener, især polybuten A, B eller C. Ved reaktivt polybuten forstår man en umættet polymer med stor kemisk ensartethed, hvorved over 10% af dobbeltbindigerne står i 10 α-stilling. I DE 2 702 604 beskrives en vej til fremstilling af sådanne polybutener. En på denne måde fremstillet polymer indeholder ca. 60% a-olefin og 30% i-polymer, trisubstitueret.
15 Middelreaktive polybutener fremkommer for det meste ved polymerisation af isobuten eller isobutenholdige (^-fraktioner med aluminiumholdige katalysatorer, de er i kemisk henseende mindre ensartede og indeholder kun ringe mæng- 13 der α-olefin, for det meste under 10%. Signalerne i C-20 NMR viser forskellen. Den i 0-stillingen foreliggende, trisubstituerede, kemisk ensartede andel andrager ved polybuten B ca. 40%, og α-andelen ca. 10%. Endelig må man betegne polybuten A som mindre reaktiv, og den udviser ikke mere nogen nævneværdig kemisk ensartede andele.
25 Særligt velegnede polybutener og polyisobutener til fremstilling af polyaminerne ifølge opfindelsen med den almene formel I og alkoholerne med den almene formel V er sådanne, som udviser en gennemsnitlig polymerisationsgrad 30 P på 10 til 100, og hvori andelen E af dobbeltbindinger, der er i stand til at reagere med maleinsyreanhydrid, andrager 60 til 90%. Herved svarer en værdi E = 100% til den beregnede teoretiske værdi i det tilfælde, at hvert molekyle af den buten- eller isobutenpolymere indeholder 35 en sådan reaktiv dobbeltbinding. Værdien E beregnes for en reaktion af polyisobutenen med maleinsyreanhydrid i et vægtforhold på 5:1 og med 4 timers opvarmning af 4 DK 169584 B1 blandingen under omrøring ved 200 °C. Yderligere enkeltheder i denne forbindelse findes i GB-A-1 592 016, hvortil der her udtrykkeligt henvises.
5 Polybutenerne er handelsprodukter.
Det ved hydroformyleringen opståede oxoprodukt foreligger normalt som aldehyd/alkohol-blanding. Det kan viderefor-arbejdes som blanding eller kan af hensyn til lagerstabi-10 liteten i forvejen blive gennemhydratiseret. Gennemhydra- tiserede produkter er mindre reaktive.
Ved den beskrevne hydroformylering dannes polybutyl-eller polyisobutylalkoholer med den almene formel V 15 R^-CI^-OH (V) hvori er en isobuten og indtil 20 vægt-% n-buten afledt polybutyl- eller polyisobutylgruppe. Disse forbindelser er f.eks. brugbare som mellemprodukter til fremstilling af forbindelserne med den almene formel I. De 20 opstår som før beskrevet ved hydroformylering af de før angivne polybutener. Man foretrækker især polybutyl-eller polyisobutylalkoholer med formel V, hvor gruppen R^ indeholder 20 til 400 carbonatomer.
25 Af økonomiske grunde er polybutyl- eller polyisobutylami-ner med den almene formel 1, hvori grupperne R2 og Rg i hvert tilfælde er hydrogen, velegnede på brændstofområdet, dvs. i brændstofblandingerne ifølge opfindelsen, især som ventilrenholdende eller -rensende additiv. Dose-30 ringen af polybutyl- eller polyisobutyl-aminerne med den almene formel 1 som brændstofadditiv andrager hensigtsmæssigt 10-2000 mg/kg, hvorved man foretrækker et område på 50-800 mg/kg. En optimal virkning kan opnås i området 100-400 ppm som additiv til Otto-brændstof til eksplo-35 sionsmotorer. Med en lige så god virkning lader ringere mængder sig dosere, når nitrogenindholdet er højere, fremfor alt ved anvendelse af polyaminer, f.eks. af DK 169584 Bl 5 dimethylaminopropylamin, eller ved anvendelse af polybu-tyl- eller polyisobutylaminer med den almene formel I med lavmolekylær polybutyl- eller polyisobutyldel, og der yderligere doseres sædvanlige bærestoffer, f.eks. polybu-5 ten, polybutylalkohol, klare remanenser fra jordolie-destillation eller andre mineralolier. Ved anvendelse af polyaminer, såsom diethylentriamin til pentaethylenhex-amin opnår man i stedet karburator-detergenter eller såkaldte askefri dispergatorer til smøreolier.
10
Halogenindholdet af polybutyl- eller polyisobutylaminerne svarer til halogenindholdet af udgangsmaterialerne. Det ligger for det meste under 30 mg/kg.
15 Opfindelsen angår yderligere en brændstof- smøremiddelblanding af den i indledningen til krav 3 beskrevne art, som er ejendommelig ved det i krav 3's kendetegnende del angivne.
20 Ved en foretrukken udførelsesform tilvejebringes en brændstof- eller smøremiddelblanding indeholdende forbindelser med den almene formel I, hvori gruppen er en af isobuten og af indtil 20 vægt-% n-buten afledet polybutyl- eller polyisobutylgruppe med 32 til 200, 25 fortrinsvis 35 til 200 carbonatomer, og hvor R2 og Rg, som kan være ens eller forskellige, er hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sek.-butyl, i-butyl, tert.-butyl, pentyl, hexyl, phenyl, -CH2-CH2-NH2, CHq / 30 -ch2-ch2-ch2-n ch3 j-CHg-CHg-NHJpCH2-CHg“NHg, hvori p er et helt tal fra 1 35 6 DK 169584 B1 til 7, især 1 til 3, -CH2-CH2-OH, £cH2-CH2-oJ-g-CH2-OH, hvori q er et helt tal mellem 1 og 30, eller sammen med det nitrogenatom, hvortil de er 5 knyttet, danner en morfolinylgruppe.
Da man i brændstofadditiver uden tab af aktiviteten kan erstatte ca. 50 vægt-% af det aktive stof med polyisobu-ten (PiB), er tilsætningen af PiB særlig fordelagtig fra 10 et økonomisk synspunkt. I forbindelse med polyisobuten kan det dreje sig om et sådant med en molekylvægt på 300 til 2000, fortrinsvis 500 til 1500.
Hvis det i forbindelse med opfindelsen drejer sig om en 15 brændstof blanding, dvs. om et brændstof til eksplosionsmotorer, kan polybutyl- eller polyisobutylaminen med den almene formel I f.eks. foreligge i en mængde mellem 10 og 2000 mg/kg brændstof, især mellem 100 og 400 mg/kg brændstof.
20 I smøremiddelblandingen ifølge opfindelsen kan polybutyl-eller polyisobutylaminen f.eks. foreligge i en mængde mellem 0,5 og 5 vægt-%, især mellem 1 og 3 vægt-%, beregnet i forhold til blandingens totale vægt.
25
Hvis der i forbindelse med den almene formel I foreligger hydroxygrupper, er disse forbindelser særligt interessante som brændstofadditiv. 1 2 3 4 5 6
Brændstof- eller smøremiddelblandingerne ifølge opfindel 2 sen udviser i forhold til kendt teknik en række fordele, 3 såsom f.eks. den kendsgerning, at det drejer sig om mæt 4 tede forbindelser, at der ikke optræder korrosionsproble 5 mer, at syntesen er billigere og mere miljøvenlig, og at 6 der ikke optræder nogen produktbelastning, på grund af chlor eller brom.
7 DK 169584 B1
Opfindelsen skal nu forklares ved de følgende eksempler. EKSEMPEL 1 5 500 g polybuten med molvægt MN = 850m 300 g dodecan og 2,8 g cobaltoctacarbonyl opvarmes i en 2,5 liter stempel-røreautoklav ved 280 bar C0/H2 1:1 under omrøring i 5 timer til 185 °C. Derpå afkøler man til stuetemperatur og fjerner katalysatoren med 400 ml 10% vandig eddikesyre.
10 Derpå vaskes der til neutralitet. Man behandler det således fremkomne oxoprodukt med 1 liter ammoniak samt 33 g ethenol og 100 g Raney-cobalt i en 5 liter Roll-autoklav med 200 bar hydrogen ved 180 °C i 5 timer. Efter afkølingen separerer man katalysatoren ved filtrering, man for-15 damper det overskydende ammoniak og separerer opløsningsmidlet ad destillativ vej.
Ved det i dette eksempel anvendte polybuten drejer det sig om et højreaktivt polybuten C, der blev fremstillet i 20 henhold til DE-A 2 702 604.
Polybutenomsætningen fremgår af den følgende tabel.
EKSEMPEL 2 25
Man arbejder som i eksempel 1, hvorved man gennemfører hydroformyleringen ved en temperatur af kun 120 °C med 0,5 g rhodiumcarbonylacetylacetonat som katalysator. I stedet for ammoniak anvender man dimethylaminopropylamin.
30 Reaktionstemperaturen af amineringstrinnet andrager kun 80 °C. Da hydroformyleringsreaktionen overvejende forløber i retning af aldehyd, lettes omsætningen med dimethylaminopropylamin. Den overskydende amin separeres sammen med opløsningsmidlet ad destillativ vej.
35 8 DK 169584 B1 EKSEMPEL 3, 4 Og 5
Man arbejder i henhold til den almene forskrift fra eksempel 1, hvorved man som aminkomponent anvender dime-5 thylaminopropylamin. som polybuten anvender man i eksempel 3 en lidet reaktiv polybuten (kaldet polybuten A), i eksempel 4 anvendes en middelreaktiv polybuten B, og i eksempel 5 anvender man en højreaktiv polybuten C. Disse polybutener udviser en molekylvægt M^ af 900-1000. Som i 10 eksempel 1 bestemmes omsætningen søjlekromatografisk præparativt over kiselgel ved gravimetri af den inddampede hexanfraktion, der kun indeholder uomsat polybuten. Renheden af denne fraktion bestemmes ved basetal og nitrogenbestemmelse .
15 EKSEMPEL 6
Man arbejder som beskrevet i eksempel 1 med undtagelse af, at man anvender 2,8 g cobaltoctacarbonyl som kataly-20 sator. Ved aminkomponenten drejer det sig om tetraethy-lenpentamin.
SAMMENLIGNINGSEKSEMPLER A og B
25 Produkterne svarende til kendt teknik fremstilledes ved chlorering af polybuten C og dehydrohalogenering i henhold til US patent nr. 3 275 554, eksempel 1. I tilfælde af sammenligningseksempel B opnåede man ved syntesevejen via polybutylenchlorid en ringere omsætning end ved 30 opfindelsen, hvilket er i overensstemmelse med DE-A nr.
2 245 918.
Brugbarheden af de stoffer, hvis fremstilling er beskrevet i det foregående, blev undersøgt i brændstofblandin-35 ger og smøremiddelblandinger. Ved eksemplerne 1 til 5 og sammenligningseksemplet A drejer det sig om undersøgelser af det additiverede brændstof, og eksempel 6 g sammenlig- 9 DK 169584 B1 ningseksemplet B angår smøremiddelblandinger.
Den ventilrensende virkning af de additiverede brændstoffer bedømtes ved hjælp af ventilaflejringer i en Opel-5 Kadett 1,2 liter motor i overensstemmelse med en som norm tjenende prøvemetode i henhold til CEC-metoden F-02-C79 efter 40 minutter.
Dispergeringsvirkningen i forbindelse med smøreolier blev 10 bestemt ved hjælp af prikkemetoden, der er beskrevet af A. Schilling i "Les Huiles Pour Meteurs et le Graissage des Moteurs", bind 1, 1962, side 89-90.
Af de i de efterfølgende tabeller 1 og 2 sammenstillede 15 data fremgår, at brændstof- eller smøremiddelblandingerne ifølge opfindelsen er overlegen i forhold til kendt teknik, hvad angår ventilrensende virkning eller disperge-ringsvirkning.
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Claims (5)
1. Polybutyl- eller polyisobutylaminer, kendeteg-5 net ved, at de har den almene formel: R2 / 2 R--CH0-N (I) 1. x R3 io hvori er en af isobuten og indtil 20 vægt-% n-buten afledt polybutyl- eller polyisobutylgruppe med 20-400 carbonato-mer, og R2 og R3, der kan være ens eller forskellige, er hydrogen, C1-C10-alkyl, phenyl, naphthyl, C^-C^-hydroxyalkyl, en aminoalkylengruppe med den almene formel II R5 / -R4-N (II)
20 XR R6 hvori R4 er en C^-C^-alkylengruppe, og R,- og Rfi, der er ens eller forskellige, er hydrogen, C. -u C^Q-alkyl, phenyl, naphthyl, C^-C^Q-hydroxyalkyl eller polybutyl eller polyisobutyl, hver med 20-400 carbonato-mer, en polyaminoalkylengruppe med den almene formel III [-ν^Λ 11“) 30 hvori grupperne R4 hver især er ens eller forskellige, grupperne Rg hver især er ens eller forskellige og grupperne R4, Rg og Rg har de ovennævnte betydninger, og m betyder et helt tal fra 1 til 7, eller 35 DK 169584 B1 en polyoxyalkylengruppe med den almene formel IV [-ν°]ιΓΗ <IV) hvori grupperne R. hver især kan være ens eller forskel- c ’ lige og har de ovennævnte betydninger, og n er et helt tal mellem 1 og 30, eller hvor og R^ sammen med det nitrogenatom, hvortil de er bundet, danner en morfolinylgruppe, og hvor polybu-tyl- eller polyisobutylaminerne er fremstillet ved hydro-formylering af de til gruppen R^ svarende polybutener eller polyisobutener efterfulgt af hydrerende aminering.
2. Fremgangsmåde til fremstilling af polybutyl- eller polyisobutylaminer med den almene formel I ifølge krav 1, kendetegnet ved, at man hydro formy lerer en polybuten eller polyisobuten med en rhodium- eller co-baltkatalysator i nærværelse af CO og ved temperaturer mellem 80 og 200 °C og et CO/H0-tryk på indtil 600 bar, 20 ^ og at man derpå gennemfører en hydrerende aminering af oxopropuktet.
3. Brændstof- eller smøremiddelblanding, kendetegnet ved, at den indeholder mindst en polybutyl-eller polyisobutylamin med den almene formel I: R2 / Δ r.-ch9-n (I) 1. x R3 30 hvori R^ er en af isobuten og indtil 20 vægt-% n-buten afledt polybutyl- eller polyisobutylgruppe med 20-400 carbonato-mer, og R2 og R^, der er ens eller forskellige, er hydrogen, C1-C1Q-alkyl, phenyl, naphthyl, C^C^Q-hydroxyalkyl, 35 en aminoalkylengruppe med den almene formel II DK 169584 B1 R5 / -R.-N (II) 4 \ R6 hvori 5 R4 er en C^-C^Q-alkylengruppe, og R5 og Rg, der er ens eller forskellige, er hydrogen, alkyl, phenyl, naphthyl, C^-C^Q-hydroxyalkyl eller polybutyl eller poly-isobutyl, hver med 20-400 carbonatomer, 10 en polyaminoalkylengruppe med den almene formel III [-R4-NR5}mR6 (111) hvori grupperne R^ hver især er ens eller forskellige, 15 grupperne Rg hver især er ens eller forskellige, og grupperne R^, Rg og Rg har de ovennævnte betydninger, og m er et helt tal fra 1 til 7, eller en polyoxyalkylengruppe med den almene formel IV 20 {R4-°}n-H <IV> hvori grupperne R^ hver især er ens eller forskellige og har de ovennævnte betydning, og n er et helt tal mellem 1 og 30, 25 eller hvor og R^ sammen med det nitrogenatom, hvortil de er bundet, danner en morfolinylgruppe, og hvor polybutyl- eller polyisobutylaminerne er fremstillet ved hydro-formylering af de til gruppen R1 svarende polybutener eller polyisobutener efterfulgt af hydrerende aminering. 30
4. Brændstofblanding ifølge krav 3, kendetegnet ved, at den indeholder polybutyl- eller polyisobutylami- nen i en mængde på mellem 10 og 2000 ppm, især 100 til 400 ppm, beregnet i forhold til blandingens totale vægt. 35 DK 169584 B1
5. Smøremiddelblanding ifølge krav 3, kendetegnet ved, at den indeholder polybutyl eller polyisobu-tylaminen i en mængde mellem 0,5 og 5 vægt-%, især mellem 1 og 3 vægt-%, beregnet i forhold til blandingens totale 5 vægt. 10 20 25 30 35
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DE3611230 | 1986-04-04 | ||
DE19863611230 DE3611230A1 (de) | 1986-04-04 | 1986-04-04 | Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen |
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DK169584B1 true DK169584B1 (da) | 1994-12-12 |
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EP (1) | EP0244616B1 (da) |
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DE (2) | DE3611230A1 (da) |
DK (1) | DK169584B1 (da) |
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Families Citing this family (263)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3838918A1 (de) * | 1988-11-17 | 1990-05-23 | Basf Ag | Kraftstoffe fuer verbrennungsmaschinen |
EP0384086A1 (en) * | 1989-02-10 | 1990-08-29 | BP Chimie Société Anonyme | Synthesis of hydrocarbyl amines |
GB8902987D0 (en) * | 1989-02-10 | 1989-03-30 | Bp Chemicals Additives | Chemical product |
US6054539A (en) * | 1998-07-31 | 2000-04-25 | Mobil Oil Corporation | Selectively hydrogenated polymer compositions: polybutadiene-isoprene-polybutadiene |
US6228817B1 (en) | 1990-01-16 | 2001-05-08 | Mobil Oil Corporation | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers |
US6248702B1 (en) | 1990-01-16 | 2001-06-19 | Mobil Oil Corporation | Dispersant and dispersant viscosity index improvers from selectively hydrogenated aryl-substituted olefin containing diene copolymers |
US6034184A (en) * | 1998-06-23 | 2000-03-07 | Mobil Oil Corporation | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: Mannich reaction products |
US6103676A (en) * | 1998-06-23 | 2000-08-15 | Mobil Oil Corporation | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: hydroformylation/reductive amination reaction products |
US6162768A (en) * | 1990-01-16 | 2000-12-19 | Mobil Oil Corporation | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: free radically initiated direct grafting reaction products |
US6488723B2 (en) * | 1990-03-05 | 2002-12-03 | Alfred Richard Nelson | Motor fuel additive composition and method for preparation thereof |
EP0518966B1 (en) * | 1990-03-05 | 1995-12-27 | Polar Molecular Corporation | Motor fuel additive composition and method for preparation thereof |
GB9007431D0 (en) * | 1990-04-03 | 1990-05-30 | Shell Int Research | Diesel fuel additives |
DE4030164A1 (de) * | 1990-09-24 | 1992-03-26 | Basf Ag | Kraftstoffe fuer verbrennungsmotoren und schmierstoffe enthaltende hochmolekulare aminoalkohole |
DE4035609A1 (de) * | 1990-11-09 | 1992-05-14 | Basf Ag | Kraftstoffe fuer ottomotoren |
CA2075716C (en) * | 1990-12-27 | 2004-02-10 | Edward T. Sabourin | Fuel compositions containing hydroxyalkyl-substituted amines |
AU1462492A (en) | 1991-02-26 | 1992-09-15 | Ferro Corporation | Halogen-free, deposit-control fuel additives comprising a hydroxypolyalkene amine, and a process for its production |
DE4135946A1 (de) * | 1991-10-31 | 1993-05-06 | Basf Ag, 6700 Ludwigshafen, De | Verfahren zur herstellung von alkanolaminen und verwendung des reaktionsprodukts als kraftstoff- oder schmierstoffadditiv |
EP0541177B1 (en) * | 1991-11-07 | 1996-01-31 | Shell Internationale Researchmaatschappij B.V. | Secondary amines and a process for their preparation |
DE69208023T2 (de) * | 1991-11-07 | 1996-07-11 | Shell Int Research | Verfahren zur Herstellung von sekundären Aminen |
DE4137852A1 (de) * | 1991-11-16 | 1993-05-19 | Basf Ag | Carbamidsaeureester, verfahren zu ihrer herstellung sowie kraft- und schmierstoffe, enthaltend die carbamidsaeureester |
FR2687159B1 (fr) * | 1992-02-07 | 1994-04-08 | Bp Chemicals Snc | Procede de fabrication d'un polybutene azote et utilisation. |
DE4208756A1 (de) * | 1992-03-19 | 1993-09-23 | Basf Ag | Diaminoalkane, verfahren zu deren herstellung sowie kraftstoffe und schmierstoffe, enthaltend die diaminoalkane |
GB9208034D0 (en) * | 1992-04-10 | 1992-05-27 | Bp Chem Int Ltd | Fuel composition |
DE4213677A1 (de) * | 1992-04-25 | 1993-10-28 | Basf Ag | Kraftstoffe und Schmierstoffe, enthaltend N-Alkyl-Carbon-säureamide |
DE4214810A1 (de) * | 1992-05-04 | 1993-11-11 | Basf Ag | µ-Aminonitrile und N-Alkyl-1,3-propylendiamine sowie deren Verwendung als Kraft- und Schmierstoffadditive |
IL107927A0 (en) | 1992-12-17 | 1994-04-12 | Exxon Chemical Patents Inc | Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same |
US5554310A (en) | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
US5516342A (en) * | 1992-12-28 | 1996-05-14 | Chevron Chemical Company | Fuel additive compositions containing poly(oxyalkylene) hydroxyaromatic ethers and aliphatic amines |
US5462567A (en) * | 1992-12-28 | 1995-10-31 | Chevron Chemical Company | Fuel additive compositions containing poly(oxyalkylene)hydroxyaromatic esters and aliphatic amines |
US5755835A (en) * | 1992-12-28 | 1998-05-26 | Chevron Chemical Company | Fuel additive compositions containing aliphatic amines and polyalkyl hydroxyaromatics |
DE4309074A1 (de) * | 1993-03-20 | 1994-09-22 | Basf Ag | Als Kraftstoffadditiv geeignete Mischungen |
DE4309271A1 (de) * | 1993-03-23 | 1994-09-29 | Basf Ag | Kraftstoffadditive, Verfahren zu ihrer Herstellung sowie Kraftstoffe für Ottomotoren, enthaltend die Additive |
DE4313088A1 (de) * | 1993-04-22 | 1994-10-27 | Basf Ag | Poly-1-n-alkenamine und diese enthaltende Kraft- und Schmierstoffzusammensetzungen |
US5346965A (en) * | 1993-08-19 | 1994-09-13 | Ferro Corporation | Process for the production of fuel additives from chlorinated polybutenes |
US5674950A (en) * | 1994-03-07 | 1997-10-07 | Exxon Chemical Patents Inc. | Polymers having terminal hydroxyl aldehyde, or alkylamino substitutents and derivatives thereof |
US5691422A (en) * | 1994-03-07 | 1997-11-25 | Exxon Chemical Patents Inc. | Saturated polyolefins having terminal aldehyde or hydroxy substituents and derivatives thereof |
US5569407A (en) * | 1994-03-25 | 1996-10-29 | Mobil Oil Corporation | Additives for fuels and lubricants |
DE4412489A1 (de) * | 1994-04-12 | 1995-10-19 | Basf Ag | Kraft- oder Schmierstoffadditive, Verfahren zu ihrer Herstellung sowie Kraft- oder Schmierstoffzusammensetzungen, enthaltend diese Additive |
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 |
US5405418A (en) † | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and an aromatic ester |
DE4423346A1 (de) | 1994-07-04 | 1996-01-11 | Basf Ag | Kupferoxid/Zirkonoxid-Katalysator |
DE4425835A1 (de) * | 1994-07-21 | 1996-01-25 | Basf Ag | Verwendung von Umsetzungsprodukten aus Polyolefinen und Stickoxiden oder Gemischen aus Stickoxiden und Sauerstoff als Additive für Kraftstoffe |
DE4426003A1 (de) | 1994-07-22 | 1996-01-25 | Basf Ag | Umsetzungsprodukte von Polyolefinen mit Vinylestern und ihre Verwendung als Kraft- und Schmierstoffadditive |
DE4427428A1 (de) | 1994-08-03 | 1996-02-29 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
DE4429547A1 (de) | 1994-08-19 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE4432038A1 (de) * | 1994-09-09 | 1996-03-14 | Basf Ag | Polyetheramine enthaltende Kraftstoffe für Ottomotoren |
US6312481B1 (en) | 1994-09-22 | 2001-11-06 | Shell Oil Company | Fuel compositions |
DE4434603A1 (de) | 1994-09-28 | 1996-04-04 | Basf Ag | Als Kraft- und Schmierstoffadditiv geeignete Mischung aus Aminen, Kohlenwasserstoffpolymeren und Trägerölen |
DE4440801A1 (de) * | 1994-11-17 | 1996-05-23 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
US5962738A (en) * | 1994-12-15 | 1999-10-05 | Petrokleen, Ltd. | Polymeric-amine fuel and lubricant additive |
US5567211A (en) * | 1995-08-03 | 1996-10-22 | Texaco Inc. | Motor fuel detergent additives |
DE19528942A1 (de) * | 1995-08-07 | 1997-02-13 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
CA2191919C (en) * | 1995-12-19 | 2006-02-21 | James A. Gray | Reductive amination process for manufacturing a fuel additive from polyoxybutylene alcohol with ethylene diamine |
DE19548145A1 (de) * | 1995-12-21 | 1997-06-26 | Basf Ag | Sekundäre Polyisobutenamine enthaltende Kraft- oder Schmierstoffzusammensetzungen |
US6165237A (en) * | 1996-02-23 | 2000-12-26 | Basf Aktiengesellschaft | Fuel and lubricant additives |
US5752990A (en) * | 1996-03-29 | 1998-05-19 | Exxon Research And Engineering Company | Composition and method for reducing combustion chamber deposits, intake valve deposits or both in spark ignition internal combustion engines |
US5669939A (en) * | 1996-05-14 | 1997-09-23 | Chevron Chemical Company | Polyalkylphenoxyaminoalkanes and fuel compositions containing the same |
DE19620262A1 (de) * | 1996-05-20 | 1997-11-27 | Basf Ag | Verfahren zur Herstellung von Polyalkenaminen |
US6909018B1 (en) | 1996-05-20 | 2005-06-21 | Basf Aktiengesellschaft | Preparation of polyalkeneamines |
US6331656B1 (en) | 1996-09-20 | 2001-12-18 | Basf Aktiengesellschaft | Hydroformylation process |
AU4355997A (en) * | 1996-09-23 | 1998-04-14 | Petrokleen, Ltd. | Method of synthesizing pure additives and the improved compositions thereby produced |
US6221116B1 (en) | 1996-09-27 | 2001-04-24 | Chevron Chemical Company | Aminocarbamates of polyalkylphenoxyalkanols and fuel compositions containing the same |
DE19645430A1 (de) * | 1996-11-04 | 1998-05-07 | Basf Ag | Polyolefine und deren funktionalisierte Derivate |
US5810894A (en) * | 1996-12-20 | 1998-09-22 | Ferro Corporation | Monoamines and a method of making the same |
DE19704482A1 (de) | 1997-02-06 | 1998-08-13 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
KR100284175B1 (ko) * | 1997-12-31 | 2001-05-02 | 이정국 | 다수의 하이드록시기가 치환된 폴리알케닐 아민 화합물과 이를함유한 연료유 조성물 |
US6215033B1 (en) | 1998-12-11 | 2001-04-10 | Mobil Oil Corporation | Dispersants and dispersant viscosity index improvers from selectively hydrogenated polymers: blends with lower molecular weight components |
US6319881B1 (en) | 1998-06-23 | 2001-11-20 | Exxonmobil Oil Corporation | Haze free oil additive compositions containing dispersants from selectively hydrogenated diene copolymers |
DE19830818A1 (de) | 1998-07-09 | 2000-01-13 | Basf Ag | Propoxilat enthaltende Kraftstoffzusammensetzungen |
DE19834593A1 (de) | 1998-07-31 | 2000-02-03 | Basf Ag | Verfahren zur Herstellung von halogenfreiem, reaktivem Polyisobuten |
WO2000020537A1 (fr) * | 1998-10-06 | 2000-04-13 | Nippon Mitsubishi Oil Corporation | Additif pour essence destinee a un moteur a essence a injection directe |
FR2786490A1 (fr) * | 1998-11-30 | 2000-06-02 | Atochem Elf Sa | Polybutyl- ou polyisobutylamines, -hydrazines ou -azides, leur procede de preparation et leurs utilisations comme detergents dans les carburants |
US6071319A (en) * | 1998-12-22 | 2000-06-06 | Chevron Chemical Company Llc | Fuel additive compositions containing aromatic esters of polyalkylphenoxyalkanols and aliphatic amines |
DE19908262A1 (de) * | 1999-02-25 | 2000-08-31 | Basf Ag | Polyalkenalkohol-Polyalkoxylate und deren Verwendung in Kraft- und Schmierstoffen |
DE19916512A1 (de) | 1999-04-13 | 2000-10-19 | Basf Ag | Polyalkenalkohol-Polyetheramine und deren Verwendung in Kraft- und Schmierstoffen |
US6193767B1 (en) * | 1999-09-28 | 2001-02-27 | The Lubrizol Corporation | Fuel additives and fuel compositions comprising said fuel additives |
EP1344784B1 (en) | 1999-11-08 | 2006-09-20 | Nippon Petrochemicals Company, Limited | Butene oligomer derivatives having terminal 1,4-butanediol functional groups |
US6224642B1 (en) | 1999-11-23 | 2001-05-01 | The Lubrizol Corporation | Additive composition |
CN1142194C (zh) | 2000-01-25 | 2004-03-17 | 阿克佐诺贝尔股份有限公司 | 胺化聚烯烃的制备方法 |
DE10003105A1 (de) * | 2000-01-25 | 2001-07-26 | Basf Ag | Kraftstoff-Wasser-Emulsionen, enthaltend Emulgatoren auf Polyisobuten-Basis |
US6210452B1 (en) | 2000-02-08 | 2001-04-03 | Hhntsman Petrochemical Corporation | Fuel additives |
US6462009B1 (en) * | 2000-04-14 | 2002-10-08 | Capital Chemical Company | Hydrophobizing microemulsions which improve the protection, drying rate and shine of surfaces |
JP2001303084A (ja) * | 2000-04-21 | 2001-10-31 | Idemitsu Kosan Co Ltd | 無鉛ガソリン組成物 |
DE10045056A1 (de) * | 2000-09-12 | 2002-03-21 | Basf Ag | Verfahren zur kontinuierlichen Hydroformylierung von Polyalkenen mit 30 bis 700 Kohlenstoffatomen |
AU2002241114A1 (en) * | 2001-03-26 | 2002-10-08 | Octel America Inc | Composition |
US7204863B2 (en) * | 2001-12-11 | 2007-04-17 | Exxonmobil Research And Engineering Company | Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits |
US7226489B2 (en) * | 2001-12-12 | 2007-06-05 | Exxonmobil Research And Engineering Company | Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits |
US20030150154A1 (en) * | 2001-12-21 | 2003-08-14 | Cherpeck Richard E. | Polyalkylphenoxyaminoalkanes and fuel compositions containing the same |
WO2003062626A1 (en) | 2002-01-23 | 2003-07-31 | Chevron Oronite Company Llc | Delivery device for removing interior engine deposits in a reciprocating internal combustion engine |
PE20030998A1 (es) * | 2002-02-12 | 2004-01-30 | Shell Int Research | Composiciones de gasolina |
DE10209830A1 (de) * | 2002-03-06 | 2003-09-18 | Basf Ag | Kraftstoffadditivgemische für Ottokraftstoffe mit synergistischer IVD-Performance |
US6660050B1 (en) | 2002-05-23 | 2003-12-09 | Chevron U.S.A. Inc. | Method for controlling deposits in the fuel reformer of a fuel cell system |
DE10239841A1 (de) * | 2002-08-29 | 2004-03-11 | Basf Ag | Additivgemische für Kraft- und Schmierstoffe |
DE10314809A1 (de) * | 2003-04-01 | 2004-10-14 | Basf Ag | Polyalkenamine mit verbesserten Anwendungseigenschaften |
DE10316871A1 (de) | 2003-04-11 | 2004-10-21 | Basf Ag | Kraftstoffzusammensetzung |
EP1651740B1 (en) * | 2003-07-15 | 2012-05-02 | Shell Internationale Research Maatschappij B.V. | Gasoline compositions |
DE10361503A1 (de) | 2003-12-23 | 2005-07-28 | Basf Ag | Verfahren zur Herstellung eines Ethylamins |
DE102004023529A1 (de) | 2004-05-13 | 2005-12-08 | Basf Ag | Verfahren zur kontinuierlichen Herstellung eines Amins |
US20050268534A1 (en) * | 2004-06-02 | 2005-12-08 | Polar Molecular Corporation | Motor fuel additive composition |
US20050268532A1 (en) * | 2004-06-02 | 2005-12-08 | Polar Molecular Corporation | Motor fuel additive composition |
US20090158642A1 (en) * | 2004-06-02 | 2009-06-25 | Polar Molecular Corporation | Motor fuel additive composition |
US20050268531A1 (en) * | 2004-06-02 | 2005-12-08 | Polar Molecular Corporation | Motor fuel additive composition |
US20090158643A1 (en) * | 2004-06-02 | 2009-06-25 | Polar Molecular Corporation | Motor fuel additive composition |
US20050268537A1 (en) * | 2004-06-02 | 2005-12-08 | Polar Molecular Corporation | Motor fuel additive composition |
US20050268533A1 (en) * | 2004-06-02 | 2005-12-08 | Polar Molecular Corporation | Motor fuel additive composition |
US20070214713A1 (en) * | 2004-08-06 | 2007-09-20 | Basf Aktiengesellschaft | Polyamine Additives For Fuels and Lubricants |
EP1640438B1 (en) | 2004-09-17 | 2017-08-30 | Infineum International Limited | Improvements in Fuel Oils |
CA2520174C (en) | 2004-09-17 | 2013-07-23 | Infineum International Limited | Additive composition for improving conductivity in fuel oils |
US20060059771A1 (en) * | 2004-09-17 | 2006-03-23 | Malfer Dennis J | Preparation of amine derivates from nitriles and phenols |
US7388033B2 (en) * | 2004-09-21 | 2008-06-17 | Capital Chemical Co. | Amine-functionalized polyisobutylenes for improved hydrophobizing microemulsions |
US20060171909A1 (en) | 2005-02-03 | 2006-08-03 | The Procter & Gamble Company | Cosmetic compositions comprising colorants with low free dye |
US20060196111A1 (en) * | 2005-03-04 | 2006-09-07 | Colucci William J | Fuel additive composition |
DE102005019540A1 (de) * | 2005-04-27 | 2006-11-09 | Basf Ag | Verfahren zur Herstellung eines Amins |
US9714371B2 (en) | 2005-05-02 | 2017-07-25 | Trican Well Service Ltd. | Method for making particulate slurries and particulate slurry compositions |
DE102005029095A1 (de) | 2005-06-23 | 2007-01-18 | Basf Ag | Verfahren zur kontinuierlichen Herstellung eines Amins |
DE102005029423A1 (de) * | 2005-06-24 | 2006-12-28 | Basf Ag | Verfahren zur Herstellung eines Polyalkenylamins |
DE102005043440A1 (de) * | 2005-09-13 | 2007-03-15 | Basf Ag | Verfahren zur Herstellung eines Ethylamins aus vergälltem Ethanol |
US20080066714A1 (en) * | 2005-09-20 | 2008-03-20 | George Robert Lee | Fuel compositions and its use |
MX2008011260A (es) | 2006-03-21 | 2008-09-10 | Basf Se | Proceso para preparar una amina. |
US8034978B2 (en) | 2006-05-31 | 2011-10-11 | Basf Se | Process for the preparation of an amine |
JP5385129B2 (ja) | 2006-06-15 | 2014-01-08 | ダウ グローバル テクノロジーズ エルエルシー | 官能化されたオレフィンインターポリマー、組成物及びそれから作製された製品、ならびにそれを作製するための方法 |
US20070294936A1 (en) * | 2006-06-23 | 2007-12-27 | Afton Chemical Corporation | Method For Producing Polyolefinic Amines and compositions Containing Same |
RU2009104738A (ru) | 2006-07-14 | 2010-08-27 | Басф Се (De) | Способ получения амина |
WO2008006750A1 (de) | 2006-07-14 | 2008-01-17 | Basf Se | Verfahren zur herstellung eines amins |
JP2009543830A (ja) * | 2006-07-14 | 2009-12-10 | ビーエーエスエフ ソシエタス・ヨーロピア | アミンの製造方法 |
CN101489980A (zh) | 2006-07-14 | 2009-07-22 | 巴斯夫欧洲公司 | 生产胺的方法 |
CN101489981B (zh) | 2006-07-14 | 2013-03-20 | 巴斯夫欧洲公司 | 生产胺的方法 |
MX2008015874A (es) * | 2006-07-20 | 2009-01-12 | Sca Hygiene Prod Ab | Un aparato y metodo para formar nucleos absorbentes tendidos al aire. |
US20080113890A1 (en) | 2006-11-09 | 2008-05-15 | The Lubrizol Corporation | Quaternary Ammonium Salt of a Polyalkene-Substituted Amine Compound |
EP1947161A1 (en) | 2006-12-13 | 2008-07-23 | Infineum International Limited | Fuel oil compositions |
ATE490299T1 (de) | 2007-03-02 | 2010-12-15 | Basf Se | Zur antistatikausrüstung und verbesserung der elektrischen leitfähigkeit von unbelebtem organischen material geeignete additivformulierung |
AR066304A1 (es) | 2007-04-26 | 2009-08-12 | Trican Well Service Ltd | Composicion de solucion acuosa espesa y metodo para controlar la arena en una formacion productora de hideocarburos para usar con dicha composicion |
DE102007046223A1 (de) | 2007-09-26 | 2009-04-02 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verringerung des Kraftstoffverbrauchs |
DE102007032120A1 (de) | 2007-07-09 | 2009-01-15 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verringerung des Kraftstoffverbrauchs |
EP2225029B1 (de) | 2007-12-21 | 2016-08-03 | Basf Se | Verfahren und katalysator zur herstellung eines amins |
US8268995B2 (en) | 2007-12-21 | 2012-09-18 | Basf Se | Processes for preparing amines and catalysts for use therein |
US8324430B2 (en) | 2007-12-21 | 2012-12-04 | Basf Se | Processes for preparing amines and catalysts for use therein |
CN101903092B (zh) | 2007-12-21 | 2013-03-20 | 巴斯夫欧洲公司 | 生产胺的方法 |
CN101959905B (zh) | 2008-02-01 | 2013-03-06 | 巴斯夫欧洲公司 | 特定的聚异丁烯胺以及它们在燃料中作为洗涤剂的用途 |
US8183314B2 (en) * | 2008-07-01 | 2012-05-22 | Exxonmobil Research And Engineering Company | Emulsion compositions with a polymeric emulsifier |
JP5656840B2 (ja) | 2008-09-19 | 2015-01-21 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | アルミニウム−銅触媒を用いた、アミンの連続的な製造方法 |
US8465560B1 (en) | 2009-02-05 | 2013-06-18 | Butamax Advanced Biofuels Llc | Gasoline deposit control additive composition |
DE102010001408A1 (de) | 2009-02-06 | 2010-08-12 | Basf Se | Verwendung von Ketonen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauches von Dieselmotoren |
DE102009001447A1 (de) | 2009-03-10 | 2010-09-16 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren zur Verbesserung des Lasttragevermögens |
DE102009001446A1 (de) | 2009-03-10 | 2010-09-23 | Evonik Rohmax Additives Gmbh | Verwendung von Kammpolymeren als Antifatigue-Additive |
US8552122B2 (en) * | 2009-03-31 | 2013-10-08 | The University Of Southern Mississippi | Amine-terminated telechelic polymers and precursors thereto and methods for their preparation |
US20100298507A1 (en) | 2009-05-19 | 2010-11-25 | Menschig Klaus R | Polyisobutylene Production Process With Improved Efficiencies And/Or For Forming Products Having Improved Characteristics And Polyisobutylene Products Produced Thereby |
US8549897B2 (en) | 2009-07-24 | 2013-10-08 | Chevron Oronite S.A. | System and method for screening liquid compositions |
DE102010039039A1 (de) | 2009-08-24 | 2011-03-03 | Basf Se | Verwendung von organischen Verbindungen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauchs von Dieselmotoren |
RU2012119830A (ru) | 2009-10-16 | 2013-11-27 | Басф Се | Блок-сополимеры в качестве термопластичных эластомеров из полиизобутеновых блоков и олигоамидных блоков |
JP5755237B2 (ja) | 2009-12-03 | 2015-07-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 触媒及びアミンの製造方法 |
EA021623B1 (ru) | 2009-12-03 | 2015-07-30 | Басф Се | Катализатор на носителе и способ получения амина |
SG181791A1 (en) * | 2009-12-18 | 2012-07-30 | Chevron Oronite Co | Polyisobutenyl alcohols and fuel compositions |
US8920524B2 (en) | 2009-12-18 | 2014-12-30 | Chevron Oronite Company Llc | Polyisobutenyl alcohols and fuel compositions |
SG178923A1 (en) * | 2009-12-18 | 2012-04-27 | Chevron Oronite Co | Carbonyl-ene functionalized polyolefins |
CN102666811A (zh) | 2009-12-21 | 2012-09-12 | Bp北美公司 | 用于减少内燃机中的摩擦的组合物和方法 |
EP2516602A1 (en) | 2009-12-21 | 2012-10-31 | BP Corporation North America Inc. | Composition and method for reducing friction in internal combustion engines |
US20110218295A1 (en) * | 2010-03-02 | 2011-09-08 | Basf Se | Anionic associative rheology modifiers |
ES2544283T3 (es) | 2010-03-02 | 2015-08-28 | Basf Se | Copolímeros de bloque y su uso |
US8673275B2 (en) | 2010-03-02 | 2014-03-18 | Basf Se | Block copolymers and their use |
EP2563822A1 (de) | 2010-04-27 | 2013-03-06 | Basf Se | Quaternisiertes terpolymerisat |
US8790426B2 (en) | 2010-04-27 | 2014-07-29 | Basf Se | Quaternized terpolymer |
JP5882308B2 (ja) * | 2010-06-01 | 2016-03-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 洗剤ブースターとしての低分子量のポリイソブチル置換したアミン |
US8637668B2 (en) | 2010-06-15 | 2014-01-28 | Basf Se | Process for preparing a cyclic tertiary methylamine |
CA2803207A1 (en) | 2010-06-25 | 2011-12-29 | Basf Se | Quaternized copolymer |
US8911516B2 (en) | 2010-06-25 | 2014-12-16 | Basf Se | Quaternized copolymer |
MX2013000054A (es) | 2010-07-06 | 2013-03-18 | Basf Se | Compuestos de nitrogeno cuaternizados libres de acido y sus uso como aditivos en combustibles y lubricantes. |
EP2439189A1 (de) | 2010-09-17 | 2012-04-11 | Basf Se | Verfahren zur Herstellung von aromatischen Aminen |
US8933223B2 (en) | 2010-10-14 | 2015-01-13 | Basf Se | Process for preparing a cyclic tertiary amine |
US8663407B2 (en) | 2010-11-17 | 2014-03-04 | 3M Innovative Properties Company | Isobutylene (Co)polymeric adhesive composition |
CA2818120C (en) | 2010-11-19 | 2019-05-14 | Chevron Oronite Company Llc | Method for cleaning deposits from an engine fuel delivery system |
US9296841B2 (en) | 2010-11-30 | 2016-03-29 | Basf Se | Preparation of isobutene homo- or copolymer derivatives |
EP4406982A3 (de) | 2010-11-30 | 2024-08-14 | Basf Se | Herstellung von isobutenhomo- oder -copolymer-derivaten |
FR2969654B1 (fr) | 2010-12-22 | 2013-02-08 | Rhodia Operations | Composition d'additif carburant a base d'une dispersion de particules de fer et d'un detergent |
US8637709B2 (en) | 2011-03-08 | 2014-01-28 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
CN103502212B (zh) | 2011-03-08 | 2016-05-18 | 巴斯夫欧洲公司 | 制备通过均相催化醇胺化获得的伯胺的方法 |
ES2544933T3 (es) | 2011-03-08 | 2015-09-07 | Basf Se | Procedimiento para la preparación de aminas primarias mediante aminación de alcohol bajo catálisis homogénea |
RU2013144822A (ru) | 2011-03-08 | 2015-04-20 | Басф Се | Способ получения ди-, три- и полиаминов аминированием спиртов при гомогенном катализе |
US8912361B2 (en) | 2011-03-08 | 2014-12-16 | Basf Se | Process for preparing di-, tri- and polyamines by homogeneously catalyzed alcohol amination |
US8785693B2 (en) | 2011-03-08 | 2014-07-22 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
US20130133243A1 (en) | 2011-06-28 | 2013-05-30 | Basf Se | Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants |
EP2540808A1 (de) | 2011-06-28 | 2013-01-02 | Basf Se | Quaternisierte Stickstoffverbindungen und deren Verwendung als Additive in Kraft- und Schmierstoffen |
EP2758498A1 (en) | 2011-09-23 | 2014-07-30 | The Lubrizol Corporation | Quaternary ammonium salts in heating oils |
EP2589647A1 (de) | 2011-11-04 | 2013-05-08 | Basf Se | Quaternisierte Polyetheramine und deren Verwendung als Additive in Kraft- und Schmierstoffen |
WO2013068272A1 (en) | 2011-11-11 | 2013-05-16 | Basf Se | Self-emulsifiable polyolefine compositions |
CN104023705B (zh) | 2011-11-11 | 2017-02-15 | 巴斯夫欧洲公司 | 可自乳化的聚烯烃组合物 |
CN103975046A (zh) * | 2011-11-23 | 2014-08-06 | 巴斯夫欧洲公司 | 胺混合物 |
EP2604674A1 (de) | 2011-12-12 | 2013-06-19 | Basf Se | Verwendung quaternisierter Alkylamine als Additive in Kraft- und Schmierstoffen |
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KR20240119070A (ko) | 2021-12-06 | 2024-08-06 | 바스프 에스이 | 폴리이소부틸렌 아크릴아미드 빗모양 공중합체를 기반으로 하는 윤활제를 위한 점도 지수 개선제 |
GB202118100D0 (en) | 2021-12-14 | 2022-01-26 | Innospec Ltd | Methods and uses relating to fuel compositions |
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WO2024149635A1 (en) | 2023-01-12 | 2024-07-18 | Basf Se | Branched amines as additives for gasoline fuels |
WO2024206634A1 (en) | 2023-03-29 | 2024-10-03 | Chevron Oronite Company Llc | Fuel additive compositions and methods for controlling carbon deposits in an internal combustion engines |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL137371C (da) * | 1963-08-02 | |||
US3574576A (en) * | 1965-08-23 | 1971-04-13 | Chevron Res | Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine |
NL176177C (nl) * | 1971-09-21 | 1985-03-01 | Shell Int Research | Werkwijze voor de bereiding van aminen geschikt als toevoegsel voor smeermiddelen en brandstoffen. |
JPS5623299B2 (da) * | 1972-09-04 | 1981-05-30 | ||
US3989476A (en) * | 1974-06-19 | 1976-11-02 | The Lubrizol Corporation | Fuels containing N-substituted morpholines |
US4094799A (en) * | 1976-12-20 | 1978-06-13 | Atlantic Richfield Company | Solid particles-containing lubricating oil composition and method for using same |
DE2702604C2 (de) * | 1977-01-22 | 1984-08-30 | Basf Ag, 6700 Ludwigshafen | Polyisobutene |
US4134344A (en) * | 1977-04-11 | 1979-01-16 | Pullman Incorporated | Railway hopper car door lock |
US4178259A (en) * | 1978-05-01 | 1979-12-11 | Chevron Research Company | Dispersant Mannich base compositions |
US4202784A (en) * | 1979-04-09 | 1980-05-13 | Standard Oil Company (Indiana) | Tertiary carbinamine modified mannich compositions and lubricants containing same |
US4312965A (en) * | 1980-02-22 | 1982-01-26 | W. R. Grace & Co. | Process for forming amine/amide containing polymers |
US4357148A (en) * | 1981-04-13 | 1982-11-02 | Shell Oil Company | Method and fuel composition for control or reversal of octane requirement increase and for improved fuel economy |
US4558101A (en) * | 1983-03-18 | 1985-12-10 | W. R. Grace & Co. | Process for the preparation of polymeric amine containing products |
US4526936A (en) * | 1983-03-18 | 1985-07-02 | W. R. Grace & Co. | Process for the preparation of polymeric amine containing products |
GB2174102A (en) * | 1985-04-24 | 1986-10-29 | Shell Int Research | Diesel fuel composition |
-
1986
- 1986-04-04 DE DE19863611230 patent/DE3611230A1/de not_active Withdrawn
-
1987
- 1987-03-25 EP EP87104371A patent/EP0244616B1/de not_active Expired - Lifetime
- 1987-03-25 DE DE8787104371T patent/DE3763421D1/de not_active Expired - Lifetime
- 1987-03-25 ES ES87104371T patent/ES2016585B3/es not_active Expired - Lifetime
- 1987-03-25 US US07/029,811 patent/US4832702A/en not_active Expired - Lifetime
- 1987-03-30 JP JP62074583A patent/JPH07103385B2/ja not_active Expired - Lifetime
- 1987-04-03 DK DK170087A patent/DK169584B1/da not_active IP Right Cessation
- 1987-04-03 NO NO871393A patent/NO168828C/no unknown
-
1995
- 1995-04-04 JP JP7079199A patent/JP2696076B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US4832702A (en) | 1989-05-23 |
DK170087A (da) | 1987-10-05 |
JPH07103385B2 (ja) | 1995-11-08 |
NO168828B (no) | 1991-12-30 |
NO871393L (no) | 1987-10-05 |
NO871393D0 (no) | 1987-04-03 |
EP0244616A2 (de) | 1987-11-11 |
DK170087D0 (da) | 1987-04-03 |
ES2016585B3 (es) | 1990-11-16 |
DE3763421D1 (de) | 1990-08-02 |
EP0244616A3 (en) | 1987-12-23 |
EP0244616B1 (de) | 1990-06-27 |
JPH08100188A (ja) | 1996-04-16 |
DE3611230A1 (de) | 1987-10-08 |
JPS62241992A (ja) | 1987-10-22 |
JP2696076B2 (ja) | 1998-01-14 |
NO168828C (no) | 1992-04-08 |
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